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
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
$3,689 SGD
Show price breakdown
for 5 nights
$3,689 SGD for 5 nights
,
·
5.0 out of 5 average rating, 34 reviews
5.0 (34)
Superhost
Superhost
Place to stay in Des Plains
H3 Cozy Room by the River
1 bedroom
1 bedroom
1 bed
,
·
1 bed
1.5 bathrooms
,
·
1.5 bathrooms
21–26 Jun
21–26 Jun
$494 SGD
Show price breakdown
for 5 nights
$494 SGD for 5 nights
Free cancellation
4.91 out of 5 average rating, 45 reviews
4.91 (45)
Top guest favourite
Guest favourite
Flat in Oak Park
Serene 1-Bedroom Suite in Oak Park (Free Parking!)
1 bedroom
1 bedroom
1 king bed
,
·
1 king bed
1 bathroom
,
·
1 bathroom
20–25 Oct
20–25 Oct
$732 SGD
$670 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 46 reviews
5.0 (46)
Top guest favourite
Guest favourite
Room in Alsip
Safe clean charming close transportation Viva!
1 queen bed
1 queen bed
1 bathroom
,
·
1 bathroom
30 Jun – 5 Jul
30 Jun – 5 Jul
$555 SGD
Show price breakdown
for 5 nights
$555 SGD for 5 nights
Free cancellation
4.91 out of 5 average rating, 268 reviews
4.91 (268)
Place to stay in Chicago
Twin Bed | Walk to Train Station | Chinatown
1 bedroom
1 bedroom
1 bed
,
·
1 bed
2 bathrooms
,
·
2 bathrooms
24–29 Jul
24–29 Jul
$329 SGD
Show price breakdown
for 5 nights
$329 SGD for 5 nights
New place to stay
New
Place to stay in Chicago
The Native Garden at the City's Edge
1 bedroom
1 bedroom
1 queen bed
,
·
1 queen bed
2 bathrooms
,
·
2 bathrooms
14–19 Jun
14–19 Jun
$531 SGD
Show price breakdown
for 5 nights
$531 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Place to stay in Chicago
Spacious Sun-Lit Suite in Chicago
2 bedrooms
2 bedrooms
2 beds
,
·
2 beds
1 bathroom
,
·
1 bathroom
23–28 Jul
23–28 Jul
$924 SGD
Show price breakdown
for 5 nights
$924 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 14 reviews
5.0 (14)
Guest favourite
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms
2 bedrooms
2 beds
,
·
2 beds
2 bathrooms
,
·
2 bathrooms
9–14 Aug
9–14 Aug
$1,666 SGD
Show price breakdown
for 5 nights
$1,666 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 76 reviews
4.96 (76)
Place to stay in Chicago
C66 -9 min to Red line, close to Loyla University
1 bedroom
1 bedroom
2 beds
,
·
2 beds
2 bathrooms
,
·
2 bathrooms
21–26 Jun
21–26 Jun
$385 SGD
Show price breakdown
for 5 nights
$385 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Guest favourite
Guest favourite
Shared room in Chicago
Snug Sofa in Great Neighborhood
1 bedroom
1 bedroom
1 sofa bed
,
·
1 sofa bed
1 shared bathroom
,
·
1 shared bathroom
6–11 Jul
6–11 Jul
$417 SGD
Show price breakdown
for 5 nights
$417 SGD for 5 nights
4.85 out of 5 average rating, 155 reviews
4.85 (155)
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
$1,217 SGD
Show price breakdown
for 5 nights
$1,217 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Flat in Chicago
2BR Avondale Apt: Free Parking + Steps to Blueline
2 bedrooms
2 bedrooms
3 beds
,
·
3 beds
1 bathroom
,
·
1 bathroom
14–19 Jun
14–19 Jun
$1,258 SGD
Show price breakdown
for 5 nights
$1,258 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
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom
1 bedroom
2 beds
,
·
2 beds
1 bathroom
,
·
1 bathroom
6–11 Sept
6–11 Sept
$1,023 SGD
Show price breakdown
for 5 nights
$1,023 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 106 reviews
4.99 (106)
Guest favourite
Guest favourite
Flat in Chicago
Modern suite w/4K TV, kitchen & fast Wi‑Fi
3 bedrooms
3 bedrooms
3 queen beds
,
·
3 queen beds
2 bathrooms
,
·
2 bathrooms
7–12 Jun
7–12 Jun
$1,394 SGD
Show price breakdown
for 5 nights
$1,394 SGD for 5 nights
4.93 out of 5 average rating, 15 reviews
4.93 (15)
Top guest favourite
Guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms
2 bedrooms
3 beds
,
·
3 beds
1.5 bathrooms
,
·
1.5 bathrooms
12–17 Jul
12–17 Jul
$1,326 SGD
Show price breakdown
for 5 nights
$1,326 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 11 reviews
5.0 (11)
Guest favourite
Guest favourite
Flat in Chicago
Easy Downtown Access from Cozy Pilsen Nest
2 bedrooms
2 bedrooms
3 beds
,
·
3 beds
2 bathrooms
,
·
2 bathrooms
7–12 Jun
7–12 Jun
$1,701 SGD
$1,366 SGD
Show price breakdown
for 5 nights
Free cancellation
4.94 out of 5 average rating, 65 reviews
4.94 (65)
Top guest favourite
Guest favourite
Home in Brookfield
Cozy Home in Brookfield
2 bedrooms
2 bedrooms
2 beds
,
·
2 beds
1 bathroom
,
·
1 bathroom
12–17 Jul
12–17 Jul
$1,549 SGD
Show price breakdown
for 5 nights
$1,549 SGD for 5 nights
4.99 out of 5 average rating, 84 reviews
4.99 (84)
Guest favourite
Guest favourite
Place to stay in Evanston
Modern Private Room |Near NU | Steps To Transit
1 bedroom
1 bedroom
1 bed
,
·
1 bed
1 bathroom
,
·
1 bathroom
28 Jun – 3 Jul
28 Jun – 3 Jul
$735 SGD
Show price breakdown
for 5 nights
$735 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 10 reviews
5.0 (10)
Top guest favourite
Guest favourite
Flat in Chicago
A Whimsical Fairy-tale Loft in Ravenswood Chicago
2 bedrooms
2 bedrooms
3 beds
,
·
3 beds
1 bathroom
,
·
1 bathroom
5–10 Jul
5–10 Jul
$1,226 SGD
Show price breakdown
for 5 nights
$1,226 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 342 reviews
4.99 (342)
1
2
3
4
…
15