
Vacation rentals in Chicago
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Top-rated vacation rentals in Chicago
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Popular amenities for Chicago vacation rentals
Chicago fishing vacation rentals

Charming, Sunny Apartment with Backyard Garden
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!!!

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA
Lovely place in a good location.

Lakeview Charmer -with parking!
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!

Chicago Bootlegger House Sleeps 10-20
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.

Executive Apartment on Lake Michigan with parking
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!

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

Near Lake Michigan & Wrigley Field
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!

The Spa of Downtown Whiting
a really awesome place. I highly recommend this place.
Apartment rentals in Chicago

Lovely 2bedroom 1bath Apt and outdoor seating.
Good location and had everything we needed. Handy to have nearby stores within walking distance. Great place and would definitely stay again.

New apartment
Loved the walkability and great access to transit and chinatown restaurants. amazing stay! thank you!

Cozy Garden Unit In Edgewater
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.

Logan Square Lookout
This was a great location, peaceful and quaint! Would definitely recommend this to friends who travel to Chicago and want to stay in the city!!! I felt right at home which is what i am looking for!

Chicago Airbnb Newly Remodeled 2-Unit Apartment!
Very nice, clean, and spacious. Easy to get around Chicago from this location either via Interstate or through neighborhoods.

Inviting 2 Bedroom Apartment in Roscoe Village
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!

BERNARD CHATEAU - LOGAN SQUARE
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.

Charming one bedroom apartment
While visiting Evanston for a family celebration in Evanston, we enjoyed Donald’s comfortable, clean, and quiet apartment. It was well-equipped for our needs and was convenient for walking to various stores, such as Target and Whole Foods, as well as local eateries and bakeries. Donald is an attentive host and communicates well by text.
Homes in Chicago

Dream Stay - Modern Bungalow Near Downtown
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!

Warm and comfortable inviting Suburban home !
Always a pleasure staying with at Rich’s place

The Country Life! Entire House.
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.

Horizon - 4 BRs, 2 BA Game Room & Gym
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!

5BR/4BA Home - Theatre, Hot Tub, Sauna, Rooftop!
This house was so beautiful and hosted my friends and I for my birthday. It was everything I hoped for!

Cozy Home by O'Hare + EV Plug
This Was A Beautiful Home With A Game Room In The Basement I’ll Love To Visit Again !

Cozy House with Gazebo
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.

A serene haven perfect for the whole family!
Her place is very nice. It’s so cozy and cute. She supplies everything you need even though I came with what I needed. She is very accommodating. I love a cozy at home feeling. Very clean as well. Thank you I definitely will be booking again.
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.
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Humboldt Park
- Six Flags Great America
- Museum of Science and Industry
- Chicago History Museum
- Lincoln Park Zoo
- The Field Museum
- 875 North Michigan Avenue
- Wicker Park
- Willis Tower
- Skokie Country Club
- Garfield Park Conservatory
- Lincoln Park
- Chicago Cultural Center
- Promontory Point
- Odyssey Fun World
- Flossmoor Golf Club
- Moraine Hills State Park
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