Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
NEW
NEW
Experiences
Experiences, new
NEW
NEW
Services
Services, new
Start your search
Location
Homes in Chicago
Check in / Check out
Any week
Guests
Add guests
Become a host
Help Centre
Become a host
It’s easy to start hosting and earn extra income.
Refer a host
Find a co-host
Log in or sign up
filters
Any
Home
Hotel
Filters
Show map
Search results; Over 1,000 homes in Chicago
Over 1,000 homes in Chicago
Top guest favourite
Guest favourite
Flat in Chicago
Gym, Garage Parking, Balcony, Sleeps 4
2 bedrooms
,
·
2 beds
,
·
2 private bathrooms
14–19 Aug
14–19 Aug
$3,527 SGD
Show price breakdown
for 5 nights
$3,527 SGD for 5 nights
,
·
5.0 out of 5 average rating, 34 reviews
5.0 (34)
Guest favourite
Guest favourite
Room in Chicago
Private Room in Norwood Park
1 bed
1 bed
1 bathroom
,
·
1 bathroom
14–19 Jun
14–19 Jun
$425 SGD
$341 SGD
Show price breakdown
for 5 nights
Free cancellation
4.97 out of 5 average rating, 37 reviews
4.97 (37)
Top guest favourite
Guest favourite
Room in Chicago
Fresh and Sunny Bed & Bath by UofC
1 queen bed
1 queen bed
1 bathroom
,
·
1 bathroom
29 Aug – 3 Sept
29 Aug – 3 Sept
$704 SGD
Show price breakdown
for 5 nights
$704 SGD for 5 nights
Free cancellation
4.91 out of 5 average rating, 255 reviews
4.91 (255)
Superhost
Superhost
Flat in Clarendon Hills
Clarendon Hills Apartment
2 bedrooms
2 bedrooms
2 beds
,
·
2 beds
1.5 bathrooms
,
·
1.5 bathrooms
22–27 Jun
22–27 Jun
$1,192 SGD
Show price breakdown
for 5 nights
$1,192 SGD for 5 nights
Free cancellation
New place to stay
New
Superhost
Superhost
Flat in Chicago
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
2 bedrooms
2 bedrooms
3 beds
,
·
3 beds
1 bathroom
,
·
1 bathroom
19–24 Jul
19–24 Jul
$1,947 SGD
Show price breakdown
for 5 nights
$1,947 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Flat in Chicago
Comfortable 2BR Stay Near Restaurants & Transit
2 bedrooms
2 bedrooms
3 beds
,
·
3 beds
1 bathroom
,
·
1 bathroom
14–19 Jun
14–19 Jun
$1,834 SGD
$1,073 SGD
Show price breakdown
for 5 nights
Free cancellation
New place to stay
New
Top guest favourite
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms
2 bedrooms
3 beds
,
·
3 beds
1.5 bathrooms
,
·
1.5 bathrooms
12–17 Oct
12–17 Oct
$1,545 SGD
Show price breakdown
for 5 nights
$1,545 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 114 reviews
4.95 (114)
Flat in Chicago
Chicago Classic•Skyline View•1BR + Den, Train Near
1 bedroom
1 bedroom
5 beds
,
·
5 beds
1 bathroom
,
·
1 bathroom
28 Jun – 3 Jul
28 Jun – 3 Jul
$1,028 SGD
Show price breakdown
for 5 nights
$1,028 SGD for 5 nights
Free cancellation
New place to stay
New
Top guest favourite
Guest favourite
Flat in Chicago
Boho City Escape | Parking + Balcony
2 bedrooms
2 bedrooms
3 beds
,
·
3 beds
2 bathrooms
,
·
2 bathrooms
28 Jun – 3 Jul
28 Jun – 3 Jul
$2,229 SGD
$2,007 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 14 reviews
5.0 (14)
Top guest favourite
Guest favourite
Apartment in Chicago
Your Chicago Retreat
3 bedrooms
3 bedrooms
3 queen beds
,
·
3 queen beds
1.5 bathrooms
,
·
1.5 bathrooms
28 Jun – 3 Jul
28 Jun – 3 Jul
$2,261 SGD
Show price breakdown
for 5 nights
$2,261 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 299 reviews
4.99 (299)
Top guest favourite
Guest favourite
Flat in Chicago
Luxe Wrigley Estate: Pool Table + Parking + Patio
4 bedrooms
4 bedrooms
7 beds
,
·
7 beds
2 bathrooms
,
·
2 bathrooms
22–27 Jun
22–27 Jun
$5,254 SGD
$4,332 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Superhost
Superhost
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms
2 bedrooms
2 beds
,
·
2 beds
2 bathrooms
,
·
2 bathrooms
5–10 Jul
5–10 Jul
$1,666 SGD
$1,510 SGD
Show price breakdown
for 5 nights
Free cancellation
4.95 out of 5 average rating, 155 reviews
4.95 (155)
Hotel in Chicago
Perfect Destination! Onsite Bar and Restaurant!
1 bedroom
1 bedroom
1 king bed
,
·
1 king bed
1 bathroom
,
·
1 bathroom
21–26 Jun
21–26 Jun
$1,720 SGD
Show price breakdown
for 5 nights
$1,720 SGD for 5 nights
Free cancellation
Guest favourite
Guest favourite
Room in North Riverside
The Albany Park Room at the Cape Cod in Riverside
1 queen bed
1 queen bed
1 bathroom
,
·
1 bathroom
17–22 Aug
17–22 Aug
$644 SGD
Show price breakdown
for 5 nights
$644 SGD for 5 nights
Free cancellation
4.93 out of 5 average rating, 255 reviews
4.93 (255)
Top guest favourite
Guest favourite
Guest suite in Chicago
Private Lincoln Square one bed+bath studio apt.
1 bedroom
1 bedroom
1 queen bed
,
·
1 queen bed
1 bathroom
,
·
1 bathroom
12–17 Oct
12–17 Oct
$1,174 SGD
Show price breakdown
for 5 nights
$1,174 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 421 reviews
4.99 (421)
Place to stay in Chicago
Private Room for 3 Guests By Grand Ave Blueline
1 bedroom
1 bedroom
2 beds
,
·
2 beds
2 bathrooms
,
·
2 bathrooms
4–9 Jul
4–9 Jul
$959 SGD
Show price breakdown
for 5 nights
$959 SGD for 5 nights
Free cancellation
Townhouse in Chicago
Walk to United Center 9 mins-Downtown FreeParking
3 bedrooms
3 bedrooms
3 beds
,
·
3 beds
3 bathrooms
,
·
3 bathrooms
14–19 Jun
14–19 Jun
$1,970 SGD
Show price breakdown
for 5 nights
$1,970 SGD for 5 nights
Free cancellation
4.67 out of 5 average rating, 6 reviews
4.67 (6)
Apartment in Chicago
The Langley Luxe modern style unit
2 bedrooms
2 bedrooms
3 beds
,
·
3 beds
1 bathroom
,
·
1 bathroom
28 Jun – 3 Jul
28 Jun – 3 Jul
$1,211 SGD
Show price breakdown
for 5 nights
$1,211 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms
2 bedrooms
2 queen beds
,
·
2 queen beds
2 bathrooms
,
·
2 bathrooms
12–17 Oct
12–17 Oct
$1,961 SGD
Show price breakdown
for 5 nights
$1,961 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 44 reviews
5.0 (44)
1
2
3
4
…
15