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Vacation rentals in Chicago

Book unique homes, vacation rentals, and more on Airbnb

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Popular amenities for Chicago vacation rentals

Stay near Chicago's top sights

O'Hare International Airport13 locals recommend
Wrigley Field152 locals recommend
United Center48 locals recommend
Millennium Park207 locals recommend
Navy Pier261 locals recommend
University of Chicago14 locals recommend

Chicago fishing vacation rentals

Guest favorite
An inviting dining area features a simple wooden table accompanied by two benches and a chair. A cozy seating arrangement includes a sofa and coffee table, framed by large windows dressed in light curtains. A ceiling fan and decorative accents add to the space.
Apartment in Lincoln Park
4.72 out of 5 average rating, 119 reviews

The Biddle House (#1)

RyanRating, 5 stars2 weeks ago
great spot, close to a brown line stop but not close enough to hear the train, clean, easy to check in, would stay there again.
Guest favorite
An inviting living area showcases a light-colored sectional sofa paired with a matching ottoman. A dark coffee table sits nearby, and a warm area rug lies underfoot. A bookshelf filled with books lines the wall, while soft lighting highlights the natural warmth of the wood flooring.
Home in Lake View
4.93 out of 5 average rating, 153 reviews

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA

JulietRating, 5 stars7 months ago
Lovely place in a good location.
Guest favorite
A cozy living area is highlighted by a red accent wall and brick details. A comfortable blue sofa faces a mounted television, with a striped chair nearby. A mirror and decorative plant are positioned against a stylish cabinet, complementing the space's inviting layout.
Apartment in Lake View
4.83 out of 5 average rating, 450 reviews

Lakeview Charmer -with parking!

KimberlyRating, 5 stars2 weeks ago
Nice location and comfortable for 4 people. Little difficult to get in from the parking space. Keypad only worked part of the time. Great to have an included parking space! Overall a nice short stay.
Guest favorite
A welcoming living space features a round dining table surrounded by four chairs, with a large artwork depicting trees on the wall. A light fixture hangs from the ceiling, and a mirror reflects the room. Natural light fills the area, enhancing the warm ambiance.
Apartment in Evanston
4.82 out of 5 average rating, 181 reviews

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private

NicholasRating, 5 stars4 weeks ago
The living room was very comfortable and provided a great space for all our group to hangout after a wedding. The extra bedding and coffee was a nice plus!
Top guest favorite
A cozy living room features a warm fireplace with a flat-screen TV mounted above. Comfortable leather chairs and a plush sofa surround a coffee table, while large windows allow natural light to fill the space. Potted plants add a touch of greenery.
Bungalow in Lake View
4.95 out of 5 average rating, 118 reviews

Chicago Bootlegger House Sleeps 10-20

ChrisRating, 5 stars3 weeks ago
We rented Will's place for a joint bachelor/bachelorette party. It was the perfect place - beautiful vintage decor, extremely spacious with ample bed spots, great amenities including a private outdoor deck with a grill, and well situated along the lake for spring activities. We highly recommend it!
Superhost
An outdoor terrace is visible, featuring seating arrangements with two orange chairs and a fire pit. The view overlooks Lake Michigan, with the calming waves in the background. A pathway leads down to the water, surrounded by the building's architecture.
Apartment in East Rogers Park
4.9 out of 5 average rating, 173 reviews

Executive Apartment on Lake Michigan with parking

FrankRating, 5 stars1 week ago
No problem except for us French to find out how the cooking utensils work and in particular the hood, a manual would be good, too bad for the bad weather the exteriors would have deserved to be used but the weather is not part of the package
Guest favorite
A spacious spa room features a modern two-person jacuzzi, surrounded by elegant marble walls. The jacuzzi is designed with a clear accent panel, and amenities such as towels are neatly arranged nearby, promoting a calming and relaxing environment.
Home in Whiting
4.85 out of 5 average rating, 155 reviews

The Spa of Downtown Whiting

MelanieRating, 5 stars1 week ago
Had a great 2 night stay. Everything was clean and exactly as pictures and described. Very cute decor/theme. The layout was great for us, family with older teens. Lots of space and TVs. Great restaurants and some shopping within walking distance. Really good value. Walk to the beach and trails. We were in town for a nearby event and really enjoyed the area this place was in. Host was very responsive and answered questions beforehand. We had no issues with our stay at all and would absolutely recommend.
Guest favorite
A modern living area features a gray sectional sofa adorned with colorful cushions. A glass coffee table is positioned on a striped area rug, complemented by a round pouf. Natural light enters through large windows, while an air conditioning unit is visible.
Apartment in Edgewater
4.86 out of 5 average rating, 123 reviews

minimal lakefront apartment

MarcusRating, 5 stars2 weeks ago
I've stayed at many Airbnbs, and this is among the best. Kenan describes it as minimal, but it has everything you need. I've rarely stayed somewhere where I didn't at least have to provide my own of something, and I appreciate Kenan for his attention to the basic needs we all have when traveling. I used to live in this neighborhood, and it was great to be right back. If you're a tourist wondering if you should stay so far from downtown, you're better off experiencing real Chicago from a real (and awesome) neighborhood next to a beach and steps from the express bus to downtown.

Pet-friendly vacation rentals in Chicago

Guest favorite
An open-concept dining and kitchen area is featured, with a long wooden table accompanied by several chairs. A spacious kitchen island with seating sits nearby, and a warm wooden floor enhances the inviting space. Natural light fills the room, highlighting the exposed brick wall.
Home in Lincoln Park
4.94 out of 5 average rating, 125 reviews

Spacious Full Home Near the Heart of Wrigleyville

JessicaRating, 5 stars2 months ago
We had an amazing stay at Dustin’s place! We had a group of 9 ladies who fit perfectly with plenty of cozy beds and linens. The location was very walkable and we felt safe. We walked over to Barcocina Lakeview on Friday, and then jumped on the train to River North on Saturday to celebrate St. Patrick’s Day. We had a couple of questions during our visit, and Dustin was speedy on the replies! Everyone in the group said the experience was 10 out of 10. We hope to visit again.
Guest favorite
A modern kitchen features sleek gray cabinetry and a spacious countertop. Stainless steel appliances, including a refrigerator and microwave, are visible. Natural light enters through a window above the sink, where a small flower arrangement is placed. The wood-inspired flooring complements the contemporary design.
Apartment in Joliet
4.95 out of 5 average rating, 208 reviews

*The Belltower Haven*Large*Family Friendly*Wi-Fi

ShivaniRating, 5 stars1 week ago
James was great and so was the airbnb, think very highly of him and his air bnb.
Guest favorite
A spacious living room features large windows allowing natural light to fill the space. A comfortable light-colored sectional sofa is situated in front of a glass coffee table, with a medium-sized rug underneath. A wooden side table and a television mounted on the wall are also visible.
Apartment in West Lake View
4.95 out of 5 average rating, 184 reviews

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

DominicRating, 5 stars3 days ago
We loved this spot! Lots to do easy easy parking, and a first floor apt. Would most certainly stay here again!!
Guest favorite
The living room features a high ceiling and a stone fireplace, with large windows allowing natural light to fill the space. Two brown leather sofas and a wooden coffee table create a cozy sitting area. The outdoor space is accessible through double doors.
Townhouse in Old Town
4.85 out of 5 average rating, 171 reviews

Downtown Elegance ✨ Private Yard Parking

SachaRating, 5 stars3 weeks ago
We were a party of 8 humans and 2 dogs, staying for the weekend. Our family had plenty of space, and the outdoor patio was a nice bonus. The kitchen was well-equipped with coffee and tea, nice new appliances, lots of dishes and utensils (we did not need a melon baller, but she had one in case we needed it!). We found it really easy to get to the L, and also convenient for walking. It was such a relief to park once and not have to drive at all. The street was nice and quiet (I mean, there were trains, because Chicago ☺️). It felt very safe, so we were comfortable taking the dogs on walks anytime. Alexandra communicated with me really well leading up to our stay, and stayed in touch throughout. We made a lot of memories, and the lovely accommodations were part of that.
Top guest favorite
Condo in Logan Square
4.92 out of 5 average rating, 346 reviews

Susie's Space. 2BR easy parking & pet friendly

MatthewRating, 5 stars1 week ago
Really liked it, nice location, plenty of room, comfortable, good kitchen. Getting around using buses and the subway was also very easy.
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, 123 reviews

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

MichaelRating, 5 stars2 days ago
Great place! Liz was really nice. I had trouble getting into the home. Liz called me, reset lock remotely and helped me get in. The house was pristine, and really cozy. We had a great time and highly recommend this to anyone interested.
Superhost
An outdoor view features a large sliding glass door leading to a spa house. A well-maintained lawn borders the entrance, complemented by decorative greenery and a stylish outdoor seating area. The serene ambiance is enhanced by the clear sky and soft lighting.
Apartment in Logan Square
4.88 out of 5 average rating, 100 reviews

Luxe Suite + Spa House! Key West Vibes 4-Seasons

CaraRating, 5 stars3 weeks ago
The place is just as described and Matt was very nice! Has a really cute dog. The hot tub was really nice. Close drive to attractions
Superhost
A charming residential street is lined with historic brick buildings, showcasing architectural details such as rounded bay windows and decorative cornices. Lush trees provide shade along the sidewalk, with parked cars and softly glowing street lamps contributing to a serene atmosphere in the early evening light.
Townhouse in Lake View
4.84 out of 5 average rating, 118 reviews

Wrigleyville townhome two blocks from ballpark

ElizabethRating, 5 stars1 week ago
We were in town for a concert at Wrigley and this could not have been more perfect for our weekend in Chicago! The neighborhood was so cute and super walkable to Wrigley and other fun spots. The house was fantastic - my daughter is a photographer and was geeking out at all of the art and collectables. Highly recommend :)

Family friendly vacation rentals in Chicago

Guest favorite
A spacious living area features a large blue sectional sofa surrounding a glass coffee table. A small blue armchair adds extra seating, while a television is positioned against the wall. Natural light is visible through the doorways leading to other rooms.
Apartment in Lake View
4.9 out of 5 average rating, 186 reviews

Clean, spacious, walk to Wrigley! Self check-in!

GeoffreyRating, 5 stars1 month ago
Amy's place is located in a perfect spot if you want to take in a game at Wrigley and spend some time in the Loop. Sensational neighborhood--safe, beautiful, convenient, etc. It's everything we needed. Thank you, Amy!
Superhost
A cozy living area features a large brown leather sectional sofa and two patterned armchairs, arranged around a circular glass-topped coffee table. Soft light filters through sheer curtains, illuminating the warm brown walls and wooden floor, creating a comfortable space for relaxation.
Apartment in North Center
4.85 out of 5 average rating, 273 reviews

Family Friendly 3BR Duplex in Roscoe Village

YoungRating, 5 stars2 weeks ago
Very nice place. Pleasant stay. Nice and quiet neighborhood with easy street parking. The only concern was that the fan in the downstairs bathroom was quite noisy, and it would be great if this can be fixed. We loved the place.
Guest favorite
A spacious living room features large windows draped with light curtains, allowing natural light to fill the space. A comfortable sofa and loveseat are positioned around a decorative area rug, with a television mounted on a cabinet. A rocking chair adds additional seating.
Apartment in Evanston
4.94 out of 5 average rating, 141 reviews

Vintage sunlit 2.5 BR apt. Perfect for families!

TomRating, 5 stars1 month ago
I enjoyed my stay at Letitia's place. I was traveling between the city and northern burbs, and Letitia's place provided a nice centralized location with easy access to both. Letitia's place is clean, charming, and comfortable. Letitia responded quickly to any questions. I recommend this as a comfortable place to explore the greater Chicagoland area.
Guest favorite
The living room features a comfortable seating arrangement, including a dark couch and a lounge chair. Large windows allow natural light to fill the space, while a television is positioned on a media console. A ceiling fan adds to the room's functionality.
Townhouse in Edgewater
4.95 out of 5 average rating, 263 reviews

The Nancy’s gorgeous , Spacious Urban Getaway

stephanieRating, 5 stars3 weeks ago
Very easy experience- host prepared a celebration for us as well. Small touches were appreciated!
Guest favorite
A living area features a cozy orange sofa and two gray armchairs set around a round coffee table. Natural light enters through large windows dressed in floral curtains, while a colorful area rug adds warmth to the space.
Apartment in Oak Park
4.92 out of 5 average rating, 185 reviews

Large sunny 3BR apt. in downtown Oak Park

AlexanderRating, 5 stars4 weeks ago
This is a great Airbnb - really clean and very pleasantly and thoughtfully furnished. In a world of Airbnbs out of an IKEA catalogue this stood out. It’s a really nice space to spend time in, with a large and sunny living/dining area. Michelle was also extremely responsive and friendly.
Guest favorite
A living room features warm yellow walls and hardwood flooring. A cozy sofa faces a decorative fireplace set into a red brick mantle. Two chairs and a small table are positioned near a large window dressed with light curtains, allowing natural light to fill the space.
Apartment in Lake View
4.94 out of 5 average rating, 118 reviews

The Wrigley Flats | Chicago Vacation Rental

SeanRating, 5 stars1 day ago
Great location. Several eating options are in the area and the neighborhood feels very safe. Would stay again!
Guest favorite
A well-maintained garden unit is framed by a neatly arranged wooden fence. A covered porch with wooden railings offers a welcoming entryway. Snow blankets the small garden at the front, and the surrounding buildings display a mix of brick and stone facades.
Apartment in Lake View
4.93 out of 5 average rating, 209 reviews

Charming Apt. near Wrigley/Cubs, Ravenswood/Uptown

Erica Rating, 5 stars1 week ago
We really enjoyed our stay at this cozy garden unit apartment. It was very comfortable, spacious, and clean, with anything you need from extra blankets and pillows to white noise machines and fully furnished kitchen. The hosts were very kind and accommodating, allowing us to check in early and leave our luggage after check out. The area was also great, very safe and walkable, and a cute neighborhood that makes you feel like a local. Highly recommend this place if you’re ever in Chicago for an event at Wrigley Field!
Guest favorite
The living room features a cozy sofa adorned with decorative pillows and a vibrant red lounge chair. A television sits on a stand near a window with natural light. Artwork is displayed on the walls, and a small lamp adds soft illumination.
Apartment in East Rogers Park
4.84 out of 5 average rating, 212 reviews

Cozy Northside Apt near Transp&Beach&Free St Prkng

AnneRating, 5 stars5 days ago
Holly & Mark are the best hosts I’ve ever had. They went above & beyond to make me feel welcome & at home. I’ve loved sharing treats & conversations with both of them! The apartment is cozy & exactly as pictured. I love the assortment of artwork, & the roof deck is a joy in the morning. The neighborhood is lovely, with plenty of delicious food options, & close to Evanston, which was perfect for my needs.

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.

  • What types of vacation rentals are available in Chicago?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Chicago. From over 6,420 apartment rentals, over 1,060 condo rentals to over 2,010 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

  • Are there vacation rentals with a dedicated workspace in Chicago?

    Yes! Work meets play with ease at over 6,880 vacation rentals in Chicago featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

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