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
Get the amount of space that is right for you
Popular amenities for Chicago apartment rentals
Weekly apartment rentals
Flat in Chicago
4.98 out of 5 average rating, 140 reviewsModern Apt with style & comfort in Pilsen Chicago
Flat in Chicago
4.95 out of 5 average rating, 117 reviewsComfortable, modern apartment 20 Min from Downtown
Flat in Logan Square
4.87 out of 5 average rating, 489 reviewsLogan Square Studio
Flat in Lincoln Square
4.96 out of 5 average rating, 325 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Flat in Chicago
4.95 out of 5 average rating, 369 reviewsA Vintage Pink House in the Heart of Chicago
Flat in Irving Park
4.96 out of 5 average rating, 257 reviewsSpacious 1BR apartment in a central location
Flat in Andersonville
4.98 out of 5 average rating, 257 reviewsAndersonville Cozy 1 bedroom basement suite
Flat in Oak Park
4.89 out of 5 average rating, 348 reviewsCharming Chicago-Style, Vintage, Tv NFL PASS
Private apartment rentals
Flat in Chicago
4.84 out of 5 average rating, 178 reviewsLa Cottage
Flat in Logan Square
4.97 out of 5 average rating, 260 reviewsLogan Square 2nd Floor Chicago Victorian
Flat in Chicago
4.96 out of 5 average rating, 104 reviewsCute, Clean, Cozy Apartment in Pilsen
Flat in Chicago
4.89 out of 5 average rating, 250 reviewsModern
Flat in Logan Square
4.89 out of 5 average rating, 351 reviewsSunny Logan Square Artists' home
Flat in Chicago
4.96 out of 5 average rating, 383 reviewsKing Bed, Huge Spa Shower, Dining Destination
Flat in Chicago
4.97 out of 5 average rating, 239 reviewsStylish First Flr. Studio. Best Location Division+Hermitage.
Flat in Chicago
4.95 out of 5 average rating, 208 reviewsHuge Apt in Uptown/Andersonville
Apartment rentals with a hot tub
Flat in Chicago
4.88 out of 5 average rating, 402 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Flat in Chicago
4.87 out of 5 average rating, 165 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Flat in West Loop
4.87 out of 5 average rating, 108 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Flat in Berwyn
4.91 out of 5 average rating, 209 reviews“Dream slice of urban homesteading.”
Flat in Chicago
4.92 out of 5 average rating, 38 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Flat in Streeterville
5.0 out of 5 average rating, 12 reviewsLake, City, & River View Condo
Flat in The Loop
5.0 out of 5 average rating, 8 reviewsThe Playwright's Palace
Flat in Chicago
4.81 out of 5 average rating, 26 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
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- Schaumburg Holiday rentals
- Flat rentals United States
- Serviced apartment rentals United States
- Rentals with a cinema Chicago
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- Flat rentals Downtown Chicago
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