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 Oak Park
4.89 out of 5 average rating, 341 reviewsCharming Chicago-Style, Vintage, Tv NFL PASS
Flat in Chicago
4.8 out of 5 average rating, 387 reviews'Secret Garden' Apartment in Wrigleyville
Flat in Logan Square
4.87 out of 5 average rating, 487 reviewsLogan Square Studio
Flat in Chicago
4.93 out of 5 average rating, 383 reviewsRavenswood Guest House Annex
Flat in Chicago
4.86 out of 5 average rating, 106 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Flat in Chicago
4.96 out of 5 average rating, 113 reviewsComfortable, modern apartment 20 Min from Downtown
Flat in Oak Park
4.85 out of 5 average rating, 536 reviewsLong stays welcome@warm&cute vintage 2BR
Flat in Forest Park
4.93 out of 5 average rating, 593 reviewsPeaceful oasis in Forest Park
Private apartment rentals
Flat in Chicago
4.96 out of 5 average rating, 380 reviewsKing Bed, Huge Spa Shower, Dining Destination
Flat in Irving Park
4.97 out of 5 average rating, 253 reviewsSpacious 1BR apartment in a central location
Flat in Chicago
4.89 out of 5 average rating, 475 reviewsiKlektik House Chicago / Robin
Flat in Chicago
4.82 out of 5 average rating, 440 reviewsLovely Andersonville Apt with Ideal Location
Flat in Andersonville
4.96 out of 5 average rating, 255 reviewsSunny, Cozy, Colorful Andersonville
Flat in Logan Square
4.9 out of 5 average rating, 287 reviewsModern Logan Square Apartment, steps from train!
Flat in Chicago
4.89 out of 5 average rating, 247 reviewsModern
Flat in West Town
4.92 out of 5 average rating, 329 reviewsBright, Modern Apartment in a Vintage Greystone
Apartment rentals with a hot tub
Flat in Chicago
4.88 out of 5 average rating, 398 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Flat in Berwyn
4.91 out of 5 average rating, 206 reviews“Dream slice of urban homesteading.”
Flat in Near South Side
4.87 out of 5 average rating, 160 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Flat in West Loop
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Flat in Chicago
4.92 out of 5 average rating, 36 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Flat in Chicago
4.78 out of 5 average rating, 23 reviewsSpacious Beautiful Condo
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
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
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Flat rentals United States
- Serviced apartment rentals United States
- Rentals with an EV charger Chicago
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- Flat rentals Downtown Chicago
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- Yurt Rentals United States
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