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
Descriptions are based on details hosts provide
Guest favourite
Guest favourite
Apartment in Chicago
Can't Beat This 2min Walk to Wrigley!
2 bedrooms
,
·
5 beds
,
·
2 private bathrooms
29 Sept – 4 Oct
29 Sept – 4 Oct
$2,942 SGD
Show price breakdown
for 5 nights
$2,942 SGD for 5 nights
,
·
4.81 out of 5 average rating, 280 reviews
4.81 (280)
Guest favourite
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4.91 out of 5 average rating, 23 reviews
4.91 (23)
,
·
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
20–25 Sept
20–25 Sept
$3,365 SGD
$2,964 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
Guest favourite
Guest favourite
Flat in Chicago
Newly renovated near Millennium Park
4.97 out of 5 average rating, 93 reviews
4.97 (93)
,
·
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
22–27 Jul
22–27 Jul
$2,978 SGD
$2,479 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
Flat in Skokie
Peaceful garden unit with private entrance
New place to stay
New
,
·
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
26–31 Jul
26–31 Jul
$1,536 SGD
$1,321 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Home in Franklin Park
Full, fun cozy house!
5.0 out of 5 average rating, 5 reviews
5.0 (5)
,
·
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
22–27 Aug
22–27 Aug
$1,396 SGD
Show price breakdown
for 5 nights
$1,396 SGD for 5 nights
Pay $0 today
Free cancellation
Guest favourite
Guest favourite
Place to stay in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
4.9 out of 5 average rating, 49 reviews
4.9 (49)
,
·
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
24–29 Oct
24–29 Oct
$748 SGD
Show price breakdown
for 5 nights
$748 SGD for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Home in Brookfield
Sunlit mid-century brick ranch, tree-lined street
4.94 out of 5 average rating, 16 reviews
4.94 (16)
,
·
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
26–31 Jul
26–31 Jul
$2,581 SGD
Show price breakdown
for 5 nights
$2,581 SGD for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Rooms in Chicago
Historic North Park home
4.97 out of 5 average rating, 113 reviews
4.97 (113)
,
·
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
1 bathroom
1 bathroom
13–18 Sept
13–18 Sept
$632 SGD
Show price breakdown
for 5 nights
$632 SGD for 5 nights
Pay $0 today
Free cancellation
Place to stay in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
New place to stay
New
,
·
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
10–15 Aug
10–15 Aug
$672 SGD
Show price breakdown
for 5 nights
$672 SGD for 5 nights
Top guest favourite
Guest favourite
Flat in Chicago
Minimal duplex with free private parking
5.0 out of 5 average rating, 13 reviews
5.0 (13)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
2–7 Aug
2–7 Aug
$2,725 SGD
Show price breakdown
for 5 nights
$2,725 SGD for 5 nights
Superhost
Superhost
Home in Chicago
Modern 6 BR 3 Baths 11 beds Sleeps 17 Birthday
6 bedrooms
6 bedrooms
,
·
11 beds
11 beds
,
·
3 bathrooms
3 bathrooms
26–31 Jul
26–31 Jul
$5,784 SGD
$3,150 SGD
Show price breakdown
for 5 nights
Guest favourite
Guest favourite
Apartment in Chicago
Modern Woodlawn condo near UChicago
4.96 out of 5 average rating, 81 reviews
4.96 (81)
,
·
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
16–21 Aug
16–21 Aug
$1,750 SGD
Show price breakdown
for 5 nights
$1,750 SGD for 5 nights
Pay $0 today
Free cancellation
Place to stay in Chicago
Self check in 24h near downtown Chicago p2
New place to stay
New
,
·
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
2 bathrooms
2 bathrooms
13–18 Aug
13–18 Aug
$4,667 SGD
Show price breakdown
for 5 nights
$4,667 SGD for 5 nights
Place to stay in Chicago
Guest room in Dunning, Chicago IL
5.0 out of 5 average rating, 3 reviews
5.0 (3)
,
·
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
19–24 Sept
19–24 Sept
$496 SGD
Show price breakdown
for 5 nights
$496 SGD for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 121 reviews
4.95 (121)
,
·
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
25–30 Oct
25–30 Oct
$1,343 SGD
$1,142 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
Place to stay in Chicago
Twin Bed | Near Train Station | McCormick Pl
New place to stay
New
,
·
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
2 bathrooms
2 bathrooms
4–9 Aug
4–9 Aug
$268 SGD
Show price breakdown
for 5 nights
$268 SGD for 5 nights
Top guest favourite
Guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
4.97 out of 5 average rating, 157 reviews
4.97 (157)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
16–21 Aug
16–21 Aug
$3,354 SGD
$2,671 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
Guest favourite
Guest favourite
Place to stay in Chicago
En suite near UChicago, 3-min to CTA
5.0 out of 5 average rating, 16 reviews
5.0 (16)
,
·
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
17–22 Aug
17–22 Aug
$581 SGD
$502 SGD
Show price breakdown
for 5 nights
Guest favourite
Guest favourite
Home in Chicago
Historic bungalow with free parking near Hyde Park
4.93 out of 5 average rating, 14 reviews
4.93 (14)
,
·
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
23–28 Aug
23–28 Aug
$1,889 SGD
Show price breakdown
for 5 nights
$1,889 SGD for 5 nights
Pay $0 today
Free cancellation
1
2
3
4
…
15