
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 West Lake View
4.95 out of 5 average rating, 106 reviewsChic retreat near the best of Lakeview & Wrigley

Flat in Joliet
4.95 out of 5 average rating, 199 reviews*The Belltower Haven*Large*Family Friendly*Wi-Fi

Flat in Lake Zurich
4.98 out of 5 average rating, 177 reviewsTake A Pebble Apartments (Studio 3)

Flat in Wicker Park
4.94 out of 5 average rating, 102 reviewsBright two bedroom garden apartment

Flat in Lincoln Square
4.91 out of 5 average rating, 186 reviewsComfortable Vintage North Side Retreat for 8

Flat in Lincoln Park
4.95 out of 5 average rating, 111 reviewsElegant Depaul Apt on Jonquil Park

Flat in Irving Park
4.94 out of 5 average rating, 231 reviewsCool and Modern Chicago Apartment near Transit

Flat in West Town
4.85 out of 5 average rating, 161 reviews*Comfortable & Spacious Home Close to Downtown*
Private apartment rentals

Flat in Oak Park
4.87 out of 5 average rating, 276 reviewsCosmopolitan Nest in Oak Park North Side

Flat in Near North Side
4.91 out of 5 average rating, 127 reviewsModern 3BR with Private Rooftop & Free Parking

Flat in Lincoln Square
4.79 out of 5 average rating, 289 reviewsCozy Garden-Subterranean Apartment

Flat in East Rogers Park
4.9 out of 5 average rating, 142 reviewsPrivate Garden Apartment GATED FREE Parking

Flat in Avondale
4.98 out of 5 average rating, 103 reviewsLovely 2bedroom 1bath Apt and outdoor seating.

Flat in Avondale
4.91 out of 5 average rating, 270 reviewsAvondale Gem: 2BR, Stylish Kitchen, Transit Nearby

Flat in Roscoe Village
4.75 out of 5 average rating, 254 reviewsNorth Side Pied-à-terre

Flat in Evanston
4.84 out of 5 average rating, 245 reviewsAdorable 1BR apartment near Northwestern
Apartment rentals with a hot tub

Flat in West Loop
4.83 out of 5 average rating, 77 reviewsQuiet but in the Heart of City walk Everywhere

Flat in The Loop
4.89 out of 5 average rating, 37 reviewsThe Areal Oasis

Flat in Lake View
New place to stayLakeview Apt Sleeps 6 - Games - Minutes to Wrigley

Flat in West Loop
4.96 out of 5 average rating, 23 reviewsSkyline Oasis: City & Lake Views

Flat in Belmont Cragin
4.99 out of 5 average rating, 88 reviewsBelmont Pleasures - hot tub / arcade gaming room

Flat in The Loop
New place to stayArt Oasis On The Chicago River

Flat in Irving Park
4.91 out of 5 average rating, 22 reviewsCozy 2Bed 2Bath with Parking, Balcony &Jacuzzi
Quick stats about flat rentals in Chicago
Total rentals
6.3K properties
Total number of reviews
297K reviews
Family-friendly rentals
3K properties are a good fit for families
Pet-friendly rentals
2.2K properties allow pets
Rentals with a pool
760 properties have a pool
Rentals with dedicated workspaces
4.2K properties have a dedicated workspace
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
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- North Side Holiday rentals
- South Bend Holiday rentals
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