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
Loft in Chicago
Elevated, open-concept loft with industrial feel
1 bedroom
,
·
4 beds
,
·
1 private bathroom
12–17 Aug
12–17 Aug
$3,812 SGD
$3,159 SGD
Show price breakdown
for 5 nights
,
·
4.78 out of 5 average rating, 40 reviews
4.78 (40)
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
16–21 Aug
16–21 Aug
$1,897 SGD
Show price breakdown
for 5 nights
$1,897 SGD for 5 nights
4.9 out of 5 average rating, 126 reviews
4.9 (126)
Guest favourite
Guest favourite
Room in Chicago
ChicagoChinatownCenterB
1 single bed
1 single bed
,
·
1 bathroom
1 bathroom
25–30 Oct
25–30 Oct
$456 SGD
Show price breakdown
for 5 nights
$456 SGD for 5 nights
4.93 out of 5 average rating, 59 reviews
4.93 (59)
Room in Chicago
Charming Room in Historic Ukrainian Village!
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
6–11 Sept
6–11 Sept
$626 SGD
Show price breakdown
for 5 nights
$626 SGD for 5 nights
New place to stay
New
Flat in Oak Park
Premier Luxe Retreat | Free Parking
1 bedroom
1 bedroom
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
7–12 Sept
7–12 Sept
$798 SGD
Show price breakdown
for 5 nights
$798 SGD for 5 nights
New place to stay
New
Top guest favourite
Guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
27 Jan – 1 Feb
27 Jan – 1 Feb
$624 SGD
Show price breakdown
for 5 nights
$624 SGD for 5 nights
5.0 out of 5 average rating, 39 reviews
5.0 (39)
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
16–21 Aug
16–21 Aug
$1,287 SGD
Show price breakdown
for 5 nights
$1,287 SGD for 5 nights
5.0 out of 5 average rating, 26 reviews
5.0 (26)
Top guest favourite
Guest favourite
Flat in Chicago
Modern Luxe Retreat in Pilsen’s Colorful Center
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
1–6 Nov
1–6 Nov
$910 SGD
$839 SGD
Show price breakdown
for 5 nights
4.98 out of 5 average rating, 51 reviews
4.98 (51)
Top guest favourite
Guest favourite
Flat in Forest Park
Walk to Oak Park from Our Sunny Turn of the Century Apt
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
23–28 Oct
23–28 Oct
$1,102 SGD
Show price breakdown
for 5 nights
$1,102 SGD for 5 nights
4.98 out of 5 average rating, 416 reviews
4.98 (416)
Top guest favourite
Guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
11–16 Nov
11–16 Nov
$891 SGD
Show price breakdown
for 5 nights
$891 SGD for 5 nights
4.96 out of 5 average rating, 309 reviews
4.96 (309)
Top guest favourite
Guest favourite
Room in Chicago
Guest room in Dunning, Chicago IL
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
19–24 Sept
19–24 Sept
$491 SGD
Show price breakdown
for 5 nights
$491 SGD for 5 nights
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Top guest favourite
Guest favourite
Flat in Oak Park
Big & Bright Treetop Oasis Near Downtown w/Parking
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
1–6 Nov
1–6 Nov
$1,475 SGD
Show price breakdown
for 5 nights
$1,475 SGD for 5 nights
4.98 out of 5 average rating, 94 reviews
4.98 (94)
Top guest favourite
Guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
2 bathrooms
2 bathrooms
6–11 Sept
6–11 Sept
$1,840 SGD
Show price breakdown
for 5 nights
$1,840 SGD for 5 nights
5.0 out of 5 average rating, 56 reviews
5.0 (56)
Guest suite in Bensenville
Private, modern room near O’hare.
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
29 Aug – 3 Sept
29 Aug – 3 Sept
$999 SGD
Show price breakdown
for 5 nights
$999 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Guest favourite
Guest favourite
Room in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
16–21 Aug
16–21 Aug
$736 SGD
$662 SGD
Show price breakdown
for 5 nights
4.87 out of 5 average rating, 15 reviews
4.87 (15)
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
27 Dec – 1 Jan
27 Dec – 1 Jan
$1,394 SGD
$1,196 SGD
Show price breakdown
for 5 nights
4.95 out of 5 average rating, 127 reviews
4.95 (127)
Guest favourite
Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
20–25 Sept
20–25 Sept
$1,408 SGD
Show price breakdown
for 5 nights
$1,408 SGD for 5 nights
4.95 out of 5 average rating, 165 reviews
4.95 (165)
Guest favourite
Guest favourite
Guest suite in Chicago
Peaceful Portage Park Apartment
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
1–6 Nov
1–6 Nov
$845 SGD
Show price breakdown
for 5 nights
$845 SGD for 5 nights
4.94 out of 5 average rating, 474 reviews
4.94 (474)
Guest favourite
Guest favourite
Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom King & Queen
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
15–20 Aug
15–20 Aug
$3,694 SGD
Show price breakdown
for 5 nights
$3,694 SGD for 5 nights
4.87 out of 5 average rating, 15 reviews
4.87 (15)
1
2
3
4
…
15
