Apartment holiday rentals in Downtown Chicago
Find and book unique apartments on Airbnb
Top-rated apartment rentals in Downtown 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 Downtown Chicago apartment rentals
Weekly apartment rentals
Apartment in Chicago
Chic and Charming Vintage Condominium in Lincoln Park
Apartment in Chicago
Humboldt Park Traveler's Lodge
Apartment in Chicago
Spacious 4 Bedroom Condo
Apartment in Chicago
Urban Luxury 1BR/2BA Logan Square Condo w/Garage
Apartment in Oak Park
Picture Perfect 3Bed Steps from Train and FLW
Apartment in Chicago
Cozy Apartment with Free On-Site Parking
Apartment in Chicago
Modern/Spacious 2BR/2BA West Town
Apartment in Chicago
Wrigleyville Inn. Historic Greystone. Parking pass
Pet-friendly apartment rentals
Apartment in Evanston
Spacious Evanston Unit - Walk to Northwestern U
Apartment in Chicago
❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D
Apartment in Chicago
2 King Bed Condo Easy Downtown Free Street Parking
Apartment in Chicago
Susie's Space. 2BR easy parking & pet friendly
Apartment in Chicago
Charming Chinatown Home by McCormick★Downtown
Apartment in Chicago
Clifton Garden Oasis 1 Min Walk to Wrigley
Apartment in Chicago
Modern Luxury In Old Town - Sleeps 4
Apartment in Chicago
Modern designed 2bed/2bath | Heart of Bronzeville!
Apartment rentals with a pool
Apartment in Chicago
Central Downtown Location-Modern 2BR Condo
Apartment in Evanston
Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Apartment in Elk Grove Village
Just remodeled apartment close to airport and mall
Apartment in Lombard
Pond View, Washer Dryer, Non Smoking, Pet Free
Apartment in Chicago
Lovely condo studio
Apartment in Chicago
1 bedroom in the heart of downtown Chicago.
Private room in Hillside
Lovely Guest Room W private bath rm.
Apartment in Evanston
"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Destinations to explore
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Chicago Holiday rentals
- Apartment rentals Chicago
- Rentals with a patio Downtown Chicago
- Hotel rentals Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- House rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Beachfront rentals Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Rentals with pools Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Rentals with lake access Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Rentals with beach access Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Waterfront rentals Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Flat rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with a cinema Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Monthly Rentals Downtown Chicago
- Loft rentals Downtown Chicago
- Townhouse 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