
Holiday rentals in Chicago
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Top-rated holiday rentals in Chicago
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Chicago
Superhost

Home in West Lawn
4.93 out of 5 average rating, 40 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 💗💗
Superhost

Apartment in The Loop
4.75 out of 5 average rating, 48 reviews2BD Central Downtown Location! Spacious & Cozy
PeggyRating, 5 stars2 weeks ago
We really enjoyed our visit to Chicago. The apartment was very close to everything. we did a lot of walking and the bus lines were very convenient. Don't let the Google reviews cause you not to stay here. You get used to the train noise within hours and you kind of miss it when you leave. There were no homeless people hanging around downstairs. As a matter of fact, I only seen a few the entire time I was there. It is a very nice place to stay and I would definitely recommend it for your next visit.
Guest favourite

Flat 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

Flat 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

Home in Logan Square
4.84 out of 5 average rating, 100 reviewsCalifornia Cottage/4br prime location Logan Square
JeniRating, 5 stars2 weeks ago
Daniel’s house was perfect for what we needed. Seven adult women were comfortable and enjoyed the open table space. Bathrooms in basement and main level were clean, and plenty of linens and towels were supplied for the three nights we were there. Nice location for easy pickups and stores with delivery nearby for quick groceries. Also check out Diversey House nearby - great food and drinks! Thanks for a great weekend getaway!
Superhost

Apartment 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 stars2 weeks 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 holiday 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
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- Lake Michigan Beach Holiday rentals
- Holland Holiday rentals
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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
- 875 North Michigan Avenue
- Six Flags Great America
- The Field Museum
- Lincoln Park
- Wicker Park
- Lincoln Park Zoo
- Museum of Science and Industry
- Willis Tower
- Chicago History Museum
- Flossmoor Golf Club
- Brookfield Zoo
- Illinois Beach State Park
- Skokie Country Club
- Garfield Park Conservatory
- Chicago Cultural Center
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