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
Apartment in Chicago
4.93 out of 5 average rating, 171 reviewsCharming Apt. near Wrigley/Cubs, Ravenswood/Uptown
Apartment in Andersonville
4.98 out of 5 average rating, 254 reviewsAndersonville Cozy 1 bedroom basement suite
Apartment in Chicago
4.89 out of 5 average rating, 141 reviewsCharming Gold Coast One-Bedroom Near Downtown!
Apartment in Wicker Park
4.95 out of 5 average rating, 175 reviewsWicker Park/Bucktown Location
Apartment in Logan Square
4.97 out of 5 average rating, 259 reviewsLogan Square 2nd Floor Chicago Victorian
Apartment in Chicago
4.96 out of 5 average rating, 113 reviewsComfortable, modern apartment 20 Min from Downtown
Apartment in Forest Park
4.93 out of 5 average rating, 593 reviewsPeaceful oasis in Forest Park
Apartment in Chicago
4.96 out of 5 average rating, 167 reviews2BR Centrally Located in Cozy Hip Logan Square
Private apartment rentals
Apartment in West Town
4.89 out of 5 average rating, 475 reviewsiKlektik House Chicago / Robin
Apartment in West Town
4.98 out of 5 average rating, 225 reviewsUkrainian Village Garden Retreat
Apartment in Chicago
4.96 out of 5 average rating, 380 reviewsKing Bed, Huge Spa Shower, Dining Destination
Apartment in Irving Park
4.97 out of 5 average rating, 253 reviewsSpacious 1BR apartment in a central location
Apartment in Lake View
4.86 out of 5 average rating, 202 reviewsPrivate Queen Bedroom and En Suite Bath
Apartment in Wicker Park
4.83 out of 5 average rating, 482 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Apartment in West Town
4.92 out of 5 average rating, 329 reviewsBright, Modern Apartment in a Vintage Greystone
Apartment in Logan Square
4.9 out of 5 average rating, 345 reviewsSunny Logan Square Artists' home
Apartment rentals with a hot tub
Apartment in Chicago
4.88 out of 5 average rating, 398 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Apartment in Berwyn
4.91 out of 5 average rating, 206 reviews“Dream slice of urban homesteading.”
Apartment in Near South Side
4.87 out of 5 average rating, 160 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Apartment in West Loop
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Apartment in Chicago
4.92 out of 5 average rating, 36 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Apartment in Chicago
4.78 out of 5 average rating, 23 reviewsSpacious Beautiful Condo
Apartment in Streeterville
5.0 out of 5 average rating, 11 reviewsLake, City, & River View Condo
Apartment in The Loop
4.8 out of 5 average rating, 10 reviewsThe Areal Oasis
Quick stats about apartment rentals in Chicago
Total rentals
5.9K properties
Rentals with dedicated workspaces
3.8K properties have a dedicated workspace
Rentals with a pool
750 properties have a pool
Pet-friendly rentals
2K properties allow pets
Family-friendly rentals
2.7K properties are a good fit for families
Total number of reviews
253K reviews
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Accommodation & holiday rentals
- Lake Michigan Beach Accommodation & holiday rentals
- Saugatuck Accommodation & holiday rentals
- Evanston Accommodation & holiday rentals
- Holland Accommodation & holiday rentals
- South Haven Holiday rentals
- Naperville Accommodation & holiday rentals
- South Side Accommodation & holiday rentals
- South Bend Accommodation & holiday rentals
- New Buffalo Holiday rentals
- Apartment rentals United States
- Serviced apartment rentals United States
- Rentals with an EV charger Chicago
- Rentals with a fireplace Chicago
- Rentals with a washing machine and dryer Chicago
- Rentals with an accessible height toilet Chicago
- Rentals with a home theatre Chicago
- Rentals with outdoor seating Chicago
- Fitness-friendly rentals Chicago
- Smoking-friendly rentals Chicago
- Private suite rentals Chicago
- Rentals with a patio Chicago
- Loft rentals Chicago
- Rentals with an accessible height bed Chicago
- Kid-friendly rentals Chicago
- Monthly Rentals Chicago
- Beachfront rentals Chicago
- Lakehouse rentals Chicago
- Rentals with a sauna Chicago
- Rentals with breakfast Chicago
- Rentals with a fire pit Chicago
- Mansion rentals Chicago
- Rentals with beach access Chicago
- Townhouse rentals Chicago
- Waterfront rentals Chicago
- House rentals Chicago
- Family-friendly rentals Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Rentals with pools Chicago
- Rentals with lake access Chicago
- Rentals with a balcony Chicago
- Condo rentals Chicago
- Rentals with a hot tub Chicago
- Bed and breakfasts Chicago
- Boutique hotel rentals Chicago
- Guesthouse rentals Chicago
- Apartment rentals Downtown Chicago
- Apartment rentals Milwaukee
- Apartment rentals Lake Geneva
- Apartment rentals Illinois
- Apartment rentals Cook County
- 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