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 Forest Park
4.93 out of 5 average rating, 584 reviewsPeaceful oasis in Forest Park
Aug 24 – 31
Apartment in Chicago
4.89 out of 5 average rating, 473 reviewsiKlektik House Chicago / Robin
Dec 10 – 17
Apartment in Chicago
4.92 out of 5 average rating, 185 reviewsTaj Ma-small at Wrigley
Mar 1 – 8
Apartment in Oak Park
4.85 out of 5 average rating, 527 reviewsLong stays welcome@warm&cute vintage 2BR
Oct 15 – 22
Apartment in Chicago
4.93 out of 5 average rating, 207 reviewsCozy Private Coach House
Jul 25 – Aug 1
Apartment in Irving Park
4.89 out of 5 average rating, 176 reviewsHistoric Chicago neighborhood flat
Nov 10 – 17
Apartment in Logan Square
4.87 out of 5 average rating, 484 reviewsLogan Square Studio
Jan 2 – 9
Apartment in Lake View
4.86 out of 5 average rating, 201 reviewsPrivate Queen Bedroom and En Suite Bath
Jul 3 – 10
Weekly apartment rentals
Apartment in Chicago
4.86 out of 5 average rating, 101 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Apr 13 – 20
Apartment in Chicago
4.84 out of 5 average rating, 175 reviewsThe Cottage
Oct 3 – 10
Apartment in Andersonville
4.98 out of 5 average rating, 249 reviewsAndersonville Cozy 1 bedroom basement suite
Nov 26 – Dec 3
Apartment in Chicago
4.9 out of 5 average rating, 283 reviewsModern Logan Square Apartment, steps from train!
Jan 1 – 8
Apartment in Chicago
4.84 out of 5 average rating, 130 reviewsPerfect Private Getaway in Perfect Pilsen
Aug 6 – 13
Apartment in Chicago
4.84 out of 5 average rating, 479 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Oct 14 – 21
Apartment in Chicago
4.95 out of 5 average rating, 106 reviewsComfortable, modern apartment 20 Min from Downtown
Mar 5 – 12
Apartment in Chicago
4.79 out of 5 average rating, 172 reviewsPerfect 1br In Lincoln Park - Steps to Depaul!
Jan 4 – 11
Private apartment rentals
Apartment in Oak Park
4.86 out of 5 average rating, 247 reviewsCosmopolitan Nest in Oak Park North Side
Sep 23 – 30
Apartment in Pilsen Historic District
4.85 out of 5 average rating, 233 reviewsTeeny Tiny Bohemian Lodge - Clean & Affordable
Aug 15 – 22
Apartment in Chicago
4.85 out of 5 average rating, 183 reviewsBucktown Retreat - Why The Buck Not? Sleeps 1-6
Jan 16 – 23
Apartment in Logan Square
4.89 out of 5 average rating, 339 reviewsSunny Logan Square Artists' home
Feb 9 – 16
Apartment in Chicago
4.89 out of 5 average rating, 242 reviewsModern
Oct 16 – 23
Apartment in Oak Park
4.88 out of 5 average rating, 128 reviewsA Little Slice of Heaven in Oak Park, IL
Feb 22 – Mar 1
Apartment in Forest Park
5.0 out of 5 average rating, 219 reviewsLike a Treehouse!
Sep 5 – 12
Apartment in Chicago
4.96 out of 5 average rating, 162 reviews2BR Centrally Located in Cozy Hip Logan Square
Oct 29 – Nov 5
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
- Rentals with a hot tub Chicago
- Pet-friendly rentals Chicago
- Rentals with pools Chicago
- Rentals with a fireplace Chicago
- Condo rentals Chicago
- Hotel rentals Chicago
- Rentals with a home theater Chicago
- Beachfront rentals Chicago
- Guesthouse rentals Chicago
- Private suite rentals Chicago
- Fitness-friendly rentals Chicago
- Kid-friendly rentals Chicago
- Loft rentals Chicago
- Rentals with an accessible height bed Chicago
- Rentals with a sauna Chicago
- Bed and breakfasts Chicago
- House rentals Chicago
- Monthly Rentals Chicago
- Rentals with an EV charger Chicago
- Rentals with a washer and dryer Chicago
- Family-friendly rentals Chicago
- Rentals with a fire pit Chicago
- Rentals with outdoor seating Chicago
- Waterfront rentals Chicago
- Rentals with breakfast Chicago
- Mansion rentals Chicago
- Rentals with a patio Chicago
- Lakehouse rentals Chicago
- Boutique hotel rentals Chicago
- Townhouse rentals Chicago
- Villa rentals Chicago
- Cottage rentals Chicago
- Rentals with beach access Chicago
- Rentals with lake access Chicago
- Smoking-friendly rentals Chicago
- Rentals with a balcony Chicago
- Apartment rentals Downtown Chicago
- Apartment rentals Milwaukee
- Apartment rentals Chicago Loop
- 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