
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

Chic N. Chicago Hideaway; Private Oasis w/ Parking

Spacious New Studio: Kitchenette, Laundry & Office

Loft-Inspired Retreat | Stylish Stay Near Downtown

Humboldt Park Retreat: Skylights & Queen Beds

Spacious 2BR Group Stay near McCormick & Wintrust

The Heart of Bucktown

Edgewater Studio on Paulina

The Norwood Nook –Walkable , Near O’Hare & Metra!
Private apartment rentals

Near 606 Trail | Free Garage Parking | W&D |LUXTEL

Fulton House #1 (2bd/ 1ba)

Spectacular Pilsen Studio for 2!

Designer Avondale Attic

Cozy guest studio, great for couples!

Loop Loft-Subway & Art Institute

*Best of Northalsted*

Modern vintage chic steps from Wrigley Field!
Apartment rentals with a hot tub

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

Spacious Beautiful Condo

Skyline Oasis: City & Lake Views

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

Penthouse Near Fulton: Skyline, Spacious

Summer Getaway in Prime Location | Pet Friendly

Belmont Pleasures - hot tub / arcade gaming room

Checkerboard Studio, Private Outdoor Hot Tub, Yard
Quick stats about apartment rentals in Chicago
Total rentals
6.4K properties
Total number of reviews
306K 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
3.9K 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
- Holland Holiday rentals
- Saugatuck Holiday rentals
- South Side Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- Rentals with an accessible height bed Chicago
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- Garfield Park Conservatory
- Washington Park Zoo
- Wicker Park
- Illinois Beach State Park
- Lincoln Park Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Things to do Chicago
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