
Vacation rentals in Chicago
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Top-rated vacation rentals in Chicago
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Charming, Sunny Apartment with Backyard Garden
Great style, great space, wonderful host. Susan was always responsive, friendly, out-going.

The Bright Retreat in Andersonville
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!

Private 3rd Floor Apartment
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.

RockStar Pad W3A BoysTown/Wrigley Field/Parking
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!

Beautiful Lincoln Park/ De Paul Complimentary Parking Permit
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.

Larimer Park Carriage House
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!

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

Cute 2 BR 10 Minutes to Downtown Chicago Sleeps 6
We had a wonderful stay at Freddy’s place
Dog friendly vacation rentals in Chicago

MiniGolfHouse-Chicago Close Warm Indoor Fun!
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

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

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

Peaceful Portage Park Apartment
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.

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

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

Home in Forest Park downstairs.
the home was beautiful and clean ! i will be returning!! the host responds quickly and very friendly!

Private apartment with retro vibe
Clean and peaceful neighborhood. Parking was not an issue
Family friendly vacation rentals in Chicago

Private suite in Lincoln Square
Great location, nice space, helpful hosts - would stay again!

Great Location Studio in the Gold Coast!!
Booked for an interview . Quiet space and responsive host . Recommend

Cozy, Quiet, Garden Getaway!
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!

Entire place with free parking.
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!

Bridgeport Garden Apartment
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!

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!

Secret Garden @ The Noble Farmhouse | Wicker Park
Wonderful place to stay! Photos seriously don’t do it justice, the outdoor area is beautiful.

'Secret Garden' Apartment in Wrigleyville
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.
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Lincoln Park
- Lincoln Park Zoo
- Willis Tower
- Illinois Beach State Park
- Wicker Park
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center
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