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Search results; Over 1,000 homes in Chicago
Over 1,000 homes in Chicago
Top guest favourite
Guest favourite
Bungalow in Lake View
Chicago Bootlegger House Sleeps 10-20
6 bedrooms
,
·
10 beds
,
·
2 private bathrooms
30 Aug – 4 Sept
30 Aug – 4 Sept
$3,310 SGD
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for 5 nights
$3,310 SGD for 5 nights
,
·
4.96 out of 5 average rating, 158 reviews
4.96 (158)
Top guest favourite
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
25–30 Jun
25–30 Jun
$2,325 SGD
$1,796 SGD
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for 5 nights
4.97 out of 5 average rating, 65 reviews
4.97 (65)
Superhost
Superhost
Flat in West Town
Modern 4BR West Town Duplex | Best for LongStays
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
3.5 bathrooms
3.5 bathrooms
22–27 Jun
22–27 Jun
$5,189 SGD
Show price breakdown
for 5 nights
$5,189 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Top 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
1–6 Jul
1–6 Jul
$480 SGD
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for 5 nights
$480 SGD for 5 nights
Free cancellation
4.94 out of 5 average rating, 139 reviews
4.94 (139)
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
30 Jun – 5 Jul
30 Jun – 5 Jul
$3,707 SGD
$3,298 SGD
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for 5 nights
5.0 out of 5 average rating, 14 reviews
5.0 (14)
Apartment in South Side
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
$1,315 SGD
$1,097 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Flat in Logan Square
Retro Logan Square Retreat • Blue Line
1 bedroom
1 bedroom
,
·
1 bunk bed
1 bunk bed
,
·
1 bathroom
1 bathroom
22–27 Aug
22–27 Aug
$918 SGD
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for 5 nights
$918 SGD for 5 nights
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Guest favourite
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms
2 bedrooms
,
·
3 queen beds
3 queen beds
,
·
2 bathrooms
2 bathrooms
7–12 Sept
7–12 Sept
$1,535 SGD
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for 5 nights
$1,535 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Superhost
Superhost
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
$1,785 SGD
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for 5 nights
$1,785 SGD for 5 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Top guest favourite
Guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
29 Aug – 3 Sept
29 Aug – 3 Sept
$2,975 SGD
$2,730 SGD
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for 5 nights
5.0 out of 5 average rating, 50 reviews
5.0 (50)
Guest favourite
Guest favourite
Flat in Wicker Park
4 Bedroom Penthouse Loft in Heart of Wicker Park
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
21–26 Jun
21–26 Jun
$4,108 SGD
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for 5 nights
$4,108 SGD for 5 nights
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Top guest favourite
Guest favourite
Flat in West Side
Easy Downtown Access from The Pilsen Haven
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
28 Jun – 3 Jul
28 Jun – 3 Jul
$1,609 SGD
$1,228 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 25 reviews
5.0 (25)
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
18–23 Oct
18–23 Oct
$1,330 SGD
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for 5 nights
$1,330 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 116 reviews
4.95 (116)
Flat in North Side
Quiet & Modern Avondale Apartment
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
15–20 Aug
15–20 Aug
$1,221 SGD
Show price breakdown
for 5 nights
$1,221 SGD for 5 nights
Superhost
Superhost
Flat in Chicago
Stunning Apt, walk to NEU, “The Bernard”
4 bedrooms
4 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
26–31 Jul
26–31 Jul
$2,317 SGD
Show price breakdown
for 5 nights
$2,317 SGD for 5 nights
Free cancellation
Superhost
Superhost
Apartment in North Side
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
15–20 Aug
15–20 Aug
$1,711 SGD
$1,589 SGD
Show price breakdown
for 5 nights
4.96 out of 5 average rating, 157 reviews
4.96 (157)
Top guest favourite
Guest favourite
Flat in Lake View
Luxe Wrigley Estate: Pool Table + Parking + Patio
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
2 bathrooms
2 bathrooms
22–27 Jun
22–27 Jun
$5,280 SGD
$4,122 SGD
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for 5 nights
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Top guest favourite
Guest favourite
Flat in Bridgeport
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$1,065 SGD
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for 5 nights
$1,065 SGD for 5 nights
4.99 out of 5 average rating, 123 reviews
4.99 (123)
Flat in Belmont Cragin
Modern 2 BR Retreat Steps From Family Park
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
12–17 Jul
12–17 Jul
$1,674 SGD
Show price breakdown
for 5 nights
$1,674 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
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