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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 Field155 locals recommend
United Center50 locals recommend
Millennium Park213 locals recommend
Navy Pier271 locals recommend
University of Chicago14 locals recommend

Chicago fishing vacation rentals

Top guest favorite
A light-filled living room features a comfortable beige sofa with an accent pillow and a light throw. Adjacent windows allow natural light to stream in, highlighting the wooden flooring and decorative area rug. A small side table holds a lamp, contributing to the calm atmosphere.
Apartment in Evanston
4.97 out of 5 average rating, 497 reviews

Charming, Sunny Apartment with Backyard Garden

RobertRating, 5 stars6 days ago
Great style, great space, wonderful host. Susan was always responsive, friendly, out-going.
Guest favorite
An inviting living area features a spacious gray couch adorned with blue and white cushions. A modern coffee table with a decorative tray sits on polished hardwood floors, while large windows allow natural light to fill the space, providing views of the surrounding greenery.
Condo in Andersonville
4.89 out of 5 average rating, 203 reviews

The Bright Retreat in Andersonville

JustinRating, 5 stars2 months ago
Alex’s place is perfect for a short stay in a very walkable area of Chicago, with plenty of restaurants and bars to walk to near by! A cozy bed awaits you at the end of the day, and on-site parking is an added bonus!
Top guest favorite
A spacious dining area features a large table surrounded by six chairs. Natural light is provided by two windows with sheer curtains. A unique light fixture hangs above, and a vase with flowers is centered on the table, contributing to the room's welcoming ambiance.
Home in Lake View
4.9 out of 5 average rating, 366 reviews

Private 3rd Floor Apartment

RickRating, 5 stars4 weeks 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.
Top guest favorite
A modern kitchen features sleek gray cabinetry and stainless steel appliances, including a refrigerator and oven. A neutral area rug complements the wood flooring. Natural light is provided by large windows, and stylish wall decor adds a contemporary touch to the space.
Condo in Lake View
4.99 out of 5 average rating, 173 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

MikeRating, 5 stars5 days ago
Great location, walking distance to Wrigley Field, even with a 3 year old. Note there was even a park for our grandson to play in nearby. Spotlessly clean, including the stairwell all the way up to the apartment. Would definitely stay there again!
Top guest favorite
A spacious living area showcases a comfortable L-shaped leather sofa adorned with decorative pillows. A glass coffee table is positioned on an elegant area rug, while framed art pieces decorate the walls. A floor lamp provides soft lighting next to a small side table with a decorative plant.
Townhouse in Ranch Triangle
4.99 out of 5 average rating, 273 reviews

Beautiful Lincoln Park/ De Paul Complimentary Parking Permit

MatthewRating, 5 stars4 days ago
Great spot to stay in Chicago! Perfect location between Wrigley and Downtown so everywhere we wanted to go was easy to get to. Jane was a great host.
Top guest favorite
A well-maintained gray exterior with white trim is presented. Surrounded by a wooden fence, the yard features a grassy area and is shaded by trees. A sunny sky with scattered clouds adds to the inviting ambiance of the outdoor space.
Home in Evanston
5 out of 5 average rating, 103 reviews

Larimer Park Carriage House

KathyRating, 5 stars2 weeks ago
If you are looking for a place to stay in Evanston, this is it! Beautiful, peaceful, and great location! Easy to walk downtown. Parking right at the house. Beautiful park behind the house. Close to the train station. Easy mile walk to the Lake Michigan parks and beaches. The house is beautifully appointed. The decor is just lovely. Comfortable beds and linens. The little touches like super soft towels, hangers in the closets, washer and dryer if needed. We will plan to use this house every time we visit Evanston!
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
Superhost
The image presents a collage of four views. A bright kitchen features modern appliances and yellow tile accents. A cozy living room showcases colorful decor and a Smart TV. A dining area with a small table is visible, along with a games corner displaying the classic Simpsons Arcade machine.
Apartment in Brighton Park
4.89 out of 5 average rating, 112 reviews

Cute 2 BR 10 Minutes to Downtown Chicago Sleeps 6

ParijataRating, 5 stars1 week ago
We had a wonderful stay at Freddy’s place

Dog friendly vacation rentals 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
4.96 out of 5 average rating, 103 reviews

MiniGolfHouse-Chicago Close Warm Indoor Fun!

Vasudeva ReddyRating, 5 stars1 week ago
It was amazing with the kids they enjoyed the mini golf a lot ….spacious bedrooms very good kitchen and cleaned washrooms …overall it was great
Guest favorite
A modern living area features a sectional sofa and two armchairs arranged around a central coffee table. Large windows allow natural light to fill the space, while decorative wall art adds visual interest. A flat-screen TV is positioned opposite the seating area.
Apartment in Melrose Park
4.94 out of 5 average rating, 121 reviews

KNG+QN 2bdrm/1parking space /18 min O’hare/Alstate

RichieRating, 5 stars5 days ago
Absolutely amazing place. It was stocked with so many things that made it feel like a ready home, the most I’ve ever felt at an AirBnB. Diana was a great and responsive host, and it felt like she cared to make it a home away from home.
Guest favorite
A cozy seating area is highlighted by a modern electric fireplace beneath a mounted television displaying streaming options. Soft cushions and a pastel throw blanket add comfort to the light-colored chair. A touch of decor is presented with wall art and a small side table.
Apartment in Oak Park
4.92 out of 5 average rating, 177 reviews

Lovely, spacious 2bd, 1bath home w/free parking

ChristinaRating, 5 stars2 days ago
Tiffany was friendly host and made sure to communicate with us to make our stay enjoyable. The place walkable distance to public transit and the neighborhood was safe enough to walk at night. It was clean and as pictured, there was coffee, utensils, plates, etc if you needed prepare food.
Guest favorite
The living area features a comfortable sofa adorned with colorful cushions, positioned beside a unique wooden coffee table. A striking piece of wall art adds visual interest, while a dining area with modern chairs is visible in the background, complemented by potted plants.
Guest suite in Portage Park
4.94 out of 5 average rating, 419 reviews

Peaceful Portage Park Apartment

KevinRating, 5 stars1 week ago
My family and I enjoyed our stay. We traveled with a one year old and the space felt like a home away from home. Aleksandra was very accommodating to all our needs. I highly recommend this stay.
Guest favorite
An outdoor seating area is presented with comfortable lounge chairs facing a lush green garden. Large glass doors lead into a spacious indoor area, enhancing the flow between indoor and outdoor spaces. Modern architectural lines create a clean and inviting environment.
Apartment in Humboldt Park
4.98 out of 5 average rating, 101 reviews

Luxe Ranch & Spa, Euro Opulence, a 4-Season Oasis

EileenRating, 5 stars2 weeks ago
We had a great time. We stayed for about 3 days got to use the hot tub for some much needed relaxing. The kitchen had a great assortment cooking pans and utensils. There was plenty of blankets for us to feel right at home. Very close to the park and the 606.
Guest favorite
A brick bungalow features a welcoming front porch adorned with a US flag. The porch includes a railing and seating area, while flower pots add greenery. Stairs lead up to the front door, which is detailed with a decorative screen.
Guest suite in Portage Park
4.94 out of 5 average rating, 161 reviews

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

JasmineRating, 5 stars1 week ago
Jamie's place was absolutely adorable—just as pictured and described. The bedrooms were very nice, and the beds were super cozy. The kitchen was fully stocked with all the gadgets you’d need to prepare whatever you'd like, plus a few condiments, which was a nice touch. The bathroom was tidy and well-kept, with fresh, clean towels and linens provided. Jamie was more than welcoming and very accommodating to any requests. Even though she lives below the rental, she was incredibly respectful of our space—warm, friendly, and never intrusive. It truly felt like having my own little apartment. Overall, a wonderful place to stay, and I will definitely be returning.
Guest favorite
A two-story apartment building is shown, featuring a light-colored exterior with dual-tone siding. Lush greenery surrounds the structure, including shrubs and grass. A staircase leads to the entrance, while the nearby homes display varying architectural styles.
Apartment in Forest Park
4.82 out of 5 average rating, 280 reviews

Home in Forest Park downstairs.

KirstenRating, 5 starstoday
the home was beautiful and clean ! i will be returning!! the host responds quickly and very friendly!
Guest favorite
A bright kitchen area features a round table with a red and white checkered tablecloth and four white chairs. A small sink and a gas stove are present, along with a refrigerator. Natural light filters through a window adorned with a red gingham curtain.
Apartment in Berwyn
4.92 out of 5 average rating, 378 reviews

Private apartment with retro vibe

ErickRating, 5 stars6 days ago
Clean and peaceful neighborhood. Parking was not an issue

Family friendly vacation rentals in Chicago

Top guest favorite
A spacious backyard is depicted, featuring a well-maintained lawn framed by lush greenery and trees. A wooden deck attached to the house is visible, along with a fenced perimeter providing privacy. Sunshine illuminates the area, creating a peaceful outdoor space.
Guest suite in Lincoln Square
4.97 out of 5 average rating, 422 reviews

Private suite in Lincoln Square

TaylorRating, 5 stars1 week ago
Great location, nice space, helpful hosts - would stay again!
Guest favorite
A studio space features a spacious bed with a patterned blanket, complemented by a decorative mirror above the headboard. A small seating area with a chair and woven basket is situated beside a window adorned with privacy blinds. The floor is covered with a textured area rug.
Apartment in Near North Side
4.89 out of 5 average rating, 448 reviews

Great Location Studio in the Gold Coast!!

RiddhiRating, 5 stars1 week ago
Booked for an interview . Quiet space and responsive host . Recommend
Top guest favorite
A bright kitchen features orange walls and white cabinetry. A white refrigerator and a black gas stove are positioned alongside a kitchen sink. A small dining table with a checkered tablecloth is set for two. Colorful artwork and a floral curtain enhance the inviting space.
Guest suite in North Center
4.92 out of 5 average rating, 472 reviews

Cozy, Quiet, Garden Getaway!

LeahRating, 5 stars4 days ago
My girlfriend and I came into town from Milwaukee for an action-packed weekend. Having previously lived in a nearby neighborhood, everything came very natural to get around on the CTA. Beth has a very spacious and clean space. Went above and beyond with amenities. Felt right at home. The surrounding neighborhood has so much to do and beautiful scenery to take in. A wonderful space to spend a weekend or any occasion. Highly recommend! Can’t wait to return!
Guest favorite
An open space is divided by sheer curtains, showcasing a king size bed with neutral bedding and a cozy queen size bed in the background. A sectional couch and a dining area with a table are visible, along with a complete kitchen featuring modern appliances.
Loft in Brighton Park
4.91 out of 5 average rating, 274 reviews

Entire place with free parking.

KieraRating, 5 stars2 weeks ago
Was a great place to stay for a quick weekend trip. The area was fairly nice and had some good dining options within walking distance or a short drive. Gina & Jose were always very quick to respond. Would definitely stay here again!
Top guest favorite
A cozy living area is highlighted by a brown sofa adorned with decorative cushions. A warm red throw drapes over the armrest. Visible at the end of the hall is the entrance to the bedroom. Light brown carpeting covers the floor, enhancing the inviting atmosphere.
Apartment in Bridgeport
4.98 out of 5 average rating, 196 reviews

Bridgeport Garden Apartment

AshRating, 5 stars1 month ago
What a wonderful place and wonderful host! Juan made sure all of our questions were answered and that we were taken care of. What a beautiful home in a beautiful city. We will stay here when we come back!
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 Uptown
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
A cozy living area features a plush green sofa adorned with patterned throw pillows. A textured rug covers the floor, while a wooden staircase leads to the lofted sleeping area. Natural light filters through the window, illuminating the space.
Guest suite in Noble Square
4.96 out of 5 average rating, 344 reviews

Secret Garden @ The Noble Farmhouse | Wicker Park

MichelaRating, 5 stars5 days ago
Wonderful place to stay! Photos seriously don’t do it justice, the outdoor area is beautiful.
Superhost
The exterior of a garden unit is visible, featuring a red door framed by large windows. A locking fence surrounds the entrance, with low shrubs and a small area of gravel alongside the pathway. The building's brick facade provides a classic urban feel.
Apartment in Wrigleyville
4.8 out of 5 average rating, 435 reviews

'Secret Garden' Apartment in Wrigleyville

KatieRating, 5 stars1 week ago
This was a great place to stay, it was easy to walk around to a lot of local shops, wrigley field, the L and they were plenty of restaurants within walking distance. This was our first time visiting the Chicago so we were very happy with how close we were to everything . The Airbnb was also a close drive to millennial park and navy pier. The owners were very friendly and gave detailed instructions to how to find the Airbnb and how to park. Would definitely try to book this place again in the future.

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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