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
Guest favourite
Guest favourite
Apartment in Chicago
The Upscale Getaway Near Downtown
2 bedrooms
,
·
3 beds
,
·
2 private bathrooms
27 Jul – 1 Aug
27 Jul – 1 Aug
$2,883 SGD
Show price breakdown
for 5 nights
$2,883 SGD for 5 nights
,
·
4.93 out of 5 average rating, 290 reviews
4.93 (290)
Superhost
Superhost
Flat in Clarendon Hills
Clarendon Hills Apartment
2 bedrooms
2 bedrooms
2 beds
,
·
2 beds
1.5 bathrooms
,
·
1.5 bathrooms
28 Jun – 3 Jul
28 Jun – 3 Jul
$1,126 SGD
Show price breakdown
for 5 nights
$1,126 SGD for 5 nights
Free cancellation
New place to stay
New
Guest favourite
Guest favourite
Flat in Chicago
LIVN West Loop Chicago King Studio Apartment
1 bedroom
1 bedroom
1 king bed
,
·
1 king bed
1 bathroom
,
·
1 bathroom
25–30 Jun
25–30 Jun
$2,120 SGD
Show price breakdown
for 5 nights
$2,120 SGD for 5 nights
Free cancellation
4.92 out of 5 average rating, 26 reviews
4.92 (26)
Superhost
Superhost
Flat in Chicago
Well Located Studio on the Red Line
1 queen bed
1 queen bed
1 bathroom
,
·
1 bathroom
5–10 Jul
5–10 Jul
$1,442 SGD
Show price breakdown
for 5 nights
$1,442 SGD for 5 nights
Free cancellation
New place to stay
New
Superhost
Superhost
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
$1,879 SGD
Show price breakdown
for 5 nights
$1,879 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Top guest favourite
Guest favourite
Flat in Oak Park
Spacious & Stylish Duplex Parking & Walkability
3 bedrooms
3 bedrooms
5 beds
,
·
5 beds
2.5 bathrooms
,
·
2.5 bathrooms
17–22 Aug
17–22 Aug
$3,499 SGD
$2,781 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 81 reviews
5.0 (81)
Top guest favourite
Guest favourite
Room in Chicago
Private Queen Bedroom with Private Bathroom
1 queen bed
1 queen bed
2.5 bathrooms
,
·
2.5 bathrooms
21–26 Jun
21–26 Jun
$1,242 SGD
$943 SGD
Show price breakdown
for 5 nights
4.95 out of 5 average rating, 196 reviews
4.95 (196)
Superhost
Superhost
Flat in Chicago
Designer Loft 3W | Heart of Gold Coast/River North
3 bedrooms
3 bedrooms
2.5 bathrooms
,
·
2.5 bathrooms
5–10 Jul
5–10 Jul
$3,189 SGD
Show price breakdown
for 5 nights
$3,189 SGD for 5 nights
4.75 out of 5 average rating, 4 reviews
4.75 (4)
Flat in Chicago
Chicago Classic•Skyline View•1BR + Den, Train Near
1 bedroom
1 bedroom
5 beds
,
·
5 beds
1 bathroom
,
·
1 bathroom
28 Jun – 3 Jul
28 Jun – 3 Jul
$983 SGD
Show price breakdown
for 5 nights
$983 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Apartment in Chicago
Wrigleyville Updated Condo with Free Parking
3 bedrooms
3 bedrooms
3 beds
,
·
3 beds
2 bathrooms
,
·
2 bathrooms
20–25 Aug
20–25 Aug
$3,435 SGD
Show price breakdown
for 5 nights
$3,435 SGD for 5 nights
5.0 out of 5 average rating, 97 reviews
5.0 (97)
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
9–14 Aug
9–14 Aug
$861 SGD
Show price breakdown
for 5 nights
$861 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 15 reviews
5.0 (15)
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
18–23 Oct
18–23 Oct
$1,426 SGD
Show price breakdown
for 5 nights
$1,426 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 115 reviews
4.95 (115)
Flat in Chicago
Bronzeville Oasis
1 bedroom
1 bedroom
3 beds
,
·
3 beds
1 bathroom
,
·
1 bathroom
15–20 Jun
15–20 Jun
$1,269 SGD
Show price breakdown
for 5 nights
$1,269 SGD for 5 nights
Free cancellation
New place to stay
New
Top guest favourite
Guest favourite
Apartment in Chicago
Your Chicago Retreat
3 bedrooms
3 bedrooms
3 queen beds
,
·
3 queen beds
1.5 bathrooms
,
·
1.5 bathrooms
28 Jun – 3 Jul
28 Jun – 3 Jul
$2,255 SGD
Show price breakdown
for 5 nights
$2,255 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 299 reviews
4.99 (299)
Top guest favourite
Guest favourite
Guest suite in Chicago
Private Lincoln Square one bed+bath studio apt.
1 bedroom
1 bedroom
1 queen bed
,
·
1 queen bed
1 bathroom
,
·
1 bathroom
12–17 Oct
12–17 Oct
$1,171 SGD
Show price breakdown
for 5 nights
$1,171 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 422 reviews
4.99 (422)
Top guest favourite
Guest favourite
Room in Chicago
Cozy Clean Large Private Room in Lincoln Square
1 double bed
1 double bed
1 bathroom
,
·
1 bathroom
22–27 Aug
22–27 Aug
$695 SGD
Show price breakdown
for 5 nights
$695 SGD for 5 nights
4.95 out of 5 average rating, 178 reviews
4.95 (178)
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
9–14 Aug
9–14 Aug
$1,360 SGD
Show price breakdown
for 5 nights
$1,360 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 62 reviews
4.97 (62)
Top guest favourite
Guest favourite
Flat in Chicago
Stylish 2BR stunner w/ unbeatable location
2 bedrooms
2 bedrooms
3 beds
,
·
3 beds
1 bathroom
,
·
1 bathroom
29 Jun – 4 Jul
29 Jun – 4 Jul
$2,070 SGD
$1,854 SGD
Show price breakdown
for 5 nights
Free cancellation
4.92 out of 5 average rating, 186 reviews
4.92 (186)
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
$766 SGD
Show price breakdown
for 5 nights
$766 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 227 reviews
4.96 (227)
1
2
3
4
…
15