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Houses in Chicago

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

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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
A recreational area features a foosball table and a billiards table, complemented by a seating area with dining chairs. Soft lighting from pendant fixtures creates a relaxed atmosphere. A variety of games and books are visible on nearby shelves, inviting guests to enjoy leisure activities.
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 stars4 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
An inviting entryway features exposed brick walls that add texture to the space. Dark stairs lead upwards, flanked by subtle lighting and framed art pieces on the right. A door with horizontal slats is present at the end of the hallway, enhancing the aesthetic.
Apartment in Lake View
4.94 out of 5 average rating, 109 reviews

Costa Lota Near Wrigley Field

ToddRating, 5 stars6 days ago
I absolutely loved this place. It was very comfortable and I appreciated all the little design touches. I loved the seperate entrace from the rest of the building. It was a very Chicago apartment. I felt right at home. The water pressure was great and appreciated having a sound machine in the bedroom. Special shout out to the character drinking glasses. The location was perfect right off Ashland and close to Clark. I would love to stay here again sometime.
Top guest favorite
Apartment in Lincoln Park
5 out of 5 average rating, 264 reviews

Explore Lincoln Park from a Polished Apartment

TomRating, 5 stars4 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
Loft in Brighton Park
4.91 out of 5 average rating, 278 reviews

Entire place with free parking.

JaspreetRating, 5 stars1 week ago
Jose was awesome and the place was perfect! I would 100% stay here again. No concerns for parking, safe area, close to what I needed. Would recommend to anyone considering this place!
Guest favorite
A vintage brick building features an inviting entrance with a maroon awning. The path is framed by well-maintained greenery, leading to dual wooden doors. Large windows are positioned above, allowing natural light to illuminate the space.
Apartment in Logan Square
4.91 out of 5 average rating, 427 reviews

The Grotto of Logan Square

Catherine Ann PorterRating, 5 stars2 weeks ago
Benjamin's place fit my needs exactly: super comfortable bed, clean bathroom, lots of surfaces for keeping stuff organized. Benjamin was super responsive upon check-in which is so helpful. I will definitely be staying there again!
Top guest favorite
Apartment in Magnificent Mile
4.98 out of 5 average rating, 160 reviews

Elegant Suite in Gold Coast

MikeRating, 5 stars1 day ago
A perfect stay! Next time I am in Chicago, this will be my first choice. I "second" all the great things that everyone else has said. I was here for a multi-day conference at a very nearby hotel, and I am so glad I chose here over the host hotel. Wonderful staff, great communication! Top notch in every respect! Thank you!
Superhost
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, 420 reviews

Berwyn Musical Apartment

MadelynRating, 5 stars1 month ago
Had a great experience, Kara the host was extremely kind and responsive with my questions and the place listed was exactly as it looked.Overall had a great stay!

Dog friendly houses in Chicago

Top guest favorite
A collage of the Mini Golf House showcases the vibrant mini golf area, a cozy lounge with arcade games, a comfortable sleeping space, and a living area featuring a large TV. The layout highlights inviting spaces designed for entertainment and relaxation.
Home in Whiting
4.95 out of 5 average rating, 107 reviews

MiniGolfHouse-Chicago Close Beach & Indoor Fun!

BrittneyRating, 5 stars1 day ago
This wasn’t really supposed to be a “fun” trip. I unfortunately had to put my mom into assisted living, but found this Airbnb close to her home. My 2 boys came with me (10 & 13) and if it wasn’t for the fun accommodations in this house, they wouldn’t have had the awesome time they did. It was a fantastic distraction, and the house felt like a home. We loved the updated bathrooms, the modern look and feel, and don’t forget the basement! We spent lots of time down there playing putt putt and arcade games. My son even hooked up his X-Box and played (which he ended up leaving behind on accident, and the host Marc actually drove it to my moms to drop it off - A SAINT!) We will likely be back at least every couple months to check on my mom and will book here from now on!
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
An inviting outdoor patio area features sleek white furniture, including a curved sofa and a coffee table atop a striped rug. A hammock is suspended nearby, surrounded by lush greenery and a wooden fence, with the warm glow of lights illuminating the space.
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
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.
Top guest favorite
A living room features a mid-century velvet sofa in a rich green hue, paired with a tan leather chair. Natural light streams through large windows, illuminating a glass coffee table and a decorative wall with layered wooden frames. The original brick fireplace adds character to the space.
Home in Berwyn
4.99 out of 5 average rating, 146 reviews

Retro Modern Bungalow | fire pit | free parking

JenniferRating, 5 stars1 week ago
This exquisite MCM GEM in Berwyn was the perfect home base for us while visiting Chicago. Every corner is curated with unique and authentic MCM touches, all with the contemporary creature comforts one could want and then some. Everything was sparkling clean and April was a superb host. We hope to come again, & highly recommend!!
Superhost
The front exterior of a single-story ranch home is displayed, featuring a brick facade and a light-colored siding. A two-car garage is present on the right, with a paved driveway leading to the entrance. Lush green grass surrounds the house, under a clear blue sky.
Home in Bolingbrook
4.93 out of 5 average rating, 134 reviews

The Sunshine Spot

AlRating, 5 stars2 weeks ago
House is centrally located . Clean. Host was responsive. 100% recommend this property !
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, 142 reviews

Quiet cul-de-sac with huge fenced in backyard

MeganRating, 5 stars3 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.

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

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