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
Cozy loft in Chicago's Uptown
1 bedroom
,
·
2 beds
,
·
1 private bathroom
16–21 Oct
16–21 Oct
$1,113 SGD
Show price breakdown
for 5 nights
$1,113 SGD for 5 nights
,
·
4.97 out of 5 average rating, 331 reviews
4.97 (331)
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
$1,216 SGD
Show price breakdown
for 5 nights
$1,216 SGD for 5 nights
Free cancellation
New place to stay
New
Guest favourite
Guest favourite
Flat in Chicago
Hancock Lookout|Steps to Beach&Transit, CHI Views
2 bedrooms
2 bedrooms
3 queen beds
,
·
3 queen beds
2 bathrooms
,
·
2 bathrooms
16–21 Aug
16–21 Aug
$3,202 SGD
$2,799 SGD
Show price breakdown
for 5 nights
Free cancellation
4.97 out of 5 average rating, 39 reviews
4.97 (39)
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
$1,940 SGD
Show price breakdown
for 5 nights
$1,940 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Guest favourite
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom
1 bedroom
1 queen bed
,
·
1 queen bed
1 bathroom
,
·
1 bathroom
11–16 Jun
11–16 Jun
$2,754 SGD
$2,391 SGD
Show price breakdown
for 5 nights
Free cancellation
4.98 out of 5 average rating, 54 reviews
4.98 (54)
Top guest favourite
Guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms
2 bedrooms
2 queen beds
,
·
2 queen beds
1 bathroom
,
·
1 bathroom
9–14 Aug
9–14 Aug
$1,369 SGD
Show price breakdown
for 5 nights
$1,369 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 61 reviews
4.97 (61)
Guest favourite
Guest favourite
Rooms in Chicago
Spacious Haven in North Park
3 bedrooms
3 bedrooms
4 beds
,
·
4 beds
1 bathroom
,
·
1 bathroom
21–26 Sept
21–26 Sept
$821 SGD
Show price breakdown
for 5 nights
$821 SGD for 5 nights
Free cancellation
4.9 out of 5 average rating, 60 reviews
4.9 (60)
Top guest favourite
Guest favourite
Apartment in Chicago
Lincoln Square Gem!
2 bedrooms
2 bedrooms
2 queen beds
,
·
2 queen beds
1 bathroom
,
·
1 bathroom
25–30 Oct
25–30 Oct
$1,075 SGD
Show price breakdown
for 5 nights
$1,075 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 488 reviews
4.97 (488)
Superhost
Superhost
Flat in Chicago
Well Located Studio on the Red Line
1 queen bed
1 queen bed
1 bathroom
,
·
1 bathroom
5–10 Jul
5–10 Jul
$1,450 SGD
Show price breakdown
for 5 nights
$1,450 SGD for 5 nights
Free cancellation
New place to stay
New
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
$1,968 SGD
Show price breakdown
for 5 nights
$1,968 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 43 reviews
5.0 (43)
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
$1,178 SGD
Show price breakdown
for 5 nights
$1,178 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 421 reviews
4.99 (421)
Top guest favourite
Guest favourite
Room in Chicago
Al's Oasis Chicago
1 queen bed
1 queen bed
1 bathroom
,
·
1 bathroom
5–10 Jul
5–10 Jul
$768 SGD
Show price breakdown
for 5 nights
$768 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 226 reviews
4.96 (226)
Top guest favourite
Guest favourite
Loft in Chicago
Lakeview Loft-Vintage Chicago, Modern Amenities
1 bedroom
1 bedroom
2 beds
,
·
2 beds
1 bathroom
,
·
1 bathroom
8–13 Nov
8–13 Nov
$1,026 SGD
Show price breakdown
for 5 nights
$1,026 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 578 reviews
4.96 (578)
Place to stay in Chicago
On The Go Travelers 1 Private Bdrm & BR
1 bedroom
1 bedroom
1 bed
,
·
1 bed
1 bathroom
,
·
1 bathroom
16–21 Jun
16–21 Jun
$540 SGD
Show price breakdown
for 5 nights
$540 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
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
$2,269 SGD
Show price breakdown
for 5 nights
$2,269 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 299 reviews
4.99 (299)
Top guest favourite
Guest favourite
Home in Oak Park
Grove Flat
2 bedrooms
2 bedrooms
2 beds
,
·
2 beds
1 bathroom
,
·
1 bathroom
15–20 Aug
15–20 Aug
$1,220 SGD
Show price breakdown
for 5 nights
$1,220 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Superhost
Superhost
Flat in Chicago
Corporate Smart Home At River Walk
1 bedroom
1 bedroom
1 queen bed
,
·
1 queen bed
1 bathroom
,
·
1 bathroom
21–26 Jun
21–26 Jun
$1,860 SGD
Show price breakdown
for 5 nights
$1,860 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Guest favourite
Guest favourite
Flat in Chicago
Lovely Lincoln Park 2BD/2BA (+parking)
2 bedrooms
2 bedrooms
3 beds
,
·
3 beds
2 bathrooms
,
·
2 bathrooms
27 Jun – 2 Jul
27 Jun – 2 Jul
$2,746 SGD
$2,070 SGD
Show price breakdown
for 5 nights
Free cancellation
4.94 out of 5 average rating, 95 reviews
4.94 (95)
Top guest favourite
Guest favourite
Flat in Chicago
Coach House in Historic Old Town Chicago
1 bedroom
1 bedroom
2 beds
,
·
2 beds
1 bathroom
,
·
1 bathroom
5–10 Jul
5–10 Jul
$1,702 SGD
Show price breakdown
for 5 nights
$1,702 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 126 reviews
4.96 (126)
1
2
3
4
…
15