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
Home in Roscoe Village
4.94 out of 5 average rating, 209 reviewsModern Home RoscoeVillage/Wrigley Free St Parking
7–14 Feb
€ 153 per night
Superhost
Flat in Chicago
4.84 out of 5 average rating, 175 reviewsLa Cottage
3–10 Oct
€ 97 per night
Guest favourite
Townhouse in Near West Side
4.85 out of 5 average rating, 275 reviewsCITY CONDO with GARAGE 7 min Walk to Train
3–10 Nov
€ 121 per night
Guest favourite
Flat in Chicago
4.98 out of 5 average rating, 128 reviewsModern Apt with style & comfort in Pilsen Chicago
10–17 Jul
€ 171 per night
Guest favourite
Guest suite in Chicago
4.98 out of 5 average rating, 111 reviewsGorgeous Studio 15 Minutes From Ohare!
13–20 Sep
€ 115 per night
Guest favourite
Flat in Uptown
4.96 out of 5 average rating, 265 reviewsCozy loft in Chicago's Uptown
16–23 Oct
€ 133 per night
Superhost
Flat in Chicago
4.79 out of 5 average rating, 66 reviewsMcCormick Place Studio/parking/sleeps up to 4
11–18 Feb
€ 103 per night
Guest favourite
Flat in Chicago
4.97 out of 5 average rating, 31 reviewsSerene Escape with King Sleep Number Bed, No Fees!
12–19 Dec
€ 124 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
- Apartment rentals Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Rentals with beach access Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Rentals with a cinema Downtown Chicago
- Flat rentals Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Monthly Rentals Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Rentals with pools Downtown Chicago
- Beachfront rentals Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Loft rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Rentals with a firepit Downtown Chicago
- House rentals Downtown Chicago
- Rentals with a patio Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Rentals with lake access Downtown Chicago
- Hotel rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Waterfront rentals 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