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
2br/2ba, A+ location by Mag mile, views & spacious
2 bedrooms
,
·
4 beds
,
·
2 private bathrooms
30 Aug – 4 Sept
30 Aug – 4 Sept
$2,243 SGD
Show price breakdown
for 5 nights
$2,243 SGD for 5 nights
,
·
4.93 out of 5 average rating, 367 reviews
4.93 (367)
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
$1,299 SGD
Show price breakdown
for 5 nights
$1,299 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 119 reviews
4.95 (119)
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
$1,191 SGD
Show price breakdown
for 5 nights
$1,191 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 54 reviews
4.96 (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
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)
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
$1,046 SGD
Show price breakdown
for 5 nights
$1,046 SGD for 5 nights
Free cancellation
4.88 out of 5 average rating, 473 reviews
4.88 (473)
Top guest favourite
Guest favourite
Room in Chicago
Spacious garden level suite
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
14–19 Mar
14–19 Mar
$649 SGD
Show price breakdown
for 5 nights
$649 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 309 reviews
4.96 (309)
Top guest favourite
Guest favourite
Guest suite in Chicago
2BR/1.5 Bath in Logan Square
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1.5 bathrooms
1.5 bathrooms
28 Nov – 3 Dec
28 Nov – 3 Dec
$1,015 SGD
Show price breakdown
for 5 nights
$1,015 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 59 reviews
4.95 (59)
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
$777 SGD
Show price breakdown
for 5 nights
$777 SGD for 5 nights
Free cancellation
4.88 out of 5 average rating, 433 reviews
4.88 (433)
Guest favourite
Guest favourite
Rooms in Chicago
Spacious Haven in North Park
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
4–9 Oct
4–9 Oct
$756 SGD
Show price breakdown
for 5 nights
$756 SGD for 5 nights
Free cancellation
4.89 out of 5 average rating, 64 reviews
4.89 (64)
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
Free cancellation
4.98 out of 5 average rating, 184 reviews
4.98 (184)
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
25–30 Oct
25–30 Oct
$827 SGD
Show price breakdown
for 5 nights
$827 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 54 reviews
5.0 (54)
Guest favourite
Guest favourite
Rooms in Oak Park
Single bedroom with Asian decor in family home
2 bedrooms
2 bedrooms
,
·
1 double bed
1 double bed
,
·
1 bathroom
1 bathroom
17–22 Aug
17–22 Aug
$448 SGD
Show price breakdown
for 5 nights
$448 SGD for 5 nights
Free cancellation
4.94 out of 5 average rating, 381 reviews
4.94 (381)
Guest favourite
Guest favourite
Flat in Chicago
Modern 2BR | Free Parking | McCormick & Chinatown
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$1,107 SGD
Show price breakdown
for 5 nights
$1,107 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 5 reviews
5.0 (5)
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
19–24 Sept
19–24 Sept
$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)
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
Free cancellation
5.0 out of 5 average rating, 5 reviews
5.0 (5)
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
$943 SGD
Show price breakdown
for 5 nights
$943 SGD for 5 nights
Free cancellation
4.93 out of 5 average rating, 336 reviews
4.93 (336)
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
$771 SGD
Show price breakdown
for 5 nights
$771 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 228 reviews
4.96 (228)
Top guest favourite
Guest favourite
Flat in Forest Park
Like a Treehouse!
1 bedroom
1 bedroom
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
30 Aug – 4 Sept
30 Aug – 4 Sept
$1,061 SGD
Show price breakdown
for 5 nights
$1,061 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 371 reviews
5.0 (371)
Top guest favourite
Guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
5–10 Jul
5–10 Jul
$2,865 SGD
$2,377 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 52 reviews
5.0 (52)
1
2
3
4
…
15