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
Apartment in Chicago
Private Lincoln Park Condo with 2 Parking Spots
4 bedrooms
,
·
4 beds
,
·
1 private bathroom
7–12 Sept
7–12 Sept
$3,109 SGD
Show price breakdown
for 5 nights
$3,109 SGD for 5 nights
,
·
4.97 out of 5 average rating, 139 reviews
4.97 (139)
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
5–10 Jul
5–10 Jul
$1,656 SGD
$1,158 SGD
Show price breakdown
for 5 nights
4.98 out of 5 average rating, 81 reviews
4.98 (81)
Top guest favourite
Guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
16–21 Aug
16–21 Aug
$1,659 SGD
Show price breakdown
for 5 nights
$1,659 SGD for 5 nights
5.0 out of 5 average rating, 12 reviews
5.0 (12)
Superhost
Superhost
Home in Chicago
Cozy Luxury Escape Amazing location private home
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
4–9 Jul
4–9 Jul
$3,882 SGD
Show price breakdown
for 5 nights
$3,882 SGD for 5 nights
New place to stay
New
Top guest favourite
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
26 Sept – 1 Oct
26 Sept – 1 Oct
$3,867 SGD
$3,401 SGD
Show price breakdown
for 5 nights
Book early to save
5.0 out of 5 average rating, 21 reviews
5.0 (21)
Home in Chicago
Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
10–15 Aug
10–15 Aug
$1,765 SGD
Show price breakdown
for 5 nights
$1,765 SGD for 5 nights
Guest favourite
Guest favourite
Flat in Chicago
Luxury Loft Collection 03 - Terrace - River North
3 bedrooms
3 bedrooms
,
·
7 beds
7 beds
,
·
3 bathrooms
3 bathrooms
16–21 Aug
16–21 Aug
$6,003 SGD
$4,177 SGD
Show price breakdown
for 5 nights
4.95 out of 5 average rating, 107 reviews
4.95 (107)
Superhost
Superhost
Flat in Chicago
Penthouse Designer Loft 4W | GoldCoast/River North
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2.5 bathrooms
2.5 bathrooms
16–21 Aug
16–21 Aug
$4,274 SGD
$3,016 SGD
Show price breakdown
for 5 nights
New place to stay
New
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
$1,372 SGD
Show price breakdown
for 5 nights
$1,372 SGD for 5 nights
4.97 out of 5 average rating, 64 reviews
4.97 (64)
Place to stay in Bridgeview
Comfortable Private Room with Easy Chicago Access
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
12–17 Jul
12–17 Jul
$457 SGD
Show price breakdown
for 5 nights
$457 SGD for 5 nights
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Top guest favourite
Guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
$2,098 SGD
Show price breakdown
for 5 nights
$2,098 SGD for 5 nights
5.0 out of 5 average rating, 19 reviews
5.0 (19)
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
27 Sept – 2 Oct
27 Sept – 2 Oct
$3,035 SGD
$2,667 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 101 reviews
5.0 (101)
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
$1,852 SGD
Show price breakdown
for 5 nights
$1,852 SGD for 5 nights
5.0 out of 5 average rating, 11 reviews
5.0 (11)
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
3.5 bathrooms
3.5 bathrooms
9–14 Aug
9–14 Aug
$3,183 SGD
$2,931 SGD
Show price breakdown
for 5 nights
New place to stay
New
Home in Chicago
Comfortable welcoming stay for business or leisure
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
4–9 Jul
4–9 Jul
$3,063 SGD
$2,567 SGD
Show price breakdown
for 5 nights
New home discount
New place to stay
New
Superhost
Superhost
Flat in Chicago
10 Min to Downtown | 3BR 2BA Spacious Home
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
5–10 Jul
5–10 Jul
$1,128 SGD
Show price breakdown
for 5 nights
$1,128 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
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
$1,350 SGD
Show price breakdown
for 5 nights
$1,350 SGD for 5 nights
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Top guest favourite
Guest favourite
Home in Evanston
1/2 mile to NU, 5min walk to Lake, Swim Spa Pool
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
3.5 bathrooms
3.5 bathrooms
5–10 Jul
5–10 Jul
$6,883 SGD
$4,704 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 10 reviews
5.0 (10)
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
$1,365 SGD
$1,250 SGD
Show price breakdown
for 5 nights
4.95 out of 5 average rating, 119 reviews
4.95 (119)
1
2
3
4
…
15