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Search results; Over 1,000 homes in Chicago
Over 1,000 homes in Chicago
Top guest favourite
Guest favourite
Room in South Side
Private BR;Parking by UofC/HydePark
1 bedroom
,
·
1 bed
,
·
1 shared bathroom
1–6 Jul
1–6 Jul
$687 SGD
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for 5 nights
$687 SGD for 5 nights
,
·
4.93 out of 5 average rating, 181 reviews
4.93 (181)
Superhost
Superhost
Home in West Side
Beautiful Chicago Greystone
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
12–17 Jul
12–17 Jul
$1,895 SGD
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for 5 nights
$1,895 SGD for 5 nights
4.93 out of 5 average rating, 137 reviews
4.93 (137)
Flat in West Rogers Park
Northside Chicago Apartment
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
12–17 Jul
12–17 Jul
$715 SGD
Show price breakdown
for 5 nights
$715 SGD for 5 nights
Free cancellation
New place to stay
New
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
3–8 Jul
3–8 Jul
$2,802 SGD
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for 5 nights
$2,802 SGD for 5 nights
5.0 out of 5 average rating, 18 reviews
5.0 (18)
Top guest favourite
Guest favourite
Bungalow in Beverly
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms
5 bedrooms
,
·
12 beds
12 beds
,
·
3.5 bathrooms
3.5 bathrooms
2–7 Jul
2–7 Jul
$6,911 SGD
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for 5 nights
$6,911 SGD for 5 nights
4.95 out of 5 average rating, 40 reviews
4.95 (40)
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
3.5 bathrooms
3.5 bathrooms
9–14 Aug
9–14 Aug
$3,240 SGD
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for 5 nights
$3,240 SGD for 5 nights
New place to stay
New
Home in West Side
Big Group Stay-Private Yard/Parking/MillenniumPark
5 bedrooms
5 bedrooms
,
·
8 beds
8 beds
,
·
3.5 bathrooms
3.5 bathrooms
9–14 Sept
9–14 Sept
$4,029 SGD
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for 5 nights
$4,029 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
16–21 Aug
16–21 Aug
$1,672 SGD
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for 5 nights
$1,672 SGD for 5 nights
5.0 out of 5 average rating, 11 reviews
5.0 (11)
Guest favourite
Guest favourite
Home in Humboldt Park
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
2–7 Jul
2–7 Jul
$3,411 SGD
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for 5 nights
$3,411 SGD for 5 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Guest favourite
Guest favourite
Apartment in South Side
The Langley Luxe modern style unit
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$1,453 SGD
$1,212 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Guest favourite
Guest favourite
Apartment in South Side
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
$1,679 SGD
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for 5 nights
$1,679 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 80 reviews
4.96 (80)
Top 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
25–30 Oct
25–30 Oct
$1,299 SGD
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for 5 nights
$1,299 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 119 reviews
4.95 (119)
Guest favourite
Guest favourite
Flat in Wicker Park
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
$1,955 SGD
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for 5 nights
$1,955 SGD for 5 nights
5.0 out of 5 average rating, 8 reviews
5.0 (8)
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
23–28 Jul
23–28 Jul
$3,884 SGD
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for 5 nights
$3,884 SGD for 5 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
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
11–16 Jul
11–16 Jul
$3,752 SGD
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for 5 nights
$3,752 SGD for 5 nights
5.0 out of 5 average rating, 15 reviews
5.0 (15)
Guest favourite
Guest favourite
Home in South Side
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
30 Aug – 4 Sept
30 Aug – 4 Sept
$3,185 SGD
$2,808 SGD
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for 5 nights
5.0 out of 5 average rating, 20 reviews
5.0 (20)
Guest favourite
Guest favourite
Flat in Wrigleyville
Bright Wrigleyville Stay | Near Transit & Parks
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
5–10 Jul
5–10 Jul
$1,626 SGD
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for 5 nights
$1,626 SGD for 5 nights
Free cancellation
4.93 out of 5 average rating, 15 reviews
4.93 (15)
Guest favourite
Guest favourite
Place to stay in South Side
Large Brand New Room in Hyde Park Close toDowntown
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
23–28 Oct
23–28 Oct
$606 SGD
$554 SGD
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for 5 nights
Free cancellation
4.95 out of 5 average rating, 20 reviews
4.95 (20)
Flat in Wicker Park
Perfect Wicker Park Stay
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
1–6 Jul
1–6 Jul
$2,358 SGD
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for 5 nights
$2,358 SGD for 5 nights
5.0 out of 5 average rating, 12 reviews
5.0 (12)
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