
Apartment holiday rentals in Chicago
Find and book unique apartments on Airbnb
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.

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

Fulton House #1 (2bd/ 1ba)

Bright & Spacious| Free Parking |Trendy Bridgeport

Humboldt Park Retreat: Skylights & Queen Beds

Loft-Inspired Retreat | Stylish Stay Near Downtown

The Heart of Bucktown

Apartment on the Lake
Private apartment rentals

KNG+QN 2bdrm/1parking space /18 min O’hare/Alstate

Charming, Sunny Apartment with Backyard Garden

Decompress on a Sophisticated Chaise at a Glamorous Hideaway

Penthouse Near Wrigley Field

Vibrant & Chic Apt On Quiet St in Andersonville

Logan Square Garden Sanctuary

Quirky Designer Apartment - Steps from Wrigley!

50th Floor Mag Mile Studio
Apartment rentals with a hot tub

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

Spacious Beautiful Condo

Skyline Oasis: City & Lake Views

Large Studio Apartment with no cleaning fee

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

Penthouse Near Fulton: Skyline, Spacious

Sentral 1 Bedroom Apt in South Loop Chicago

Belmont Pleasures - hot tub / arcade gaming room
Quick stats about flat 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 beach access Chicago
- Rentals with an accessible-height bed Chicago
- Smoking-friendly rentals Chicago
- Fitness-friendly rentals Chicago
- Rentals with an EV charger Chicago
- Lakehouse rentals Chicago
- Rentals with lake access Chicago
- Rentals with a cinema Chicago
- Rentals with outdoor seating Chicago
- Rentals with a balcony Chicago
- Beachfront rentals Chicago
- Rentals with pools Chicago
- Waterfront rentals Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Loft rentals Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Rentals with breakfast Chicago
- Rentals with a firepit Chicago
- House rentals Chicago
- Rentals with a fireplace Chicago
- Rentals with a patio Chicago
- Rentals with a sauna Chicago
- Rentals with a washing machine and dryer Chicago
- Bed and breakfasts Chicago
- Ski-in/ski-out rentals Chicago
- Mansion rentals Chicago
- Townhouse rentals Chicago
- Family-friendly rentals Chicago
- Villa rentals Chicago
- Private suite rentals Chicago
- Flat rentals Cook County
- Flat rentals Illinois
- Flat rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Humboldt Park
- Six Flags Great America
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Brookfield Zoo
- Illinois Beach State Park
- Wicker Park
- Washington Park Zoo
- The 606
- Raging Waves Waterpark
- Flossmoor Golf Club
- Things to do Chicago
- Food and drink Chicago
- Tours Chicago
- Sightseeing Chicago
- Art and culture Chicago
- Nature and outdoors Chicago
- Things to do Cook County
- Food and drink Cook County
- Tours Cook County
- Sightseeing Cook County
- Art and culture Cook County
- Things to do Illinois
- Sightseeing Illinois
- Art and culture Illinois
- Nature and outdoors Illinois
- Food and drink Illinois
- Tours Illinois
- Things to do United States
- Sightseeing United States
- Food and drink United States
- Wellness United States
- Nature and outdoors United States
- Art and culture United States
- Tours United States
- Sports activities United States
- Entertainment United States