Find the best vacation rental

ACCOMMODATION TYPES

Save Up To 76%

Airbnb, Vacation rentals and hotel deals in Chicago, IL

8.0 (929 reviews)
Freehand Chicago
Hotel · 2 Guests · 1 Bedroom
$134 /night
View deal
Found Chicago powered by Sonder | Double Bunk Room
Apartment · 2 Guests · 1 Bedroom
$97 /night*
View deal
8.8 (994 reviews)
Arlo Chicago
Hotel · 2 Guests · 1 Bedroom
$88 /night
View deal
9.1 (549 reviews)
Aloft Chicago Downtown River North
Hotel · 2 Guests · 1 Bedroom
$127 /night
View deal
6.5 (1291 reviews)
Travelodge by Wyndham Downtown Chicago
Hotel · 2 Guests · 1 Bedroom
$78 /night
View deal
8.8 (665 reviews)
Hyatt Centric The Loop Chicago
Hotel · 2 Guests · 1 Bedroom
$128 /night
View deal
9.0 (672 reviews)
citizenM Chicago Downtown
Hotel · 2 Guests · 1 Bedroom
$104 /night
View deal
9.0 (1022 reviews)
Fairfield Inn and Suites Chicago Downtown-River North
Hotel · 2 Guests · 1 Bedroom
$112 /night
View deal
8.5 (1981 reviews)
River Hotel
Hotel · 2 Guests · 1 Bedroom
$99 /night
View deal
8.6 (7 reviews)
Found Chicago powered by Sonder | Bunk Room
Apartment · 2 Guests · 1 Bedroom
$85 /night*
View deal
8.3 (159 reviews)
The Buckingham Hotel
Hotel · 2 Guests · 1 Bedroom
$122 /night
View deal
9.6 (4 reviews)
Found Chicago powered by Sonder | Queen Room
Apartment · 2 Guests · 1 Bedroom
$117 /night*
View deal
8.7 (997 reviews)
Hyatt Place Chicago River North
Hotel · 2 Guests · 1 Bedroom
$108 /night
View deal
Found Chicago powered by Sonder | Queen Room w/ Bunk Bed
Apartment · 2 Guests · 1 Bedroom
$120 /night*
View deal
8.4 (1137 reviews)
Homewood Suites By Hilton Chicago Downtown South Loop
Hotel · 2 Guests · 1 Bedroom
$105 /night
View deal
8.2 (850 reviews)
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hotel · 2 Guests · 1 Bedroom
$93 /night
View deal
8.4 (1074 reviews)
Hampton Inn Chicago Downtown/N Loop/Michigan Ave
Hotel · 2 Guests · 1 Bedroom
$109 /night
View deal
7.5 (2804 reviews)
Best Western Grant Park Hotel
Hotel · 2 Guests · 1 Bedroom
$83 /night
View deal
8.7 (788 reviews)
The Allegro Royal Sonesta Hotel Chicago Loop
Hotel · 2 Guests · 1 Bedroom
$122 /night
View deal
8.5 (912 reviews)
Homewood Suites by Hilton Chicago Downtown
Hotel · 2 Guests · 1 Bedroom
$118 /night
View deal

Airbnb, Vacation Rentals, House with Full Kitchen, and Other Rental Options in Chicago, IL

Getaway with Friends! 2 Great Units, Shop at Shops at Northbridge
Holiday home · 2 Guests · 1 Bedroom
$317 /night*
View deal
Downtown Getaway! 2 Relaxing Units, Parking, Pets Allowed, Art Galleries Onsite!
Holiday home · 2 Guests · 1 Bedroom
$345 /night*
View deal
What Are The Top Amenities at Chicago, IL?
Amenity Overview in Chicago, IL
+
There are in total of 15 rental amenities in Chicago, shown above with the property numbers. In Chicago, 1671 rentals offer Internet or Wifi, 1453 rentals offer Air Conditioning, 1386 rentals offer TV. So, if you need Internet or Wifi during your vacation, use the Internet or Wifi filter to compare these properties. Two amenities that are not typical are Hot Tub, Fireplace.
Which Price Range Is Considered As A Good Deal in Chicago, IL Area?
Vacation Rentals Price Information in Chicago, IL
+
The graph shows the percentages of vacation homes in each price bucket. Chicago has the largest percentage (27.59%) of homes in $100 - $150 price range.
$0 to 50
$0 to 50
$50 to 100
$50 to 100
$100 to 150
$100 to 150
$150 to 200
$150 to 200
$200 to 250
$200 to 250
$250 to 300
$250 to 300
$300 to 350
$300 to 350
$350 to 400
$350 to 400
$400 to 450
$400 to 450
$450 to 500
$450 to 500
$500 +
$500 +
What Are The Most Liked Rental Accommodations in Chicago, IL?
Most Picked Accommodations in Chicago, IL
+
Before visiting Chicago, it is a good idea to explore all the accommodation types in this area, and pick the one that fits your group well. All the available accommodation types are: Apartment, House, Studio, Condo, Townhome, Guest House, Hotel, Building, Bungalow, Corporate Apartment, Tower, Resort, Bed And Breakfast, Yacht, Hotel Suites, Estate, Cottage. Apartment is the most-liked rental type, with the largest percentage of 57.42%. The biggest home in this area available for rent is around 21528 square feet.The least popular accommodation in Chicago is Cottage rentals
How Many Accommodations Are Pets Allowed in Chicago, IL?
Pets Allowed vs Not Allowed in Chicago, IL
+
17.57% of vacation homes in Chicago are pet friendly. Make sure you select the pet friendly home filter when you are going to bring your pet(s) for the upcoming vacation.
Trail Recommendations in Chicago, IL Area?
Must Visit Trails In Chicago, IL
+
If you like outdoor activities, we highly recommend you to visit those famous trails: Wicker Park Trail, Chicago Riverwalk to Grant Park Trail, Public Outdoor Art Walking Tour, Millennium Park Trail, Museum and Lakefront Walking Tour, Chicago Riverwalk, Navy Pier Walk, Magnificent Mile and Navy Pier - Chicago, Lincoln Park Trail, Wrigleyville Cultural Walking Tour.
Where Are The Campgrounds in Chicago, IL Area?
Top Rated Campgrounds In Chicago, IL
+
For campgrounds in Chicago, here are our recommendations: Indian Creek, Lakeshore East, Illinois Beach Campground, Chicago Northwest KOA, Cliffside Park Campground, Indiana Dunes Campground, Cedar Lake, Kankakee River Campground, Warren Dunes Campground, Rutherford Mountain Campground.
Which Airports Should I Choose To Get To Chicago, IL?
Suggested Airports in Chicago, IL
+

Airbnb, Vacation Rentals, Condo with Pool in Chicago, IL

Level Chicago River North
Apartment · 2 Guests · 1 Bedroom
$248 /night
View deal
9.6 (21 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Apartment · 2 Guests · 1 Bedroom
$340 /night*
View deal
* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
See all offers