
Apartment holiday rentals in Chicago
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Top-rated apartment rentals in Chicago
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Holiday rentals for every style
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Popular amenities for Chicago apartment rentals
Weekly apartment rentals

Breathtaking & Bright: Designer 2bd with Garage

Kasa | Studio, Walk to Grant Park | South Loop

Humboldt Park Retreat: Skylights & Queen Beds

Loft-Inspired Retreat | Stylish Stay Near Downtown

Chic & Cozy Boho Vibe in Heart of Logan Square

Darling Flat Walk to OP

"Hope of Evanston" 2BDR/2BTH

Sonder Onterie | King Studio Apartment
Private apartment rentals

Hidden Gem:Artsy Speakeasy in Historic Bronzeville

Vibrant & Chic Apt On Quiet St in Andersonville

Andersonville Bicycle Studio

Modern+Spacious W/King Bed, Walk to Town-Park Free

Quirky Designer Apartment - Steps from Wrigley!

Explore Chicago from an Urban Sanctuary with Free Parking

Newly Renovated, Spacious 2BR in Andersonville

Brand new 2 bed 2 bath apartment in Lincoln Square
Apartment rentals with a hot tub

The Areal Oasis

Spacious Beautiful Condo

5 Minutes to Wrigley - Sauna + Games - Sleeps 6

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

Skyline Oasis: City & Lake Views

Penthouse Near Fulton: Skyline, Spacious

Spacious 1 BR Garden Unit-1 FREE Garage Parking

2Bed 2Bath 15min to Wrigley with Parking& Balcony
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
- Indianapolis Holiday rentals
- Downtown Chicago Holiday rentals
- Platteville Holiday rentals
- St. Louis Holiday rentals
- Detroit Holiday rentals
- Louisville Holiday rentals
- Columbus Holiday rentals
- Southern Indiana Holiday rentals
- Cincinnati Holiday rentals
- Milwaukee Holiday rentals
- Wisconsin River Holiday rentals
- Windsor Holiday rentals
- Family-friendly rentals Chicago
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- Flat rentals Cook County
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- Humboldt Park
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- 875 North Michigan Avenue
- The Field Museum
- Illinois Beach State Park
- Washington Park Zoo
- Wicker Park
- Brookfield Zoo
- Garfield Park Conservatory
- Museum of Science and Industry
- Lincoln Park Zoo
- Raging Waves Waterpark
- Willis Tower
- The 606
- The Beverly Country Club
- Things to do Chicago
- Sports activities Chicago
- Food and drink Chicago
- Tours Chicago
- Sightseeing Chicago
- Nature and outdoors Chicago
- Art and culture Chicago
- Things to do Cook County
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- Things to do Illinois
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- Things to do United States
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