
Vacation rentals in Chicago
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Top-rated vacation rentals in Chicago
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Popular amenities for Chicago vacation rentals
Other great vacation rentals in Chicago
Superhost

Home in West Lawn
4.92 out of 5 average rating, 39 reviewsFamily Friendly Duplex/9 min from MDW/Free Parking
JoannaRating, 5 stars2 weeks ago
Came for c2e2 with my friends and it was perfect for all of us! Would recommend 💗💗
Guest favourite

Apartment in West Town
4.85 out of 5 average rating, 130 reviewsCondo with private terrace, free WIFI and parking
OlesyaRating, 5 stars2 weeks ago
The place looked much better than on the pictures! It has rooftop patio, spacious, clean, with a unique interior design (vintage). It had plenty of towels, dishes, comforters, so we will definitely come back there when we are in Chicago.
Top guest favourite

Home in Schaumburg
5 out of 5 average rating, 51 reviewsGreat location-King beds-Kids playroom
AdamRating, 5 stars2 weeks ago
Ninna's place was fantastic! It was exactly as described, and the process was proactive. Ninna communicated very well and anticipated questions we may have. We had friends from the area join us for dinner, and Ninna was accommodating of that request. Her place was perfect, with everything we may need during our stay. The kitchen was stocked with all the things we needed, and the coffee nook was a nice touch! The kids enjoyed the little playroom upstairs, and the mattresses were very comfortable.
Guest favourite

Apartment in Albany Park
4.86 out of 5 average rating, 42 reviewsElegant 4Bedroom with Free Parking in Albany Park
MatthewRating, 5 stars2 months ago
Wonderful stay as always, thank you so much!
Superhost

Apartment in Jefferson Park
4.63 out of 5 average rating, 24 reviewsCity Gem: Stylish 3BR for Urban Explorers
AnnikaRating, 5 stars1 month ago
Peaceful, felt like home, very spacious and comfortable
Superhost

Condo in East Rogers Park
4.79 out of 5 average rating, 29 reviewsSpacious condo with open floor plan and fireplace
TatianaRating, 5 stars4 months ago
This place was spacious and perfect for our family (two kids and a baby), with plenty of room for everyone to spread out. The hosts were fantastic! They encountered an issue with the fridge not working just before our arrival but handled it professionally, providing excellent support until it was fixed. We really appreciated their responsiveness and care. We highly recommend this space for families and large groups. One small suggestion: if you’re a light sleeper or have kids, consider bringing a noise machine, as some sound from the upstairs neighbors can be heard. However, this wasn’t a problem for us and is to be expected when staying in a condo.
Top guest favourite

Home in Lombard
5 out of 5 average rating, 25 reviewsSpacious Home in Chicago Suburbs
JenniferRating, 5 stars2 weeks ago
It was great! The house was lovely and looked newly renovated. It was much roomier than I expected. The beds were very comfortable.
Top guest favourite

Home in Chicago
5 out of 5 average rating, 21 reviewsComfy Home Away From Home
ZakiRating, 5 stars1 week ago
This home completely transformed our view of Chicago. We arrived a little nervous, but the moment we walked in, we were greeted by a space that was warm, welcoming, and absolutely stunning. Every detail was thoughtfully curated, from the sleek kitchen to the plush pillows on the sectional. The kitchen is modern and fully stocked, perfect for cooking and gathering. The living room is beautifully styled and cozy, and the bedrooms felt like luxurious retreats with spa-like linens and calming decor. The basement lounge was a standout with its oversized sectional and elegant bar area, so perfect for relaxing after a long day. We especially loved the little reading nook with the blue chairs. Every corner of this home radiates peace and intentionality. It truly felt like a sanctuary. We left feeling inspired, rested, and already planning our return.
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
Destinations to explore
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- Six Flags Great America
- Museum of Science and Industry
- 875 North Michigan Avenue
- Chicago History Museum
- Lincoln Park Zoo
- The Field Museum
- Wicker Park
- Flossmoor Golf Club
- Garfield Park Conservatory
- Skokie Country Club
- Brookfield Zoo
- Willis Tower
- Lincoln Park
- Chicago Cultural Center
- Promontory Point
- Washington Park Zoo
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