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
4.97 out of 5 average rating, 251 reviewsSpacious 1BR apartment in a central location
Apartment in Chicago
4.9 out of 5 average rating, 372 reviewsGreat Location Studio in the Gold Coast!!
Apartment in Forest Park
4.98 out of 5 average rating, 286 reviewsWalk to Oak Park from Our Sunny Turn of the Century Apt
Apartment in Chicago
4.86 out of 5 average rating, 202 reviewsPrivate Queen Bedroom and En Suite Bath
Apartment in Chicago
4.95 out of 5 average rating, 110 reviewsComfortable, modern apartment 20 Min from Downtown
Apartment in Chicago
4.87 out of 5 average rating, 104 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Apartment in Forest Park
5.0 out of 5 average rating, 225 reviewsLike a Treehouse!
Apartment in Chicago
4.91 out of 5 average rating, 373 reviewsThe Grotto of Logan Square
Weekly apartment rentals
Apartment in Chicago
4.99 out of 5 average rating, 181 reviewsNW Chicago Apartment in Safe Neighborhood
Apartment in Chicago
4.81 out of 5 average rating, 370 reviewsWESTERN AVE ARTISTS LOFTS- Park Free
Apartment in Chicago
4.98 out of 5 average rating, 132 reviewsModern Apt with style & comfort in Pilsen Chicago
Apartment in Des Plaines
4.83 out of 5 average rating, 99 reviewsNewly Renovated, Safe, 1 Bdrm, Self Check-in
Apartment in Chicago
4.86 out of 5 average rating, 325 reviewsThe Avondale Garden Unit
Apartment in Oak Park
4.86 out of 5 average rating, 248 reviewsCosmopolitan Nest in Oak Park North Side
Apartment in Chicago
4.9 out of 5 average rating, 283 reviewsModern Logan Square Apartment, steps from train!
Apartment in Chicago
4.96 out of 5 average rating, 249 reviewsNewly remodeled 1BR! Only 5 MIN walk to BLUE LINE!
Private apartment rentals
Apartment in Oak Park
4.92 out of 5 average rating, 106 reviewsLovely, spacious 2bd, 1bath home w/free parking
Apartment in Chicago
4.82 out of 5 average rating, 440 reviewsLovely Andersonville Apt with Ideal Location
Apartment in Chicago
4.79 out of 5 average rating, 173 reviewsPerfect 1br In Lincoln Park - Steps to Depaul!
Apartment in Chicago
4.86 out of 5 average rating, 175 reviewsAttic apartment in a hip neighborhood!
Apartment in Chicago
4.79 out of 5 average rating, 107 reviewsWelcome Chez Moi
Apartment in Berwyn
4.87 out of 5 average rating, 387 reviewsBerwyn Musical Apartment
Apartment in Chicago
4.84 out of 5 average rating, 480 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Apartment in Chicago
4.82 out of 5 average rating, 273 reviews*Entire City Apartment 1 block to Train Park Free
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
- Apartment rentals United States
- Serviced apartment rentals United States
- Fitness-friendly rentals Chicago
- Rentals with lake access Chicago
- Rentals with an accessible height bed Chicago
- Rentals with a washer and dryer Chicago
- Rentals with an EV charger Chicago
- Rentals with a home theater Chicago
- Rentals with outdoor seating Chicago
- Rentals with a sauna Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Rentals with breakfast Chicago
- Rentals with a fire pit Chicago
- Loft rentals Chicago
- Kid-friendly rentals Chicago
- Beachfront rentals Chicago
- Townhouse rentals Chicago
- Rentals with beach access Chicago
- Rentals with pools Chicago
- Rentals with a fireplace Chicago
- Boutique hotel rentals Chicago
- Guesthouse rentals Chicago
- Bed and breakfasts Chicago
- House rentals Chicago
- Condo rentals Chicago
- Rentals with a hot tub Chicago
- Private suite rentals Chicago
- Monthly Rentals Chicago
- Rentals with a balcony Chicago
- Rentals with a patio Chicago
- Mansion rentals Chicago
- Waterfront rentals Chicago
- Smoking-friendly rentals Chicago
- Lakehouse rentals Chicago
- Family-friendly 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