
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

Pristine Gold Coast 3BD|2BA | Free Parking| Beach.

Spacious Studio in Little Italy, Near West Loop

Chic 2BR 2BA Condo with Balcony - River North Chic

Fulton House #1 (2bd/ 1ba)

Loft-Inspired Retreat | Stylish Stay Near Downtown

Humboldt Park Retreat: Skylights & Queen Beds

NEW Jade Haven in Berwyn/Riverside

Darling Flat Walk to OP
Private apartment rentals

The Bell House: Apartment #1

Spectacular Pilsen Studio for 2!

Large condo w/ amazing roof deck

*Best of Northalsted*

Chic 1 BR w Parking

Grace Place in Wrigleyville

Chicago Luxury Long Term 30+

Fantastic West Loop 2 bedroom
Apartment rentals with a hot tub

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

The Areal 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
Quick stats about flat 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
- 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
- Loft rentals Chicago
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- Rentals with a sauna Chicago
- Townhouse rentals Chicago
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- Rentals with a fireplace Chicago
- Rentals with a washing machine and dryer Chicago
- Rentals with lake access Chicago
- Ski-in/ski-out rentals Chicago
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- Mansion rentals Chicago
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- Rentals with an EV charger Chicago
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- Private suite rentals Chicago
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- Beach Cabins United States
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- Dog-Friendly Cottages United Kingdom
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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
- Wicker Park
- Washington Park Zoo
- Illinois Beach State Park
- Lincoln Park Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Things to do Chicago
- Food and drink Chicago
- Nature and outdoors Chicago
- Sightseeing Chicago
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- Art and culture Chicago
- Things to do Cook County
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