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
Filters
Price
Type of place
Show map
Search results; Over 1,000 homes in Chicago
Over 1,000 homes in Chicago
Superhost
Superhost
Apartment in Chicago
Spacious 5-BR Apt next to transit Free Parking
5 bedrooms
,
·
5 beds
,
·
1.5 shared bathrooms
18–23 Oct
18–23 Oct
$1,825 SGD
Show price breakdown
for 5 nights
$1,825 SGD for 5 nights
,
·
4.89 out of 5 average rating, 114 reviews
4.89 (114)
Top guest favourite
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
25–30 Oct
25–30 Oct
$1,353 SGD
$1,163 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
4.95 out of 5 average rating, 119 reviews
4.95 (119)
Guest favourite
Guest favourite
Home in Chicago
Chicago Row House Garden Apartmt
1 bedroom
1 bedroom
,
·
1 bed
1 bed
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,144 SGD
Show price breakdown
for 5 nights
$1,144 SGD for 5 nights
Pay $0 today
Free cancellation
4.91 out of 5 average rating, 58 reviews
4.91 (58)
Top guest favourite
Guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
30 Aug – 4 Sept
30 Aug – 4 Sept
$1,390 SGD
Show price breakdown
for 5 nights
$1,390 SGD for 5 nights
Pay $0 today
Free cancellation
4.97 out of 5 average rating, 64 reviews
4.97 (64)
Top guest favourite
Guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
27 Sept – 2 Oct
27 Sept – 2 Oct
$2,073 SGD
Show price breakdown
for 5 nights
$2,073 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 19 reviews
5.0 (19)
Guest favourite
Guest favourite
Flat in Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
2 bedrooms
2 bedrooms
16–21 Aug
16–21 Aug
$2,662 SGD
$1,982 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
4.95 out of 5 average rating, 19 reviews
4.95 (19)
Top guest favourite
Guest favourite
Flat in Chicago
A Whimsical Fairy-tale Loft in Ravenswood Chicago
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
30 Aug – 4 Sept
30 Aug – 4 Sept
$1,407 SGD
$1,245 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
4.99 out of 5 average rating, 348 reviews
4.99 (348)
Guest favourite
Guest favourite
103
Reviews
4.91
Stars
Rating
15
Years hosting
Room in Chicago
Lovely Front Room in a New Renovated Apartment
2 single beds
2 single beds
22–27 Sept
22–27 Sept
$504 SGD
Show price breakdown
for 5 nights
$504 SGD for 5 nights
Pay $0 today
Free cancellation
4.91 out of 5 average rating, 103 reviews
4.91 (103)
Guest favourite
Guest favourite
Flat in Chicago
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
9–14 Aug
9–14 Aug
$1,640 SGD
Show price breakdown
for 5 nights
$1,640 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Superhost
Superhost
5
Reviews
4.4
Stars
Rating
8
Months hosting
Place to stay in Chicago
Woodlawn Beauty: Room 2
3 bedrooms
3 bedrooms
,
·
3 queen beds
3 queen beds
3–8 Aug
3–8 Aug
$366 SGD
Show price breakdown
for 5 nights
$366 SGD for 5 nights
Pay $0 today
Free cancellation
4.4 out of 5 average rating, 5 reviews
4.4 (5)
Top guest favourite
Guest favourite
Home in Chicago
West Town Gem: 2BR w/ Patio, W/D + Free Parking
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
15–20 Aug
15–20 Aug
$2,204 SGD
Show price breakdown
for 5 nights
$2,204 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 12 reviews
5.0 (12)
Guest favourite
Guest favourite
Flat in Chicago
NW Chicago Garden Apartment
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
8–13 Sept
8–13 Sept
$887 SGD
Show price breakdown
for 5 nights
$887 SGD for 5 nights
Pay $0 today
Free cancellation
4.92 out of 5 average rating, 51 reviews
4.92 (51)
Top guest favourite
Guest favourite
Flat in Forest Park
1 bedroom garden apartment in Forest Park
1 bedroom
1 bedroom
,
·
2 beds
2 beds
28 Sept – 3 Oct
28 Sept – 3 Oct
$897 SGD
Show price breakdown
for 5 nights
$897 SGD for 5 nights
Pay $0 today
Free cancellation
4.98 out of 5 average rating, 186 reviews
4.98 (186)
Guest favourite
Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
15–20 Aug
15–20 Aug
$1,704 SGD
$1,565 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
4.96 out of 5 average rating, 161 reviews
4.96 (161)
Top guest favourite
Guest favourite
Guest suite in Chicago
Cozy, Quiet, Garden Getaway!
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
29 Aug – 3 Sept
29 Aug – 3 Sept
$916 SGD
Show price breakdown
for 5 nights
$916 SGD for 5 nights
Pay $0 today
Free cancellation
4.92 out of 5 average rating, 529 reviews
4.92 (529)
Top guest favourite
Guest favourite
Apartment in Chicago
Bright, new 2BR in the heart of East Lakeview
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
23–28 Aug
23–28 Aug
$1,503 SGD
Show price breakdown
for 5 nights
$1,503 SGD for 5 nights
Pay $0 today
Free cancellation
4.99 out of 5 average rating, 128 reviews
4.99 (128)
Top guest favourite
Guest favourite
113
Reviews
4.97
Stars
Rating
3
Years hosting
Rooms in Chicago
Historic North Park home
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
13–18 Sept
13–18 Sept
$649 SGD
Show price breakdown
for 5 nights
$649 SGD for 5 nights
Pay $0 today
Free cancellation
4.97 out of 5 average rating, 113 reviews
4.97 (113)
Place to stay in Chicago
Guest room in Dunning, Chicago IL
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
16–21 Aug
16–21 Aug
$423 SGD
Show price breakdown
for 5 nights
$423 SGD for 5 nights
Pay $0 today
Free cancellation
New place to stay
New
Home in Chicago
Modern Cozy Studio Near Dining & Transit
1 king bed
1 king bed
8–13 Aug
8–13 Aug
$1,105 SGD
$805 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
New place to stay
New
1
2
3
4
…
15