Vacation rentals in Chicago

Book unique homes, vacation rentals, and more on Airbnb

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Stay near Chicago's top sights

O'Hare International Airport122 locals recommend
Wrigley Field1,004 locals recommend
Boystown92 locals recommend
Logan Square174 locals recommend
United Center200 locals recommend
Millennium Park1,243 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, 487 reviews

Charming, Sunny Apartment with Backyard Garden

LauraRating, 5 stars1 day ago
Susan’s place was amazing! It was clean, inviting, and full of natural light. You had everything you would need for a comfortable stay. Not only was the inside gorgeous, her yard was beautiful too. We will definitely stay here again when in the Chicago area!!!
Top 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 stars6 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, 441 reviews

Lakeview Charmer -with parking!

LisaRating, 5 stars2 weeks ago
Great location! Felt safe and easy to get around. Close to the Vic Theater and the El. The space was very comfortable for 3 of us. Once we figured out the codes/keys, it was easy enough. I would definitely stay again. Cathy is super easy to talk to and very responsive. Thank you, Cathy!
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, 111 reviews

Chicago Bootlegger House Sleeps 10-20

ElisaRating, 5 stars2 days ago
Will’s place was perfect for our stay in Chicago! I brought a group of friends out for my 30th birthday, and there was ample room for all 11 of us. The place was extremely clean and in a perfect location. Would definitely stay there again.
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
4.89 out of 5 average rating, 166 reviews

Executive Apartment on Lake Michigan with parking

DebraRating, 5 stars1 month ago
This was a beautiful place with an excellent view of Lake Michigan. Both rooms had comfortable beds and setup with everything you need. Kitchen is well stocked, but we mostly ordered Grub Hub, lol. Loved spending time here and great place to hangout and chat with friends. It is right on the water and we really enjoyed watching the waves crash against the barrier. It is on the 2nd floor, but the stairs are not bad at all. Felt very safe and having the parking space is a great perk. Very commutative and checked in with us to make sure everything was fine. Would definitely stay here again!
Superhost
A rustic kitchen and dining area features wooden cabinets and a large island with stainless steel appliances. A dining table with six wooden chairs is illuminated by natural light from the large windows. Exposed brick walls add character to the space.
Loft in Lake View
4.89 out of 5 average rating, 794 reviews

2bd/2bath Urban Loft w/ 2 pkg spots 1 blk to train

BennieRating, 5 stars2 days ago
Jay's place was perfect for the Chicago experience we were looking for! The location was walkable to any grocery needs, easy access to transportation and the area had great restaurants and bars that were in walking distance, not to mention an easy walk to Wrigley Field! I would recommend this to anyone!
Top guest favorite
A spacious living area is presented, featuring a large gray sectional sofa. Natural light enters through expansive windows, illuminating the room. A fireplace and a mounted television are visible on the wall, with plants enhancing the decor around the space.
Condo in Uptown
4.98 out of 5 average rating, 269 reviews

Near Lake Michigan & Wrigley Field

RjayRating, 5 stars4 days ago
Brian’s place was great! Had everything I needed for my stay. The location and neighborhood were great too. Seeing that this was my first time somewhere they required street parking, it was tricky for me to get the hang of at first but Brian was very helpful with that. Overall I will be back Chicago again and if this listing is available I will stay here again!
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
4.84 out of 5 average rating, 152 reviews

The Spa of Downtown Whiting

SantiagoRating, 5 stars1 day ago
a really awesome place. I highly recommend this place.

Apartment rentals in Chicago

Guest favorite
A modern living space features a dark sofa adorned with colorful cushions. A round coffee table sits in front, accompanied by a small side table with a decorative vase. A large mirror reflects the cozy atmosphere, while a vibrant city skyline artwork adds visual interest to the wall.
Apartment in Avondale
4.97 out of 5 average rating, 106 reviews

Lovely 2bedroom 1bath Apt and outdoor seating.

JillRating, 5 stars1 month ago
Good location and had everything we needed. Handy to have nearby stores within walking distance. Great place and would definitely stay again.
Guest favorite
A modern living area features a beige sectional sofa and a round coffee table set on a patterned rug. A large flat-screen TV is mounted on the wall, and a potted plant adds a touch of greenery. Natural light illuminates the space.
Apartment in Chinatown
4.83 out of 5 average rating, 184 reviews

New apartment

Gary QilieunRating, 5 stars5 months ago
Loved the walkability and great access to transit and chinatown restaurants. amazing stay! thank you!
Guest favorite
A small entryway is illuminated by soft natural light filtering through a lace curtain. A vase of white roses sits atop a white table, with a radiator located below it. Beige walls with a minimalist aesthetic offer a warm welcome.
Apartment in East Rogers Park
4.84 out of 5 average rating, 386 reviews

Cozy Garden Unit In Edgewater

BriannaRating, 5 stars1 week ago
The garden apartment is exactly as described and is a wonderful home away from home while visiting Chicago. Edgewater is a great neighborhood with access to diverse restaurants, several grocery stores, train stops, and the lake shore. I felt right at home upon arrival.
Superhost
The kitchen includes modern appliances, white cabinetry, and a tiled floor. A view into the adjoining living area reveals a comfortable seating arrangement. Natural light enters through a nearby window, enhancing the functional kitchen space.
Apartment in Avondale
4.86 out of 5 average rating, 541 reviews

Logan Square Lookout

BrendaRating, 5 stars2 weeks ago
Clean and cozy place to stay at while visiting Chicago for the first time! Close to the L station which was very convenient. Great local restaurants nearby and an easily walkable neighborhood. Would love to stay here again if I plan on coming back!
Guest favorite
A spacious living area is furnished with a dark sectional sofa, accented by decorative pillows. A round coffee table rests on an area rug, while a television is placed on a dark wooden stand. Natural light filters through large windows with sheer curtains.
Apartment in Chicago
4.98 out of 5 average rating, 210 reviews

Chicago Airbnb Newly Remodeled 2-Unit Apartment!

David AaronRating, 5 stars2 days ago
Very nice, clean, and spacious. Easy to get around Chicago from this location either via Interstate or through neighborhoods.
Top guest favorite
A bright living room is highlighted by large windows that invite natural light. A comfortable brown leather sofa and a beige loveseat are positioned around a colorful area rug. A wooden coffee table and a wall-mounted TV complement the inviting space.
Apartment in Roscoe Village
4.97 out of 5 average rating, 145 reviews

Inviting 2 Bedroom Apartment in Roscoe Village

GaryRating, 5 stars1 week ago
We really enjoyed our stay! We really like Roscoe Village and this apartment was perfectly located. Close to shops, coffee and restaurants. The check in process was easy and the apartment was well appointed with everything we needed. Parking was very easy as well. This was a great find for us and we will plan to visit again!
Guest favorite
A modern living area features a light-colored sofa adorned with decorative pillows. A small coffee table sits at the center, complemented by a decorative globe and a plant. Two windows allow natural light, while a mirror and dining area are visible in the background.
Apartment in Logan Square
4.83 out of 5 average rating, 262 reviews

BERNARD CHATEAU - LOGAN SQUARE

HyunjinRating, 5 stars1 day ago
it was my first Airbnb experience and it was very pleasant. The location is perfect to get to the place, but perfectly peaceful in the night.
Guest favorite
A cozy living area features a green sectional sofa adorned with yellow accent pillows. A wooden coffee table sits in the center, complemented by a light grey armchair. Natural light streams in through a skylight, highlighting the rich brown flooring.
Apartment in Avondale
4.91 out of 5 average rating, 102 reviews

Avondale Cozy 1 Bedroom Attic Apartment 4th FL

MarionRating, 5 stars1 month ago
It was a great apartment! The bed was so comfy I couldn’t quite believe how well I slept for two weeks. Very calm neighbor. My biggest worry was the heat because it was winter and it was not a problem at all. Good hot water, and the place was easy to warm up or cool down as needed. Really, it was a great stay. Thank you!

Homes in Chicago

Guest favorite
The exterior of the bungalow features a modern white facade with large windows, allowing for natural light. A covered porch is visible, offering shaded seating space. Surrounding trees cast gentle shadows on the ground, enhancing the tranquility of the setting.
Home in Homewood
4.89 out of 5 average rating, 18 reviews

Dream Stay - Modern Bungalow Near Downtown

MarcRating, 5 stars1 month ago
Urania’s place was in a great neighborhood, which was quiet and the people I encountered were friendly. The house itself was well maintained on the outside and inside, and the couch and chairs were comfortable,along with the beds. Everything was spotless and clean, and we loved the space upstairs and downstairs. Urania responded quickly when I couldn’t figure out how to lock the outside door, and she talked me through it. We all throughly enjoyed our stay, and had no complaints whatsoever. I would highly recommend Urania’s home if you’re coming to the Chicagoland area, and I will definitely stay there again on any return trips to Chicago or the surrounding areas!
Guest favorite
A cozy living room features a brick fireplace as a focal point, surrounded by comfortable leather seating arranged for relaxation. Light-colored curtains frame large windows, while a plush area rug adds warmth to the wooden floor. A wooden door and wall decor complement the inviting space.
Home in Glen Ellyn
4.92 out of 5 average rating, 147 reviews

Home in Glen Ellyn

KellyRating, 5 stars1 week ago
We enjoyed our night here. It provided a calm place to rest and plenty of space. Host was wonderful to work with.
Superhost
The image presents a two-story home with framed cedar bevel siding. A welcoming front porch features wooden railings and steps leading to the entrance. Surrounding greenery adds a natural touch, while the well-maintained pathway and lawn contribute to the property’s inviting exterior.
Home in Blue Island
4.81 out of 5 average rating, 193 reviews

Warm and comfortable inviting Suburban home !

MarcusRating, 5 stars1 day ago
Always a pleasure staying with at Rich’s place
Superhost
A comfortably arranged living room features a gray sofa with multiple cushions and two teal accent chairs. Natural light enters through large windows dressed in light curtains, while a wooden floor adds warmth to the space. A flat-screen TV is mounted on the white wall.
Home in Markham
4.73 out of 5 average rating, 124 reviews

The Country Life! Entire House.

DeniseRating, 5 stars1 month ago
Cathy was a great host, very responsive! House was great, it accommodated our family size perfect. The only thing in my opinion that was missing was washer and dryer access in the home. We were traveling with toddlers and couldn’t wash a load of clothes. But aside from that everything else was great.
Superhost
The living area features a modern gray sofa with yellow and gold accent pillows, complemented by two blue armchairs. A low white coffee table sits atop a patterned black and white rug. Natural light enters through large windows, illuminating a wall-mounted TV and a decorative plant.
Home in Homewood
4.71 out of 5 average rating, 42 reviews

Horizon - 4 BRs, 2 BA Game Room & Gym

NicoleRating, 5 stars1 week ago
Blaine was a gracious host, excellent response time and very accommodating! The place was clean and comfortable and we thoroughly enjoyed our stay! The home is located on a busy street, so parking and ease of access was challenging but workable. Also, the space was considerably smaller than expected from the photos. Overall, we had no complaints!
Top guest favorite
The inviting entryway features sleek, modern details, including a stylish wooden door with glass panels. Two shiny, rounded chairs are positioned beside a small, artistic table, while a vibrant sofa and contemporary fireplace are visible in the background. Large windows allow natural light to fill the space.
Home in Portage Park
4.97 out of 5 average rating, 111 reviews

Ultra Modern, 2800 SQ Ft, Outdoor Gazebo Sleeps 14

AlisonRating, 5 stars2 days ago
this spot was great! We had plenty of sleeping space for everyone and it was a good central location to get all over the city.
Superhost
A charming house features a sloping roof and a light-colored exterior, complemented by a welcoming front porch. Outdoor seating is arranged on a spacious deck, surrounded by a wooden railing. Warm lights are strung overhead, creating an inviting atmosphere in the surrounding grassy area.
Home in Des Plaines
4.85 out of 5 average rating, 100 reviews

Cozy Home by O'Hare + EV Plug

ShitakiaRating, 5 stars1 week ago
This Was A Beautiful Home With A Game Room In The Basement I’ll Love To Visit Again !
Guest favorite
The charming exterior of a two-story brick home features a welcoming front porch with a green door and large windows framed by black shutters. Lush greenery and seasonal decorations, including a pumpkin, enhance the inviting curb appeal.
Home in Munster
4.92 out of 5 average rating, 103 reviews

Cozy House with Gazebo

HannahRating, 5 stars7 months ago
Sarah was a great host and had such a cute little home. She was very quick to respond and the place was nice and clean. Perfect for a group of 4. The neighborhood was also nice and many restaurants nearby.

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 2,010 house rentals, over 1,060 condo rentals to over 6,420 apartment 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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