Holiday rentals in Downtown Chicago
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Downtown Chicago
Guests agree: these stays are highly rated for location, cleanliness and more.
0 of 0 items showing
1 of 3 pages
1 of 3 pages
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Downtown Chicago holiday rentals
Other great holiday rentals in Downtown Chicago
Guest favourite
Loft in Lake View
4.96 out of 5 average rating, 420 reviewsLakeview Loft-Vintage Chicago, Modern Amenities
22–29 Mar
£156 per night
Guest favourite
Flat in Little Italy
4.98 out of 5 average rating, 199 reviewsSpacious 2BR on Quiet St - Free Park/Late Checkout
20–27 Jan
£185 per night
Guest favourite
Home in Roscoe Village
4.94 out of 5 average rating, 210 reviewsModern Home RoscoeVillage/Wrigley Free St Parking
23 Feb – 2 Mar
£134 per night
Guest favourite
Flat in Chicago
4.98 out of 5 average rating, 130 reviewsModern Apt with style & comfort in Pilsen Chicago
5–12 Jul
£145 per night
Superhost
Flat in Near West Side
4.81 out of 5 average rating, 270 reviewsThe Banksy-Greystone Rooftop Firepit United Center
Guest favourite
Guest suite in East Pilsen
4.92 out of 5 average rating, 115 reviewsEntirely Private Suite - Urban Oasis - Pilsen/UIC
6–13 Jul
£127 per night
Superhost
Flat in Chicago
4.84 out of 5 average rating, 175 reviewsLa Cottage
26 Sept – 3 Oct
£82 per night
Guest favourite
Flat in Cicero
4.98 out of 5 average rating, 202 reviewsCOZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
25 Feb – 4 Mar
£116 per night
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
- Rentals with pools Downtown Chicago
- Rentals with a patio Downtown Chicago
- Flat rentals Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Waterfront rentals Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Loft rentals Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Rentals with beach access Downtown Chicago
- Rentals with lake access Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Monthly Rentals Downtown Chicago
- Hotel rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Beachfront rentals Downtown Chicago
- House rentals Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Rentals with a cinema Downtown Chicago
- 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