Apartment vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago apartment rentals
Apartment rentals with air conditioning
Apartment in Chicago
4.96 out of 5 average rating, 113 reviewsComfortable, modern apartment 20 Min from Downtown
Apartment in Oak Park
4.85 out of 5 average rating, 536 reviewsLong stays welcome@warm&cute vintage 2BR
Apartment in Chicago
4.87 out of 5 average rating, 487 reviewsLogan Square Studio
Apartment in Chicago
4.93 out of 5 average rating, 383 reviewsRavenswood Guest House Annex
Apartment in Chicago
4.96 out of 5 average rating, 380 reviewsKing Bed, Huge Spa Shower, Dining Destination
Apartment in Andersonville
4.98 out of 5 average rating, 254 reviewsAndersonville Cozy 1 bedroom basement suite
Apartment in Wicker Park
4.95 out of 5 average rating, 176 reviewsWicker Park/Bucktown Location
Apartment in Logan Square
4.97 out of 5 average rating, 259 reviewsLogan Square 2nd Floor Chicago Victorian
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 Chicago
4.87 out of 5 average rating, 160 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
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 Chicago
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
Apartment in West Loop
5.0 out of 5 average rating, 11 reviewsSkyline Oasis: City & Lake Views
Weekly apartment rentals
Apartment in Chicago
4.99 out of 5 average rating, 183 reviewsNW Chicago Apartment in Safe Neighborhood
Apartment in Chicago
4.89 out of 5 average rating, 475 reviewsiKlektik House Chicago / Robin
Apartment in Logan Square
4.9 out of 5 average rating, 287 reviewsModern Logan Square Apartment, steps from train!
Apartment in Chicago
4.89 out of 5 average rating, 247 reviewsModern
Apartment in Chicago
4.92 out of 5 average rating, 329 reviewsBright, Modern Apartment in a Vintage Greystone
Apartment in Chicago
4.96 out of 5 average rating, 255 reviewsSunny, Cozy, Colorful Andersonville
Apartment in Chicago
4.84 out of 5 average rating, 133 reviewsPerfect Private Getaway in Perfect Pilsen
Apartment in Lake View
4.86 out of 5 average rating, 202 reviewsPrivate Queen Bedroom and En Suite Bath
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 Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
- Saugatuck Vacation rentals
- Evanston Vacation rentals
- Holland Vacation rentals
- South Haven Vacation rentals
- Naperville Vacation rentals
- South Side Vacation rentals
- South Bend Vacation rentals
- New Buffalo Vacation rentals
- Serviced apartment rentals United States
- Apartment rentals United States
- Rentals with lake access Chicago
- Rentals with an accessible height bed Chicago
- Rentals with an EV charger Chicago
- Rentals with a balcony Chicago
- Rentals with a washer and dryer Chicago
- Rentals with a fireplace Chicago
- Family-friendly rentals Chicago
- Rentals with a sauna Chicago
- Kid-friendly rentals Chicago
- Rentals with a patio Chicago
- Loft rentals Chicago
- Rentals with a home theater Chicago
- Rentals with outdoor seating Chicago
- Lakehouse rentals Chicago
- Rentals with an accessible height toilet Chicago
- Fitness-friendly rentals Chicago
- Rentals with breakfast Chicago
- Rentals with a fire pit Chicago
- Private suite rentals Chicago
- Smoking-friendly rentals Chicago
- Rentals with pools Chicago
- Rentals with beach access Chicago
- Townhouse rentals Chicago
- Boutique hotel rentals Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Guesthouse rentals Chicago
- Waterfront rentals Chicago
- Beachfront rentals Chicago
- House rentals Chicago
- Monthly Rentals Chicago
- Condo rentals Chicago
- Rentals with a hot tub Chicago
- Bed and breakfasts Chicago
- Mansion 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