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
Home in Chicago
Chicago Row House Garden Apartmt
1 bedroom
,
·
1 bed
,
·
1 private bathroom
12–17 Oct
12–17 Oct
$1,190 SGD
Show price breakdown
for 5 nights
$1,190 SGD for 5 nights
,
·
4.95 out of 5 average rating, 55 reviews
4.95 (55)
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
25–30 Oct
25–30 Oct
$1,386 SGD
Show price breakdown
for 5 nights
$1,386 SGD for 5 nights
Pay $0 today
Free cancellation
4.95 out of 5 average rating, 119 reviews
4.95 (119)
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
16–21 Aug
16–21 Aug
$1,374 SGD
Show price breakdown
for 5 nights
$1,374 SGD for 5 nights
Pay $0 today
Free cancellation
4.97 out of 5 average rating, 64 reviews
4.97 (64)
Guest favourite
Guest favourite
Room in Chicago
ChicagoChinatownCenterB
1 single bed
1 single bed
,
·
1 bathroom
1 bathroom
6–11 Aug
6–11 Aug
$483 SGD
Show price breakdown
for 5 nights
$483 SGD for 5 nights
Pay $0 today
Free cancellation
4.93 out of 5 average rating, 54 reviews
4.93 (54)
Guest favourite
Guest favourite
Place to stay in Chicago
Large Brand New Room in Hyde Park Close toDowntown
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
23–28 Oct
23–28 Oct
$606 SGD
$554 SGD
Show price breakdown
for 5 nights
Extended stay discount
Pay $0 today
Free cancellation
4.95 out of 5 average rating, 21 reviews
4.95 (21)
Top guest favourite
Guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
5–10 Jul
5–10 Jul
$2,030 SGD
Show price breakdown
for 5 nights
$2,030 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 19 reviews
5.0 (19)
Top guest favourite
Guest favourite
Flat in Chicago
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$918 SGD
Show price breakdown
for 5 nights
$918 SGD for 5 nights
Pay $0 today
Free cancellation
4.93 out of 5 average rating, 337 reviews
4.93 (337)
Superhost
Superhost
Place to stay in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
24–29 Oct
24–29 Oct
$830 SGD
Show price breakdown
for 5 nights
$830 SGD for 5 nights
Pay $0 today
Free cancellation
4.89 out of 5 average rating, 45 reviews
4.89 (45)
Guest favourite
Guest favourite
Room in Chicago
Lovely Front Room in a New Renovated Apartment
2 single beds
2 single beds
,
·
1 bathroom
1 bathroom
22–27 Sept
22–27 Sept
$496 SGD
Show price breakdown
for 5 nights
$496 SGD for 5 nights
Pay $0 today
Free cancellation
4.91 out of 5 average rating, 102 reviews
4.91 (102)
Top guest favourite
Guest favourite
Flat in Forest Park
1 bedroom garden apartment in Forest Park
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
28 Sept – 3 Oct
28 Sept – 3 Oct
$898 SGD
Show price breakdown
for 5 nights
$898 SGD for 5 nights
Pay $0 today
Free cancellation
4.98 out of 5 average rating, 184 reviews
4.98 (184)
Top guest favourite
Guest favourite
Room in Chicago
Cozy Room for One In The Company of Cats -Blueline
1 single bed
1 single bed
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$481 SGD
Show price breakdown
for 5 nights
$481 SGD for 5 nights
Pay $0 today
Free cancellation
4.94 out of 5 average rating, 140 reviews
4.94 (140)
Top guest favourite
Guest favourite
Room in Chicago
Spacious & serene in hip spot. Sleeps 4.
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
16–21 Aug
16–21 Aug
$714 SGD
$550 SGD
Show price breakdown
for 5 nights
Free cancellation
4.92 out of 5 average rating, 519 reviews
4.92 (519)
Top guest favourite
Guest favourite
Flat in Chicago
Fun & cozy getaway w/POOL/game room/FREE parking
1 bedroom
1 bedroom
,
·
3 queen beds
3 queen beds
,
·
1 bathroom
1 bathroom
12–17 Jul
12–17 Jul
$2,756 SGD
Show price breakdown
for 5 nights
$2,756 SGD for 5 nights
4.98 out of 5 average rating, 156 reviews
4.98 (156)
Guest favourite
Guest favourite
Flat in Chicago
Upscale High-Rise Apt · Rooftop Pool + Views
1 bedroom
1 bedroom
,
·
1 double bed
1 double bed
,
·
1 bathroom
1 bathroom
27 Sept – 2 Oct
27 Sept – 2 Oct
$2,025 SGD
$1,811 SGD
Show price breakdown
for 5 nights
Free cancellation
4.97 out of 5 average rating, 31 reviews
4.97 (31)
Guest favourite
Guest favourite
Apartment in Chicago
Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
5–10 Jul
5–10 Jul
$986 SGD
$884 SGD
Show price breakdown
for 5 nights
Free cancellation
4.88 out of 5 average rating, 475 reviews
4.88 (475)
Guest favourite
Guest favourite
Flat in Chicago
NW Chicago Garden Apartment
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
8–13 Sept
8–13 Sept
$905 SGD
Show price breakdown
for 5 nights
$905 SGD for 5 nights
Pay $0 today
Free cancellation
4.92 out of 5 average rating, 50 reviews
4.92 (50)
Guest favourite
Guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
6–11 Sept
6–11 Sept
$1,353 SGD
Show price breakdown
for 5 nights
$1,353 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Guest favourite
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
15–20 Aug
15–20 Aug
$1,981 SGD
Show price breakdown
for 5 nights
$1,981 SGD for 5 nights
Pay $0 today
Free cancellation
4.95 out of 5 average rating, 62 reviews
4.95 (62)
Top guest favourite
Guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
1 bathroom
1 bathroom
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, 112 reviews
4.97 (112)
1
2
3
4
…
15