
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

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

Lakeview Charmer -with parking!
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.

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

Chicago Bootlegger House Sleeps 10-20
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!

Executive Apartment on Lake Michigan with parking
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!

Near Lake Michigan & Wrigley Field
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.

The Spa of Downtown Whiting
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.

Cozy Andersonville Cabin
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

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
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.

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
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.

Downtown Elegance ✨ Private Yard Parking
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!

Large sunny 3BR apt. in downtown Oak Park
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!

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

Cozy Northside Apt near Transp&Beach&Free St Prkng
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

Lovely 2bedroom 1bath Apt and outdoor seating.
A very nice and welcoming place to stay!

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

Chicago Airbnb Newly Remodeled 2-Unit Apartment!
Neat, clean, great location! Heads up for anyone parking: there's a Thursday morning parking restriction. Learned that the hard way with a fine.

Inviting 2 Bedroom Apartment in Roscoe Village
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.

Victorian Home in Old Town
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!

BERNARD CHATEAU - LOGAN SQUARE
Perfect weekend stay for our girls trip. Place was small but beautiful. Quiet neighborhood. Close enough to both downtown and Wrigley!

Avondale Cozy 1 Bedroom Attic Apartment 4th FL
Great place, beautiful attic and great amenities from host!

Spaulding Oasis on 4 lots In Humboldt Park!
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.
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- Six Flags Great America
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park Zoo
- Flossmoor Golf Club
- Museum of Science and Industry
- Willis Tower
- Wicker Park
- Lincoln Park
- Chicago History Museum
- Skokie Country Club
- Illinois Beach State Park
- Washington Park Zoo
- Brookfield Zoo
- Promontory Point
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