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Search results; Over 1,000 homes in Westchester

Guest favourite
Home in Westchester
Modern 2Bdrm Westchester/Chicago Home.With Hot tub
2 bedrooms, 3 beds, 1 private bathroom
4–9 Oct
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4.87 out of 5 average rating, 103 reviews
Guest favourite
Home in Westchester
Jacuzzi, King Beds, Easy Access to DT Chicago!
4 bedrooms, 4 beds, 2.5 bathrooms
19–25 Oct
4.96 out of 5 average rating, 132 reviews
Guest favourite
Home in Westchester
Quiet Suburban Westchester Home
3 bedrooms, 3 beds, 2 bathrooms
18–23 Oct
4.98 out of 5 average rating, 60 reviews
Guest favourite
Home in Brookfield
Homey Brookfield Gem — 4 Beds, 2 Baths, Great Yard
4 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.95 out of 5 average rating, 20 reviews
Top guest favourite
Home in Berwyn
Chic Bungalow Near Chicago - Stained Glass Gem
4 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Home in Brookfield
Cozy Home in Brookfield
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 107 reviews
Top guest favourite
Flat in Oak Park
Comfortable & Easy
2 bedrooms, 3 queen beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Apartment in Berwyn
Red Door
4 bedrooms, 4 queen beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Addison
Private & quiet🌲 O'Hare 8mi✈️ D/T Chicago 22mi 🏙
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
4.99 out of 5 average rating, 92 reviews
Top guest favourite
Home in Maywood
Stunning 4BR | 2 living rooms & game area
4 bedrooms, 5 queen beds, 2 bathrooms
28 Sept – 3 Oct
4.95 out of 5 average rating, 20 reviews
Top guest favourite
Home in Chicago
Chicago Home (1st floor) by Midway near Downtown
3 bedrooms, 3 beds, 1 bathroom
24–29 Oct
4.95 out of 5 average rating, 110 reviews
Top guest favourite
Home in Bensenville
Grand 6BR, 4.5BA Game Rm Near O’Hare, & Down Town
5 bedrooms, 8 beds, 4.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Flat in Oak Park
Frank Lloyd Wright District | King Bed + Parking
2 bedrooms, 4 beds, 1 bathroom
1–6 Nov
4.98 out of 5 average rating, 98 reviews
Top guest favourite
Room in North Riverside
The Albany Park Room at the Cape Cod in Riverside
1 queen bed, 1 bathroom
7–12 Sept
4.93 out of 5 average rating, 272 reviews
Top guest favourite
Home in Itasca
RANCH, House-tel: updated full kitchen, comfy beds
3 bedrooms, 3 queen beds, 2 bathrooms
28 Sept – 3 Oct
4.99 out of 5 average rating, 90 reviews
Top guest favourite
Flat in Oak Park
Large sunny 3BR apt. in downtown Oak Park
3 bedrooms, 5 beds, 1 bathroom
25–30 Oct
4.92 out of 5 average rating, 208 reviews
Top guest favourite
Flat in Berwyn
A cosy apartment 20 min by car from Chicago
1 bedroom, 1 queen bed, 1 bathroom
19–24 Oct
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Room in Elmhurst
Cozy room with private bathroom.
1 queen bed, 1 bathroom
28 Sept – 3 Oct
4.99 out of 5 average rating, 157 reviews
Room in Elmhurst
Close to Oakbrook and O’Hare + Bistro. Pool. Gym.
2 double beds, 1 bathroom
6–11 Sept