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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 Downtown Chicago
Chicago Vintage & Chic Living
2 bedrooms
,
·
2 beds
,
·
1 private bathroom
12–17 Oct
12–17 Oct
$3,268 SGD
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for 5 nights
$3,268 SGD for 5 nights
,
·
4.98 out of 5 average rating, 66 reviews
4.98 (66)
Guest favourite
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
18–23 Jan
18–23 Jan
$974 SGD
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for 5 nights
$974 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 132 reviews
4.95 (132)
Top guest favourite
Guest favourite
Flat in North Side
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
15–20 Nov
15–20 Nov
$1,316 SGD
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for 5 nights
$1,316 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 39 reviews
4.97 (39)
Top guest favourite
Guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
$2,025 SGD
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for 5 nights
$2,025 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 32 reviews
5.0 (32)
Top guest favourite
Guest favourite
Home in Logan Square
Spacious Retro Logan Square Loft
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
7–12 Sept
7–12 Sept
$2,232 SGD
$1,562 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 34 reviews
5.0 (34)
Guest favourite
Guest favourite
Flat in South Side
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
28 Sept – 3 Oct
28 Sept – 3 Oct
$1,524 SGD
$1,311 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 28 reviews
5.0 (28)
Superhost
Superhost
Flat in West Side
Easy Downtown Access from Cozy Pilsen Nest
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,371 SGD
$1,089 SGD
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for 5 nights
Free cancellation
4.93 out of 5 average rating, 70 reviews
4.93 (70)
Guest favourite
Guest favourite
Flat in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2.5 bathrooms
2.5 bathrooms
25–30 Oct
25–30 Oct
$1,772 SGD
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for 5 nights
$1,772 SGD for 5 nights
5.0 out of 5 average rating, 14 reviews
5.0 (14)
Flat in Downtown Chicago
Kasa Lake Shore Chicago | Two Bedroom Double Queen
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
6–11 Sept
6–11 Sept
$3,159 SGD
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for 5 nights
$3,159 SGD for 5 nights
New place to stay
New
Home in Lincoln Park
Charming Historic Row Home | Lincoln Park
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
15–20 Nov
15–20 Nov
$1,688 SGD
Show price breakdown
for 5 nights
$1,688 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Flat in Logan Square
Prime Logan Square apartment
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,649 SGD
$1,446 SGD
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for 5 nights
Free cancellation
4.98 out of 5 average rating, 43 reviews
4.98 (43)
Top guest favourite
Guest favourite
Flat in Bridgeport
Designer Garden Unit in Bridgeport
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
25–30 Oct
25–30 Oct
$1,376 SGD
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for 5 nights
$1,376 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 73 reviews
4.97 (73)
Top guest favourite
Guest favourite
Home in Bridgeport
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
28 Nov – 3 Dec
28 Nov – 3 Dec
$791 SGD
$696 SGD
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for 5 nights
Free cancellation
4.96 out of 5 average rating, 312 reviews
4.96 (312)
Top guest favourite
Guest favourite
Flat in Ukrainian Village
Bright Cozy Modern-Chic Condo in Trendy West Town
1 bedroom
1 bedroom
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
25–30 Oct
25–30 Oct
$965 SGD
$838 SGD
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for 5 nights
Free cancellation
4.98 out of 5 average rating, 253 reviews
4.98 (253)
Top guest favourite
Guest favourite
Room in Chicago
Guest room in Dunning, Chicago IL
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
23–28 Sept
23–28 Sept
$617 SGD
$545 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 10 reviews
5.0 (10)
Top guest favourite
Guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
15–20 Nov
15–20 Nov
$2,219 SGD
$1,955 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 61 reviews
5.0 (61)
Guest favourite
Guest favourite
Flat in Ravenswood
Stylish Modern-Chic Apartment in Lincoln Square
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
15–20 Nov
15–20 Nov
$901 SGD
$805 SGD
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for 5 nights
Free cancellation
4.95 out of 5 average rating, 235 reviews
4.95 (235)
Guest favourite
Guest favourite
Room in Irving Park
Cozy Room for One In The Company of Cats -Blueline
1 single bed
1 single bed
,
·
1 bathroom
1 bathroom
24–29 Nov
24–29 Nov
$384 SGD
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for 5 nights
$384 SGD for 5 nights
Free cancellation
4.93 out of 5 average rating, 150 reviews
4.93 (150)
Top guest favourite
Guest favourite
Guest house in West Side
Pilsen Gem Near the Loop & Chinatown
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
27 Oct – 1 Nov
27 Oct – 1 Nov
$1,094 SGD
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for 5 nights
$1,094 SGD for 5 nights
5.0 out of 5 average rating, 27 reviews
5.0 (27)
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