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 Airport13 locals recommend
Wrigley Field152 locals recommend
Boystown18 locals recommend
Logan Square43 locals recommend
United Center48 locals recommend
Millennium Park207 locals recommend

Chicago fishing vacation rentals

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
4.84 out of 5 average rating, 443 reviews

Lakeview Charmer -with parking!

CindyRating, 5 stars2 weeks ago
Excellent host who provided very detailed instructions and local recommendations! Great location close to the El trains, and it was so nice to have a parking spot. So many places within walking distance as well.
Superhost
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
4.83 out of 5 average rating, 179 reviews

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

SkylarRating, 5 stars1 month ago
Craig was extremely nice and accommodating when it came to my birthday weekend. He responds quickly to all questions asked and makes sure we’re comfortable at all times. This home was clean, accurately described, and had the perfect “home feeling”. Overall, when visiting the area I will be booking here again !
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, 115 reviews

Chicago Bootlegger House Sleeps 10-20

AshbyRating, 5 stars1 week ago
Will’s place was perfect for my group of coworkers who traveled in from various cities to stay together. His instructions for check-in and check-out were thorough and helpful. We had plenty of room to spread out but enjoyed being together in the large common areas. We even took advantage of the ample supply of board games one evening while sitting around the fireplace. Given that two of us drove, having a two-car garage for off-street parking was greatly appreciated. The house is immaculately clean and super comfortable. We took advantage of the walkable neighborhood and the nearby restaurants and stores. We all commented on how quiet the house is despite being near major thoroughfares. The well-equipped kitchen inspired one of my coworkers to get up early and cook us a full breakfast. The location allowed for a quick, shared-ride service to the Loop. All of us would highly recommend Will’s place and would be happy to make a return visit. Grateful for a wonderful stay!
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, 168 reviews

Executive Apartment on Lake Michigan with parking

DevinRating, 5 stars1 week ago
me and my fiance stayed just a few days and I didn’t want to leave! The space was even better than expected. Having almost everything you’d need to cook, plenty of towels, clean bedding. It was so clean and beautiful inside and the view from the balcony was gorgeous. Felt just like home. The neighborhood was very nice and peaceful as well. We will 100% be back!
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, 273 reviews

Near Lake Michigan & Wrigley Field

AmandaRating, 5 stars3 days ago
We loved our stay at Brian’s condo. We felt at home right away. There are lots of modern amenities and the location is great.
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, 153 reviews

The Spa of Downtown Whiting

YesyRating, 5 stars3 weeks ago
Thank you for allowing us to enjoy your home. It was a wonderful experience. It is incredible. The place is very cozy. You feel an atmosphere of relaxation and peace.
Top guest favorite
The living room features warm pine walls, offering a cozy atmosphere. A dark, spacious sofa is positioned alongside a wooden coffee table. Two lamps illuminate the space, framed artwork adorns the walls, and potted plants are placed on the windowsill, adding a touch of greenery.
Guest suite in Andersonville
4.98 out of 5 average rating, 126 reviews

Cozy Andersonville Cabin

CydneyRating, 5 stars3 weeks ago
Loved staying here! Super cozy, easy to find, and Matt was always responsive and gracious letting me check in early and check out late. There’s a bathtub, a desk by a window perfect for working, and lots of great books. The hosts even left a complimentary bottle of wine and bag of chips! 10/10

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, 184 reviews

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

GeoffreyRating, 5 stars1 week 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, 268 reviews

Family Friendly 3BR Duplex in Roscoe Village

CaitlinRating, 5 stars2 weeks ago
I travel frequently back to the city and have stayed in a few Airbnb’s in the general area. This was by far my favorite! This space was great for my mini family reunion and was like a home away from home. All of the rooms are comfortable and it is fully equipped with anything you’d need for cooking, hanging out as a group and has plenty of space to yourself. The neighborhood is beautiful, safe, a few minutes walk to Hamlin Park and very close to all public transportation and grocery stores. If you’re traveling here by car, rest assured there is plenty of parking right out in front of the apartment. John was a great host and very responsive. This is a perfect spot for a couple of travelers or a whole family! I would love to return and will highly recommend this space for anyone needed a place to stay while they’re in the city.
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 week 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, 261 reviews

The Nancy’s gorgeous , Spacious Urban Getaway

MaryRating, 5 stars2 weeks ago
Nancy was an amazing host! Always so prompt to reply to our questions, and very thoughtful with all the goodies she left for us to enjoy. Her place was very spacious and clean, great location. It was perfect for a wedding at the Firehouse venue 2 blocks away. We enjoyed our week in Chicago at this convenient location and her thoughtfulness.
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, 169 reviews

Downtown Elegance ✨ Private Yard Parking

JohnRating, 5 stars2 weeks ago
Alex was great at communicating and following up. We had some questions and she was responsive. Also goes beyond expectations on things like forgetting coats :0) - thank you! The location is great. Short walk to a Main Street of bars and restaurants, kid friendly too - happy campers pizza joint was a great reco! Also close to the brown line train station and not too far into town - we walked it with children and it was fine. House is really large, spacious. I know some have mentioned about hearing the train, but that is part of city living, it was more than fine. Enjoyed the stay, would recommend it and would go back again if visiting Chicago. Thanks Alex!
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, 182 reviews

Large sunny 3BR apt. in downtown Oak Park

CraigRating, 5 stars1 month ago
This was a beautiful place! it had everything we needed. Oak Park downtown is walkable and has everything you could want. It is an upstairs unit so be prepared for some steps. Parking was easy. Michelle was great! Downtown Chicago is only 15m (if there's no traffic.). We would definitely come back!
Top guest favorite
A sunlit living area features large windows framed by wooden accents, allowing natural light to illuminate the space. A comfortable futon is positioned alongside an armchair and a glass coffee table on a textured rug, with a small television and simple wooden furniture completing the layout.
Apartment in Logan Square
4.95 out of 5 average rating, 511 reviews

2nd floor of 1908 brick two-flat in Logan Square

KateRating, 5 stars5 days ago
Extremely clean and centrally located in Logan Square neighborhood. We drove into the city, but found parking in a street nearby. The apartment was also very close to blue line stops. Would recommend and hope to stay again!
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, 211 reviews

Cozy Northside Apt near Transp&Beach&Free St Prkng

ElijahRating, 5 stars1 month ago
Holly and Mark are great hosts. Very responsive and went above and beyond to offer additional help and recommendations for travel, food, etc during our stay.

Apartment rentals in Chicago

Guest favorite
A cozy living area features a modern black sectional sofa adorned with colorful throw pillows. A large photograph of a city skyline hangs on the wall. A small coffee table rests on a patterned rug, while a desk and chair are positioned beside a plant and shelves.
Apartment in Avondale
4.97 out of 5 average rating, 107 reviews

Lovely 2bedroom 1bath Apt and outdoor seating.

DarenRating, 5 stars1 week ago
A very nice and welcoming place to stay!
Superhost
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
4.82 out of 5 average rating, 185 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 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, 214 reviews

Chicago Airbnb Newly Remodeled 2-Unit Apartment!

SreejithRating, 5 stars1 day ago
Neat, clean, great location! Heads up for anyone parking: there's a Thursday morning parking restriction. Learned that the hard way with a fine.
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, 147 reviews

Inviting 2 Bedroom Apartment in Roscoe Village

ChadRating, 5 stars3 days ago
Great place! Loved the area. Plenty of things to do within walking distance, would definitely recommend. Place is very clean, and even though there’s another unit above I barely heard any noise.
Guest favorite
An open living area features a dark leather sofa and a small wooden table atop a vibrant area rug. Natural light floods through two tall windows, framed by wooden shutters. A decorative fireplace is situated to one side, adding to the room's charm.
Apartment in Lincoln Park
4.93 out of 5 average rating, 505 reviews

Victorian Home in Old Town

AlexRating, 5 stars5 months ago
I really enjoyed my stay! I loved the art and decor of the space. I am a solo traveler and I felt safe being here. There are written instructions on the door and in the home that explain almost everything I needed. I felt safe in the neighborhood! I would get back late and felt safe doing so. There are multiple stores within walking distance so it was easy to grab food or any items I may have needed. I didn't have a car and found it very easy to get to everywhere I wanted to go. Shampoo/Conditioner/Body Wash was a pleasant surprise to have! Along with the teas and coffee items. The space was a great size and I had everything I needed. It was easy to come and go and check in was very easy. I would stay here again, Lynn was super responsive, helpful, and kind! The bedroom area doesn't get much light, but it wasn't an issue for me. Bed was comfy, home was beautiful, and I loved my stay. Thank you so much Lynn!
Guest favorite
An open concept living space is displayed, featuring a modern kitchen with white cabinets and stainless steel appliances. A dining table with four chairs is situated next to the kitchen island, while a comfortable seating area with a sofa and Smart TV is seen in the background.
Apartment in Logan Square
4.83 out of 5 average rating, 264 reviews

BERNARD CHATEAU - LOGAN SQUARE

KimRating, 5 stars1 week ago
Perfect weekend stay for our girls trip. Place was small but beautiful. Quiet neighborhood. Close enough to both downtown and Wrigley!
Guest favorite
The open-concept living space features natural light streaming through skylights and a mix of wooden accents and plants. A comfortable green sofa and a chair are positioned along the walls, while a sliding barn door leads to the adjacent bedroom area.
Apartment in Avondale
4.9 out of 5 average rating, 104 reviews

Avondale Cozy 1 Bedroom Attic Apartment 4th FL

CatherineRating, 5 stars1 month ago
Great place, beautiful attic and great amenities from host!
Guest favorite
A modern dining area is presented, featuring a white rectangular table surrounded by six chairs. A decorative centerpiece sits on the table. The open layout connects to a bright living space with a couch and shelving in the background, enhancing the inviting feel of the apartment.
Apartment in Humboldt Park
4.83 out of 5 average rating, 114 reviews

Spaulding Oasis on 4 lots In Humboldt Park!

DariusRating, 5 stars2 weeks ago
Happy with my stay

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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