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
Featured hotel
Featured hotel
Hotel in Chicago
King - city view
1 bedroom
,
·
1 bed
,
·
1 private bathroom
27 Jul – 1 Aug
27 Jul – 1 Aug
$3,091 SGD
Show price breakdown
for 5 nights
$3,091 SGD for 5 nights
,
·
4.75 out of 5 average rating, 190 reviews
4.75 (190)
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
$1,413 SGD
Show price breakdown
for 5 nights
4.97 out of 5 average rating, 77 reviews
4.97 (77)
Superhost
Superhost
Home in Chicago
Cozy Luxury Escape Amazing location private home
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
1–6 Jul
1–6 Jul
$4,120 SGD
Show price breakdown
for 5 nights
$4,120 SGD for 5 nights
Free cancellation
New place to stay
New
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
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)
Guest favourite
Guest favourite
Apartment in Chicago
The Langley Luxe modern style unit
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$1,298 SGD
Show price breakdown
for 5 nights
$1,298 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Guest favourite
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms
2 bedrooms
,
·
3 queen beds
3 queen beds
,
·
2 bathrooms
2 bathrooms
23–28 Aug
23–28 Aug
$1,886 SGD
Show price breakdown
for 5 nights
$1,886 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 10 reviews
5.0 (10)
Guest favourite
Guest favourite
Flat in Chicago
Modern 2 BR Retreat Steps From Family Park
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
14–19 Jul
14–19 Jul
$1,684 SGD
Show price breakdown
for 5 nights
$1,684 SGD for 5 nights
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Top guest favourite
Guest favourite
Room in Oak Park
Antique Filled Home
1 bed
1 bed
,
·
1 bathroom
1 bathroom
1–6 Oct
1–6 Oct
$550 SGD
Show price breakdown
for 5 nights
$550 SGD for 5 nights
4.94 out of 5 average rating, 443 reviews
4.94 (443)
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)
Guest favourite
Guest favourite
Room in Niles
Private Furnished Bedroom in Chicago Surburb
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
6–11 Jul
6–11 Jul
$426 SGD
$374 SGD
Show price breakdown
for 5 nights
4.82 out of 5 average rating, 89 reviews
4.82 (89)
Superhost
Superhost
Flat in Chicago
Modern 4BR West Town Duplex | Best for LongStays
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
3.5 bathrooms
3.5 bathrooms
8–13 Jul
8–13 Jul
$6,808 SGD
$5,654 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 7 reviews
5.0 (7)
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
$3,080 SGD
$2,565 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 52 reviews
5.0 (52)
Room in Chicago
Comfortable bed with Smart stand
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
13–18 Jul
13–18 Jul
$408 SGD
Show price breakdown
for 5 nights
$408 SGD for 5 nights
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Guest favourite
Guest favourite
Room in Alsip
Safe clean charming close transportation Viva!
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
11–16 Jul
11–16 Jul
$556 SGD
Show price breakdown
for 5 nights
$556 SGD for 5 nights
Free cancellation
4.91 out of 5 average rating, 269 reviews
4.91 (269)
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
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, 7 reviews
5.0 (7)
Guest favourite
Guest favourite
Home in Norridge
Modern Ranch | 5 Min to O'Hare, 25 to Chicago
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
18–23 Jul
18–23 Jul
$2,472 SGD
Show price breakdown
for 5 nights
$2,472 SGD for 5 nights
4.92 out of 5 average rating, 13 reviews
4.92 (13)
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
4–9 Jul
4–9 Jul
$1,450 SGD
Show price breakdown
for 5 nights
$1,450 SGD for 5 nights
5.0 out of 5 average rating, 17 reviews
5.0 (17)
1
2
3
4
…
15