
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

Designer Lakeview Haven. Private Rooftop Oasis!

Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

Susie's Space. 2BR easy parking & pet friendly

University of Chicago Condo-Upgraded and Spacious

Cozy Kitties in the City 1BR by Park/Sox/Transit

Peaceful & Airy Modern-Chic Condo in Trendy Pilsen

Luxury Penthouse w/ HOT TUB & Amazing Roof Deck
Pet-friendly apartment rentals

Chic and Charming Vintage Condominium in Lincoln Park

816 PLZN Luxury Apartment| Rooftop| Garage Parking

Cozy Lincoln Park Condo near the lake.

Spacious 3BR • Great for Groups • Fast WiFi • Pets

Luxuriously bright 3-bedroom condo: The Treehouse

Picture Perfect 3Bed Steps from Train and FLW

Spacious & Stylish Home at the ♥ of Wicker Park

Steps from the Lake, Lovely 3-Bedroom Condo
Apartment rentals with a pool

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

Just remodeled apartment close to airport and mall

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

Pond View, Washer Dryer, Non Smoking Community

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

Iconic Style, Charming Lake View
Quick stats about apartment rentals in Chicago
Total rentals
1K properties
Nightly prices starting at
$26 SGD before taxes and fees
Total number of reviews
70K reviews
Family-friendly rentals
630 properties are a good fit for families
Pet-friendly rentals
300 properties allow pets
Rentals with a pool
80 properties have a pool
Destinations to explore
- Indianapolis Holiday rentals
- Downtown Chicago Holiday rentals
- Platteville Holiday rentals
- St. Louis Holiday rentals
- Detroit Holiday rentals
- Columbus Holiday rentals
- Louisville Holiday rentals
- Southern Indiana Holiday rentals
- Cincinnati Holiday rentals
- Milwaukee Holiday rentals
- Wisconsin River Holiday rentals
- Windsor Holiday rentals
- Rentals with lake access Chicago
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- 875 North Michigan Avenue
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Garfield Park Conservatory
- Illinois Beach State Park
- Lincoln Park Zoo
- Washington Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
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- Nature and outdoors Chicago
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