
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

River North | Private Deck With In&Out Parking

Fulton House #1 (2bd/ 1ba)

Pilsen Modern Chic Retreat

Spacious New Studio: Kitchenette, Laundry & Office

Loft-Inspired Retreat | Stylish Stay Near Downtown

McCormick Place Studio/parking/sleeps up to 4

Private Garden APT/ Cozy/Warm

Chic & Cozy Boho Vibe in Heart of Logan Square
Private apartment rentals

Stunning Corner 2BR in the Loop | City & Lake View

Spectacular Pilsen Studio for 2!

Lincoln Paradise– Steps to Park & Zoo!

【Central】- Eclectic Fun 1BR APT in Wicker Park

Breathtaking & Chic Oasis Loc in Desirable Old Twn

Logan Square Cozy 2BR Basement Apartment

1BR South Loop Loft I SuperHost + Top Rated!
Bright, Modern Apartment in a Vintage Greystone
Apartment rentals with a hot tub

Luxe Ranch & Spa, Euro Opulence, a 4-Season Oasis

Spacious Beautiful Condo

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

Skyline Oasis: City & Lake Views

Penthouse Near Fulton: Skyline, Spacious

Summer Getaway in Prime Location | Pet Friendly

Belmont Pleasures - hot tub / arcade gaming room

The Parkside Panorama
Quick stats about apartment rentals in Chicago
Total rentals
6.3K properties
Total number of reviews
299K reviews
Family-friendly rentals
3.1K properties are a good fit for families
Pet-friendly rentals
2.2K properties allow pets
Rentals with a pool
840 properties have a pool
Rentals with dedicated workspaces
3.8K properties have a dedicated workspace
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- South Haven Holiday rentals
- Saugatuck Holiday rentals
- Holland Holiday rentals
- South Side Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- Rentals with a home theatre Chicago
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- Oak Street Beach
- Humboldt Park
- Shedd Aquarium
- Frank Lloyd Wright Home and Studio
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Washington Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Illinois Beach State Park
- Garfield Park Conservatory
- Wicker Park
- Lincoln Park Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Things to do Chicago
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