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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
The Woodsman's Gallery at OHC
3 bedrooms
,
·
4 beds
,
·
2 private bathrooms
26–31 Jul
26–31 Jul
$3,646 SGD
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for 5 nights
$3,646 SGD for 5 nights
,
·
4.9 out of 5 average rating, 621 reviews
4.9 (621)
Flat in Chicago
Northside Chicago Apartment
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
4–9 Sept
4–9 Sept
$832 SGD
Show price breakdown
for 5 nights
$832 SGD for 5 nights
Free cancellation
New place to stay
New
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
2–7 Jul
2–7 Jul
$6,911 SGD
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for 5 nights
$6,911 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 40 reviews
4.95 (40)
Top guest favourite
Guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
3–8 Jul
3–8 Jul
$2,777 SGD
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for 5 nights
$2,777 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 18 reviews
5.0 (18)
Superhost
Superhost
Home in Chicago
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
Free cancellation
4.93 out of 5 average rating, 137 reviews
4.93 (137)
Home in Chicago
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 Chicago
ChiCasa Wicker Park Paradise
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
5–10 Jul
5–10 Jul
$2,865 SGD
$2,377 SGD
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for 5 nights
5.0 out of 5 average rating, 52 reviews
5.0 (52)
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
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)
Flat in Chicago
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
Top guest favourite
Guest favourite
Flat in Chicago
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
Apartment in Chicago
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
Home in Norridge
Modern Ranch | 5 Min to O'Hare, 25 to Chicago
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
6–11 Jul
6–11 Jul
$2,473 SGD
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for 5 nights
$2,473 SGD for 5 nights
Free cancellation
4.92 out of 5 average rating, 12 reviews
4.92 (12)
Flat in Berwyn
Spacious 2BD w/Game Table for 7 near City+Airport
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
16–21 Jul
16–21 Jul
$1,994 SGD
Show price breakdown
for 5 nights
$1,994 SGD for 5 nights
New place to stay
New
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
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
Home in Chicago
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 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
$1,969 SGD
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for 5 nights
$1,969 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Top guest favourite
Guest favourite
Flat in Westchester
At the Pac House, You can Play, Stay and Discover.
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
21–26 Aug
21–26 Aug
$1,213 SGD
Show price breakdown
for 5 nights
$1,213 SGD for 5 nights
Free cancellation
4.92 out of 5 average rating, 13 reviews
4.92 (13)
Guest favourite
Guest favourite
Flat in Evanston
NEW Fam-Frndly 3 bd 1 bth w/ EZ Parking near NU
3 bedrooms
3 bedrooms
,
·
1 bathroom
1 bathroom
3–8 Jul
3–8 Jul
$2,150 SGD
$1,691 SGD
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for 5 nights
Free cancellation
4.94 out of 5 average rating, 163 reviews
4.94 (163)
Guest favourite
Guest favourite
Flat in Chicago
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
Show price breakdown
for 5 nights
$1,626 SGD for 5 nights
Free cancellation
4.93 out of 5 average rating, 15 reviews
4.93 (15)
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