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
Rental unit in Chicago
Bright, Modern Apartment in a Vintage Greystone
Rental unit in Chicago
Roscoe Village One Bed Lux Apartment Near Wrigley
Rental unit in Chicago
Modern Apt with style & comfort in Pilsen Chicago
Rental unit in Chicago
King Bed, Huge Spa Shower, Dining Destination
Rental unit in Chicago
Comfortable, modern apartment 20 Min from Downtown
Rental unit in Chicago
Lovely Andersonville Apt with Ideal Location
Rental unit in Chicago
Sunny Logan Square Artists' home
Rental unit in Chicago
Cozy Garden Apartment in Heart of Pilsen
Private apartment rentals
Rental unit in Chicago
*Entire City Apartment 1 block to Train Park Free
Rental unit in Chicago
Relaxed Bucktown/Wicker Park 1B Apt
Rental unit in Chicago
Your brand new Chicago suite (unit 1F)
Rental unit in Chicago
Explore Lincoln Park from a Polished Apartment
Rental unit in Chicago
Cute, Clean, Cozy Apartment in Pilsen
Rental unit in Chicago
Cozy loft in Chicago's Uptown
Rental unit in Chicago
McCormick 2B/2Ba w opt parking for up to 6 guests
Rental unit in Chicago
Avondale Cozy 1 Bedroom Attic Apartment 4th FL
Apartment rentals with a hot tub
Rental unit in Chicago
Checkerboard Studio with Private Outdoor Hot Tub and Yard
Rental unit in Berwyn
“Dream slice of urban homesteading.”
Rental unit in Chicago
Skyline Serenity: Sauna, Hot Tub, Peloton, Views
Rental unit in Chicago
Cloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Rental unit in Chicago
Luxe Suite + Spa House Retreat! Pets Welcome
Rental unit in Chicago
Lake, City, & River View Condo
Rental unit in Chicago
The Areal Oasis
Rental unit in Chicago
Spacious Beautiful Condo
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
- Flat rentals United States
- Serviced apartment rentals United States
- Flat rentals Chicago
- Rentals with a patio Downtown Chicago
- Waterfront rentals Downtown Chicago
- Rentals with pools Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Beachfront rentals Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Townhouse rentals Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Loft rentals Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Monthly Rentals Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with a cinema Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Rentals with lake access Downtown Chicago
- Rentals with beach access Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Hotel rentals Downtown Chicago
- House rentals Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Flat rentals Milwaukee
- Flat rentals Lake Geneva
- Flat rentals Illinois
- Flat 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