Apartment holiday rentals in Chicago
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Top-rated apartment rentals in Chicago
Guests agree: these apartments are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Chicago apartment rentals
Weekly apartment rentals
Flat in Forest Park
5.0 out of 5 average rating, 229 reviewsLike a Treehouse!
Flat in Chicago
4.79 out of 5 average rating, 178 reviewsPerfect 1br In Lincoln Park - Steps to Depaul!
Flat in Chicago
4.93 out of 5 average rating, 383 reviewsRavenswood Guest House Annex
Flat in Chicago
4.99 out of 5 average rating, 107 reviewsNewly Renovated, Spacious 2BR in Andersonville
Flat in Near North Side
4.89 out of 5 average rating, 379 reviewsGreat Location Studio in the Gold Coast!!
Flat in Chicago
4.78 out of 5 average rating, 130 reviewsChic & Fully Furnished Studio Apt with Laundry
Flat in Little Italy
4.98 out of 5 average rating, 202 reviewsSpacious 2BR on Quiet St - Free Park/Late Checkout
Flat in Logan Square
4.87 out of 5 average rating, 488 reviewsLogan Square Studio
Private apartment rentals
Flat in Chicago
4.86 out of 5 average rating, 107 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Flat in Irving Park
4.97 out of 5 average rating, 253 reviewsSpacious 1BR apartment in a central location
Flat in Lake View
4.86 out of 5 average rating, 203 reviewsPrivate Queen Bedroom and En Suite Bath
Flat in Chicago
4.89 out of 5 average rating, 143 reviewsCharming Gold Coast One-Bedroom Near Downtown!
Flat in Skokie
4.91 out of 5 average rating, 538 reviewsCozy Garden Unit in Quiet Neighborhood
Flat in Wicker Park
4.95 out of 5 average rating, 259 reviewsHeart of Bucktown
Flat in Logan Square
4.89 out of 5 average rating, 347 reviewsSunny Logan Square Artists' home
Flat in Logan Square
4.97 out of 5 average rating, 259 reviewsLogan Square 2nd Floor Chicago Victorian
Apartment rentals with a hot tub
Flat in Chicago
4.88 out of 5 average rating, 399 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Flat in Berwyn
4.91 out of 5 average rating, 208 reviews“Dream slice of urban homesteading.”
Flat in Near South Side
4.87 out of 5 average rating, 163 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Flat in West Loop
4.87 out of 5 average rating, 107 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Flat in Chicago
4.92 out of 5 average rating, 37 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Flat in Streeterville
5.0 out of 5 average rating, 11 reviewsLake, City, & River View Condo
Flat in The Loop
4.8 out of 5 average rating, 10 reviewsThe Areal Oasis
Flat in Chicago
4.8 out of 5 average rating, 25 reviewsSpacious Beautiful Condo
Quick stats about flat rentals in Chicago
Total rentals
5.9K properties
Rentals with dedicated workspaces
3.8K properties have a dedicated workspace
Rentals with a pool
750 properties have a pool
Pet-friendly rentals
2K properties allow pets
Family-friendly rentals
2.7K properties are a good fit for families
Total number of reviews
253K reviews
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
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