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
Guest suite in Chicago
Boutique Garden Suite • Pilsen • 10 Min to Loop
1 bedroom
,
·
1 bed
,
·
1 private bathroom
1–6 Jul
1–6 Jul
$2,289 SGD
Show price breakdown
for 5 nights
$2,289 SGD for 5 nights
,
·
4.95 out of 5 average rating, 220 reviews
4.95 (220)
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
$1,351 SGD
Show price breakdown
for 5 nights
$1,351 SGD for 5 nights
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
Free cancellation
4.97 out of 5 average rating, 64 reviews
4.97 (64)
Top guest favourite
Guest favourite
Home in Chicago
Chicago Row House Garden Apartmt
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
12–17 Oct
12–17 Oct
$1,190 SGD
Show price breakdown
for 5 nights
$1,190 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 55 reviews
4.95 (55)
Top guest favourite
Guest favourite
Room in Chicago
NEW,Roscoe Village,Cubs, Pvt Bath, Pvt Entrance
3 beds
3 beds
,
·
1 bathroom
1 bathroom
25–30 Oct
25–30 Oct
$796 SGD
$719 SGD
Show price breakdown
for 5 nights
Free cancellation
4.95 out of 5 average rating, 678 reviews
4.95 (678)
Guest favourite
Guest favourite
Room in Chicago
ChicagoChinatownCenterB
1 single bed
1 single bed
,
·
1 bathroom
1 bathroom
6–11 Aug
6–11 Aug
$482 SGD
Show price breakdown
for 5 nights
$482 SGD for 5 nights
4.93 out of 5 average rating, 55 reviews
4.93 (55)
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
3–8 Jul
3–8 Jul
$2,383 SGD
$1,414 SGD
Show price breakdown
for 5 nights
4.97 out of 5 average rating, 76 reviews
4.97 (76)
Guest favourite
Guest favourite
Guest suite in Chicago
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
16–21 Aug
16–21 Aug
$775 SGD
Show price breakdown
for 5 nights
$775 SGD for 5 nights
4.88 out of 5 average rating, 433 reviews
4.88 (433)
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
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
$2,048 SGD
Show price breakdown
for 5 nights
$2,048 SGD for 5 nights
5.0 out of 5 average rating, 19 reviews
5.0 (19)
Guest favourite
Guest favourite
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
$1,836 SGD
Show price breakdown
for 5 nights
$1,836 SGD for 5 nights
5.0 out of 5 average rating, 8 reviews
5.0 (8)
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
$895 SGD
Show price breakdown
for 5 nights
$895 SGD for 5 nights
4.93 out of 5 average rating, 337 reviews
4.93 (337)
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
$1,968 SGD
Show price breakdown
for 5 nights
$1,968 SGD for 5 nights
4.95 out of 5 average rating, 64 reviews
4.95 (64)
Top guest favourite
Guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms
3 bedrooms
,
·
3 queen beds
3 queen beds
,
·
2 bathrooms
2 bathrooms
5–10 Jul
5–10 Jul
$2,289 SGD
Show price breakdown
for 5 nights
$2,289 SGD for 5 nights
5.0 out of 5 average rating, 15 reviews
5.0 (15)
Home in Chicago
Comfortable welcoming stay for business or leisure
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
1–6 Jul
1–6 Jul
$3,595 SGD
$3,006 SGD
Show price breakdown
for 5 nights
Free cancellation
New place to stay
New
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
$885 SGD
Show price breakdown
for 5 nights
$885 SGD for 5 nights
4.88 out of 5 average rating, 475 reviews
4.88 (475)
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
5.0 out of 5 average rating, 6 reviews
5.0 (6)
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
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
Free cancellation
4.94 out of 5 average rating, 140 reviews
4.94 (140)
1
2
3
4
…
15