
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

The Biddle House (#1)
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.

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

Lakeview Charmer -with parking!
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.

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

Chicago Bootlegger House Sleeps 10-20
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!

Executive Apartment on Lake Michigan with parking
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

The Spa of Downtown Whiting
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.

minimal lakefront apartment
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

Spacious Full Home Near the Heart of Wrigleyville
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.

*The Belltower Haven*Large*Family Friendly*Wi-Fi
James was great and so was the airbnb, think very highly of him and his air bnb.

Sun drenched 2 bedroom 1 bath with Kitchen & W/D
We loved this spot! Lots to do easy easy parking, and a first floor apt. Would most certainly stay here again!!

Downtown Elegance ✨ Private Yard Parking
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.

Susie's Space. 2BR easy parking & pet friendly
Really liked it, nice location, plenty of room, comfortable, good kitchen. Getting around using buses and the subway was also very easy.

Dog Friendly Cozy North Naperville 3 BED/2 BA Home
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.

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

Wrigleyville townhome two blocks from ballpark
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

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

Family Friendly 3BR Duplex in Roscoe Village
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.

Vintage sunlit 2.5 BR apt. Perfect for families!
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.

The Nancy’s gorgeous , Spacious Urban Getaway
Very easy experience- host prepared a celebration for us as well. Small touches were appreciated!

Large sunny 3BR apt. in downtown Oak Park
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.

The Wrigley Flats | Chicago Vacation Rental
Great location. Several eating options are in the area and the neighborhood feels very safe. Would stay again!

Charming Apt. near Wrigley/Cubs, Ravenswood/Uptown
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!

Cozy Northside Apt near Transp&Beach&Free St Prkng
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.
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Humboldt Park
- Guaranteed Rate Field
- Six Flags Great America
- 875 North Michigan Avenue
- The Field Museum
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Lincoln Park Zoo
- Willis Tower
- Lincoln Park
- Wicker Park
- Illinois Beach State Park
- Flossmoor Golf Club
- Brookfield Zoo
- The 606
- Washington Park Zoo
- Moraine Hills State Park
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