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
Superhost
Superhost
Home in Chicago
Beautiful Chicago Greystone
4 bedrooms
,
·
4 beds
,
·
1 private bathroom
21–26 Sept
21–26 Sept
$1,698 SGD
Show price breakdown
for 5 nights
$1,698 SGD for 5 nights
,
·
4.93 out of 5 average rating, 137 reviews
4.93 (137)
Home in Chicago
The Dorchester | Steps to the Obama Center & Beach
5 bedrooms
5 bedrooms
,
·
10 beds
10 beds
,
·
3.5 bathrooms
3.5 bathrooms
1–6 Jul
1–6 Jul
$9,335 SGD
$6,611 SGD
Show price breakdown
for 5 nights
Free cancellation
New place to stay
New
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
1–6 Jul
1–6 Jul
$6,271 SGD
$5,680 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Flat in Chicago
Modern 2 BR Retreat Steps From Family Park
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
12–17 Jul
12–17 Jul
$1,677 SGD
Show price breakdown
for 5 nights
$1,677 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Home in Chicago
Newly Renovated Home 4BD/3BTH with garage!
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
4–9 Aug
4–9 Aug
$4,749 SGD
Show price breakdown
for 5 nights
$4,749 SGD for 5 nights
Free cancellation
New place to stay
New
Top guest favourite
Guest favourite
Room in Chicago
NEW,Roscoe Village,Cubs, Pvt Bath, Pvt Entrance
3 beds
3 beds
,
·
1 bathroom
1 bathroom
25–30 Oct
25–30 Oct
$789 SGD
$682 SGD
Show price breakdown
for 5 nights
Free cancellation
4.95 out of 5 average rating, 677 reviews
4.95 (677)
Top guest favourite
Guest favourite
Flat in Oak Park
Airy & Sunny Treetop Oasis Best Location & Parking
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
17–22 Aug
17–22 Aug
$2,077 SGD
$1,609 SGD
Show price breakdown
for 5 nights
Free cancellation
4.98 out of 5 average rating, 82 reviews
4.98 (82)
Guest favourite
Guest favourite
Apartment in Chicago
Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
5–10 Jul
5–10 Jul
$1,155 SGD
Show price breakdown
for 5 nights
$1,155 SGD for 5 nights
Free cancellation
4.88 out of 5 average rating, 473 reviews
4.88 (473)
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
$1,384 SGD
Show price breakdown
for 5 nights
$1,384 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 63 reviews
4.97 (63)
Guest favourite
Guest favourite
Home in Chicago
Cozy 4BR with Spa Tub Near UChicago & Obama Center
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
20–25 Sept
20–25 Sept
$3,686 SGD
$3,244 SGD
Show price breakdown
for 5 nights
Book early to save
Free cancellation
5.0 out of 5 average rating, 19 reviews
5.0 (19)
Flat in Chicago
Chic 3BR Sun-Filled Oasis: Wicker & Logan Square
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
12–17 Jul
12–17 Jul
$2,902 SGD
Show price breakdown
for 5 nights
$2,902 SGD for 5 nights
Free cancellation
New place to stay
New
Top guest favourite
Guest favourite
Flat in Chicago
Easy Downtown Access from The Pilsen Haven
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
4–9 Jul
4–9 Jul
$1,603 SGD
$1,331 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 26 reviews
5.0 (26)
Flat in Berwyn
Spacious 2BD w/Game Table for 7 near City+Airport
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$1,218 SGD
Show price breakdown
for 5 nights
$1,218 SGD for 5 nights
Free cancellation
New place to stay
New
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
3–8 Jul
3–8 Jul
$2,824 SGD
Show price breakdown
for 5 nights
$2,824 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 17 reviews
5.0 (17)
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
$3,234 SGD
Show price breakdown
for 5 nights
$3,234 SGD for 5 nights
Free cancellation
New place to stay
New
Top guest favourite
Guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
1 bathroom
1 bathroom
13–18 Sept
13–18 Sept
$648 SGD
Show price breakdown
for 5 nights
$648 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 109 reviews
4.97 (109)
Top guest favourite
Guest favourite
Flat in Chicago
2BR Avondale Apt: Free Parking + Steps to Blueline
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
11–16 Aug
11–16 Aug
$1,384 SGD
Show price breakdown
for 5 nights
$1,384 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 8 reviews
5.0 (8)
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
$1,127 SGD
Show price breakdown
for 5 nights
$1,127 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Guest favourite
Guest favourite
Place to stay in Chicago
The Native Garden at the City's Edge
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
4–9 Aug
4–9 Aug
$497 SGD
Show price breakdown
for 5 nights
$497 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 7 reviews
5.0 (7)
1
2
3
4
…
15