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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 Logan Square
Best in Chicago, private, amazing garden space
2 bedrooms
,
·
3 beds
,
·
1 private bathroom
9–14 Aug
9–14 Aug
$2,304 SGD
$1,917 SGD
Show price breakdown
for 5 nights
,
·
4.95 out of 5 average rating, 749 reviews
4.95 (749)
Guest favourite
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
4.97 out of 5 average rating, 76 reviews
4.97 (76)
,
·
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
1–6 Jul
1–6 Jul
$2,742 SGD
$1,381 SGD
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for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 119 reviews
4.95 (119)
,
·
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
25–30 Oct
25–30 Oct
$1,386 SGD
Show price breakdown
for 5 nights
$1,386 SGD for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Room in Irving Park
Cozy Room for One In The Company of Cats -Blueline
4.94 out of 5 average rating, 140 reviews
4.94 (140)
,
·
1 single bed
1 single bed
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$481 SGD
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for 5 nights
$481 SGD for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Flat in West Side
Easy Downtown Access from The Pilsen Haven
5.0 out of 5 average rating, 26 reviews
5.0 (26)
,
·
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
4–9 Jul
4–9 Jul
$1,286 SGD
$995 SGD
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for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Room in South Side
Private BR;Parking by UofC/HydePark
4.93 out of 5 average rating, 181 reviews
4.93 (181)
,
·
1 double bed
1 double bed
,
·
1 bathroom
1 bathroom
7–12 Sept
7–12 Sept
$548 SGD
$491 SGD
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for 5 nights
Pay $0 today
Free cancellation
Guest favourite
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
5.0 out of 5 average rating, 10 reviews
5.0 (10)
,
·
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
23–28 Aug
23–28 Aug
$1,886 SGD
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for 5 nights
$1,886 SGD for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
5.0 out of 5 average rating, 12 reviews
5.0 (12)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
3–8 Jul
3–8 Jul
$2,278 SGD
Show price breakdown
for 5 nights
$2,278 SGD for 5 nights
Guest favourite
Guest favourite
Apartment in South Side
The Langley Luxe modern style unit
5.0 out of 5 average rating, 7 reviews
5.0 (7)
,
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2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$1,556 SGD
$1,298 SGD
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for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Flat in South Side
Stylish Hyde Park/Kenwood Brownstone Garden Apt
5.0 out of 5 average rating, 17 reviews
5.0 (17)
,
·
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
4–9 Jul
4–9 Jul
$1,450 SGD
Show price breakdown
for 5 nights
$1,450 SGD for 5 nights
Pay $0 today
Free cancellation
Luxe
Luxe
Flat in Chicago Loop
Luxury Downtown 4BR | Exclusive Design PH
4.97 out of 5 average rating, 39 reviews
4.97 (39)
,
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4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3.5 bathrooms
3.5 bathrooms
2–7 Jul
2–7 Jul
$19,751 SGD
Show price breakdown
for 5 nights
$19,751 SGD for 5 nights
Free cancellation
Guest favourite
Guest favourite
Room in Norwood Park
Private Room in Norwood Park
4.98 out of 5 average rating, 41 reviews
4.98 (41)
,
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1 bed
1 bed
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$431 SGD
$367 SGD
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for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Home in South Side
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
5.0 out of 5 average rating, 21 reviews
5.0 (21)
,
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4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
20–25 Sept
20–25 Sept
$3,032 SGD
$2,614 SGD
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for 5 nights
Book early to save
Free cancellation
Hotel in Downtown Chicago
Perfect Destination! Onsite Bar and Restaurant!
1 bedroom
1 bedroom
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$1,394 SGD
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for 5 nights
$1,394 SGD for 5 nights
Pay $0 today
Free cancellation
Guest favourite
Guest favourite
Apartment in South Side
The Modern Woodlawn 2 Bed 2 Bath
4.96 out of 5 average rating, 80 reviews
4.96 (80)
,
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2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
16–21 Aug
16–21 Aug
$1,679 SGD
Show price breakdown
for 5 nights
$1,679 SGD for 5 nights
Pay $0 today
Free cancellation
Home in West Town
Comfortable welcoming stay for business or leisure
New place to stay
New
,
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3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
1–6 Jul
1–6 Jul
$3,595 SGD
$3,006 SGD
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for 5 nights
New home discount
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Room in Roscoe Village
Spacious garden level suite
4.96 out of 5 average rating, 311 reviews
4.96 (311)
,
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1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
1–6 Nov
1–6 Nov
$649 SGD
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for 5 nights
$649 SGD for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
5.0 out of 5 average rating, 52 reviews
5.0 (52)
,
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3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
5–10 Jul
5–10 Jul
$3,079 SGD
$2,559 SGD
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for 5 nights
Top guest favourite
Guest favourite
Flat in South Side
Luxury Living in Bronzeville with Massive Roofdeck
5.0 out of 5 average rating, 15 reviews
5.0 (15)
,
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3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
5–10 Jul
5–10 Jul
$2,290 SGD
Show price breakdown
for 5 nights
$2,290 SGD for 5 nights
Pay $0 today
Free cancellation
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