Home Vacation Home Rentals By Owner In Chicago, IL

Showing 80 Of 354 Vacation Rentals
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Exceptional(9)

$974.57

/ Nightly
Private Vacation Home

NEW! Large/Beautiful Home with 6BDS/4BTH + Garage!

Chicago, Illinois, United States

NEW HOME/NEWLY FURNISHED! This 6 bed single family home is ready to host! My space accomodates 12 guests with 6 beds and 4 full baths. You will find a fully stocked kitchen, comfortable beds, a furnished back deck, grill, ping pong table, spacious gathering rooms, a 1 car garage, driveway, and free street parking at the home! Both MDW and ORD airports are only 20-30 min from our place. Great for family gatherings, corporate groups, reunions, and large group getaways!brbrMy place is great for multiple families, business travelers, large groups, or couples! This single family home is situated on a residential street with planty of free street parking for your convenience. With comfortable and stylish furnishings we want you to feel this is your home away from home!brbrbrTop Floor:br1st bedroom - 2 queen bedsbr2nd bedroom - 1 king Bedbr3rd bedroom - 1 king Bedbr2 full bathroomsbrbrMain Floor:br1st bedroom - 1 queen bedbr1 full bathroombrbrBottom Floor:br1st bedroom - 1 queen bedbr1 full bathroombrbrbrIn addition I provide the following amenities to all my guests!br- My cleaners are professionally trained and follow a tightly regimented cleaning and sanitizing checklist.brThey are equipped with a full complement of professional cleaning tools and chemicals including abrhospital-grade disinfectant.br- Fresh towels and linensbr- Wireless internet is always availablebr- TV with streaming optionsbr- Kitchen appliances including a microwave, coffee pot with a reusable filter,brtea kettle, and toasterbr- Keurig and coffee makerbr- My place is FULLY STOCKED with all the amenities of home like shampoo,brconditioner, body wash, paper towels, toilet paper, tissue, sponges, handbrsoap and dish soap.br-The full sized kitchen is stocked with cookware, utensils, glasses, cutlery, sharp knives, cutting boards,brbaking sheets and all the basic tools like wine openers, cheese graters, vegetable peelers, pizza cutters, etc.br- Hair dryerbr- Luggage racks and hangersbrbrCheck-in is effortless and 100% contact-free. Your private access code works on all exterior door keypads, allowing you to arrive and settle in on your own schedule. We’ve designed the process to be completely autonomous, though our team is always just a message away if you need us!brbr*This home is professionally curated by Hosty Co, Chicago’s premier boutique management team. We specialize in high-touch service, 5-star aesthetics, and seamless stays.*brbr**Follow the journey: Find us on social @hosty_co_chibnb for a look at our full portfolio and `insider only` Chicago neighborhood guides.**brbrTo protect the quality of our home and the harmony of our neighborhood, we specifically host:br*Corporate Travelers seeking a refined, reliable home base.br*Families visiting for holidays or major Chicago milestones.br*Urban Explorers who value a quiet, high-end retreat.brbrBooking Requirements: We operate under a strict `Good Neighbor` policy. To ensure we are the right fit for your trip:br*Tell Us Your Story: When inquiring, please include a brief note about your trip and your group. We love knowing how to best prep the space for your arrival!br*Vetting: We prioritize guests with 100% ID verification and a track record of positive reviews.br*Zero Tolerance: To maintain our home`s integrity, parties and unauthorized gatherings are strictly prohibited.brNo events brNo shoes on in the homebrNo guests outside of the group in the homebrNo smoking of anykind indoors
Bed 5

Bed

Bath 4

Bath

Sleep 12

Sleeps

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$902.93

/ Nightly
Private Vacation Home

Beautiful, cozy, stylish Bucktown, Wicker Park House, perfect Chicago location.

Chicago, Illinois, United States

Welcome to Rainbow Guest House. This is a designer owned, fully decorated house located in a perfect Bucktown/Wicker Park location, central to all of Chicago. Come relax and enjoy a lovely quiet neighborhood with easy access to all of Chicago. There is a lovely private back yard and huge deck off of the kitchen to enjoy meals outside, or a bbq on the grill. Easily get to all parts of the city form this convenient location, only ten minutes to central downtown or the lakefront beaches. Walk to parks, tons of great restaurants, and shops within minutes. brbrA bespoke home that fuses original 1890’s woodwork and details with a new artful design. Relax in the very private backyard and walk to everything Wicker Park and Bucktown has to offer in this quiet charming central Chicago neighborhood.brbrThe home is fully furnished with a fully stocked kitchen for everything needed to cook your heart out, all new beds, mattresses, sheets, towels, everything is new, plus some gorgeous antiques and artworks from the owners personal collection. Lovely fully landscaped front and back gardens, upstairs deck off of family room, huge back deck for entertaining and eating outside with new bbq qrill off of the kitchen, two car garage, and easy permit street parking.brThere is one bedroom downstairs, along with the kitchen, living and dining spaces. Upstairs there is a living room with wood burning fireplace, kids play area, kids bedroom with bunk beds, primary bedroom with office area, ample closets, siting room, and wonderful bathroom.brThe home is light filled because of the large windows and five skylights filling the home with natural light all day. The location is convenient to get to all parts of the city from this truly peaceful oasis filled with light, color and great design offering wonderful comfort in the heart of Chicago’s vibrant Bucktown/Wicker Park neighborhood.brAvailable now for any amount of days or months brMessage with any questions, thanks!
Bed 3

Bed

Bath 1

Bath

Sleep 10

Sleeps

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Exceptional(8)

$1346.69

/ Nightly
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

Bed

Bath 3

Bath

Sleep 17

Sleeps

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Exceptional(5)

$318.73

/ Nightly
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
Bed 2

Bed

Bath 3

Bath

Sleep 6

Sleeps

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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

Bed

Bath 3

Bath

Sleep 12

Sleeps

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Exceptional(15)

$265.54

/ Nightly
Private Vacation Home

Vintage Escape 1BR Two Blocks Away From Beach

Chicago, Illinois, United States

1st-floor unit with one flight of stairs. Older building with radiant heat managed by the building.brbrConveniently located in the heart of Chicago's most popular northernmost neighborhood. The location is perfect and minutes from anywhere you may want to go in the city. Parks, coffee shops, restaurants, museums.. all just steps away! Spend your days soaking up the sun at Loyola Beach or spend the afternoon at Pottawatomie Park which are few minutes away. You'll also discover the brightly-painted murals, theaters, art galleries, and even a sculpture garden in the Glenwood Avenue Arts District.brbrGuest Access:brYou’ll have access the the entire unit during your stay.brbrOther details to note:brWe do not have a designated parking space. That said, please take care to read any signs indicating no parking or tow zones to avoid any issues. Parking availability can fluctuate depending on the time of day, and if you arrive later in the evening, there’s a chance that spots might be harder to find.brbrIn case you run into this situation, we suggest using the SpotHero app or ParkWhiz to easily locate an affordable and convenience parking spot nearby.brbr**HOUSE RULES**brbrWe want you to have a comfortable and enjoyable stay! To help keep the space safe, clean, and pleasant for everyone, please review and follow the house rules below. Failure to comply may result in cancellation or additional charges.brbrShoes off, please. Kindly remove shoes upon entering the unit.brbrNo smoking anywhere inside the unit or on the property. Smoking will result in immediate cancellation and a $200 damage fee.brbrNo drugs, including marijuana.brbrNo illegal activities anywhere on the property.brbrNo parties or events.brbrNo outside visitors.brbrNo overnight guests without prior approval from the host.brbrFood storage: Please store all food in designated areas and do not leave food out to help prevent pests.brbrKitchen use: Feel free to use the kitchen, but please clean up after yourself. Wash dishes, wipe counters, stove, and microwave. No dirty dishes left in the sink overnight.brbrDamages: If anything is broken or damaged, please let us know right away so we can arrange repair or replacement.brbrCheckout cleaning:brPlease wash dishes, return moved furniture to its original place, and take out the trash before checkout.brThe standard cleaning fee covers normal turnover cleaning. If the unit is left excessively dirty (dirty dishes, trash left throughout the unit, etc.), an additional cleaning fee of up to $100 may apply.brbrTowels & linens: Provided for your entire stay. If you need extras, please let us know in advance. A $50 fee applies to cover the cleaner’s trip. Paid laundry facilities are available in the building.brbrLost keys: A $300 fee applies for lock and key replacement. Please note that lost keys cannot be replaced immediately, and you may temporarily lose access to the unit and building amenities.brbrQuiet hours: Please observe quiet hours from 10:00 PM – 8:00 AM.brbrLate checkout: Checkout time is 11:00 AM. Late checkout without prior approval will incur a $50 fee, which covers the cleaner’s waiting time.brbrThank you for your understanding and cooperation -we truly appreciate it and look forward to hosting you!
Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps

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$155.89

/ Nightly
Private Vacation Home

1 Block to Red Line Station: Walkable Chicago Home

Chicago, Illinois, United States

Off-Street Parking | Work From Home Friendly | Easy Hwy AccessbrbrImmerse yourself in the charm and excitement of the Windy City with a stay at this family-friendly vacation rental in Chicago, perfect for extended stays! The 4-bedroom, 3-bath home is designed for comfortable stays — complete with a full kitchen, home gym, and private patio. When you're not relaxing by the fire pit, take the expressway or hop the Red Line for quick access to Lake Michigan, downtown adventures, and Chicago eats!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 1 queen bedbr- Bedroom 3: 1 queen bedbr- Bedroom 4: 1 futonbrbrKITCHENbr- Stove/oven, refrigerator, microwave, dishwasherbr- Drip coffee maker (coffee provided)br- Blender, toaster, spicesbr- Cooking basics, dishware & flatwarebr- Trash bags/paper towelsbrbrINDOOR LIVINGbr- Smart TVs, fireplacebr- Board gamesbr- Home gymbr- Dining tablebrbrOUTDOOR LIVINGbr- Fenced-in backyardbr- Patio, dining table, gas grillbr- Fire pitbrbrGENERALbr- Central heating & A/Cbr- Washer/dryer, laundry detergentbr- Linens/towels, iron/boardbr- Complimentary toiletries, hair dryerbr- Free WiFibr- Keyless entrybrbrFAQbr- 1 exterior security camera (facing out)br- Quiet hours (8:00 PM-8:00 AM)brbrACCESSIBILITYbr- Split-level home w/ basement, 3 exterior steps to enterbr- All bedrooms on upper & basement levelsbrbrPARKINGbr- Driveway (1 vehicle)br- No street parkingbrbr-- THE LOCATION --brbr- Easy access to I-57 & I-94br- Walk to 95th Red Line Station & Abbott Parkbr- 6 miles to the University of Chicagobr- 7 miles to Griffin Museum of Science and Industrybr- 9 miles to Rate Field & Soldier Fieldbr- 10 miles to McCormick Place & Shedd Aquariumbr- 12 miles to Millennium Park & Navy Pierbr- 13 miles to United Center & 17 miles to Wrigley Fieldbr- 10 miles to Chicago Midway Int’l Airport & 27 miles to O’Hare Int’l Airportbrbr-- 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- Please observe quiet hours from 8:00 PM to 8:00 AMbrbrADDITIONAL INFORMATIONbr- This split-level home requires 3 steps to enter. Interior stairs are required to access all bedrooms on the upper level and the basement levelbr- Your safety matters. This property features a Ring doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video and sound when motion is detected by the device
Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps

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Exceptional(30)

$1543.39

/ Nightly
Private Vacation Home

3-Levels.11Beds.Sleeps 20. 10min walk to Train. Rooftop+Spa Bath+Garage.

Chicago, Illinois, United States

An ideal retreat for special occasions in Wicker Park. This spacious home is a celebration of contrasts. An eclectic style carefully gathers various periods, styles & interesting recycled elements while creating cohesiveness with modern design. A wide and long, open-floor concept in the heart of the city, with three separate floors. An ideal retreat with tons of light, space and privacy should you prefer to close your bedroom. Perfect for a relaxing vacation or special occasion. A fully equipped chef’s kitchen + wet bar + family room leading to your outdoor deck and rooftop garage. The rooftop garage deck is equipped w/ a Weber grill and sectional seating. brbrTotal bed count: seven queen size beds, two twin foldout bed cots (memory foam), one twin, one floor air mattress, one full size futon, one twin trundle. Three bedrooms are on the second floor with two full bathrooms, vaulted ceilings, washer+dryer. Two bedrooms and third bathroom in the lower level (in-law suite), with an additional living room and kitchenette.brbrAll beds have been comfortably laid out with plenty of room to spread out; Plush beds and cozy organic sheets, large walk-in closets to store luggage. A private spa-like Primary Bath features Italian travertine stone, Zero-entry Steam Shower, oversized jetted Jacuzzi tub fit for two, double sink Vanities. The home has been upgraded with a tankless water heater so your guests never run out of hot water.brbr10 min walk to Blue line (Western or Damen Stops). The 606 Trail is only 2 blocks away; a 2.7 mile trail and green space for runners and families alike. 5-10 drive to other popular neighborhoods- Logan Square, Bucktown, Humboldt Park, Ukrainian Village; 10-15 min drive to Wrigleyville, Lakeview, Lincoln Park; 15-20 min drive to Fulton Market/West Loop/River North. 25-40 min drive to either O'hare or Midway International Airports. brbrRestaurants and bars are within a 10 min walk to the popular corners of North Ave/Milwaukee/Damen. 20min Uber to: The Mag Mile,Navy Pier, Soldier/ Wrigley Field, United Center, Millenium Park, McCormick Pl, and Museum Campus. brbrFast fiber optic Wifi- 250 mbps. The home is smart temperature controlled with room sensors to help manage hot+cold spots for your comfort, plus a Nest smoke+carbon monoxide detector.brbrPlease note the garage comfortably fits two midsize vehicles or one large SUV.
Bed 5

Bed

Bath 3

Bath

Sleep 20

Sleeps

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Exceptional(54)

$1071.32

/ Nightly
Private Vacation Home

Modern Logan Square Luxury: 5 bedroom - sleeps 16!

Chicago, Illinois, United States

Finally, a home that actually fits the whole group! Our stunning, newly-constructed Logan Square retreat was designed for connection, offering sprawling common areas for your family or friends to gather comfortably. Step outside and you`re in the heart of Chicago’s trendiest neighborhood, surrounded by top-tier eateries and local charm, all while being just minutes from the city center.`brbrExperience the perfect blend of luxury and convenience in this expansive, designer-built home. Located on the desirable East end of Logan Square, this property is specifically designed to host large groups comfortably under one roof. Whether you are planning a multi-generational family gathering, a corporate retreat, or a reunion with friends, this home offers the space you need to create lasting memories.brbrThe LayoutbrThe home is thoughtfully designed across three levels of living space:brbrThe Main Level (Gathering Hub): Flooded with natural light, this open-concept floor plan features a spacious living area, a formal dining space, and a chef-inspired kitchen. A convenient half-bath is located on this level for guests.brbrThe Upper Level (Sleeping Quarters): Features four well-appointed bedrooms:brbrPrimary Suite: King-sized bed with a private ensuite bathroom.brbrBedroom 2 & 3: Queen-sized beds with premium linens.brbrBedroom 4: Two Twin-sized beds, perfect for kids or singles.brbrGuest Bath: A full, modern bathroom serving the additional bedrooms.brbrThe Lower Level (Entertainment Zone): Boasting dramatic 14-foot ceilings, this level feels incredibly airy and spacious. It includes a large family room, two additional bedrooms, and a full bathroom.brbrHigh-End AmenitiesbrWe’ve curated every detail to ensure a seamless stay:brbrSleep in Comfort: Every bedroom features brand-new memory foam mattresses for a restful night`s sleep.brbrTech-Ready: High-speed Wi-Fi, three 4K Smart TVs, Sonos speakers, and Alexa integration throughout the home.brbrThe Kitchen: Fully stocked with high-end utensils and cookware, ready for everything from quick breakfasts to gourmet dinners.brbrEssentials Provided: Bathrooms are stocked with premium shampoo, conditioner, body wash, and plush towels. A new washer/dryer with detergent is also available for your use.brbrPrime Location & AccessbrSkip the commute! Being on the East side of Logan Square puts you closer to Downtown Chicago while keeping you in a safe, upscale residential pocket.brbrTransit: A short walk to the Blue Line train and seconds away from highway access.brbrLocal Vibes: Steps away from the Michelin-rated dining and vibrant nightlife that makes Logan Square famous.brbrParking: Includes a private 2-car garage—no need to worry about street parking.brbrCheck-in is effortless and 100% contact-free. Your private access code works on all exterior door keypads, allowing you to arrive and settle in on your own schedule. We’ve designed the process to be completely autonomous, though our team is always just a message away if you need us!brbrAlways ready to assist -- do not hesitate to text/call/email/message. You can see from my reviews that I pride myself on making sure you have a wonderful experience from start to finish. I`m also flexible with check-in and check-outs when possible and will do my best to accommodate requests.brbrBoasting gorgeous boulevards and a constantly expanding selection of restaurants and bars, Logan Square is one of the city`s trendiest neighborhoods, balancing family-friendly amenities with a thriving nightlife. Walk along Milwaukee Avenue and you`ll find cocktail bars and gastropubs as well as dive bars and late night eateries, all packed with young crowds watching local bands or playing vintage arcade games. The variety of diversions present in Logan Square attracts record lovers, musicians, pinball wizards and dining aficionados to this scenic section of Chicago.brbrThis Northwest Side neighborhood is rich in working class traditions and low-key charm. Its industrial character continues to evolve as longtime residents welcome the influx of artists, young professionals and new families drawn to the area`s affordable homes, easy access to downtown and multicultural heritage.brbrWe`re a 10 minute walk to the Logan Square blue line station, and just steps to the Diversey and California Ave. buses - you won`t have any trouble getting around town without a car from here! If you do bring your car, however, we offer on-premises garage parking and a close shot to highway on-ramp. Most of our guests grab an Uber / Lyft and enjoy the quick ride to downtown Chicago!brbr*This home is professionally curated by Hosty Co, Chicago’s premier boutique management team. We specialize in high-touch service, 5-star aesthetics, and seamless stays.*brbr**Follow the journey: Find us on social @hosty_co_chibnb for a look at our full portfolio and `insider only` Chicago neighborhood guides.**brbrTo protect the quality of our home and the harmony of our neighborhood, we specifically host:br*Corporate Travelers seeking a refined, reliable home base.br*Families visiting for holidays or major Chicago milestones.br*Urban Explorers who value a quiet, high-end retreat.brbrBooking Requirements: We operate under a strict `Good Neighbor` policy. To ensure we are the right fit for your trip:br*Tell Us Your Story: When inquiring, please include a brief note about your trip and your group. We love knowing how to best prep the space for your arrival!br*Vetting: We prioritize guests with 100% ID verification and a track record of positive reviews.br*Zero Tolerance: To maintain our home`s integrity, parties and unauthorized gatherings are strictly prohibited.brNo guests outside of your group in the homebrNo shoes inside the housebrPlease be courteous to our neighbors and observe quiet hours from 10pm - 8ambrNo smoking of any kind indoorsbrNo events or parties
Bed 4

Bed

Bath 3

Bath

Sleep 16

Sleeps

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Exceptional(1)

$951.92

/ Nightly
Private Vacation Home

Giant 5-Bedroom Home w/ Pool Table, 15 Min to Wrigley & Downtown

Chicago, Illinois, United States

Bring the whole crew to this spacious Irving Park home packed w/fun! Shoot pool, kick back with smart TVs in almost every room, spread out in the huge living/dining areas, and cook up a storm in the fully-equipped kitchen. Sleeps comfortably with multiple bedrooms and bathrooms. Just 15–25 min Uber to Wrigley Field, Downtown, The Bean, Soldier Field, United Center, Salt Shed, Riverwalk, and more. Perfect for families, friend groups, Cubs trips, concert weekends, or a relaxed Chicago home base!brbrClassic early-1900s Chicago Craftsman Foursquare loaded with vintage charm, beautifully preserved with iconic Chicago front porch. brbrSTEP INSIDE THIS CLASSIC CHICAGO HOME AND FEEL THE FLOWbrbrLiving RoombrbrAs you enter the cozy foyer, the staircase to the second floor is on your right. To your left, you’ll find the bright “frunchroom” (Chicago speak for living room) with an oversized L-shaped sectional, 65” Fire TV & soundbar – perfect for movie nights. brbrKitchen & Dining AreabrbrStraight ahead is the dining area with a large leather banquet and table – ideal for family meals, morning coffee, or getting some work done. brbrThe dining area seamlessly flows into the chef’s kitchen, fully equipped with everything you need to cook for a crowd (holiday feasts, game-day spreads, you name it). An 8-foot peninsula doubles as extra prep space or a casual snack bar (with power at either ends of the peninsula). brbrCoffee BarbrbrThe kitchen is fully equipped to cater to all your coffee and tea needs! You’ll find a 12-cup drip coffee maker, a Keurig single-serve coffee maker, a French Press, and even a coffee bean grinder for freshly ground coffee. To make things easier for you, we’ve stocked the coffee station with Keurig pods, packets of sugar and Splenda, as well as Nestlé Coffee Mate creamer singles.brbrFor tea lovers, there’s an electric tea kettle available for use, perfect for brewing tea or preparing other hot beverages.brbrGame RoombrbrOn the other side of the peninsula is the game room: Bar box pool table, 75” smart TV & soundbar, and plenty of space to watch the game, shoot pool, or just hang out. The open layout keeps everyone connected while still giving distinct zones for relaxing, dining, and playing. It’s the perfect mix of vintage Chicago charm and modern hangout vibes!brbrYOUR SLEEP & COMFORT IS OUR PRIORITYbrbrThe home has five private bedrooms with luxury hotel-quality bedding:brbr-100% organic cotton sheets br-Allergen-free duvets (cool in summer, warm in winter) br-Pillow mix for side, back & stomach sleepers br-Room darkening blinds in every bedroom br-Bedside charging outlets/USBbrbrSECOND FLOOR (3 bedrooms + large full bathroom) brBright shared bath with plenty of natural light brHooks lining the hallway & inside every walk-in closet – great for towels, hoodies, robesbrbr-Bedroom 1: King bed, two nightstands, walk-in closet, ceiling fan, two mid-century chairs for a private retreatbr-Bedroom 2: Two full-size beds, one nightstand, ceiling fan, two small benches, 55” Fire TV, huge walk-in closet, full-length mirrorbr-Bedroom 3: Queen bed, two nightstands, ceiling fan, large walk-in closet off hallway, leather chaise brbrFIRST FLOOR bedroom suite (1 bedroom + full bathroom) brBedroom 4 is located just off the kitchenbrPrivate bathroom with walk-in shower, high toilet & support barbrHooks lining the wall brbrBedroom 4: br-Full-over-full bunk bed supports 1,000 lbs of distributed weight, plenty of headroom on bottom, sturdy 18 wide stairs lead to top bunk which has 30 headroom,br-Walk-in closet, 55” Fire TV, desk/table, backyard views, room darkening blindsbrbrBASEMENT (1 bedroom + full bathroom) brPrivate bath with walk-in showerbrFull-size washer & dryer right outside the bedroombrbrBedroom 5:br-Two twin bedsbr-40” TV with two comfy bean bags, wall tic-tac-toe and checkersbr-Fun cotton-canvas tent playhouse (kids love it!) brbrSleep well wherever you land!brbrHI-TECH & HASSLE-FREE HOMEbrbrStay connected and comfortable with smart tech throughout:br-Blazing-fast Wi-Fi powered by enterprise-grade Unifi access points on every level – perfect for streaming, work calls, or group FaceTimes br-Nest thermostat (located in 1st floor game room) monitors the temperature on each floorbr-Keyless entry via Schlage smart lock – your own unique code sent before check-in (no keys to lose!) br-All TVs hardwired with Cat6 + smart soundbars (Bluetooth-ready for Spotify, Apple Music, etc.) br-Exterior security cameras for peace of mindbrbrPlay hard, stream harder, relax completely – the tech just works.
Bed 5

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Bath 3

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Sleep 14

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Exceptional(11)

$675.89

/ Nightly
Private Vacation Home

ENVITAE Hotel, 4BR Luxury Modern Apartments

Chicago, Illinois, United States

Summary:brbrWelcome to your chic, new retreat in downtown Chicago! This brand new luxury space is meticulously designed for comfort and style. Enjoy fully equipped kitchens, tranquil bedrooms with plush bedding, and state-of-the-art amenities. Steps from top dining, shopping, and attractions with easy public transport access. Discover your perfect Chicago getaway!brbrbrbrThe Space:brbr• Master Suite: King bed, en-suite bathroombrbr• Guest Suite: King bed, en-suite bathroombrbr• Second Guest Suite: King bedbrbr• Third Guest Suite: King bedbrbr• Queen floor mattress availablebrbr• Huge windows offering spectacular views of the citybrbr• Washer & dryerbrbr• Fully-equipped kitchen brbr• Flat Screen TV/Cablebrbr• High-speed Internetbrbr• Stainless steel appliancesbrbr• Spacious, walk-in closetsbrbr• Individually controlled heat and airbrbr• Shampoo, conditioner, & body wash in bathroomsbrbr• Hair dryerbrbr• Iron/ironing boardbrbrbrbrAs part of our commitment to providing a premium experience, we offer complimentary starter items to kickstart your stay like shampoo, body wash, conditioner, hand soap, toilet paper, laundry detergent and kitchen supplies like coffee, tea, cooking oil, paper towels and seasonings. These items are thoughtfully provided to ensure you have everything you need upon arrival. However, please note that they are starter supplies and not be replenished during your stay. If you require additional supplies beyond the initial offering, we recommend local stores or delivery services for your convenience.brbrbrbrGuest Access:brbrEasy and convenient self check-in is available at this property. You’ll have full access to the apartment and building amenities during your stay.brbrbrbrThe Neighborhood:brbrPerfectly positioned at the crossroads of Old Town, Lincoln Park, and the Clybourn Corridor, this location lets you experience Chicago’s best mix of shopping, dining, and culture. Step outside to explore the New City shopping plaza, enjoy a show at the Second City Theater, or stroll along the North Branch Trail toward the lakefront. Within minutes, you’ll find stylish boutiques, gyms, Whole Foods Market, Trader Joe’s, and some of the city’s most beloved restaurants and coffee houses.brbrbrbrTransit: Multiple bus lines and the Red Line train nearby for direct access downtown and to the Loop.brbrCoffee: Sweetwaters Coffee & Tea (3 min), Printer’s Row Coffee (5 min).brbrDining: Boka, Ada Street, and Armitage Alehouse all within a short walk.brbrParks: Oz Park and the Lincoln Park Boardwalk are nearby for morning runs or weekend strolls.brbrbrbrWhether you’re here for work, leisure, or family time, you’ll love how easily connected this area is to River North nightlife, the Magnificent Mile, and Lake Michigan’s scenic paths.brbrbrbrGetting Around:brbrYou are minutes away from bus and train stops. brbrbrbrWe find some of our guests prefer to use Uber or Lyft, which is a very convenient and cheap way to get around the city.brbrbrbrOther Things to Note:brbrPlease note:brbrThis listing includes multiple 4-bedroom homes with the same layout, bed sizes, and amenities, though furnishings and décor may vary slightly. Guests will be assigned one of the available homes prior to check-in, and all homes meet the same standard shown in the photos.brbrbrbr- The building features a central HVAC system that provides year-round comfort. Heating and cooling operate seasonally to keep the temperature pleasant. Guests can adjust the in-unit temperature within the range set by the building.brbr- Building maintenance staff may occasionally need access, but we’ll always provide advance notice whenever possible.brbr- Daily housekeeping isn’t included, though it can be arranged for an additional fee.brbr- Early check-in or late check-out may be available for $149 per service, depending on availability.brbr- On-site parking is available for $69 per night, per spot. Multiple spots can be reserved based on availability. Spots are limited and fill up fast - we recommend securing yours as early as possible. Please message us with your dates to reserve.brbr- Package delivery availability may vary by building - message us for details.brbr- Date changes that shorten or move a reservation follow the standard cancellation policy.brbrbrbrFor your security and a smooth check-in process:brbr- A refundable $500 security deposit is required.brbr- A valid government-issued ID and matching credit card must be provided before check-in.brbr- A short rental agreement will be sent electronically after booking.brbr- Some buildings may require a brief background check as part of management policy.brbr- Local residents (within two hours of the property) cannot book for same-day arrival.brbrbrbrWhile we strive to offer a peaceful experience, please be aware that city or building maintenance, construction, or temporary water/elevator servicing may occasionally occur. These events are outside our control and do not qualify for compensation.brbrbrbrInteraction with Guests:brbrOur online team is available 24/7 to assist you every step of the way - from booking to checkout, ensuring a smooth and comfortable stay.
Bed 4

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Bath 3

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Sleep 10

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Exceptional(5)

$739.11

/ Nightly
Private Vacation Home

Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly

Chicago, Illinois, United States

Stay in a historic home in Old Town, within walking distance of Downtown, the Magnificent Mile, restaurants, bars, boutiques, Lincoln Park, and North Ave Beach. Enjoy an open floor plan with a spacious living, dining, and sitting area with a cozy fireplace. The home offers 3 bedrooms, 2.5 baths, a fully stocked kitchen, 2-car garage, backyard, and laundry. Pets are welcome! Perfect for a relaxing city escape. Message me with any questions!brbrPlease turn to the photos to get enchanted by this stunning space and to see the floor plan with layout and sleeping arrangements.brbr** SPECIAL FEATURES ** br• Large open-plan living/dining area with a fireplacebr• Covered porch br• Large enclosed backyardbrbr**OTHER AMENITIES** br- Washer and dryer br- Air conditioning and central heating br- Detached 2-car garage br- Free Wi-Fi throughout the property br- Free luggage storage in the garage and extended free parking (before check-in and after check-out, if available) br- Free EV chargerbrbrbr**BEDS** br- Bedroom 1: 1 king and 1 single br- Bedroom 2: 2 queen-size beds br- Bedroom 3: 1 single brPlus a small double futon, 4 single floor mattresses and a crib brbr**EXTRAS** br- Late check-out at 1 pm: $80 br- Early check-in at 1 pm: $80 br- Worry-free cleaning package: $80 (details below) br***IMPORTANT** Payment arrangements must be made in advance for these services. I do not have access to your credit card.brbr**ACCESSIBILITY** br8 steps to the front door, 15 steps from the main floor to the second.brbr**NOISE** brThe Brown Line train runs nearby, so you may hear it in certain parts of the house.brbr**HOUSE RULES** br- Unregistered guests are not allowed on the property. The presence of more than 14 guests is unlawful. A guest is anyone at the property, staying the night, or just visiting. br- Minors need to have a responsible adult present. br- Primary booker is required to stay on the property and provide an ID. Also, IDs will need to be provided prior to your arrival for everyone spending any time at the property. br- There is a counter installed to identify the number of guests at the house. I utilize a private security firm. If the counter shows more than the registered number of people or if I get a noise complaint from neighbors, security will be immediately dispatched. A $200 dispatch fee will be charged from your security deposit. Should they be unsuccessful in removing you from the premises, they will involve the police. br- This is not a place for a local house party.brbr**WORRY-FREE CLEANING PACKAGE** brAt check-out you will need to take care of trash overflow, dishes, exuberant messes, and any food you brought. The worry-free package covers any and all cleaning. Just walk out in the morning (you do need to move furniture back if you make any changes to layout). Note that this fee is additional to my regular cleaning fee you pay when you book the place. This package is best for those who want to decorate, cook a lot, are traveling as a group, and would rather split the extra fee than worry about anything in the morning.brbr**DECORATING THE HOUSE** brFeel free to decorate but use paint-safe tape and remove it before departure. Glitter or confetti incurs a $200 cleaning fee.brbr**WILDLIFE** brYou will encounter wildlife while staying at the property. Here is what you can expect most commonly:brSpiders and ants are common in Chicago. They get as high as 95th floor of John Hancock building. While we do our best to combat them, it is nearly impossible during high season.brBees, wasps, yellow jackets are abundant throughout the city. While we take care of any nests on the property, I cannot control them in the air and beyond my boundaries.brbr**BREAKDOWNS** brWe strive to keep all equipment in good working order but can’t guarantee that things won’t break. Mechanical failures, weather, interruptions of utilities, or issues with TV/Internet won’t be grounds for refunds or rental adjustments. If anything malfunctions, we’ll work to resolve it as soon as possible.
Bed 3

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Bath 2

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Sleep 14

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Exceptional(35)

$1214.16

/ Nightly
Private Vacation Home

Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10

Chicago, Illinois, United States

Chic Lincoln Park Townhome w/ Rooftop Deck | Sleeps 10 brbrStay in the heart of Lincoln Park, Chicago, just steps from the Lincoln Park Zoo, DePaul University, and Lake Michigan. This modern, design-forward 3-bedroom, 2-bath townhome sleeps up to 10 guests and features a private rooftop deck with bar, luxury king suite, glam vanity, and walkable access to Chicago’s best dining, nightlife, and attractions.brbrPerfect for families, bachelorette groups, DePaul visitors, corporate stays, and weekend getaways.brbrPrime Lincoln Park LocationbrbrExperience one of Chicago’s most iconic neighborhoods, where tree-lined streets meet world-class restaurants, boutique shopping, and vibrant nightlife.brbr✔ Walk to Lincoln Park Zoo & lakefront trailsbr✔ Minutes to DePaul Universitybr✔ Easy access to Downtown, Wrigleyville & CTA linesbrbrThe SpacebrbrSpread across three levels of living space, this stylish Chicago vacation rental offers plenty of room to relax, gather, and unwind.brbrSleeping Arrangementsbrbr3 Bedrooms | 2 Full Bathroomsbrbr1 King Bed, 3 Full Beds, 1 Twinbrbr2 air mattresses are also available if needed.brbrSleeps up to 10 guests comfortablybrbrEvery detail is thoughtfully designed with modern décor, high ceilings, and a boutique hotel feel, perfect for both cozy nights in and photo-worthy moments.brbrRooftop Deck & EntertainingbrA guest favorite feature:brbrPrivate rooftop deckbrBuilt-in bar with mini-fridge on 3rd floorbrLounge seating for morning coffee or evening cocktailsbrIdeal for relaxing, celebrating, and enjoying the city atmospherebrbrVanity & Coffee Bar FavoritesbrbrFull vanity / makeup bar with boutique toiletries, perfect for getting ready togetherbrbrCoffee bar station with Nespresso, Keurig, French Press, drip coffee, and essentialsbrbrHome AmenitiesbrbrFully equipped kitchen with stainless-steel appliancesbrSmart TVs in every bedroom and living spacebrDedicated workspace for remote work or trip planningbrWasher & dryer for longer staysbrHigh-speed Wi-Fi throughoutbrSelf check-in for easy arrivalbrbrIdeal for Groups, Families & Special OccasionsbrbrWhether you’re planning a bachelorette weekend, visiting DePaul, celebrating a milestone, or exploring Chicago with family, this home offers the perfect balance of luxury, space, and location.brbrEnjoy rooftop mimosas, walk to brunch, or explore Lincoln Park’s renowned restaurant scene, all just outside your door.brbrNeighborhood HighlightsbrbrWalk to Lincoln Park Zoo, lakefront paths & seasonal farmers marketbrTrader Joe’s, Target & The Fresh Market within 2 blocksbrSurrounded by top cafés, brunch spots & cocktail barsbrWalk to CTA Red, Brown & Purple LinesbrSteps to Divvy bikes, buses & ride share accessbrbrThis Lincoln Park vacation rental combines quiet residential charm with easy access to city energy.brbrParking & Check-InbrbrResidential street parking pass provided for one vehiclebrSelf check-in with detailed arrival instructionsbrExterior cameras at entryways only (for safety)brNoise monitoring (no cameras) to ensure a peaceful staybrbrGuest ComfortsbrWe provide everything you need for a comfortable stay:brbrPlush towels, hotel-grade linens & extra blanketsbrBoutique toiletries & hair dryersbrWelcome snacks upon arrivalbrIron, cleaning supplies & stocked essentialsbrProfessionally cleaned and sanitized between staysbrbrGuest Reviewsbrbr“Perfect for our bachelorette weekend — the rooftop was amazing and the location couldn’t be better!”br“Beautifully decorated, spotless, and walkable to everything.”br“The host thought of every detail — coffee bar, toiletries, even welcome snacks!brbrBook Your Lincoln Park StaybrbrWhether you’re visiting Chicago for a celebration, campus visit, or family vacation, this Lincoln Park townhome with rooftop deck delivers space, style, and an unbeatable location.brbrBook now and experience Chicago like a local, comfortably and in style.
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Bath 2

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Sleep 10

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