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 Andersonville
4.82 out of 5 average rating, 441 reviewsLovely Andersonville Apt with Ideal Location
Flat in Chicago
4.84 out of 5 average rating, 177 reviewsLa Cottage
Flat in Andersonville
4.98 out of 5 average rating, 256 reviewsAndersonville Cozy 1 bedroom basement suite
Flat in Chicago
4.87 out of 5 average rating, 207 reviewsSpectacular Pilsen Studio for 2!
Flat in Forest Park
5.0 out of 5 average rating, 229 reviewsLike a Treehouse!
Flat in Oak Park
4.85 out of 5 average rating, 537 reviewsLong stays welcome@warm&cute vintage 2BR
Flat in Chicago
4.96 out of 5 average rating, 380 reviewsKing Bed, Huge Spa Shower, Dining Destination
Flat in Chicago
4.86 out of 5 average rating, 106 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Private apartment rentals
Flat in Chicago
4.89 out of 5 average rating, 479 reviewsiKlektik House Chicago / Robin
Flat in Andersonville
4.96 out of 5 average rating, 257 reviewsSunny, Cozy, Colorful Andersonville
Flat in Chicago
4.87 out of 5 average rating, 276 reviewsHistoric Old Town Flat - Minutes from Downtown!
Flat in Logan Square
4.9 out of 5 average rating, 287 reviewsModern Logan Square Apartment, steps from train!
Flat in Logan Square
4.97 out of 5 average rating, 259 reviewsLogan Square 2nd Floor Chicago Victorian
Flat in Chicago
4.91 out of 5 average rating, 170 reviewsA Novel Situation at Wrigley
Flat in Near North Side
4.82 out of 5 average rating, 488 reviewsGreat Location Studio II
Flat in Chicago
4.96 out of 5 average rating, 102 reviewsCute, Clean, Cozy Apartment in Pilsen
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, 207 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, 37 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Flat in Chicago
4.79 out of 5 average rating, 24 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
- Serviced apartment rentals United States
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- Rentals with a patio Chicago
- Lakehouse rentals Chicago
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- Rentals with an EV charger Chicago
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- Rentals with an accessible-height bed Chicago
- Rentals with a washing machine and dryer Chicago
- Smoking-friendly rentals Chicago
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- Townhouse rentals Chicago
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- House rentals Chicago
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- Flat rentals Downtown Chicago
- Flat rentals Milwaukee
- Flat rentals Lake Geneva
- Flat rentals Illinois
- Flat rentals Cook County
- Yurt Rentals United States
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- Castle Rentals United States
- Houseboats United States
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- Farm Houses United States
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- Holiday Chalets United Kingdom
- Cottage Rentals United States
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- Mansion Rentals United States
- Villa Rentals United Kingdom
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- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
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- Big House Rentals United States
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