Home Vacation Rentals By Owner In Chicago, IL

Showing 580 Of 2640 Vacation Rentals
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Exceptional(3)

$354.24

/ Nightly
Apartment

The Norwood Nook – Walkable Stay Near O’Hare & Metra!

Chicago, Illinois, United States

-5 miles to O’Hare Airport 10 minutes drive without trafficbr-2nd Floor Apartment within a two-unit building** You will need to walk upstairs to your unit*br-Blackout curtains br-Updated Kitchen with Quartz Countertopsbr-Utilities included! br-Keypad Entrybr-Walking Distance to Norwood Park Metra Station (half a mile away). br-Quiet Neighborhood br-4.7 Miles (12-minute drive) to Lutheran General Hospitalbr- Owner lives on the first floor with children***brbrVRBO Premier Host: 200+ reviews, 4.99 rating!brbrThe Space:brFully stocked apartment with everything you’ll need! Room darkening drapes in the bedrooms. Work from home with a large desk in the airy and bright apartment. The air conditioning we provide is 1 window unit a/c in the primary bedroom and 1 window unit a/c in the living area. Street parking is available without a permit.brbrBuilding & Neighbors:brThis is a second-floor unit in a well-maintained building with long-term residents. Quiet, respectful community atmosphere.brbrGeneral Amenities: br- Smart TV in the living roombr- Complimentary WiFibr- Central air conditioningbr- Towels and linens providedbr- Washer/DryerbrSupplies/Essentials: (We provide starter amounts of)br- Toilet paper & paper towelsbr- Hand soap & dish detergentbr- Laundry detergent & K-cupsbr**Guests manage their own refills after the starter package.brbrCheck-In Info:br- Standard check-in is 4 PM. Early check-in may be available starting 5 days before arrival:br- 10 AM to 4 PM: Additional half-nightly ratebrbrThe $45 Management Fee serves as an accidental damage waiver, covering up to $500 in accidental damages. It does not cover negligence. or pet damage.**br-The cleaning fee covers a standard turnover. If the home requires excessive cleaning beyond normal use (including but not limited to excessive trash, stains, bodily fluids, excessive dirt, moving furniture, or evidence of unapproved additional guests), the additional cleaning costs will be documented and charged through the Resolution Center.brbrPet Policy:br- NO PETS allowedbrbrNoise Monitoring:br- Minut device monitors noise and smoke (not audio/video) to help prevent parties.brbrPlease note there is a floodlight security camera on the house.brbrGuest Verification and Rental Agreement:br- To ensure a smooth check-in experience and to comply with current short-term rental regulations, we ask that you complete a guest verification process. This step helps us provide enhanced protection for both our guests and our property. This process includes a real-time selfie and ID check, as well as a safety search.br- Additionally, you will need to e-sign our short-term rental agreement, which outlines the house rules and important information about your stay.br***Please complete both the verification and the agreement within 72 hours of booking for a quick and seamless check-in.***br- Minimum booking age is 18. This home is located in a quiet residential area and is not suitable for parties or events.br- Minimum booking age is 18. This home is located in a quiet residential area and is not suitable for parties or events.brbrThank you for your cooperation and understanding!
Bed 2

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Bath 1

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Sleep 4

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$387.2

/ Nightly
Hotel

Family-Friendly 3BR Retreat Near UIC & West Loop

Chicago, Illinois, United States

Experience the best of Chicago living in this modern 3-bedroom, 2-bathroom home — a spacious, sunlit retreat perfect for families, business travelers, and groups. Tucked away in a peaceful neighborhood yet just minutes from downtown, this stylish getaway blends comfort, sophistication, and convenience for an unforgettable stay.brbr Sleeps up to 8 guests comfortably with spacious rooms and premium bedsbr Book your stay today!br We can’t wait to host you in the heart of beautiful ChicagobrbrSurprise your loved one with our Romantic Experience, launching this February for Valentine’s Day. brbrEnjoy a beautifully styled romantic setup with elegant décor, soft candlelight, and a stunning photo backdrop—perfect for proposals, anniversaries, or an unforgettable Valentine’s stay.brbrCheck the other details to note for more info brbrbrEvery detail has been designed with your comfort in mind — from the custom furnishings and large open spaces to the fully equipped kitchen and cozy bedrooms. Whether you’re in town for work, a concert, a conference, or a weekend getaway, you’ll find this home is the perfect place to relax, recharge, and make lifelong memories.brbrStep into a warm and welcoming environment that feels like home from the moment you arrive. The open-concept layout creates a bright and inviting space — perfect for gathering with family, working remotely, or unwinding after a day exploring the city.brbr Accommodation Features:br• 3 Spacious Bedrooms with Plush King Beds br• Cozy Sofa Bed in the Living Room br• 2 Full Bathrooms with Modern Fixtures br• Large Windows Bringing in Beautiful Natural Light br• Custom Furnishings and Thoughtful Design Details br• Fully Equipped Kitchen with Stainless Steel Appliances br• Central Heating & Cooling for Year-Round Comfort br• Large Dining Area — Perfect for Family Meals or Remote Work br• Plenty of Closet Space for Longer Stays br• FREE Parking for 1 Vehicle (limited availability, first-come, first-served) brbrThe home’s decor is a balance of modern design and cozy charm — ideal for guests seeking a relaxing and elevated stay.brbr✦ Entertainment & Comfort ✦brStay entertained or productive throughout your visit:br• Roku Smart TVs in the Living Room & Bedrooms br• Netflix, Hulu, Disney+, and More Ready to Stream br• Fast WiFi and a Comfortable Workspace for Remote Workers br• Thoughtfully Placed Lighting for a Cozy Ambiance brbrWhether you’re watching your favorite show, catching up on work, or sharing a meal with loved ones, this home offers everything you need for a comfortable, stress-free experience.brbr✦ Location Highlights ✦brEnjoy the convenience of being close to Chicago’s top attractions while coming home to a peaceful retreat at the end of the day.brbr Nearby Attractions:br• 10–15 min walk to Pink Line Subway Stationbr• 8 min drive to United Center (Home of the Bulls & Blackhawks)br• 10–15 min drive to Museum Campus (Shedd Aquarium, Field Museum, Adler Planetarium)br• 12 min drive to Millennium Park & The Iconic “Bean”br• 15 min drive to Navy Pierbr• 14 min drive to McCormick Place Convention Centerbrbr Nearby Restaurants & Dining:br• Dusek’s Tavern – award-winning gastropub favorites br• Pilsen Yards – tacos, craft cocktails, and outdoor dining br• Giordano’s Pizza – famous Chicago deep-dish br• Thalia Hall – iconic venue with live music and dining brbrShopping & Essentials:br• Target, Walgreens, and local markets just minutes awaybrbrGuests have full private access to the entire accommodation — no shared spaces! brbrParking:brFree designated parking spot for 1 vehicle (limited availability, first-come, first-served).brbr Laundry:brWasher & dryer available for guest use.brbr Self-Check-In:brConvenient and secure self-check-in with detailed instructions provided before arrival.brbr Romantic Experience – Available for $350/staybrbrOur Romantic Experience Package is designed to elevate your stay with a thoughtfully curated romantic setup, perfect for Valentine’s Day, anniversaries, or special celebrations. All décor will be professionally arranged before your arrival for a seamless and memorable surprise.brbr What’s Included (as shown in photos):br• Elegant table throw for a romantic dining setupbr• Light-up LOVE sign and small romantic décor accentsbr• Large heart-shaped backdrop (8–10 ft) ideal for photosbr• Flameless candles and rose petals for a warm, cozy ambiancebr• Romantic heart-shaped dining setbr• Decorative rose wine glassesbr• 100 faux roses for styling and photosbr• Clear decorative vase for floral displaybrbr Important Notes:brbr• This is a decor experience only (no food or beverages included)br• Items are for décor and photos and must remain in the accommodationbr• Setup is completed prior to check-inbr• Available February only for Valentine’s seasonbr• Must be requested in advance and added as a paid experiencebrbrThis experience is perfect for creating unforgettable moments and stunning photos during your stay.brbrbrAbout the Neighborhood:brWelcome to South Fairfield Avenue, located near the heart of Chicago’s vibrant Pilsen area — a neighborhood known for its rich culture, colorful murals, historic charm, and fantastic dining scene! brbrNeighborhood Highlights:br• Artistic and Culturally Rich: Pilsen is a creative hub filled with art galleries, stunning murals, and indie shops. br• Foodie's Paradise: Enjoy authentic Mexican restaurants, cozy cafes, and local breweries nearby. br• Close to Everything: Just a few minutes to downtown, the Pink Line subway, and Chicago’s top attractions! brbr Important to Know:brThe surrounding neighborhood is still undergoing development and revitalization. Like many growing urban areas, we encourage guests to be mindful when exploring, especially after dark. brWhile many guests feel perfectly comfortable, we recommend using rideshare services (Uber/Lyft) at night instead of walking.brbrYour Safety is Our Priority:br• Our building is professionally secured 24/7 with on-site security staff and monitored cameras throughout.br• The interior of the building and parking area are completely private and secure for your peace of mind. brbrMany guests choose our location because it offers an authentic Chicago experience with easy access to the city's most popular destinations — all while enjoying a safe and modern living space.brbr FAQsbrIs the neighborhood safe br Absolutely! It’s calm, family-friendly, and monitored 24/7.brbrDo you provide towels, linens, and toiletries br Yes! Fresh towels, bed linens, hair dryer, toothbrushes, toothpaste, and a starter kit of toiletries are provided.brbrWhat are the check-in and check-out times br Check-In: 4:00 PM | Check-Out: 11:00 AMbrEarly check-in/late check-out may be available upon request for an additional fee.brbrIs the accommodation professionally cleaned br Yes, every stay is thoroughly cleaned and sanitized.brbrAre the beds comfortable brGuests often rave about how cozy the mattresses are — many even ask where they can buy the same ones!brbrbr Why Guests Love This Staybr Spacious, Modern, and Family-Friendlybr TVs + Netflix in Every Bedroombr Super-Fast WiFi and Comfortable Workspacesbr Close to Downtown, Attractions, Dining, and Shoppingbr Great Value Compared to Hotels
Bed 3

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Bath 2

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Sleep 8

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$357.76

/ Nightly
Hotel

Pilsen Family-Friendly 3BR Retreat with Free Parking

Chicago, Illinois, United States

Welcome to your perfect Chicago getaway! This spacious and modern 3-bedroom, 2-bathroom home is ideal for families, business travelers, and groups seeking a stylish, comfortable stay. Thoughtfully designed with custom furnishings and art-deco touches, it offers all the comforts of home — plus luxurious extras.brbr Book Your Stay Today!brWe can’t wait to host you in Chicago. brFeel free to message us anytime if you have any questions!brbrStep inside a warm, welcoming environment designed for comfort, style, and relaxation.brbr Accommodation Features:br• 3 Spacious Bedrooms with King Beds br• Cozy Sofa Bed in the Living Room br• 2 Full Bathrooms br• Large Windows offering natural sunlight br• Custom Furnishings and Stylish Decor br• Remodeled Flooring & Modern Touches br• Contemporary Kitchen with Stainless Steel Appliances br• Central Heating & Cooling br• Large Dining Table — perfect for meals or work br• Plenty of Closet Space for Long Stays br• FREE Parking for 1 car (limited availability, first-come, first-served)brEntertainment:br• Roku Smart TVs in Living Room & Bedroomsbr• Netflix, Hulu, and other streaming apps ready-to-gobrbrbr Location HighlightsbrStay close to everything while enjoying a quiet and calm home base:brbr Nearby Attractions:br• 10–15 min walk to Pink Line Subway Stationbr• 8 min drive to (Bulls & Blackhawks Games)br• 10–15 min drive to Museum Campus (Shedd Aquarium, Field Museum, Adler Planetarium)br• 15 min drive to Navy Pierbr• 12 min drive to Millennium Park & The Beanbr• 14 min drive to McCormick Place Convention Centerbrbr Top Restaurants Nearby:br• Dusek’s Tavern – 1227 W 18th St (gastropub favorites)br• Pilsen Yards – 1163 W 18th St (hip tacos & cocktails)br• Giordano’s Pizza – 1340 W 31st St (famous Chicago deep-dish)br• Thalia Hall – 1807 S Allport St (live music venue)brbr Shops & Essentials:br• Target, Walgreens, and local markets within 10 minutes brbrbr Why Guests Love This Staybr Spacious, Modern, and Family-Friendlybr TVs + Netflix in Every Bedroombr Super-Fast WiFi and Comfortable Workspacesbr Close to Downtown, Attractions, Dining, and Shoppingbr Great Value Compared to HotelsbrbrGuests have full private access to the entire accommodation — no shared spaces! brbr Parking:brFree parking spot for 1 vehicle (limited availability, first-come, first-served)brbr Laundry:brIn-suite washer & dryer available for guest use.brbr Self-Check-In:brConvenient and secure self-check-in with detailed instructions provided before arrival.brbrWe're available on an app and over the phone if needed.brbrAbout the Neighborhood:brbrWelcome to South Fairfield Avenue, located near the heart of Chicago’s vibrant Pilsen area — a neighborhood known for its rich culture, colorful murals, historic charm, and fantastic dining scene! brbr Neighborhood Highlights:br• Artistic and Culturally Rich: Pilsen is a creative hub filled with art galleries, stunning murals, and indie shops. br• Foodie's Paradise: Enjoy authentic Mexican restaurants, cozy cafes, and local breweries nearby. br• Close to Everything: Just a few minutes to downtown, the Pink Line subway, and Chicago’s top attractions! brbr Important to Know:brThe surrounding neighborhood is still undergoing development and revitalization. Like many growing urban areas, we encourage guests to be mindful when exploring, especially after dark. brWhile many guests feel perfectly comfortable, we recommend using rideshare services (Uber/Lyft) at night instead of walking.brbrYour Safety is Our Priority:br• Our building is professionally secured 24/7 with on-site security staff and monitored cameras throughout.br• The interior of the building and parking area are completely private and secure for your peace of mind. brbr Many guests choose our location because it offers an authentic Chicago experience with easy access to the city's most popular destinations — all while enjoying a safe and modern living space.brbrbrFAQsbrIs the neighborhood safe br Absolutely! It’s calm, family-friendly, and monitored 24/7.brbrDo you provide towels, linens, and toiletries br Yes! Fresh towels, bed linens, hair dryer, toothbrushes, toothpaste, and a starter kit of toiletries are provided.brbrWhat are the check-in and check-out times br Check-In: 4:00 PM | Check-Out: 11:00 AMbrEarly check-in/late check-out may be available upon request for an additional fee.brbrIs the accommodation professionally cleaned br Yes, every stay is thoroughly cleaned and sanitized.brbrAre the beds comfortable br Guests often rave about how cozy the mattresses are — many even ask where they can buy the same ones!
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Bath 2

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Sleep 8

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Exceptional(4)

$118.93

/ Nightly
Hotel

Upscale City Center Stay | Prime Locale | City Views | Pets Allowed

Chicago, Illinois, United States

Walk to Magnificent Mile, Navy Pier, parks. Near shops, dining, transit, arts.brbrThis listing is for a room within a hotel.brbr✦ Your room is 375 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services availability and frequency vary by staybrbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 18 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 02:00 pm.brbr✦ Fitness center is available.brbr✦ Paid valet parking – 1 space(s), available for $75 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $125 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $93.57 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00 (per pet). $75 plus tax per pet per stay Dogs only, maximum 2brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.
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Bath 1

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Sleep 2

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Exceptional(1)

$175.91

/ Nightly
Hotel

The Chicago Hotel Collection, Mag Mile, Deluxe Double Queen - Premium Option

Chicago, Illinois, United States

Walk to Magnificent Mile, Navy Pier, parks. Near shops, dining, transit, arts.brbrThis listing is for a room within a hotel.brbr✦ Your room is 425 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services availability and frequency vary by staybrbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 18 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 02:00 pm.brbr✦ Fitness center is available.brbr✦ Paid valet parking – 1 space(s), available for $75 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $125 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $93.57 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00 (per pet). $75 plus tax per pet per stay Dogs only, maximum 2brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.
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Bath 1

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Sleep 4

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$501.76

/ Nightly
Hotel

The Chicago Hotel Collection Magnificent Mile, 3 Standard King Rooms

Chicago, Illinois, United States

Walk to Magnificent Mile, Navy Pier, parks. Near shops, dining, transit, arts.brbrThis listing is for 3 separate rooms within a hotel. The price shown in the listing covers all 3 rooms.brbr✦ Each room is 375 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services availability and frequency vary by staybrbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 18 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 02:00 pm.brbr✦ Fitness center is available.brbr✦ Paid valet parking – 1 space(s), available for $75 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $375 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $93.57 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00 (per pet). $75 plus tax per pet per stay Dogs only, maximum 2brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.
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Bath 3

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Sleep 12

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Exceptional(8)

$1346.69

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Private Vacation Home

Relax with family in a super deluxe single family home. West town.

Chicago, Illinois, United States

“ Hello Again, Chicago” is a strikingly appointed, turn-key single-family home in the heart of West Town. This stunning developer's home blends a modern aesthetic with unparalleled comfort. brbrLocated on a quiet block across the street from Snowberry Park, this home boasts over 4300sf of finished living space across four levels, featuring 5 generously sized bedrooms, 3 full and 1 half bath. brbrAt the heart of the home is the enormous chef's kitchen that features custom cabinetry, a 16' island w/ quartz countertops, an over-the-top luxury appliance package including a 48 Wolf range and hood, Miele coffee maker, and Subzero refrigerator/freezer, and a temperature-controlled, fully-enclosed floor-to-ceiling glass 1200 bottle wine cellar. This luxurious kitchen is open to a sitting area/ entertaining area w/ a gas fireplace and massive dining table.. The rear deck anchors the large outdoor space with a wood-burning fireplace. Bistro lights hang over the large turfed yard for exquisite outdoor entertaining. Then down the hall is a huge family room with 55” TV and office area complete with business printer. brbrThe second floor features 2 guest beds that share a handsome full bathroom. Bedroom 1 has two queen beds and the next has 2 twin beds. A full laundry room down the hall and a master suite to make anyone envious. The master features large windows, built-in speakers, a huge walk-in closet w/ custom shelving, a spa-like bathroom with floor-to-ceiling designer tile, a steam shower, and a Kohler bubble jet massage tub. brbrThe third floor has a wet-bar that leads to the rooftop deck. Deck provides 360-degree views of the city from the pergola-covered seating area that includes a 55” Outdoor TV. brbrThe lower level features 2 more bedrooms, one with 2 queens and the other with 1 full bed and one twin beds. These rooms share 1 full bath. incredible media room with a high-definition projection home theater system w/ 144 screen. There's also a full wet bar w/ a wine fridge and a full commercial gym setup complete with cable machine, free weights and commercial treadmill. brbrThere are currently 2 garage spaces included with your rental. The home has custom lighting, window treatments, Closet-organization systems. Both outdoor areas have built-in speakers and there is a natural gas Weber grill on the back deck. This fantastic location is centrally located being just west of downtown Chicago and close to just about everything. brbr-2 miles straight down Chicago Ave to the Magnificent Milebr-4 miles to Wrigley Fieldbr-6 miles to Guaranteed Rate Stadiumbr-5 miles to Soldier Fieldbr-1 mile to United Centerbr-1 mile walk to the Blue Line L train br-Just steps from Chicago's super hip bars, restaurants, and nightlife on Chicago and Division streets.brbrThe home has been stocked with every amenity thinking of anything and everything that a discerning traveler like yourself could possibly need. New couches and all new furniture, new high quality linens, organic or natural mattresses and bedding and the home was very thoughtfully decorated and stocked with every convenience item imaginable. brbrI’ve hosted thousands of groups and have a host for the past 11 years and I hope that you’ll choose “Hello, Again” for your home base while you make memories in Chicago. brbrbrbrbr** A note about extra guest fee's. 6 guests are included in the per night price, it’s $69 per person per night thereafter. The reason for this is the higher cost incurred from larger groups. The costs are higher in electricity, gas, water, consumables, wear and tear on the home and insurance liability. Thanks for your understanding.
Bed 5

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Bath 3

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Sleep 17

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Exceptional(5)

$318.73

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Private Vacation Home

Game Room, Deck & Yard: Chicago Home

Chicago, Illinois, United States

Retreat to The Windy City and book this 2-bedroom, 3.5-bath Chicago vacation rental! This abode features an updated interior with new finishes, a full kitchen, and a private outdoor space fit for the whole crew. Stay local and tour the Irish American Heritage Center or enjoy a riverfront picnic at Gompers (Samuel) Park! After, hop on the Blue Line and head downtown for shopping and live entertainment. Back home, adults can sip drinks on the deck while the kids play cornhole in the fenced yard.brbr-- THE PROPERTY --brbrR25000134193 | Air Hockey Table | Charcoal Grill | 1 Mi to Montrose Train Station (Blue Line) | Easy Access to I-90brbrBedroom 1: Queen Bed | Bedroom 2: Queen Bed | Game Room: Sleeper Sofa | Additional Sleeping: Pack 'n PlaybrbrINDOOR LIVING: 2 Smart TVs w/ cable, gas fireplace, wet bar w/ wine cooler, dining table, breakfast bar, basketball arcade machine, dartboard, punching bag, books, board games, heated floors, ceiling fansbrOUTDOOR LIVING: Furnished deck, cornhole, fenced yardbrKITCHEN: Refrigerator, stove/oven, dishwasher, dishware/flatware, cooking basics, spices, drip coffee maker, blender, microwave, water filter, ice makerbrGENERAL: Free WiFi, keyless entry, central A/C & heating, linens/towels, iron/board, washer/dryer, laundry detergent, trash bags, paper towels, hair dryer, complimentary toiletriesbrFAQ: Quiet hours (8:00 PM-8:00 AM), 4 exterior security cameras (facing out)brACCESSIBILITY: 2-story home w/ basement, step-free entry, 2nd-floor bedrooms onlybrPARKING: Concrete pad (1 vehicle, access via alley)brbr-- THE LOCATION --brbrAREA ATTRACTIONS: Irish American Heritage Center (0.8 miles), Logan Square (4 miles), Concord Music Hall (5 miles), Wrigley Field (5 miles), Lincoln Park Zoo (8 miles), Navy Pier (10 miles), The Art Institute of Chicago (11 miles), Soldier Field (14 miles)brDOWNTOWN (~10 miles): Magnificent Mile, Willis Tower, Skydeck Chicago, Millennium Park, Little Italy, Greektown, Chicago RiverwalkbrPARKS & REC: Gompers (Samuel) Park - North Branch Chicago River (0.8 miles), Palmer Square Park (5 miles), Humboldt Park (6 miles), Lincoln Park (7 miles), North Avenue Beach (8 miles), Oak Street Beach (9 miles), Grant Park (11 miles)brAIRPORTS: O'Hare International Airport (8 miles), Chicago Midway International Airport (18 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: Please observe quiet hours from 8:00 PM to 8:00 AMbr- NOTE: Your safety matters. This property features 4 exterior security cameras located on each corner of the home facing the front yard, side yards, and backyard. These cameras are outward facing and record sound and video continuously while guests are in residencebr- NOTE: While this 2-story home with a basement offers step-free entry, both bedrooms and the sleeper sofa are located on the 2nd floor or in the game room in the basement and require interior stairs to access
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Bath 3

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Sleep 6

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Exceptional(10)

$1182.49

/ Nightly
Private Vacation Home

Historic Edgewater Home Steps to the Beach

Chicago, Illinois, United States

*Reduced new listing price February-March*brbrThis 6-bedroom, 3.5 bath home is full of Chicago charm. The house was built in 1896 as part of the original Edgewater development under JL Cochran. We bought this property in 2015 and with hard work and love we have turned it into a wonderful home.brbrWe have added all the modern conveniences while retaining the original character of the home. In the years we have lived here, we have had three amazing boys, so as you can imagine, the home is very special to us.brbrThe home is ideally located for visitors to explore all that Chicago has to offer. We are two blocks away from the Chicago lakefront with 16 miles of running and biking trails as well as parks and beaches. We are one block away from public transportation and the red-line. We are just steps away from the restaurants, shops and bars of Edgewater/Andersonville area. In addition, get on Lakeshore Drive and you are only a quick commute to the mag mile and downtown Chicago.brbrBack at the house, you will find the interior just as special as the outside. We have updated the flooring with dark stained oak throughout. The dining room and living room are open up to each other. The dining table can extend to seat up to 12 and a large sectional in the living room is nice for gathering. There is an office space on this floor which offers additional seating and a pull out sofa bed should it be needed. The kitchen is fully updated and includes a large 8' island, gorgeous Carrara counter tops, Wood Mode cabinetry and SubZero/Wolf appliances. Every gadget and accessory has been provided so you will not need to worry about bringing/buying utensils to cook. brbrOff the kitchen you have a large back deck with pergola that can seat up to 10 ppl for a dinner al fresco. The deck overlooks the back yard which is fully fenced in where your kids can play, shoot hoops or adults can relax on an additional sunken patio with a bbq grill. We back up to the train offering a uniquely Chicago experience and you will see and hear it pass from the back yard. brbrWe have 6 bedrooms on the two additional floors. The second floor has 4 bedrooms. The master has a king size bed, closet space and full master bath. The additional bedrooms share a large bathroom with tub/shower. Of the three one has a bunk bed perfect for kids, two twins in our boys room and a full bed in the last bedroom. We also have a laundry room on this floor, making any laundry washing that needs to be done a breeze. The third floor has been converted into two bedrooms with a large shared bath. One bedroom has a king sized bed and the other has a sitting area with daybed and trundle. There is also a kitchenette on this floor with refrigerator, coffee maker and small microwave. brbrAdditionally, the home has free WiFi. On your arrival, you'll find the home stocked with a starter supply of the essentials so that you can unpack without stress. brbrWe have a no smoking, no parties and a no pet policy. We rent a minimum of 4 night stays during the summer.
Bed 6

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Bath 3

Bath

Sleep 12

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Exceptional(12)

$286.93

/ Nightly
Apartment

Sacramento - Stylish 2BR Apt in Irving Park

Chicago, Illinois, United States

pWelcome to our charming basement unit in the heart of Irving Park! This inviting space is perfect for small families, couples, or friends looking for a comfortable and convenient place to stay in Chicago. Located in the vibrant Irving Park neighborhood, this basement unit offers easy access to a variety of local attractions, restaurants, and shops. You'll be just a short drive or train ride away from downtown Chicago, making it convenient to explore all the city has to offer. Welcome to your cozy retreat in the heart of Irving Park! This basement unit offers everything you need for a comfortable stay. Bedrooms: This unit features two inviting bedrooms. The first bedroom is furnished with a comfortable full bed, while the second bedroom offers a spacious queen bed, providing restful sleep for all guests. Bathroom: The full bathroom includes a bathtub, perfect for soaking and relaxation after a busy day. Entertainment: The living area is equipped with a flat-screen TV with Netflix, ensuring endless entertainment options for cozy nights in. Make yourself at home in this charming space, designed for comfort and convenience. Parking: Enjoy the convenience of free street parking available right outside the property. Entry: Access the unit easily with a lockbox containing the key. You'll receive a unique code before your arrival for a seamless check-in experience. -We will try our best, but Early Check-Ins and Late Check-Outs are difficult to accommodate, especially during the summer. If you need additional time, please consider booking an extra day. -No parties, noise or loud music. We have cancelled reservations due to complaints in the past. -Quiet hours must be observed from 10pm to 8am -No smoking. In the event that the unit is smoked in, there will be an automatic $500 cleaning & deodorizing fee applied. -Guest should be mindful to not run or walk hard in the apartment to not disturb other tenants. -Local guests are permitted to book on an exception basis only. Local groups looking to use the property for a party, gathering or other group event are expressly prohibited and your reservation will be canceled. -Bath towels are provided per number of guests not per number of stay -We have duvet covers on our beddings (no top sheets). -A Security Deposit may be required on some bookings. -If there's an issue during your stay, please report it real time so we can address it right away. -Pets are allowed: Small Dogs or Cats at $50 per pet, per stay./p
Bed 2

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Bath 1

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Sleep 3

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Exceptional(35)

$773.36

/ Nightly
Condo

Ukrainian Village 3BR/3BA • Private Patio, Parking

Chicago, Illinois, United States

Welcome to Ohio St — your private Chicago home, designed for guests who want genuine space, real comfort, and one of the city's most vibrant neighborhoods right outside the door.brThe entire home is yours. Three bedrooms, three full bathrooms, multiple living areas — a layout that works effortlessly for families, friend groups, business travelers, and anyone who needs room to breathe without feeling crowded.brThe master bedroom is your private retreat — featuring a luxurious jet tub that turns a regular night into something exceptional. After a full day exploring Chicago, there is nothing quite like it.brStep outside to the front patio — relax in the hammock, enjoy your morning coffee, and watch the neighborhood come alive. Around back, fire up the gas grill on the back porch and settle into the outdoor dining area. Two distinct outdoor spaces, both private, both exceptional for a Chicago property.brParking in Chicago is never easy. Here, it's solved. A gated private parking spot directly behind the unit accommodates 2 cars tandem — one of the rarest amenities in the city. Free street parking is also available directly in front.brThe fully equipped kitchen has everything you need for real cooking — refrigerator, stove, oven, dishwasher, microwave, coffee maker, and all the utensils and cookware you need. Fresh coffee and tea are stocked and waiting for your arrival.brYou're in Ukrainian Village — one of Chicago's most walkable, characterful neighborhoods. Wicker Park's restaurants and nightlife, Bucktown's boutiques, West Town's coffee shops, and Downtown Chicago are all minutes away.brThis is the kind of home you'll want to come back to.
Bed 3

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Bath 3

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Sleep 7

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$10980.21

/ Nightly
Hotel

Cozy 2BR Unit Near Garfield Park & United Center

Chicago, Illinois, United States

Welcome to your relaxing home base in Chicago. Offers a spacious and inviting environment designed for travelers who want both comfort and convenience while visiting the city.brbrWhether you're visiting Chicago for sightseeing, work, sporting events, or a weekend getaway with friends and family, this thoughtfully designed apartment provides everything you need to feel at home. After a day exploring the city’s iconic attractions, you’ll love returning to a calm and cozy space where you can unwind.brbrTHE PROPERTYbrStretch out on comfortable king beds, stream your favorite shows on Smart TVs, cook a home-style meal in the kitchen, or relax in the bathtub after a long day. With a layout that balances open living areas and private bedrooms, the apartment is perfect for groups who want to spend time together while still enjoying their own space.brbrWith sleeping space for up to 6 guests, Unit 4 is ideal for families, friends traveling together, business professionals, and extended stays.brbr⦿ Comfortable Sleeping Spaces ⦿brbrEach bedroom is designed to provide restful sleep and privacy.brbrBoth bedrooms feature luxurious king-size beds and their own TVs, creating a relaxing place to recharge at the end of the day. The living room offers additional sleeping space with a sofa bed, making the home comfortable for larger groups.brbr- 2 King Bedsbr- Sofa Bed in Living Roombr- TVs in Bedroomsbr- Smart TV in Living Roombr- Sleeps up to 6 guests comfortablybrbr⦿ Fully Equipped Kitchen & Dining ⦿brbrThe full kitchen includes everything needed to prepare meals during your stay. Whether you're making breakfast before heading out or enjoying dinner together in the evening, you'll have access to cookware, utensils, appliances, and dishes.brbrThe dining table with seating for six is perfect for shared meals, remote work sessions, or planning your next Chicago adventure.brbrKitchen highlights include:brbr• Refrigerator & freezerbr• Stove & ovenbr• Microwavebr• Coffee maker with coffee providedbr• Dishes, silverware & wine glassesbrbr⦿ Bathroom & Essentials ⦿brbrThe apartment features a full bathroom with a bathtub, allowing you to relax and recharge after a busy day. Fresh linens, towels, and toiletries are provided to ensure a comfortable stay.brbr⦿ Perfect for Work or Long Stays ⦿brbrTraveling for work or planning an extended visit The apartment includes several features that make longer stays easy:brbr- Dedicated workspacebr- High-speed WiFibr- Ethernet connectionbr- In-unit washer & dryerbr- Air conditioning & heatingbrbrEverything you need to stay productive while enjoying the comfort of a full apartment.brbr⦿ Additional Amenities ⦿brbr• Private entrancebr• Private living roombr• High chair available upon requestbr• Pack ’n Play travel crib available upon requestbr• Clothing storage and closet spacebr• Long-term stays allowed (28+ days)brbr⦿ Convenient Chicago Location ⦿brbrThis location gives you quick access to some of the city’s most popular destinations:brbr- About 10–12 minutes to United Center for concerts and gamesbrbr- About 8 minutes to Humboldt Park, one of Chicago’s largest and most beautiful parksbrbr- About 12–15 minutes to downtown Chicagobrbr- Around 15 minutes to The Magnificent Milebrbr- Around 15 minutes to Millennium Park and Cloud Gate (The Bean)brbrYou’ll also find restaurants, grocery stores, and public transportation options nearby, making it easy to get around the city.brbrGUEST ACCESSbrGuests have full private access to the entire apartment.brbrFeatures a private entrance with convenient self check-in.br brGUEST INTERACTIONbrWe’re always available through messaging if you need assistance, local recommendations, or help during your stay. Our goal is to make your visit to Chicago smooth, comfortable, and memorable.
Bed 2

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Bath 1

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Sleep 6

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$362.87

/ Nightly
Hotel

Stylish Cozy 3BR Retreat Near Pilsen with Free Parking

Chicago, Illinois, United States

Imagine stepping into a sunlit home where style meets comfort — soft light pouring through large windows, elegant art-deco touches around every corner, and the inviting scent of freshly brewed coffee from your fully stocked kitchen. This isn’t just a stay — it’s your Chicago experience waiting to unfold.brbrPerfect for families, business travelers, and small groups, this spacious 3-bedroom, 2-bathroom home offers the perfect balance between downtown excitement and peaceful relaxation.brbrSurprise your loved one with our Romantic Experience, launching this February for Valentine’s Day. brbrEnjoy a beautifully styled romantic setup with elegant décor, soft candlelight, and a stunning photo backdrop—perfect for proposals, anniversaries, or an unforgettable Valentine’s stay.brbrCheck the other details to note for more info brbrbrWhether you’re here for a convention, a concert, or a foodie weekend, you’ll find everything you need to feel right at home — plus a few luxurious extras.brbrAfter a day exploring the city, sink into one of the plush king beds, stream your favorite movie on the Smart TV, or gather around the dining table for a late-night meal and laughter. Every detail — from the contemporary furnishings to the central heating and cooling — is designed with your comfort in mind.brbrStep inside a bright, modern home designed for connection and relaxation.brbrAccommodation Features:br• 3 Spacious Bedrooms with King Beds br• Cozy Sofa Bed in the Living Room br• 2 Modern Bathrooms br• Large Windows with Natural Sunlight br• Custom Art-Deco Furnishings br• Fully Equipped Kitchen with Stainless Steel Appliances br• Central Heating & Cooling br• Large Dining Table – perfect for shared meals or remote work br• Spacious Closets for Long Stays br• Free parking for 1 vehicle (limited availability, first-come, first-served)br• Washer & Dryer brbr Entertainment:br• Roku Smart TVs in Living Room & Bedrooms br• Netflix, Hulu, and Streaming Apps Ready-to-Go br• Fast Wi-Fi for Work or Play brbr The LocationbrbrYour home is nestled along South Fairfield Avenue, just minutes from the vibrant Pilsen neighborhood — one of Chicago’s most artistic and culturally rich areas. brbrHere, you’ll find colorful murals, indie galleries, live music, and some of the city’s best Mexican food. The area is filled with creative energy, blending local charm with urban edge. Whether you’re wandering through art-lined streets, exploring nearby museums, or catching a game at United Center, you’re perfectly positioned for it all.brbr Nearby Attractions:br• 10–15 min walk to Pink Line Subway Stationbr• 8 min drive to United Center (Bulls & Blackhawks)br• 10–15 min drive to Museum Campus (Shedd, Field, Adler)br• 15 min drive to Navy Pierbr• 12 min drive to Millennium Park & “The Bean”br• 14 min drive to McCormick Placebrbr Top Local Restaurants:br• Dusek’s Tavern – Gastropub classics & craft beer br• Pilsen Yards – Tacos, cocktails & a vibrant patio br• Giordano’s Pizza – Famous Chicago deep-dish br• Thalia Hall – Historic live music & dining venue brbrShops & Essentials:br• Target, Walgreens, and local markets within 10 minutesbrbrGuests have full private access to the entire accommodation — no shared spaces! brbr Parking:brFree designated parking for 1 vehicle (limited availability, first-come, first-served).brbr Laundry:brWasher & dryer available for guest use.brbrSelf-Check-In:brConvenient and secure self-check-in with detailed instructions provided before arrival.brbr Romantic Experience – Available for $350/staybrbrOur Romantic Experience Package is designed to elevate your stay with a thoughtfully curated romantic setup, perfect for Valentine’s Day, anniversaries, or special celebrations. All décor will be professionally arranged before your arrival for a seamless and memorable surprise.brbr What’s Included (as shown in photos):br• Elegant table throw for a romantic dining setupbr• Light-up LOVE sign and small romantic décor accentsbr• Large heart-shaped backdrop (8–10 ft) ideal for photosbr• Flameless candles and rose petals for a warm, cozy ambiancebr• Romantic heart-shaped dining setbr• Decorative rose wine glassesbr• 100 faux roses for styling and photosbr• Clear decorative vase for floral displaybrbr Important Notes:brbr• This is a decor experience only (no food or beverages included)br• Items are for décor and photos and must remain in the accommodationbr• Setup is completed prior to check-inbr• Available February only for Valentine’s seasonbr• Must be requested in advance and added as a paid experiencebrbr This experience is perfect for creating unforgettable moments and stunning photos during your stay.brbrAbout the Neighborhood:brbrWe are located near the heart of Chicago’s vibrant Pilsen area — a neighborhood known for its rich culture, colorful murals, historic charm, and fantastic dining scene! brbr Neighborhood Highlights:br• Artistic and Culturally Rich: Pilsen is a creative hub filled with art galleries, stunning murals, and indie shops. br• Foodie's Paradise: Enjoy authentic Mexican restaurants, cozy cafes, and local breweries nearby. br• Close to Everything: Just a few minutes to downtown, the Pink Line subway, and Chicago’s top attractions! brbr Important to Know:brThe surrounding neighborhood is still undergoing development and revitalization. Like many growing urban areas, we encourage guests to be mindful when exploring, especially after dark.brWhile many guests feel perfectly comfortable, we recommend using rideshare services (Uber/Lyft) at night instead of walking.brbrYour Safety is Our Priority:br• Our building is professionally secured 24/7 with on-site security staff and monitored cameras throughout.br• The interior of the building and parking area are completely private and secure for your peace of mind. brbr Many guests choose our location because it offers an authentic Chicago experience with easy access to the city's most popular destinations — all while enjoying a safe and modern living space.brbr FAQsbrIs the neighborhood safe br Absolutely! It’s calm, family-friendly, and monitored 24/7.brbrDo you provide towels, linens, and toiletries br Yes! Fresh towels, bed linens, hair dryer, toothbrushes, toothpaste, and a starter kit of toiletries are provided.brbrWhat are the check-in and check-out times br Check-In: 4:00 PM | Check-Out: 11:00 AMbrEarly check-in/late check-out may be available upon request for an additional fee.brbrIs the accommodation professionally cleaned brYes, every stay is thoroughly cleaned and sanitized.brbrAre the beds comfortable brGuests often rave about how cozy the mattresses are — many even ask where they can buy the same ones!brbr Hot Water NotebrThe suite is supplied by an 80-gallon hot water tank. If fully used, reheating may take 1–2 hours. We kindly ask guests to use water responsibly .brbrWhy Guests Love This Stay Spacious, Modern, and Family-FriendlybrTVs + Netflix in Every BedroombrSuper-Fast WiFi and Comfortable WorkspacesbrClose to Downtown, Attractions, Dining, and ShoppingbrGreat Value Compared to Hotels
Bed 3

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Bath 2

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Sleep 8

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Exceptional(4)

$1024.47

/ Nightly
Apartment

Luxury Designer Penthouse 3803 | Pool | Gold Coast

Chicago, Illinois, United States

Summary:brbrNEW PENTHOUSE IN THE HEART OF GOLD COAST!brbrbrbrEnjoy your own penthouse in Chicago's Gold Coast-the city's center of nightlife, restaurants, and shopping. Sitting 38 stories in the sky, your 3 bedroom/2 bathroom penthouse offers some of the best views in all of Chicago. The highly secure building includes elevator, rooftop pool, full gym, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!brbrbrbrThe Space:brbrLocated in a full-service building with elevator access and just steps from Michigan Avenue, your penthouse apartment was professionally designed, sleeping up to 12 people and is perfectly situated for groups, families, and those traveling for work. Everything flows around the spacious and open living room and kitchen which have some of the most breathtaking views of all of Chicago and the Lake, and features high-end cooking appliances and designer level finishes, which creates a unique environment for entertaining and gathering with your group.brbrbrbrYour spacious living/dining room combo is decorated in mid-century modern furniture and features a large sofa (which folds out into another bed), accent chairs, dining table for 8+ people, and smart TV (Netflix, Hulu, Prime, etc. compatible). brbrbrbrAttached to the living area, the high end designer quality chef's kitchen is outfitted with stainless steel stove, oven, restaurant sized refrigerator and freezer, plenty of cabinetry, plates, cups, and cutlery in addition to state-of-the-art kitchen appliances including a Nespresso coffee maker, amongst others.brbrbrbrThis one of a kind apartment comfortably sleeps 12 people and has 3 bedrooms and 2 full bathrooms. The main bedroom with a king bed, full bath. An additional bedroom with a queen bed. One additional bedroom featuring two twin-over-twin bunk beds. brbrbrbrSleeping arrangements/room layout:brbrMain bedroom (bedroom 1): King Bed, full bathroombrbrBedroom 2: King bedbrbrBedroom 3: Two Bunk Beds (twin over twin)brbrLiving Room: Air MatressbrbrbrbrWe offer one free parking space in a secured parking garage just a couple blocks away. There are ample parking solutions in the area should you need additional parking and you can park in the lot where we provide the one space for a fee that is paid for at the garage.brbrbrbrOur units are made up fresh before each guest and their group arrives. Our professional cleaning service that we use on all of our properties do a thorough job of cleaning all areas, focusing on high touch point areas. Each bed is stripped and all sheets, pillow covers, and duvet covers are washed thoroughly after each stay.brbrbrbrTo abide by all legal requirements and building security rules, you may be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, pass through our verification portal and, in some instances, complete a criminal background check.brbrbrbrImportant note: The information is collected for screening and verification only and is not stored or used for any other purposes.brbrbrbrPlease be advised that all guests will be asked to sign a rental usage agreement that governs the terms of the stay. By completing the reservation you agree to the following:brbrbrbr-You agree to be bound by our rental terms and conditions.brbr-You acknowledge that you will be required to provide a copy of a valid government-issued ID and matching credit card prior to check-in.brbr-You acknowledge that you may be required to undergo a background check if mandated by the property management company or the building, as stated in accordance with your rental agreement and the condition of the booking.brbr-You understand that your check-in instructions might be withheld until you have successfully completed our verification portal.brbrbrbrGuest Access:brbrYou will have full access to all rooms and spaces inside the unit, except for one utility closet. Temporary access codes will be shared 24 hours before rental commencement by email.brbrbrbrInteraction with Guests:brbrWe pride ourselves on making our guest's stay as enjoyable as possible. We live in Chicago and are available should anything come up.
Bed 3

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Bath 2

Bath

Sleep 10

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