Vacation Home Rentals By Owner In Chicago, IL

$1955.43

New, Mega Dream Home in Wicker Park Bucktown - Sleeps 21

Chicago, Illinois, United States

Perfect for groups and families!brbrWelcome to our massive 6-bedroom Bucktown Wicker Park haven! brbr• Unbeatable location in Bucktown/Wicker Park -- walk to tons of stores and restaurants, 5 minute walk to public train for O'Hare Airport/Downtown, 10 minute Uber to Downtown and Randolph Stbr• 6 bedrooms and 4.5 bathsbr• Fully stocked kitchen br• Blazing fast gigabit WiFi, perfect for work or streamingbr• Private 2 car garage with super fast Tesla 240V chargerbrbrGuests will have access to the entire 4,500 sq ft home over 5 levels. Easy electronic check-in. *NOTE: This is a split level home so expect many stairs*brbrSleeping:brBedroom 1: King Bed, 1 Twin Daybed (Sleeps 3), en suite bathroombrBedroom 2: King Bed (Sleeps 2), en suite bathroombrBedroom 3: King Bed (Sleeps 2), shared bathroombrBedroom 4: King Bed (Sleeps 2), shared bathroombrBedroom 5: Queen Bunk Beds (Sleeps 4), shared bathroombrBedroom 6: 2x Queen Bunk Beds (Sleeps 8), en suite bathroombr(A Pack'n'Play crib can be provided if requested.)brbrAll bathrooms are fully-stocked with fluffy towels, washcloths, & body wash, shampoo, conditioner products.brbrHouse Rules:brOutdoor Quiet Hours of 10pm-9am will be STRICTLY ENFORCED. You must agree to not congregate in any outdoor space during Quiet Hours.brbrWhile we want our guests to have fun and enjoy the space as much as possible, there is no tolerance for any behavior that will disrupt our neighbors. brbrOutdoor noise is monitored via automated sensors and violating quiet hours may result in a canceled reservation and/or penalty fines.brbr100% Smoke Free Property. Any smoking must be done on the street in front of the house.

6

Bed

4

Bath

21

Sleeps

$792.12

/ Nightly

Private Vacation Home

Modern 4-Bedroom Home – Newly Built - Sleeps 10!

Chicago, Illinois, United States

Modern 4-Bedroom Retreat – Newly Renovated, Steps from the Train!brbrWelcome to your home away from home! This beautifully renovated and fully furnished 4-bedroom home is designed for comfort, style, and convenience. With 5 beds total, it’s perfect for families, friend groups, or business travelers looking for space and flexibility.brbrbr4 spacious bedroomsbr5 comfy beds (ideal for up to 10 guests)brModern decor, quality mattresses, and cozy linensbrbrEnjoy a fresh, contemporary feel throughout the house. From sleek flooring to updated bathrooms and a fully equipped kitchen, everything has been thoughtfully designed to meet today’s standards.brbr Convenient Transit Access:brLocated just a 5-minute walk to the CTA Green Line (Kedzie station), you’ll have quick access to downtown Chicago, West Loop, and beyond—ideal for exploring the city or commuting with ease.brbr Neighborhood Highlights:brbrQuiet, residential block with a growing community vibebrbrGarage + Easy/free street parkingbrbrClose to Garfield Park Conservatory—a local gem and perfect for a relaxing day outbrbrNearby shops, local eateries, and grocery storesbrbrQuick access to I-290 Eisenhower Expresswaybrbr High-speed Wi-Fibr❄️ Central heating & A/Cbr Smart TVbr ️ Fully stocked kitchenbrbrWhether you`re here for a weekend getaway or an extended stay, this home offers the space and amenities you need—with the city just minutes away.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!brbrGuest will receive a keypad code (keypads are located on the door) and guests will check in on their own, no assistance or in person interaction is required.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.

4

Bath

10

Sleeps

$390.32

/ Nightly

Private Vacation Home

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Chicago, Illinois, United States

HOT HOT HUMBOLDT PARK WEST BUCKTOWN! This comfortable and welcoming, NEWLY CONSTRUCTED 5 bedroom duplex condo (2 units combined) is the ideal location for your Chicago stay. With easy access to some of Chicago's hottest attractions like the 606 nature trail (just a block away) and Chicago's prized Humboldt Park (right outside!) you're also not far from the action of downtown, a 15 minute drive! Located right off popular North Ave, minutes away from lively Division St and Wicker ParkbrThe spacebrI want to ensure everyone who stays at my place feels like they are at home and can settle right in, so I provide the following amenities to all my guests!brbr-Newly constructed duplex condo that is great for large gatherings for friends or family to rest in during your stay in Chicago. Prime Chicago location for commuting, restaurants and nightlife. brbr-Brand new high end laminate flooring, white, quartz kitchen counters, stainless-steel, high-end appliances, 2 (yes, 2!) kitchens spread across 2 floors, new bathroom vanities, tubs and toilets, and ample common areas on each floor for gatherings.brbrFully furnished and kitchen is ready for use and cooking with large fridge!brbr- My cleaners are professionally trained and follow a tightly regimented cleaning and sanitizing checklist. They are equipped with a full complement of professional cleaning tools and chemicals including a hospital-grade disinfectant.br- Fresh towels and linens which are professionally laundered and ironed by a hotel linen companybr- Wireless internet is always availablebr- TV with streaming optionsbr- Kitchen appliances including a microwave, coffee pot with a reusable filter, tea kettle, and toasterbr- My place is FULLY STOCKED with all the amenities of home like eco friendly shampoo, conditioner, and body wash, paper towels, toilet paper, tissue, sponges & Method brand hand soap and dish soap. You name it, we provide it to make you feel at home!br-The full sized kitchen is stocked with cookware, utensils, glasses, cutlery, sharp knives, cutting boards, baking sheets and all the basic tools like wine openers, cheese graters, vegetable peelers, pizza cutters, etc.br- Hair dryerbr- Luggage racks and hangersbrGuest accessbrGuest will recieve a keypad code (keyads are located on the door) and guests will check in on their own, no assitance or in person interaction is required.brOther things to notebr**COVID 19 News** Unfortunately, during the pandemic, we have had a significant rise in guests that want to rent the house for large gatherings / parties. Our home is meant for people that are traveling for business, families visiting from out of state for holidays and guests interested in exploring the city, and small gatherings. It is not meant for large parties. We would like to see verifications and good reviews before renting the house. We do require all of our inquiries contact us with details about their trip because want to insure the people renting are renting it for the right reasons.brLicense numberbrR22000078499

Bed

Bath

Sleeps

$341.03

/ Nightly

Private Vacation Home

Stay, Relax & Explore Chicago

Chicago, Illinois, United States

Unwind in a serene, upscale space where comfort meets elegance. This modern Chicago escape features refined finishes, plush bedding, and curated amenities to elevate your stay. Ideal for guests who value peace, quality, and style—with quick access to the city’s top spots. Inspired by the art of intentional living, it’s more than a stay—it’s a lifestyle.

Bed

Bath

Sleeps

$128.54

/ Nightly

Private Vacation Home

4/20 Friendly 12PM Check Out 1 Bedroom Basement

Chicago, Illinois, United States

I Have A 1 Bedroom Private Full Apartment Located In My Basement Its Connected Too My House But Blocked Off You Have Your Own Privacy & Your Own Door Too Get In & Out & Wont See Me In Your Way While Hosting Im 4/20 Friendly Soo You Can Smoke Im Not As Strick As Most Other Host Soo Your Free Too Do Your Own Thang With Out Being Harassed All I Ask Is You Be Respectful If You Need Anythang Dont Be Afraid Too Ask & Enjoy Your Stay At The Palace & Please Leave Me A Good Review ( Currently Having Plumbing Issues With The Bath Tub Soo I Lowered My Original Price Everything Else Works In The Bathroom Except The Shower/Tub Soo Intill I Get It Fixed Im Sharing My Tub Upstairs Which Is The Same Exact Jacuzzi Tub In The Pictures I Will Respect Your Time When Needed Too Use The Tub At Any Time I Am Very Sorry For The Inconvenience & Hope That You Still Enjoy Your Stay)

1

Bed

1

Bath

3

Sleeps

$164.68

/ Nightly

Private Vacation Home

Cozy Chicago Retreat Near All The Action

Chicago, Illinois, United States

Discover this 1-bedroom 2-flat in Chicago. The upper level space features a terrific bedroom with two Queen beds, a dinning area with a full sized day bed and a cozy office area that includes a futon. This unit sleeps 6 guests comfortably and is 420 friendly.NO tobacco smoking is allowed in the unit. Small touches like a curling wand, hair dryer and iron add convenience to your stay. We even offer pots, pans, and utensils for our guests who love to cook! After spending the day downtown Chicago ( just 20 minutes away depending on your desired destination) unwind in the jacuzzi bathtub! Whether you’re relaxing indoors or working remotely, this fantastic spot offers a welcoming vibe. It’s easy to see why you’ll be able to unwind at our place.

1

Bed

1

Bath

6

Sleeps

$912.85

/ Nightly

Private Vacation Home

4 BR • Theater Room • Gym • Walk to Lincoln Park!

Chicago, Illinois, United States

✨ I highly recommend this location. The home is beautiful and quaint. The location is perfect. The neighbor is very quiet you are very close to shops and eateries.✨brbr✔️ Situated on a tree-lined in the heart of Old Town Chicagobrbrbr✔️ 3-5 min drive:brbr✔️ Lincoln Park and Zoobr✔️ Immersive Van Gogh Exhibitbr✔️ North Avenue Beachbr✔️ Chicago History Museumbrbr⭐ HIGHLIGHTS ⭐br▪️ 4 Bedrooms: 1 King Bed, 4 Queen Bedsbr▪️ 2 Full Bathrooms and 1 Half Bath w/ Complimentary Toiletriesbr▪️ Full Kitchen w/ High End Appliancesbr▪️ Spacious living area w/ couch + Smart TVbr▪️ Free Wi-Fi + Multiple laptop-friendly surfacesbr▪️ Central Air Conditioning and Heatingbr▪️ On-site washer and dryerbr▪️ Patiobr▪️ Free parkingbr▪️ Furry friends are welcomed!br▪️ Family-friendly amenities: Pack ‘n Play, high chair, children’s dinnerware, extra pillows + more (upon request)br▪️ Maximum Capacity: 12brbrNote: Before booking, please ensure that you have reviewed the “Other Things to Note” and “House Rules” sections.brbr✨A five star host and a five star stay!✨ brbr✨ EAGER TO KNOW MORE READ BELOW! ✨brbrbr⭐ BEDROOMS ⭐br▪️Master Bedroom: King Bedbr✔️ Lounge areabr✔️ Smart TVbr✔️ Full body mirrorbr✔️ En-suite bathroombrbr▪️ Bedroom 2: Queen Bedbr▪️ Bedroom 3: Queen Bedbrbr▪️ Bedroom 4 (Basement): Two Queen Bedsbr✔️ Large lounge areabr✔️ Smart TVbrbr✔️Clean and fresh beddingbr✔️ Room-darkening shadesbr✔️ Extra pillows and blankets (upon request)brbrbr⭐ BATHROOMS ⭐brOur home offers three beautifully designed bathrooms, each equipped with modern fixtures and stylish finishes to enhance your stay.br▪️ Bathroom 1: Full Bathroom - Main Levelbr▪️ Bathroom 2: Full Bathroom - Second Floor br▪️ Bathroom 3: Half Bathroom - Lower Levelbr✔️ Fresh towelsbr✔️ Shampoo, conditioner and body washbr✔️ Hair Dryerbrbrbr⭐ KITCHEN and DINING ⭐brOur home features a beautifully designed dining area that comfortably seats sevenbr✔️ High-end appliancesbr✔️ Full size fridgebr✔️ Stove, oven, microwave, dishwasherbr✔️ Toaster, coffee/tea maker, water kettlebr✔️ Spicesbr✔️ Dishware, flatware, and dining utensilsbr✔️ Essential cooking utensilsbr✔️ Stocked with basic supplies: paper towels, trash bags, etc.br✔️ Kitchen Islandbr✔️ Dining table for 7brbrbr⭐ LIVING ROOM ⭐brOur home boasts two inviting spaces for relaxation and entertainment:br▪️ Main living areabr✔️ Large sectional sofabr✔️ Smart TV with Disney+, Netflix, Amazon Prime, Hulu + HBO + morebr✔️ Board gamesbrbr▪️ Lower-level lounge.br✔️ Large sectional sofabr✔️ Smart TV with Disney+, Netflix, Amazon Prime, Hulu + HBO + morebr✔️ Indoor Basketballbr✔️ Arcadebrbrbr⭐ BASEMENT⭐br✔️ In-suite washer and dryerbr✔️ Iron and ironing boardbrbrbr✨ Don’t miss out on this fantastic vacation home! Book now to experience the best of Chicago with all the comforts of a home away from home. ✨ brbr✨ Book Today and Let Us Take Care Of You In Chicago! ✨brbr✔️ Please take a moment to read our House Rules in the House Rules section.br✔️ This property comfortably accommodates up to 10 guests, but we are happy to consider hosting up to 12 guests if needed.br✔️ Travelling with little ones We’ve got you covered with supplies available upon request, including a Pack ’n Play/travel crib, highchair, and board games. Fees may apply upon the host's discretion.br✔️ We offer options for early check-in and late check-out, subject to availability. Please note, there is a fee for early check-in and late check-out.br✔️ Mid-stay cleaning and other concierge services are available upon request for an additional fee.br✔️ For guests’ convenience, those with early arrivals or late departures can drop off their luggage with host approval before standard check-in time.br✔️ Surveillance or recording devices on property - We use a noise monitoring device; It does NOT record actual sounds or conversations, it simply monitors the noise level (measured in decibels). Video recording devices only monitor the exterior of the home and not any of the interior.brbr✔️ Unregistered guests are not allowed. Additional fees may apply.br✔️ Pets are welcome, but must be registered and reported to the host. Ensure that they are well-behaved and that you take necessary precautions to prevent any damage. Pet owners will be responsible for any damages caused. A pet fee will apply.br✔️ No smoking inside the property. br✔️ No parties, events, or large gatherings allowed br✔️ Please observe quiet hours from 10 PM to 8 AM.br✔️ Respect the neighbors. Do not park on their premises.br✔️ Do not leave food or debris that can attract pests. Maintain cleanliness throughout your stay.br✔️ Do not flush anything down the toilet to avoid plumbing issues.br✔️ Please report anything that is not working or broken upon check-in.br✔️ Follow the guidebook instructions.br✔️ Adhere to the standard check-in and check-out time. Early check-in and late checkout are subject to the host's approval. br✔️ Must be at least 21 years old to bookbr✔️ View Rental Agreement, Photo ID, and Security Deposit may be required upon check-in.br✔️ We reserve the right to charge a fee if ANY of the policy is violated.br✔️ Any unauthorized moving of furniture that results in additional cleaning, repairs, or setup may incur a fee of up to $1000.

5

Bed

2

Bath

12

Sleeps

$1143.83

/ Nightly

Private Vacation Home

Stylish 3BR Townhouse with 2 Jacuzzi and 1 private garage spot

Chicago, Illinois, United States

About this spacebr!!1 CAR PRIVATE GARAGE PARKING INCLUDED!!brbrWelcome to this stylish urban home that will make you feel at home! This modern and beautifully furnished apartment offers a perfect blend of comfort and style, making it an ideal choice for your stay in the Vibrant City of Chicago.brThe spacebrOur property is a 4-story townhouse, with 3 -stories of living space and ground level is a private 1-car parking garage. Access to the parking is included with your stay so you do not have to worry about parking at any time during your stay.brbrThe living space is a 3 bedroom + game room and 2.5 bathroom. We have comfortable accommodation for 12 guests.brbrLiving Room: Relax in the spacious and inviting living room, complete with a plush sectional sofa, two cozy mustard-colored chairs, and a warm fireplace that sets the perfect ambiance. The large windows allow plenty of natural light to flood the space, and the flat-screen TV is mounted above the fireplace, ready for your favorite shows and movies.brbrKitchen & Dining: The fully equipped kitchen features sleek dark wood cabinetry, stainless steel appliances, and a granite island with comfortable barstools for casual dining or morning coffee. The adjacent dining area offers a chic wooden table set for six, perfect for enjoying meals with family or friends.brbrMaster Bedroom: Located on the 3rd floor, this room features a king bed and has access to a shared bathroom.brbrBedroom 2: Also on the 3rd floor, this room offers a queen bed and shares the attached bathroombrbrBedroom 3: Located on the 4th floor, this room includes two queen beds and has its own private bathroom. There are 2 roll out beds placed in both the closets that you will be able to use for your stay.brbrGame Room: Located on the 4th floor, just across from Bedroom 3, this room is perfect for enjoying quality time with your group.brbrPatio: Our outdoor patio is furnished with comfortable furniture, offering a great spot to relax and enjoy the fresh air during your stay.brGuest accessbrThe guest will have access to the all 4-floors of the townhouse during their stay. The garage is included with the stay. The main garage entrance is shared with our townhouses of the community, so we expect guests to be respectful of the shared area and close the garage doors when they arrive and exit.brOther things to notebrThe unit is located on the main street, so please be aware that there will be traffic noise during the day and little bit at night, however the building has very good sound proofing to minimize the noise.brRegistration DetailsbrR24000116759

Bed

Bath

Sleeps

$1536.17

/ Nightly

Private Vacation Home

El Motel United in Logan Square that Sleeps 24 with Large Entertaining Patio + Grill

Chicago, Illinois, United States

Bed

Bath

Sleeps

Select Dates for Price

Private Vacation Home

Wicker Park Entire House, Private Yard and Parking

Chicago, Illinois, United States

Summary:brbrRenovated 4 bed 3 bath home in the heart Wicker Park. PRIVATE FREE PARKING! Incredible backyard with outdoor kitchen and gas fire pit. There is no better location than this, just a few steps from all that Wicker Park and Bucktown have to offer. Just a few hundred feet from Collectivo Coffee Shop and the countless restaurants and shops and attractions that the area has to offer. Also a very quick walk to the blue line train (goes west to O'Hare International Airport, east to Downtown Chicago).brbrbrbrThe Space:brbrYou will be renting the entire single family home, there are no adjoining units! There are 4 bedrooms and 3 bathrooms:brbrbrbr1st floor : 1 full bathroom with shower/tub combobrbr2nd floor : 2 private bedrooms, each with a king bed. 1 full bathroom with stand up showerbrbr3rd floor : 2 private bedrooms: 1 with two double beds and 1 XL twin. 1 with 1 double bed and 1 XL twin. 1 full bathroom with shower/tub combobrbrbrbrThe entire fenced in back yard is your private oasis to enjoy!brbrbrbrThere is a parking pad in the rear of the home that can fit at least 2 vehicles and has a private gated entry into the back yard and back door to the home.brbrbrbrGuest Access:brbrThe entire home, back yard, and private parking area will be available only to you during your stay. Truly a private oasis in the perfect location in the city, and you have it all to yourself!brbrbrbrThe Neighborhood:brbrLocated in vibrant Wicker Park, you're steps from trendy cafes, top-rated restaurants, unique boutiques, and lively nightlife. Easy access to downtown via the Blue Line or a quick drive. Explore nearby parks, galleries, and music venues. A perfect spot for foodies, creatives, and city explorers alike!brbrbrbrGetting Around:brbrLocated in Chicago’s vibrant Wicker Park, 1235 N Damen offers easy access to the Blue Line ‘L’ train—just steps away—getting you downtown or to O’Hare in minutes. Walk to trendy shops, cafes, and nightlife. Great for Airbnb guests without a car; bike lanes, Divvy stations, and rideshares are all nearby. Urban, walkable, and super convenient for exploring Chicago.brbrbrbrOther Things to Note:brbr**The backyard amenities (BBQ grill, gas firepit, seating areas) are winterized by November 15th and are not reopened until April 15th**brbrbrbrPlease note that this house is right in the heart of Wicker Park, on the main road which makes it absolutely ideal for walkability and for enjoyment of the many restaurants, bars, coffee shops, retail stores, art studios etc. nearby. However, since it is right in the city, there is city noise and plenty of traffic and hustle and bustle. We want to make sure guests know this prior to booking.brbrbrbrInteraction with Guests:brbrWe will be available for any issues that arise, please contact us through the booking app and we will promptly respond. We will let you do your thing but you can reach us whenever you may need back up!

4

Bed

3

Bath

12

Sleeps

$1164.44

/ Nightly

Private Vacation Home

Bohome Chicago | 4BR + Sauna + Chefs Kitchen

Chicago, Illinois, United States

Designer, plant-infused 4BR/3.5BA home in Wicker Park—crafted for retreat, work, and play. Unwind in the private sauna, gather on the deck with a fire pit, and cook in the chef-ready kitchen. Enjoy a Sonos sound system, smart mood lighting, fast Wi-Fi, a dedicated workspace, and multiple projectors for movie nights. Sleeps eight comfortably across three king bedrooms + 1 queen Murphy; two king suites feature ensuite baths—minutes to Division St. dining, boutiques, and the 606 trail. Events and productions are available upon request and require prior approval, a signed agreement, separate rates/fees, and proof of insurance (COI).brbrChicago — The Home + HighlightsbrWelcome to Bohome Chicago — calm, curated, and plant-forward with room to breathe. Wellness is a cornerstone here and across our sister locations. Think morning espresso, afternoon sauna, dinner on the deck, a movie on the projector, then exhale with a warm bath. Thoughtfully designed for families, small groups, retreats, or creative getaways, the home blends warm textures with modern minimalism across a multi-level layout that keeps each bedroom wing feeling private. Wellness touches—a massage table, foot-soak tub, and a fitness/meditation room with yoga mats—make restoration effortless between city adventures.brbrHighlightsbrWellness: private sauna; jetted tubs; massage table; foot-soak; fitness/meditation room with yoga matsbrSleep: 4BR / 3.5BA — 3 king beds + 1 queen Murphy; hotel-quality linens and tranquil designbrSuites: two king bedrooms with ensuite baths (tub + shower)brLiving & A/V: Sonos sound system throughout; multiple projectors for cinema nightsbrChef setup: espresso station, juicer, Vitamix, high-quality cookwarebrWork-ready: fast Wi-Fi + dedicated deskbrIndoor fireplaces: for added cozy effectsbrSmart comforts: voice-controlled lighting (Alexa) and smart home touchesbrInstruments: grand piano, guitars, hand drums, plug-and-playbrbrCDJs (by request)brAdded comfort: throw blankets, plush robes, bedside phone chargersbrbrOutdoors: deck with pergola, seating, and fire pitbrParking: street parking typically available out front; nearby garages within walking distancebrbrLayout & SectionsbrRooms & Bathsbr4 bedrooms / 3.5 bathsbrKing Suite 1 — ensuite (jetted tub + shower)brKing Suite 2 — ensuite (jetted tub + shower)brKing Bedroom 3 — shares hallway bath (with sauna access)brBedroom 4 — Queen Murphy; shares hallway bath (with sauna access)brbrPlus a main-level powder roombrTwo bedrooms are on the 3rd (top) level; two are on the lower (garden) level. The lower level also includes a wellness lounge with sauna access, a family room, and plug-and-play CDJs for guests who want to DJ.brbrCulinary & GatherbrThe main level offers open living/dining anchored by a chef-ready kitchen—espresso/tea station, juicer, Vitamix, and quality cookware—set up for real cooking and effortless hosting. Open living/dining flows to the deck and Spanish-inspired backyard for alfresco dinners, brunch, or sunbathing.brbrLivingbrComfortable, calm seating areas with room to gather or decompress. Multiple projector setups for movie nights.brbrWork & Wind-DownbrFast Wi-Fi and a focused workspace support remote days. After hours, step into the sauna or cue up a movie with the projector + Sonos. Smart-home features include Alexa to control lighting (dimness and colors) and music throughout the house to set the perfect ambiance.brbrWellness & WorkoutbrPrivate gym/meditation room (punching bag + light equipment), massage table, and foot-soak tub. Ideal for restorative stays.brbrTechbrSonos sound system; Alexa voice controls for lighting and music; multiple projectors (100 in the living room and in three bedrooms) for streaming.brbrGroundsbrIn the heart of Wicker Park, you’re a block from Division St. restaurants, cafés, vintage/boutique shopping, the 606 trail, and easy transit via the Blue Line and CTA buses. Evenings on the deck pair perfectly with tacos at Big Star or cocktails on Division or Milwaukee. (Walk/Bike-score fans, you’ll be happy here.) Nature time is close by at Wicker Park and the beautiful, vast Humboldt Park.brbrGuest accessbrYou’ll have access to the entire home and outdoor areas, except for any clearly locked owner storage. Garage access only if discussed in advance. Smart keypad for easy self-check-in.brbrThings to Know + Extras + EventsbrWe welcome gatherings, celebrations, private dinners, pop-ups, productions, and meetings; all require prior host approval, a signed agreement, separate rates/fees, and proof of insurance (COI). Handled case by case—please inquire in the Vrbo message thread.brbrCameras: No indoor cameras. Outdoor devices (e.g., doorbell and entrance cameras) may be present and are disclosed.brQuiet hours: Please be mindful and kind to neighbors.brPets: Require approval and a pet fee.brParking: Please let us know if you have specific parking needs. Typically, there’s plenty of free street parking in front; nearby garages are within walking distance.brCleaning fee: An additional $350 cleaning fee applies and will be requested after booking via Airbnb’s Resolution Center.brBonus: High-rating/repeat guests may qualify for select perks or discounts—mention prior stays or your rating in your inquiry.brbrElevated extras (by request)brPrivate chef dinnersbrCurated floral welcomes or celebration setupsbrWelcome, chef-made charcuterie, grazing table, banana pudding, or ice creambrGuided wellness sessionsbrProfessional photo shootsbrSound baths + healingsbrMassage coordinationbrRetreat or small-event packages (weddings considered)brbrWe’re happy to help customize your stay—send a message in the Vrbo thread and we’ll co-create the ideal experience.brbrEvents, productions & policies (Vrbo-compliant)brPre-approval via the Vrbo message threadbrSigned location/use agreementbrSeparate rates/fees and proof of insurance (COI) requiredbrbr(Unapproved events/parties are not allowed.)brbrChicago — House RulesbrNo outside shoes indoors (slippers available upon request).brNo glitter or confetti.brKeep the front gate closed.brNo smoking indoors.brQuiet, respectful use of outdoor areas.brOnly registered guests on the property unless pre-approved.brbrEvents/productions require prior approval, a signed agreement, separate rates/fees, and proof of insurance (COI).brFollow the check-in/out checklist: start the dishwasher, remove trash, return furniture to its original positions, and report issues promptly so we can help.brbrBonus: High-rating/repeat guests may qualify for select perks or discounts—mention prior stays or your rating in your inquiry.

4

Bed

4

Bath

8

Sleeps

$381.28

/ Nightly

Private Vacation Home

Wonderful 4-bedroom house with AC in charming Chicago

Chicago, Illinois, United States

This comfortable and spacious 4-bed, 2-bath house is the perfect spot for families, groups, or anyone who just wants a relaxed place to unwind while staying close to everything.brbrAs soon as you walk in, you’ll feel the easy, home-like vibe. There’s plenty of room for everyone to spread out, a cozy living area for movie nights, and a full kitchen if you’d rather cook than eat out. Whether you’re here for a weekend or a longer stay, the layout makes it super easy to settle in.brbrWhat guests love about this place:brbrLots of space – Four bedrooms and two full bathrooms mean no squeezing in and no waiting in line in the mornings.brbrComfortable living areas – Warm, inviting, and perfect for hanging out after a day of exploring.brbrGreat for families & groups – Easy, functional, and designed to fit everyone comfortably.brbrConvenient location – Close to restaurants, shops, and local attractions, but still in a quiet area where you can relax.brbrEasy parking & stress-free stay – Parking on site, simple check-in, and a host who’s quick to help with anything you need.brbrThis home is set up to make your stay smooth from start to finish. Whether you’re here to explore the city, visit family, or just enjoy a change of scenery, we’d love to host you and make your trip as comfortable as possible.

Bed

Bath

Sleeps

$1216.05

/ Nightly

Private Vacation Home

Pet-Friendly w/Pool Table: Walk to Wrigley Field

Chicago, Illinois, United States

Pedestrian-Friendly Location | Walk to the Red Line | Off-Street ParkingbrbrStep into this North Side vacation rental, where Cubs spirit runs deep and game-day energy fills the air! Just 3 blocks from Wrigley Field, this 4-bed, 2-bath townhouse is set in the heart of Chicago’s most vibrant neighborhood. Ready to explore more of the city Step outside and you’re practically at Sheridan Station — putting the university, museums, and Millennium Park within easy reach. Book today!brbr-- THE PROPERTY --brbrR25000134678brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 queen bed, 1 full sleeper sofabr- Bedroom 3: 1 queen bedbr- Bedroom 4: 1 queen bedbrbrMAIN FEATURESbr- TVsbr- Pool tablebr- Wood-burning fireplacebr- Dining tablebr- Keurig coffee bar (starter coffee provided)br- DeckbrbrKITCHENbr- Refrigerator, stove/oven, dishwasherbr- Microwavebr- Dishware/flatware, trash bags/paper towelsbrbrGENERALbr- Free WiFibr- Central A/C & heat, ceiling fanbr- Linens/towels, shampoo & conditioner, body washbrbrFAQbr- Pet fee (paid pre-trip)br- Quiet hours (8:00 PM-8:00 AM)br- 1 exterior security camera (facing front entry)brbrACCESSIBILITYbr- 2-story townhouse, exterior steps to enterbr- 2 bedrooms & 1 bathroom on main floorbrbrPARKINGbr- Carport (1 vehicle)br- Free street parking (first-come, first-served)brbr-- THE LOCATION --brbr- Walkable to essential shopping, restaurants & nightlifebr- 0.1 miles to Sheridan Stationbr- 2 miles to Lincoln Park, Montrose Beach: Lake Michigan accessbr- 7 miles to Millennium Parkbr- 14 miles to The University of Chicagobr- 14 miles to Chicago O'Hare International 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- Pet friendly w/ $50 fee (+ fees & taxes)br- No events, parties, or large gatheringsbr- Please observe quiet hours from 8:00 PM to 8:00 AMbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This 2-story townhouse requires exterior steps to enter; it has 2 bedrooms and 1 bathroom on the main floorbr- Your safety matters. This property features 1 exterior security camera on the front door facing the front outdoor entry. The camera does not look into any interior spaces. It records video and sound when activated by motion

Bed

Bath

Sleeps

$593.02

/ Nightly

Private Vacation Home

Cozy Home in the heart of Chicago W/Private Backyard & Games Room-Free parking.

Chicago, Illinois, United States

*** Welcome to Whipple Haven, your home away from home ! ***brbrOur home comfortably sleeps 10 guests and is located in the heart of historic Logan Square, Chicago. We hope you enjoy your time here and make the most of everything the neighborhood has to offer.brbr* Perfect for EventsbrWe’re just a short walk from Stan Mansion, a popular wedding venue. If you’re attending a celebration there, our home is the ideal place to stay.brbr* Traveling with a Larger Group brOur next-door neighbour’s home is also available to rent on Airbnb! Together, the two homes offer space for up to 8 bedrooms total. Reach out if you’d like help arranging a larger group booking.brbr* Foodie ParadisebrLogan Square is home to award-winning dining, all within walking distance:brbrLula Café – James Beard Award–winning and a true neighborhood gem.brbrGiant – Michelin-starred modern American dining.brbrGretel – Known for craft cocktails and elevated pub fare.brbrParson’s Chicken & Fish – Famous for fried chicken and frozen cocktails.brbrBixi Beer – Asian-inspired brews and bites.brbrDaisies – Celebrated pasta-focused, vegetable-driven cuisine.brbrWhether you’re here for a wedding, a foodie adventure, or a family gathering, Whipple Haven is the perfect home base for your Chicago stay. brbr* About our home:brbrOur spacious, sun-drenched family-friendly retreat has everything you need for a relaxing stay—whether you’re traveling with kids, friends, or extended family. Spread across three levels, the home is designed for comfort, fun, and unforgettable gatherings.brbr* Upper LevelbrbrMaster Suite: Unwind in the king-sized bed with an en-suite bathroom featuring a full tub, drawers, and a clothing rail. Fresh sheets, fluffy towels, shampoo, conditioner, and body wash are all provided.brbrGuest Bedroom: A queen bed, blackout blinds, and a small walk-in closet make this room cozy and restful. Bathroom access included with toiletries and linens.brbrKid-Friendly Bedroom: A dream space for little ones—twin-over-double bunk bed plus an additional twin, a walk-in closet, blackout blinds, and a library stocked with children’s books.brbr* Lower LevelbrbrGames Room: Challenge your friends and family to a round of pool, table football, axe throwing (plastic) or a game of darts! Fully stocked with kids games/puzzles, books and even a barbie dream house. brbrGuest Suite: Queen bed with private bathroom, plus a travel crib for infants or toddlers. All linens and bath essentials provided.brbrOffice Space: Need to work while away A desk, chair, and printer (with ink and paper) are ready for you. High-speed WiFi covers the entire house.brbr* Main LevelbrbrChef’s Kitchen: Cook with ease using Viking appliances, a Smeg coffee maker, Nespresso machine, toaster, kettle, and fully stocked cookware. Spices and condiments are also on hand.brbrDining Room: Gather around the full-length dining table that seats 6–8 comfortably.brbrCozy Living Room: Curl up by the electric fireplace with a book or enjoy the curated art collection from Vietnam, China, and Ireland.brbrTV Lounge: A 60-inch TV by the breakfast nook makes it easy to stream your favorite shows and movies together.brbr* Outdoor HavenbrOur favorite spot! Dine under the shaded pergola, fire up the grill, and host your very own family feast. The perfect place for long evenings, laughter, and making memories.brbrThis home blends comfort, style, and practicality—whether you’re here to relax, explore, or celebrate together.brbrOur home is also pet friendly with enclosed back yard. brbr* Local nature: Enjoy walking or biking on 'The 606'/ Bloomingdale Trail. Walk half a block to Palmer Square Park, great to play with dogs and kids or swing on a hammock and read a book. We provide hammock in front cloak room at entrance. brbr* Fun breweries walking distance:brRevolution, Maplewood, Hopewell, Solemn Oath and Middle Brow Bungalow. brbrYou will not run out of things to do in Logan Square. brbr* Public Transport brbrThe bus to Lincoln park which connects to downtown (73) is on our doorstep (2 min walk on Armitage St) and we are a ten minute walk from the California stop on the Blue line (The 'L) if you have plans to sightsee downtown! It is easy and safe to travel this way. brbrIf you're driving by car here, there is free parking out front on Whipple Street.brbrSome info about the neighborhood:brbrWelcome to Logan Square, one of Chicago’s most vibrant and historic neighborhoods. Known for its tree-lined boulevards, classic greystone architecture, and lively arts scene, Logan Square beautifully blends history with modern culture.brbr*A Bit of HistorybrbrNamed after General John A. Logan, a Civil War hero, the neighborhood is part of Chicago’s historic Boulevard System, which is listed on the National Register of Historic Places.brbrThe iconic Illinois Centennial Monument, designed by renowned architect Henry Bacon (who also designed the Lincoln Memorial), stands proudly at the heart of Logan Square.brbrWhat to See & Do:brbrStroll the Logan Boulevard Historic District with its stately homes and green medians.brbrBrowse local shops, vintage stores, and art galleries sprinkled throughout the neighborhood.brbrCatch live music at The Logan Theatre, a beautifully restored 100-year-old movie house that now features indie films, craft beer, and events. Another amazing spot walking distance for live music is Rosa's Lounge on Armitage St with live jazz and blues music! Perfect spot for a date night!brbrSpend a Sunday morning at the Logan Square Farmers Market, one of the city’s best, packed with local produce, baked goods, and artisanal finds.brbrA favourite date-night venue of my husband and I is to grab a glass of wine and charcuterie at Lardon and head to the speakeasy next door called Blue Bird. This is about a 8-10 minute walk from our home. brbrA bit of Trivia for you!brbr**Just steps from Logan Square, Chicago has deep ties to two icons of imagination. Walt Disney was born in 1901 at a modest home on Tripp Avenue in nearby Hermosa—only a couple miles from here. And in 1899, L. Frank Baum penned The Wonderful Wizard of Oz while living on Humboldt Boulevard, right next door to Logan Square. Together, these neighborhood connections remind us that Chicago is not just a city of architecture and food—it’s also a birthplace of timeless stories that shaped childhoods around the world. brbrHappy exploring Logan Square, Chicago and its surrounding neighborhoods! brbrIf you have any questions please don't hesitate to reach out!

4

Bed

3

Bath

10

Sleeps

Vacation Home Rentals By Owner In Chicago, IL

$1955.43

$792.12

$390.32

$341.03

$128.54

$164.68

$912.85

$1143.83

$1536.17

$1164.44

$381.28

$1216.05

$593.02

Rent a place that suits your needs

Most popular vacation rentals in Chicago

$2319.21

$2427.16

$2731.80

$2999.50

$3259.71

$3780.16

$320.07

$317.86

$318.18

$318.68

Most Popular Cities in Illinois