Vacation rentals in Downtown Chicago
Find and book unique accommodations on Airbnb
Top-rated vacation 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
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Downtown Chicago vacation rentals
Other great vacation rentals in Downtown Chicago
Guest favourite
Townhouse in Chicago
4.85 out of 5 average rating, 275 reviewsCITY CONDO with GARAGE 7 min Walk to Train
Nov. 3 – 10
$175 CAD per night
Guest favourite
Guest suite in Lincoln Square
4.97 out of 5 average rating, 361 reviewsPrivate suite in Lincoln Square
Dec. 30 – Jan. 6
$192 CAD per night
Guest favourite
Apartment in Lincoln Park
4.83 out of 5 average rating, 208 reviewsCozy Lincoln Park Studio - Steps to Zoo!
Jan. 10 – 17
$195 CAD per night
Guest favourite
Guest suite in Chicago
4.91 out of 5 average rating, 358 reviewsContemporary, private suite w fireplace
Oct. 22 – 29
$138 CAD per night
Superhost
Apartment in Chicago
4.81 out of 5 average rating, 86 reviewsMcCormick Pl 420 friendly 1br/1ba parking/sleeps 4
Jan. 1 – 8
$178 CAD per night
Guest favourite
Apartment in Chicago
4.89 out of 5 average rating, 76 reviewsMcCormick 2B/2Ba for up to 6 guests w Skyline view
Jan. 20 – 27
$190 CAD per night
Guest favourite
Apartment in Portage Park
4.96 out of 5 average rating, 51 reviewsComfy & Private Chicago Studio
Sep. 26 – Oct. 3
$159 CAD per night
Guest favourite
Condo in Lake View
4.95 out of 5 average rating, 20 reviewsChic & Comfy • Close to Wrigley
Jan. 15 – 22
$214 CAD per night
Destinations to explore
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
- Saugatuck Vacation rentals
- Evanston Vacation rentals
- Holland Vacation rentals
- South Haven Vacation rentals
- Naperville Vacation rentals
- South Side Vacation rentals
- South Bend Vacation rentals
- New Buffalo Vacation rentals
- Chicago Vacation rentals
- Monthly Rentals Downtown Chicago
- Rentals with lake access Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Hotel rentals Downtown Chicago
- Kid-friendly rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Rentals with a patio Downtown Chicago
- House rentals Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Rentals with a washer and dryer Downtown Chicago
- Rentals with beach access Downtown Chicago
- Beachfront rentals Downtown Chicago
- Waterfront rentals Downtown Chicago
- Rentals with pools Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Condo rentals Downtown Chicago
- Rentals with a home theater Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Loft 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