Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
Experiences
Experiences
Services
Services
Start your search
Location
Homes in Westchester
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 Westchester
Over 1,000 homes in Westchester
Guest favourite
Guest favourite
Home in Westchester
Quiet Suburban Westchester Home
3 bedrooms
,
·
3 beds
,
·
2 private bathrooms
18–23 Oct
18–23 Oct
$2,627 SGD
Show price breakdown
for 5 nights
$2,627 SGD for 5 nights
,
·
4.98 out of 5 average rating, 60 reviews
4.98 (60)
Guest favourite
Guest favourite
Home in Westchester
Jacuzzi, King Beds, Easy Access to DT Chicago!
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
14–20 Sept
14–20 Sept
$4,001 SGD
Show price breakdown
for 6 nights
$4,001 SGD for 6 nights
4.96 out of 5 average rating, 132 reviews
4.96 (132)
Guest favourite
Guest favourite
Home in Brookfield
Homey Brookfield Gem — 4 Beds, 2 Baths, Great Yard
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
7–12 Sept
7–12 Sept
$2,808 SGD
$2,491 SGD
Show price breakdown
for 5 nights
4.95 out of 5 average rating, 20 reviews
4.95 (20)
Top guest favourite
Guest favourite
Home in Berwyn
Chic Bungalow Near Chicago - Stained Glass Gem
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
28 Sept – 3 Oct
28 Sept – 3 Oct
$2,644 SGD
Show price breakdown
for 5 nights
$2,644 SGD for 5 nights
5.0 out of 5 average rating, 26 reviews
5.0 (26)
Superhost
Superhost
Flat in Westchester
Near Brookfield Zoo - King Bed - Sleeps 6
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
7–12 Sept
7–12 Sept
$1,405 SGD
$1,160 SGD
Show price breakdown
for 5 nights
4.5 out of 5 average rating, 4 reviews
4.5 (4)
Top guest favourite
Guest favourite
Home in Bensenville
Grand 6BR, 4.5BA Game Rm Near O’Hare, & Down Town
5 bedrooms
5 bedrooms
,
·
8 beds
8 beds
27 Sept – 2 Oct
27 Sept – 2 Oct
$5,661 SGD
$4,454 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 21 reviews
5.0 (21)
Top guest favourite
Guest favourite
Flat in Oak Park
Comfortable & Easy
2 bedrooms
2 bedrooms
,
·
3 queen beds
3 queen beds
7–12 Sept
7–12 Sept
$1,305 SGD
Show price breakdown
for 5 nights
$1,305 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 10 reviews
5.0 (10)
Top guest favourite
Guest favourite
Home in Chicago
Chicago Home (1st floor) by Midway near Downtown
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
24–29 Oct
24–29 Oct
$1,174 SGD
$1,045 SGD
Show price breakdown
for 5 nights
Free cancellation
4.95 out of 5 average rating, 110 reviews
4.95 (110)
Luxe
Luxe
Apartment in Oak Park
Architect-Designed 3BR Oak Park Flat
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
8–13 Sept
8–13 Sept
$3,954 SGD
Show price breakdown
for 5 nights
$3,954 SGD for 5 nights
5.0 out of 5 average rating, 17 reviews
5.0 (17)
Top guest favourite
Guest favourite
Room in Elmhurst
Cozy room with private bathroom.
1 queen bed
1 queen bed
28 Sept – 3 Oct
28 Sept – 3 Oct
$1,177 SGD
$1,031 SGD
Show price breakdown
for 5 nights
Free cancellation
4.99 out of 5 average rating, 157 reviews
4.99 (157)
Top guest favourite
Guest favourite
Room in North Riverside
The Albany Park Room at the Cape Cod in Riverside
1 queen bed
1 queen bed
7–12 Sept
7–12 Sept
$621 SGD
Show price breakdown
for 5 nights
$621 SGD for 5 nights
Free cancellation
4.93 out of 5 average rating, 272 reviews
4.93 (272)
Top guest favourite
Guest favourite
Home in Brookfield
Coffee Bar •Game Room •Walk to Train •Garage
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
12–17 Oct
12–17 Oct
$3,656 SGD
Show price breakdown
for 5 nights
$3,656 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 36 reviews
4.97 (36)
Superhost
Superhost
Home in Bellwood
Near O'Hare huge home for all occasions
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
7–12 Sept
7–12 Sept
$2,895 SGD
$2,546 SGD
Show price breakdown
for 5 nights
Top guest favourite
Guest favourite
Flat in Oak Park
SuperHost and Super Location Central OP
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
20–25 Sept
20–25 Sept
$1,507 SGD
$1,329 SGD
Show price breakdown
for 5 nights
4.98 out of 5 average rating, 144 reviews
4.98 (144)
Top guest favourite
Guest favourite
Home in Brookfield
Cozy Home in Brookfield
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
20–25 Sept
20–25 Sept
$1,535 SGD
Show price breakdown
for 5 nights
$1,535 SGD for 5 nights
4.99 out of 5 average rating, 107 reviews
4.99 (107)
Top guest favourite
Guest favourite
Home in Itasca
RANCH, House-tel: updated full kitchen, comfy beds
3 bedrooms
3 bedrooms
,
·
3 queen beds
3 queen beds
28 Sept – 3 Oct
28 Sept – 3 Oct
$2,319 SGD
$2,052 SGD
Show price breakdown
for 5 nights
Free cancellation
4.99 out of 5 average rating, 90 reviews
4.99 (90)
Top guest favourite
Guest favourite
Home in Maywood
Stunning 4BR | 2 living rooms & game area
4 bedrooms
4 bedrooms
,
·
5 queen beds
5 queen beds
28 Sept – 3 Oct
28 Sept – 3 Oct
$2,402 SGD
Show price breakdown
for 5 nights
$2,402 SGD for 5 nights
4.95 out of 5 average rating, 20 reviews
4.95 (20)
Guest favourite
Guest favourite
Apartment in Berwyn
Red Door
4 bedrooms
4 bedrooms
,
·
4 queen beds
4 queen beds
20–25 Sept
20–25 Sept
$3,063 SGD
$2,764 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Guest favourite
Guest favourite
Room in Forest Park
Cozy City Get-away on Marengo
1 double bed
1 double bed
30 Sept – 5 Oct
30 Sept – 5 Oct
$482 SGD
Show price breakdown
for 5 nights
$482 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 5 reviews
5.0 (5)
1
2
3
4
…
15