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Search results; Over 1,000 homes in Chicago
Over 1,000 homes in Chicago
Guest favourite
Guest favourite
Apartment in Chicago
The Upscale Getaway Near Downtown
2 bedrooms
,
·
3 beds
,
·
2 private bathrooms
27 Jul – 1 Aug
27 Jul – 1 Aug
$2,869 SGD
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for 5 nights
$2,869 SGD for 5 nights
,
·
4.93 out of 5 average rating, 290 reviews
4.93 (290)
Superhost
Superhost
Flat in Clarendon Hills
Clarendon Hills Apartment
2 bedrooms
2 bedrooms
2 beds
,
·
2 beds
1.5 bathrooms
,
·
1.5 bathrooms
28 Jun – 3 Jul
28 Jun – 3 Jul
$1,126 SGD
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for 5 nights
$1,126 SGD for 5 nights
Free cancellation
New place to stay
New
Superhost
Superhost
Flat in Chicago
Well Located Studio on the Red Line
1 queen bed
1 queen bed
1 bathroom
,
·
1 bathroom
5–10 Jul
5–10 Jul
$1,442 SGD
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for 5 nights
$1,442 SGD for 5 nights
Free cancellation
New place to stay
New
Top guest favourite
Guest favourite
Flat in Chicago
Sun drenched 2 bedroom 1 bath with Kitchen & W/D
2 bedrooms
2 bedrooms
2 beds
,
·
2 beds
1 bathroom
,
·
1 bathroom
23–28 Aug
23–28 Aug
$2,282 SGD
$1,994 SGD
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for 5 nights
Free cancellation
4.95 out of 5 average rating, 258 reviews
4.95 (258)
Top guest favourite
Guest favourite
Apartment in Chicago
Wrigleyville Updated Condo with Free Parking
3 bedrooms
3 bedrooms
3 beds
,
·
3 beds
2 bathrooms
,
·
2 bathrooms
20–25 Aug
20–25 Aug
$3,435 SGD
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for 5 nights
$3,435 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 98 reviews
5.0 (98)
Superhost
Superhost
Flat in Chicago
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
2 bedrooms
2 bedrooms
3 beds
,
·
3 beds
1 bathroom
,
·
1 bathroom
19–24 Jul
19–24 Jul
$1,852 SGD
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for 5 nights
$1,852 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Top guest favourite
Guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms
5 bedrooms
12 beds
,
·
12 beds
3.5 bathrooms
,
·
3.5 bathrooms
23–28 Jun
23–28 Jun
$6,034 SGD
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for 5 nights
$6,034 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 40 reviews
4.95 (40)
Top guest favourite
Guest favourite
Apartment in Chicago
Your Chicago Retreat
3 bedrooms
3 bedrooms
3 queen beds
,
·
3 queen beds
1.5 bathrooms
,
·
1.5 bathrooms
28 Jun – 3 Jul
28 Jun – 3 Jul
$2,255 SGD
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for 5 nights
$2,255 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 299 reviews
4.99 (299)
Top guest favourite
Guest favourite
Flat in Oak Park
Spacious & Stylish Duplex Parking & Walkability
3 bedrooms
3 bedrooms
5 beds
,
·
5 beds
2.5 bathrooms
,
·
2.5 bathrooms
17–22 Aug
17–22 Aug
$3,499 SGD
$2,781 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 81 reviews
5.0 (81)
Flat in Chicago
Chicago Classic•Skyline View•1BR + Den, Train Near
1 bedroom
1 bedroom
5 beds
,
·
5 beds
1 bathroom
,
·
1 bathroom
28 Jun – 3 Jul
28 Jun – 3 Jul
$962 SGD
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for 5 nights
$962 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 Chicago
Pilsen Modern Chic Retreat
2 bedrooms
2 bedrooms
3 beds
,
·
3 beds
1.5 bathrooms
,
·
1.5 bathrooms
18–23 Oct
18–23 Oct
$1,425 SGD
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for 5 nights
$1,425 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 115 reviews
4.95 (115)
Top guest favourite
Guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms
2 bedrooms
2 queen beds
,
·
2 queen beds
1 bathroom
,
·
1 bathroom
9–14 Aug
9–14 Aug
$1,360 SGD
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for 5 nights
$1,360 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 62 reviews
4.97 (62)
Top guest favourite
Guest favourite
Place to stay in Chicago
Spacious Sun-Lit Suite in Chicago
2 bedrooms
2 bedrooms
2 beds
,
·
2 beds
1 bathroom
,
·
1 bathroom
9–14 Aug
9–14 Aug
$861 SGD
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for 5 nights
$861 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 15 reviews
5.0 (15)
Top guest favourite
Guest favourite
Room in Chicago
Cozy Clean Large Private Room in Lincoln Square
1 double bed
1 double bed
1 bathroom
,
·
1 bathroom
22–27 Aug
22–27 Aug
$695 SGD
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for 5 nights
$695 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 178 reviews
4.95 (178)
Top guest favourite
Guest favourite
Room in Chicago
Al's Oasis Chicago
1 queen bed
1 queen bed
1 bathroom
,
·
1 bathroom
5–10 Jul
5–10 Jul
$766 SGD
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for 5 nights
$766 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 227 reviews
4.96 (227)
Top guest favourite
Guest favourite
Guest suite in Chicago
Private Lincoln Square one bed+bath studio apt.
1 bedroom
1 bedroom
1 queen bed
,
·
1 queen bed
1 bathroom
,
·
1 bathroom
18–23 Oct
18–23 Oct
$1,171 SGD
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for 5 nights
$1,171 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 422 reviews
4.99 (422)
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
13–18 Jul
13–18 Jul
$1,903 SGD
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for 5 nights
$1,903 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 78 reviews
4.96 (78)
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
23–28 Jun
23–28 Jun
$2,453 SGD
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for 5 nights
$2,453 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 58 reviews
4.98 (58)
Top guest favourite
Guest favourite
Home in Chicago
Big house in the BEST Location!
3 bedrooms
3 bedrooms
3 beds
,
·
3 beds
2.5 bathrooms
,
·
2.5 bathrooms
24–29 Aug
24–29 Aug
$2,103 SGD
Show price breakdown
for 5 nights
$2,103 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 57 reviews
4.98 (57)
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