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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 Chicago Loop
Lavish 2BR/2BA Loft I Next to Grant Park & Museums
2 bedrooms
,
·
2 beds
,
·
2 private bathrooms
24–30 Aug
24–30 Aug
$4,525 SGD
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for 6 nights
$4,525 SGD for 6 nights
,
·
4.94 out of 5 average rating, 251 reviews
4.94 (251)
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
$1,659 SGD
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for 5 nights
$1,659 SGD for 5 nights
5.0 out of 5 average rating, 12 reviews
5.0 (12)
Top guest favourite
Guest favourite
Bungalow in Beverly
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms
5 bedrooms
,
·
17 beds
17 beds
,
·
3.5 bathrooms
3.5 bathrooms
3–8 Jul
3–8 Jul
$6,463 SGD
Show price breakdown
for 5 nights
$6,463 SGD for 5 nights
4.95 out of 5 average rating, 41 reviews
4.95 (41)
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
$1,367 SGD
$1,252 SGD
Show price breakdown
for 5 nights
4.95 out of 5 average rating, 119 reviews
4.95 (119)
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
4–9 Jul
4–9 Jul
$1,958 SGD
$1,242 SGD
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for 5 nights
4.98 out of 5 average rating, 80 reviews
4.98 (80)
Superhost
Superhost
Flat in West Side
10 Min to Downtown | 3BR 2BA Spacious Home
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
5–10 Jul
5–10 Jul
$1,129 SGD
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for 5 nights
$1,129 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
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
21–26 Jul
21–26 Jul
$2,617 SGD
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for 5 nights
$2,617 SGD for 5 nights
5.0 out of 5 average rating, 26 reviews
5.0 (26)
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
$1,297 SGD
Show price breakdown
for 5 nights
$1,297 SGD for 5 nights
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
$1,677 SGD
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for 5 nights
$1,677 SGD for 5 nights
4.96 out of 5 average rating, 81 reviews
4.96 (81)
Flat in West Rogers Park
Northside Chicago Apartment
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
7–12 Sept
7–12 Sept
$743 SGD
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for 5 nights
$743 SGD for 5 nights
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
5–10 Jul
5–10 Jul
$2,027 SGD
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for 5 nights
$2,027 SGD for 5 nights
5.0 out of 5 average rating, 19 reviews
5.0 (19)
Top guest favourite
Guest favourite
Flat in South Side
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms
3 bedrooms
,
·
3 queen beds
3 queen beds
,
·
2 bathrooms
2 bathrooms
5–10 Jul
5–10 Jul
$2,291 SGD
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for 5 nights
$2,291 SGD for 5 nights
5.0 out of 5 average rating, 15 reviews
5.0 (15)
Home in Chicago
Blonde Beauty Cozy Home Near Downtown Attractions
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
12–17 Jul
12–17 Jul
$2,401 SGD
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for 5 nights
$2,401 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Guest favourite
Guest favourite
Flat in South Side
Sunny Penthouse - Oakwood Beach
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
15–20 Aug
15–20 Aug
$1,914 SGD
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for 5 nights
$1,914 SGD for 5 nights
4.95 out of 5 average rating, 64 reviews
4.95 (64)
Guest favourite
Guest favourite
Apartment in West Side
Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
16–21 Aug
16–21 Aug
$1,338 SGD
$1,244 SGD
Show price breakdown
for 5 nights
4.88 out of 5 average rating, 476 reviews
4.88 (476)
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
$1,854 SGD
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for 5 nights
$1,854 SGD for 5 nights
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Superhost
Superhost
Flat in South Loop
Paradise Lounge South loop 3br W/ Balcony
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
9–14 Aug
9–14 Aug
$1,885 SGD
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for 5 nights
$1,885 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
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
23–28 Aug
23–28 Aug
$1,854 SGD
Show price breakdown
for 5 nights
$1,854 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
5–10 Jul
5–10 Jul
$2,827 SGD
Show price breakdown
for 5 nights
$2,827 SGD for 5 nights
5.0 out of 5 average rating, 7 reviews
5.0 (7)
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