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 Forest Park
4.93 out of 5 average rating, 584 reviewsPeaceful oasis in Forest Park
24 – 31 Aug
Apartment in West Town
4.89 out of 5 average rating, 473 reviewsiKlektik House Chicago / Robin
10 – 17 Dec
Apartment in Chicago
4.92 out of 5 average rating, 186 reviewsTaj Ma-small at Wrigley
1 – 8 Mar
Apartment in Oak Park
4.85 out of 5 average rating, 527 reviewsLong stays welcome@warm&cute vintage 2BR
15 – 22 Oct
Apartment in Logan Square
4.93 out of 5 average rating, 207 reviewsCozy Private Coach House
25 July – 1 Aug
Apartment in Irving Park
4.89 out of 5 average rating, 176 reviewsHistoric Chicago neighborhood flat
10 – 17 Nov
Apartment in Logan Square
4.87 out of 5 average rating, 484 reviewsLogan Square Studio
2 – 9 Jan
Apartment in Lake View
4.86 out of 5 average rating, 201 reviewsPrivate Queen Bedroom and En Suite Bath
3 – 10 July
Private apartment rentals
Apartment in Chicago
4.86 out of 5 average rating, 101 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
13 – 20 Apr
Apartment in Chicago
4.84 out of 5 average rating, 175 reviewsThe Cottage
3 – 10 Oct
Apartment in Andersonville
4.98 out of 5 average rating, 249 reviewsAndersonville Cozy 1 bedroom basement suite
26 Nov – 3 Dec
Apartment in Logan Square
4.9 out of 5 average rating, 283 reviewsModern Logan Square Apartment, steps from train!
1 – 8 Jan
Apartment in Chicago
4.84 out of 5 average rating, 130 reviewsPerfect Private Getaway in Perfect Pilsen
6 – 13 Aug
Apartment in Wicker Park
4.84 out of 5 average rating, 479 reviewsRelaxed Bucktown/Wicker Park 1B Apt
14 – 21 Oct
Apartment in Chicago
4.95 out of 5 average rating, 106 reviewsComfortable, modern apartment 20 Min from Downtown
5 – 12 Mar
Apartment in Chicago
4.79 out of 5 average rating, 172 reviewsPerfect 1br In Lincoln Park - Steps to Depaul!
4 – 11 Jan
Apartment rentals with a hot tub
Apartment in Berwyn
4.91 out of 5 average rating, 201 reviews“Dream slice of urban homesteading.”
9 – 16 Feb
Apartment in Chicago
4.88 out of 5 average rating, 393 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
16 – 23 July
Apartment in Chicago
4.86 out of 5 average rating, 155 reviewsStunning Panoramic Chicago Views & Free Parking
2 – 9 Nov
Apartment in West Loop
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
15 – 22 May
Apartment in Chicago
4.93 out of 5 average rating, 28 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
10 – 17 Mar
Apartment in Chicago
5.0 out of 5 average rating, 16 reviewsSpacious Beautiful Condo
10 – 17 Sept
Apartment in Streeterville
5.0 out of 5 average rating, 9 reviewsLake, City, & River View Condo
6 – 13 May
Apartment in Chicago
4.79 out of 5 average rating, 24 reviewsThe Professional's Playground
2 – 9 Jan
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
- Bed and breakfasts Chicago
- Rentals with a patio Chicago
- Rentals with breakfast Chicago
- Rentals with pools Chicago
- Rentals with a balcony Chicago
- Rentals with an accessible height bed Chicago
- Monthly Rentals Chicago
- Rentals with lake access Chicago
- Beachfront rentals Chicago
- Rentals with beach access Chicago
- Rentals with a washing machine and dryer Chicago
- Townhouse rentals Chicago
- Rentals with a sauna Chicago
- Waterfront rentals Chicago
- Family-friendly rentals Chicago
- Kid-friendly rentals Chicago
- Loft rentals Chicago
- Rentals with a home theatre Chicago
- Villa rentals Chicago
- Rentals with a fire pit Chicago
- Rentals with outdoor seating Chicago
- Fitness-friendly rentals Chicago
- House rentals Chicago
- Boutique hotel rentals Chicago
- Rentals with an EV charger Chicago
- Rentals with a hot tub Chicago
- Hotel rentals Chicago
- Lakehouse rentals Chicago
- Pet-friendly rentals Chicago
- Guesthouse rentals Chicago
- Private suite rentals Chicago
- Condo rentals Chicago
- Smoking-friendly rentals Chicago
- Mansion rentals Chicago
- Rentals with a fireplace Chicago
- Cottage rentals 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