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
Flat in Chicago
Best in Chicago, private, amazing garden space
2 bedrooms
,
·
3 beds
,
·
1 private bathroom
9–14 Aug
9–14 Aug
$2,304 SGD
$1,917 SGD
Show price breakdown
for 5 nights
,
·
4.95 out of 5 average rating, 749 reviews
4.95 (749)
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
$1,447 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
4.97 out of 5 average rating, 76 reviews
4.97 (76)
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
Pay $0 today
Free cancellation
New place to stay
New
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
Pay $0 today
Free cancellation
4.94 out of 5 average rating, 140 reviews
4.94 (140)
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
$1,318 SGD
$1,018 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 26 reviews
5.0 (26)
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
Pay $0 today
Free cancellation
4.95 out of 5 average rating, 119 reviews
4.95 (119)
Top guest favourite
Guest favourite
Room in Chicago
Private BR;Parking by UofC/HydePark
1 double bed
1 double bed
,
·
1 bathroom
1 bathroom
7–12 Sept
7–12 Sept
$548 SGD
$491 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
4.93 out of 5 average rating, 181 reviews
4.93 (181)
Guest favourite
Guest favourite
Home in Chicago
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
5–10 Jul
5–10 Jul
$2,831 SGD
Show price breakdown
for 5 nights
$2,831 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (6)
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
3–8 Jul
3–8 Jul
$2,278 SGD
Show price breakdown
for 5 nights
$2,278 SGD for 5 nights
5.0 out of 5 average rating, 12 reviews
5.0 (12)
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
$1,556 SGD
$1,298 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 7 reviews
5.0 (7)
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
Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Flat in Chicago
2BR/1BA Apt w/ Modern Amenities Rogers Park
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
1–6 Jul
1–6 Jul
$1,287 SGD
Show price breakdown
for 5 nights
$1,287 SGD for 5 nights
Pay $0 today
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
8–13 Jul
8–13 Jul
$6,808 SGD
$5,654 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 7 reviews
5.0 (7)
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
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 15 reviews
5.0 (15)
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
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 10 reviews
5.0 (10)
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
Pay $0 today
Free cancellation
4.94 out of 5 average rating, 443 reviews
4.94 (443)
Top guest favourite
Guest favourite
Home in Chicago
New Home | O'Hare Airport
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
11–16 Jul
11–16 Jul
$3,536 SGD
Show price breakdown
for 5 nights
$3,536 SGD for 5 nights
5.0 out of 5 average rating, 15 reviews
5.0 (15)
Guest favourite
Guest favourite
Flat in Evanston
New 3bd/1.5 bth Apt w/private prkg
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
5–10 Jul
5–10 Jul
$1,980 SGD
$1,509 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
4.91 out of 5 average rating, 188 reviews
4.91 (188)
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
Pay $0 today
Free cancellation
4.91 out of 5 average rating, 269 reviews
4.91 (269)
1
2
3
4
…
15