Houses in Chicago

Book unique boutique hotel rooms, houses, and more on Airbnb

0 of 0 items showing
1 of 3 pages

Stay near Chicago's top sights

O'Hare International Airport14 locals recommend
Wrigley Field158 locals recommend
United Center50 locals recommend
Millennium Park213 locals recommend
Navy Pier274 locals recommend
University of Chicago14 locals recommend

Boutique hotel rooms in Chicago

Superhost
An entertainment area features a foosball table and a billiards table, inviting relaxation and socialization. Surrounding seating areas with tables are available for games or gatherings. Soft lighting from overhead fixtures creates a comfortable environment for guests to enjoy leisure activities.
Hotel room in The Loop
4.82 out of 5 average rating, 33 reviews

King Room in Theatre District

AlexRating, 5 stars2 months ago
I had a great stay. Clean, check-in was easy, and the room is conveniently located to many Chicago attractions.
Superhost
A recreational area is presented, featuring a foosball table and a billiards table. The space includes comfortable seating arrangements and a dining table, illuminated by pendant lighting. The walls are adorned with artwork, creating an engaging atmosphere for social gatherings.
Hotel room in The Loop
4.74 out of 5 average rating, 62 reviews

Charming King Bedroom in Loop

JavierRating, 5 stars2 months ago
Absolutely! Go ahead and send me the Airbnb review you want expanded, and I’ll enhance it with more detail, warmth, or whatever tone you’re going for.
Superhost
An outdoor rooftop space features comfortable seating arranged in a conversational layout, surrounded by greenery. A wooden pergola provides shade over the area, while decorative cushions add color. The deck's wooden flooring complements the serene setting, creating an inviting space for relaxation.
Hotel room in Andersonville
4.67 out of 5 average rating, 6 reviews

1BD/1BA steps away from local shops, entertainment

SusanRating, 5 stars34 months ago
A wonderful place, clean, well equipped, friendly, and located in a great neighborhood. We will return the next time we go to Chicago!
Superhost
A recreational area features a billiards table with colorful balls scattered across the felt. Surrounding seating includes several modern chairs at a long table, with shelves displaying games and books in the background. Warm lighting from overhead fixtures enhances the inviting space.
Hotel room in The Loop
4.67 out of 5 average rating, 9 reviews

Charming Private Room in Downtown

RenaRating, 5 stars17 months ago
This is wonderfully located , clean and nice place! It is the second time that I stay there and it is still lovely! Thank you!
Superhost
An entertainment area features a billiards table with colorful balls positioned on it, complemented by seating at a dining table in the background. Modern light fixtures illuminate the space, which includes games on shelves and a cozy lounge area with plush chairs and decorative wall elements.
Hotel room in The Loop
4.52 out of 5 average rating, 25 reviews

King Bedroom in Theatre District

KellyRating, 5 stars4 months ago
Cambria hotel was super convenient. Instructions for check in were clear. Room was as shown in the photos. Super close to everything and easily walkable to the theaters! Will stay again.
Superhost
A modern communal space is highlighted by several round wooden tables and comfortable seating. Soft lighting illuminates the area, where a large television and shelves filled with books are visible. Large windows allow natural light to fill the room, creating a bright atmosphere.
Hotel room in The Loop
4.64 out of 5 average rating, 45 reviews

Private King Bedroom in Heart of Downtown Chicago

JoseRating, 5 stars5 months ago
Enjoyed our stay, thank you Paul for having us!
Superhost
The exterior of the Cambria Chicago Loop - Theatre District is featured, showcasing a stylish entrance under a canopy. The vibrant sign of the Oriental Theatre is visible, along with pedestrians walking along a well-lit sidewalk, creating an inviting atmosphere in an urban setting.
Hotel room in The Loop
4.79 out of 5 average rating, 14 reviews

Private King Room in Theatre District

MadelineRating, 5 stars4 months ago
Staff were incredibly helpful during our stay. Checking in and out was super smooth and efficient. The location is super convenient and walkable to many fun activities and restaurants. We didn’t have to be on public transit for more than a half hour for anything we couldn’t walk to.
Superhost
An inviting lobby features four plush orange armchairs arranged around a central coffee table. A decorative rug lies beneath, adding a pop of color. A sleek fireplace is framed by dark cabinetry, while shelves display various decorative items and refreshments, creating a welcoming atmosphere.
Hotel room in Uptown
4.98 out of 5 average rating, 44 reviews

Bright 1BR w/ shared Roof Deck, close to beach

TylerRating, 5 stars30 months ago
FANTASTIC Andersonville place to stay, walkable to all the best the neighborhood has to offer! Rick is super responsive, helpful, kind, and generous! Highly recommended, and hope to return soon :)

Places to stay in Chicago

Guest favorite
A well-equipped kitchen features wooden cabinets and a stainless steel stove. Open shelving displays white dishware and cooking essentials. The space includes a sink with dish drying rack and a countertop with a toaster, creating a functional area for meal preparation.
Apartment in Chicago
4.95 out of 5 average rating, 151 reviews

Cute, Clean, Cozy Apartment in Pilsen

AnnetteRating, 5 stars5 days ago
I was very impressed and pleased with all of the thoughtful details and extras like Keurig pods, filtered water and parking stickers. The space was cozy and perfect for our small family. It had every possible amenity needed to make ourselves at home for a week and cooking was a breeze. The location was ideal both due to the proximity to our daughter’s place, but also very quiet and walkable to everything you need including restaurants, stores, light rail and bus lines. Leigh-Anne was super responsive and flexible. The only word of caution would be that guests who are very tall (like over 6’) might find the ceilings too low, though they were perfect for us. We would definitely stay here again on a future trip.
Guest favorite
A modern kitchen countertop displays a sleek air fryer beside a stainless steel toaster. The appliances are set against a backdrop of white tile and dark cabinetry, with gold accents on the hardware adding a touch of elegance.
Home in North Park
4.96 out of 5 average rating, 174 reviews

Chicago River House -BBQ Oasis now open!

ThomasRating, 5 stars2 weeks ago
Even more spacious than in the photos! Well-kept place, with a fully stocked kitchen, projector, BOSE speaker, and great backyard. Double shower in the master bedroom, and strong water pressure. Entry is easy with a code. Finally, the host is VERY accommodating, flexible, and responsive. Recommended!
Top guest favorite
A spacious living area features a comfortable black leather sofa and a distinctive black chair. Natural light filters through large windows, illuminating the mid-century cabinetry and vibrant area rug. Light-colored curtains frame the windows, and a circular coffee table sits at the center.
Guesthouse in Little Italy
4.99 out of 5 average rating, 858 reviews

Polk Street Coach House Apartment, Little Italy/Medical Dist

VickyRating, 5 stars3 weeks ago
the airbnb was so lovely and spacious for our party of 4! we had 0 trouble finding the home and had the best weekend in chicago reuniting with our friends from college. would def recommend - it is a quieter part of chicago. the walk to little italy is quite lovely and is a quick uber from the west loop
Top guest favorite
A light-filled living area features a gray sectional sofa adorned with blue and yellow cushions. Two large windows provide perspectives of the outdoors. A world map hangs on the wall, complemented by a small coffee table and a patterned area rug, contributing to a cozy setting.
Apartment in Lincoln Park
5 out of 5 average rating, 264 reviews

Explore Lincoln Park from a Polished Apartment

TomRating, 5 stars5 days ago
There is no way I/we can do a review of Elizabeth's beautiful apartment in just 1,000 characters. Met Elizabeth personally, made a wonderful connection. It's the most awesome airbnb we've ever stayed at. The apartment has been beautifully remodeled. As a retired general contractor, I was very impressed. The neighborhood is fantastic; great for walking, shopping, and there are restaurants galore. The location is fantastic for touring Chicago. The neighborhood is beautiful with lovely architecture and interesting shops. There are lots of families; couples walking, biking, babies-buggying. We enjoyed walking around the neighborhood after a walk to dinner or lunch. The bed/bedding is very comfortable and we slept very well. Great temp control, lots of windows, and a 65"flat screen TV. The bathroom is large and airy with a walk-in shower. The unit is very quiet, with dual-pane windows and black-out shades for sleeping in late. Stay here for the best Chicago experience.
Guest favorite
A charming brick exterior is presented, featuring a welcoming front porch with seating. Lush green landscaping surrounds the entryway, with well-maintained grass and shrubs adding to the outdoor appeal. The roofline is accented with a gabled feature, enhancing the overall character of the home.
Guest suite in Portage Park
4.95 out of 5 average rating, 125 reviews

Eddy Street Upstairs Apartment

TrinityRating, 5 stars1 week ago
Joe was awesome at communicating and hosting. He even allowed us to bring our reactive dog and we didn’t even have one bad interaction. It was awesome and I appreciate it. It will get warm during the summer time but that’s okay with us. We were happy to just bring our furbabies with us 💕
Superhost
A wooden balcony features a round table with two folding chairs, complemented by various potted plants arranged along the railing. The background includes a view of neighboring buildings and lush greenery, creating a serene outdoor seating area.
Apartment in Logan Square
4.77 out of 5 average rating, 368 reviews

Private Logan Square Studio

MirandaRating, 5 stars5 months ago
very private and fit the description exactly!
Superhost
A compact kitchen is equipped with a black refrigerator and a black gas stove, featuring a microwave and various kitchen appliances. Natural light streams through a window above the countertop, illuminating the organized counter space.
Apartment in Berwyn
4.86 out of 5 average rating, 421 reviews

Berwyn Musical Apartment

WillRating, 5 stars2 days ago
We stayed here for 2-weeks and it was perfect for our family of three. All of the amenities were as described and the washer/dryer proved extremely helpful during out time here. The location can't be beat, there's so much to do! It is very walkable to local bars, restaurants and parks. Train access is also a huge plus. We look forward to staying here again soon. Berwyn forever!
Guest favorite
A sunlit kitchen area with white cabinetry and stainless steel appliances is showcased. A bright yellow wall complements mid-century-style furniture, featuring a light blue chair. Large doors open to the balcony, allowing natural light to fill the space.
Loft in Pilsen Historic District
4.9 out of 5 average rating, 394 reviews

Pilsen Modernist, Creative, Lightfilled Loft

JasmineRating, 5 stars1 week ago
Really nice stay in Chicago. Very quiet and safe neighborhood. Daniel is very friendly to reach out. We’d choose to stay here again next time visiting Chicago.

Dog friendly houses in Chicago

Guest favorite
An outdoor space is showcased featuring a hot tub under a pergola with string lights, providing a relaxed ambiance. Comfortable seating is arranged around a firepit table, complemented by a gas grill visible in the background.
Home in Bridgeport
4.96 out of 5 average rating, 123 reviews

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

KristenRating, 5 stars1 week ago
Staying at Matt’s Air BnB was a fantastic experience. We stayed with our two kids and another couple and the space was perfect for our group. The spacious, fenced in yard made for a great hangout space for our toddler to safely run around. The house looks exactly like the pictures and was extremely clean. We will definitely stay here again! Thank you, Matt!
Top guest favorite
A cozy living area features large windows that invite natural light, complemented by red and orange accents. A television is mounted on the wall above a stylish wooden cabinet, while a colorful rug adds warmth to the space. A compact closet offers additional storage.
Home in Uptown
4.9 out of 5 average rating, 367 reviews

Private 3rd Floor Apartment

RickRating, 5 stars1 month ago
Very comfy apartment in a great neighborhood. We were in town for a baseball game and it’s a terrific place for that, just about a 20-minute walk to Wrigley Field. The only thing to be concerned about is the stairs: there are two flights to get into the apartment and they’re fairly steep and small, so if you have mobility issues that would be a concern. I don’t and had no problem. Karen is a lovely host and was very helpful when I was getting into the place and unloading my stuff from my car. There are tons of restaurants and coffee shops in the area, so it’s a great place to explore and hang out.
Guest favorite
Home in Avondale
4.94 out of 5 average rating, 148 reviews

BoHo House - A Chic, 1903 Chicago Workers Cottage

niratiRating, 5 stars3 weeks ago
Adam was a great host and very responsive. We loved our stay. The house was clean and the house is easily accessible to everything. Would definitely recommend!
Top guest favorite
The exterior of a restored Victorian house is presented, featuring a striking red front door and large windows that invite natural light. A welcoming porch is adorned with seating, surrounded by meticulously landscaped greenery and plants, creating an engaging atmosphere.
Home in East Rogers Park
4.98 out of 5 average rating, 100 reviews

Victorian House in Heart of Rogers Park

LukeRating, 5 stars1 week ago
We had an excellent stay here. hosts went above and beyond to make sure we had everything we needed. beautiful house and parking spot was ideal.
Superhost
The exterior of a single-story home is framed by lush green grass and dark mulch landscaping. A welcoming pathway leads to the front door, adorned with a seasonal wreath. A large tree provides shade, and a white fence marks the boundary of the yard.
Home in Naperville
4.85 out of 5 average rating, 126 reviews

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

MicahRating, 5 stars2 weeks ago
Nice place tucked into a quiet, safe neighborhood. Backyard was outstanding. (We wish the weather had cooperated so we could have spent more time outside) One level home with comfy beds and furniture throughout. Kitchen was spacious and clean. Plenty of extra towels and blankets.
Top guest favorite
The modern kitchen showcases sleek white cabinetry and a spacious island topped with a white marble surface. Stainless steel appliances, including a gas stove and a refrigerator, are complemented by glass-front cabinets displaying elegant dishware. Soft blue lighting highlights the room's contemporary design.
Home in Portage Park
4.97 out of 5 average rating, 117 reviews

Ultra Modern, 2800 SQ Ft, Outdoor Gazebo Sleeps 14

ErikaRating, 5 stars1 week ago
The house is very beautiful. My family and I loved the place and how spacious it is.
Guest favorite
A corner jacuzzi whirlpool tub is positioned against a wall, featuring multiple jets for relaxation. A white toilet and a small wooden stool are visible nearby. Light gray walls are complemented by a window covered with a light-colored curtain, allowing natural light to filter in.
Home in Chicago Ridge
4.91 out of 5 average rating, 143 reviews

Quiet cul-de-sac with huge fenced in backyard

MeganRating, 5 stars4 days ago
Tom's place was really nice and exactly as described. The backyard was perfect for our pup and the neighborhood was really nice to take him on the walk. We would defintely stay there again if we are in the area.
Guest favorite
An open-concept living space features a large sectional sofa in front of a vibrant area rug, with exposed wooden beams overhead. Large windows allow natural light to fill the room, revealing glimpses of the dining area and a staircase adorned with artwork.
Home in Logan Square
4.95 out of 5 average rating, 152 reviews

The Grand Kimball Lodge, Logan Square, Sleeps 14

AlexRating, 5 stars4 weeks ago
Staying at the Grand Kimball Lodge was fantastic! From Bob's proactive communication to his flexibility around check in times, the stay was as seamless as it was memorable. We had a group of 9 and everyone had their own bed, which is rare being so centrally located. The sauna was an excellent bonus, and we'd be happy to come back, thanks again!

Quick stats about vacation rentals in Chicago

  • Total rentals

    11K properties

  • Total number of reviews

    542K reviews

  • Family-friendly rentals

    5.2K properties are a good fit for families

  • Pet-friendly rentals

    3.6K properties allow pets

  • Rentals with a pool

    1.2K properties have a pool

  • Rentals with dedicated workspaces

    6.9K properties have a dedicated workspace

Your guide to Chicago

All About Chicago

Settled along the banks of Lake Michigan, the Windy City of Chicago offers world-class dining, exciting architecture, a top performing arts scene, and plenty of excellent museums. With more than 200 neighborhoods calling this city home, there’s a unique aura found in each.

You’ll find historic mansions and upscale shopping in Gold Coast, Gothic-style university buildings in Hyde Park, cool cocktail bars and quirky shops in hip Logan Square, and incredible comedy clubs in Old Town. Enjoy time outside lounging on the city beaches, catch a baseball game at Wrigley Field, shop along the Magnificent Mile, or sample the celebrated dining scene in this dynamic city, the third-largest metropolis in the United States.


The best time to stay in a vacation rental in Chicago

Chicago’s summers are warm and sunny, which means the rooftops and patios are buzzing, and the days are filled with music and food festivals. This is also when the city's lakeside beaches are at their best, so it’s a popular time for booking Chicago vacation rentals. Fall is chilly but pleasant. Winters are downright cold, and you can expect plenty of snow between the months of December and April, but there’s also plenty of opportunity for ice skating in rinks and snowshoeing and sledding down hills in city parks. There are also wonderful Christmas lights at Navy Pier and throughout the city. Expect relatively cool temperatures and a decent amount of rainfall in spring, and pack your waterproof layers.


Top things to do in Chicago

The Art Institute of Chicago

The Art Institute is one of the best museums in the United States with more than 300,000 permanent artworks and many traveling exhibits. Take shelter from the city’s infamous wind and check out world-famous paintings from French Impressionists and modern American masterpieces. Cafes and restaurants are on-site for coffee breaks and leisurely lunches, and the museum also hosts regular lectures and events.

Willis Tower

The tallest building in the world for almost 25 years, the Willis Tower is a 110-story skyscraper that’s now the second-tallest building in the U.S. For a view that can reach Wisconsin and Michigan on a clear day, visit The Willis Tower observation deck. It’s located on the 103rd floor of the building, and you can even step inside glass observation boxes that extend four feet over the street below.

Millennium Park

Located across from the Art Institute, this city park is one of the most recognizable areas in Chicago thanks to the iconic Cloud Gate sculpture, lovingly known as “The Bean.” Rotating sculpture exhibitions and the naturalistic Lurie Garden make for lovely visits in spring and fall. During the summer months, the park comes alive with outdoor concerts, film screenings, dance performances, and even public yoga classes.

Frequently Asked Questions

  • How is the weather in Chicago?

    Chicago experiences a wide range of weather, from hot summers that can reach 95°F (35°C) to chilly winters that can drop to 20°F (-6°C). The city exhibits four distinct seasons, with beautiful spring blossoms, sunny summers, colorful autumns, and snow-dusted winters, perfect for ice skating in Millennium Park.

  • What are some of the best things to do in Chicago?

    In Chicago, you can explore iconic sights like Navy Pier, Cloud Gate in Millennium Park, and Willis Tower's SkyDeck for breathtaking city views. Cultural enthusiasts can immerse themselves in the Art Institute of Chicago or catch an engaging show at the Second City comedy club.

  • What is the best time of year to visit Chicago?

    Summer, from June to August, is often recommended to visit Chicago. During this season, the city hosts various events, including the Chicago Blues Festival and Taste of Chicago, attracting food and music enthusiasts alike. However, the city is vibrant year-round, with winter activities such as ice skating and holiday markets.

  • What are the best places to stay in Chicago?

    Popular areas to stay in Chicago include the vibrant neighborhoods of River North and Gold Coast for their proximity to dining and shopping. Lincoln Park and Lakeview are also often recommended for their leafy streets, local cafes, and proximity to the lake.

  • What are the best places to visit in Chicago?

    Popular places to visit in Chicago include the culturally rich neighborhoods like Chinatown, Little Italy, and Pilsen. Navy Pier, the Magnificent Mile shopping district, as well as green spaces like Grant Park and Lincoln Park, are also frequently suggested.

  • What are some hiking trails in Chicago?

    While Chicago is an urban city, it still has some scenic hiking trails. The Chicago Lakefront Trail, a 18-mile (29 km) path along Lake Michigan, and the North Branch Trail System in the Forest Preserves of Cook County are popular among outdoor enthusiasts.

  • What are some family activities to do in Chicago?

    Families often enjoy exploring the Shedd Aquarium, the Field Museum of Natural History, and the interactive exhibits at the Chicago Children's Museum. A boat tour along the Chicago River, highlighting the city's architectural marvels, is another frequently suggested activity for families.

  • What are some of the best day trip ideas in Chicago?

    For day trips from Chicago, consider a visit to the Indiana Dunes National Park for some beach fun and hiking, or explore the charming town of Geneva for a relaxed pace with boutique shopping. Rockford, with its Anderson Japanese Gardens and Burpee Museum of Natural History, is also a viable option.

  • How much does it cost to stay in boutique hotel rentals in Chicago?

    Experience the best of Chicago with our boutique hotel rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there boutique hotel rentals with a dedicated workspace in Chicago?

    Yes! Work meets play with ease at over 30 boutique hotel rentals in Chicago featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago