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Search results; Over 1,000 homes in Chicago
Over 1,000 homes in Chicago
Top guest favourite
Guest favourite
Flat in Chicago
Cozy loft in Chicago's Uptown
1 bedroom
,
·
2 beds
,
·
1 private bathroom
16–21 Oct
16–21 Oct
$1,124 SGD
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for 5 nights
$1,124 SGD for 5 nights
,
·
4.97 out of 5 average rating, 331 reviews
4.97 (331)
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
12–17 Oct
12–17 Oct
$1,549 SGD
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for 5 nights
$1,549 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 114 reviews
4.95 (114)
Guest favourite
Guest favourite
Room in Chicago
Private Room in Norwood Park
1 bed
1 bed
1 bathroom
,
·
1 bathroom
14–19 Jun
14–19 Jun
$426 SGD
$342 SGD
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for 5 nights
Free cancellation
4.97 out of 5 average rating, 37 reviews
4.97 (37)
Flat in Chicago
Retro Logan Square Retreat • Blue Line
1 bedroom
1 bedroom
1 bunk bed
,
·
1 bunk bed
1 bathroom
,
·
1 bathroom
15–20 Aug
15–20 Aug
$916 SGD
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for 5 nights
$916 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
$790 SGD
$711 SGD
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for 5 nights
Free cancellation
4.96 out of 5 average rating, 674 reviews
4.96 (674)
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
5–10 Jul
5–10 Jul
$3,096 SGD
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for 5 nights
$3,096 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Flat in Chicago
3BR Vintage Apt • Patio • Walk to McKinley Park
3 bedrooms
3 bedrooms
3 queen beds
,
·
3 queen beds
1 bathroom
,
·
1 bathroom
21–26 Jun
21–26 Jun
$1,812 SGD
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for 5 nights
$1,812 SGD for 5 nights
Free cancellation
New place to stay
New
Apartment in Chicago
The Langley Luxe modern style unit
2 bedrooms
2 bedrooms
3 beds
,
·
3 beds
1 bathroom
,
·
1 bathroom
28 Jun – 3 Jul
28 Jun – 3 Jul
$1,215 SGD
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for 5 nights
$1,215 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
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
17–22 Jun
17–22 Jun
$3,154 SGD
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for 5 nights
$3,154 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 56 reviews
4.98 (56)
Room in Chicago
Comfortable bed with Smart stand
1 queen bed
1 queen bed
1 bathroom
,
·
1 bathroom
6–11 Jul
6–11 Jul
$418 SGD
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for 5 nights
$418 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Top guest favourite
Guest favourite
Flat in Chicago
Boho City Escape | Parking + Balcony
2 bedrooms
2 bedrooms
3 beds
,
·
3 beds
2 bathrooms
,
·
2 bathrooms
28 Jun – 3 Jul
28 Jun – 3 Jul
$2,247 SGD
$2,025 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 14 reviews
5.0 (14)
Top guest favourite
Guest favourite
Flat in Oak Park
Historic Hotspot: Downtown Oak Park w/parking spot
2 bedrooms
2 bedrooms
2 queen beds
,
·
2 queen beds
1 bathroom
,
·
1 bathroom
12–17 Jul
12–17 Jul
$1,662 SGD
$1,295 SGD
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for 5 nights
Free cancellation
4.99 out of 5 average rating, 80 reviews
4.99 (80)
Guest favourite
Guest favourite
Flat in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
1 bedroom
1 bedroom
1 bed
,
·
1 bed
1 bathroom
,
·
1 bathroom
24–29 Oct
24–29 Oct
$817 SGD
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for 5 nights
$817 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 40 reviews
5.0 (40)
Top guest favourite
Guest favourite
Apartment in Chicago
Wrigleyville Inn. Historic Greystone, Free Parking
3 bedrooms
3 bedrooms
3 queen beds
,
·
3 queen beds
2 bathrooms
,
·
2 bathrooms
5–10 Jul
5–10 Jul
$2,304 SGD
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for 5 nights
$2,304 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 135 reviews
4.99 (135)
Superhost
Superhost
Home in Schaumburg
Chicagoland-Schaumburg/ORD 3BR Ranch Home, sleeps7
3 bedrooms
3 bedrooms
4 beds
,
·
4 beds
1 bathroom
,
·
1 bathroom
6–11 Jul
6–11 Jul
$2,126 SGD
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for 5 nights
$2,126 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Top guest favourite
Guest favourite
Guest house in Evanston
Welcome to Serenity.
1 bedroom
1 bedroom
1 queen bed
,
·
1 queen bed
1 bathroom
,
·
1 bathroom
12–17 Jul
12–17 Jul
$669 SGD
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for 5 nights
$669 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 17 reviews
5.0 (17)
Top guest favourite
Guest favourite
Flat in Chicago
Rustic Sanctuary
2 bedrooms
2 bedrooms
2 queen beds
,
·
2 queen beds
1 bathroom
,
·
1 bathroom
14–19 Jun
14–19 Jun
$2,278 SGD
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for 5 nights
$2,278 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 43 reviews
5.0 (43)
Guest favourite
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms
2 bedrooms
2 beds
,
·
2 beds
2 bathrooms
,
·
2 bathrooms
16–21 Aug
16–21 Aug
$1,671 SGD
Show price breakdown
for 5 nights
$1,671 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 78 reviews
4.96 (78)
Flat in Chicago
Close to Wrigley Field, The Beach & Downtown
1 bedroom
1 bedroom
3 beds
,
·
3 beds
1 bathroom
,
·
1 bathroom
19–24 Jul
19–24 Jul
$1,412 SGD
Show price breakdown
for 5 nights
$1,412 SGD for 5 nights
Free cancellation
New place to stay
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