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Search results; Over 1,000 homes in Chicago
Over 1,000 homes in Chicago
Top guest favourite
Guest favourite
Apartment in Chicago
Fulton Market Loft | Rooftop Fire Pit | Parking
3 bedrooms
,
·
3 beds
,
·
2.5 private bathrooms
22–27 Aug
22–27 Aug
$6,293 SGD
$5,706 SGD
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for 5 nights
,
·
4.96 out of 5 average rating, 282 reviews
4.96 (282)
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
20–25 Sept
20–25 Sept
$3,456 SGD
$3,044 SGD
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for 5 nights
Book early to save
4.95 out of 5 average rating, 22 reviews
4.95 (22)
Guest favourite
Guest favourite
Apartment in Chicago
Ultimate Group Experience Entire Building Chicago
9 bedrooms
9 bedrooms
,
·
15 beds
15 beds
,
·
6 bathrooms
6 bathrooms
29 Aug – 3 Sept
29 Aug – 3 Sept
$7,314 SGD
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for 5 nights
$7,314 SGD for 5 nights
Free cancellation
4.8 out of 5 average rating, 10 reviews
4.8 (10)
Top guest favourite
Guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms
5 bedrooms
,
·
18 beds
18 beds
,
·
3.5 bathrooms
3.5 bathrooms
2–7 Aug
2–7 Aug
$6,214 SGD
$5,591 SGD
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for 5 nights
4.95 out of 5 average rating, 41 reviews
4.95 (41)
Guest favourite
Guest favourite
Flat in Chicago
Bronzeville Hidden Oasis
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
22–27 Sept
22–27 Sept
$2,206 SGD
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for 5 nights
$2,206 SGD for 5 nights
4.98 out of 5 average rating, 183 reviews
4.98 (183)
Guest favourite
Guest favourite
Home in Chicago
Beautiful Chicago Greystone
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
7–12 Sept
7–12 Sept
$1,804 SGD
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for 5 nights
$1,804 SGD for 5 nights
4.94 out of 5 average rating, 141 reviews
4.94 (141)
Apartment in Chicago
Ukrainian Village 2 Bd/2ba - Steps from Division!
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
2 bathrooms
2 bathrooms
22–27 Aug
22–27 Aug
$1,720 SGD
Show price breakdown
for 5 nights
$1,720 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
2–7 Aug
2–7 Aug
$2,618 SGD
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for 5 nights
$2,618 SGD for 5 nights
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Home in Forest Park
Renovated 2 bedroom - 1.5 bath Coach House
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
6–11 Aug
6–11 Aug
$1,968 SGD
Show price breakdown
for 5 nights
$1,968 SGD for 5 nights
New place to stay
New
Guest favourite
Guest favourite
Flat in Chicago
Easy Downtown Access from Cozy Pilsen Nest
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
18–23 Aug
18–23 Aug
$1,962 SGD
$1,666 SGD
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for 5 nights
Free cancellation
4.94 out of 5 average rating, 66 reviews
4.94 (66)
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
$1,755 SGD
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for 5 nights
$1,755 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 81 reviews
4.96 (81)
Guest favourite
Guest favourite
Flat in Berwyn
Cozy, Sunny, and Clean Apt 3 bd Free Parking
3 bedrooms
3 bedrooms
,
·
3 double beds
3 double beds
,
·
1 bathroom
1 bathroom
2–7 Aug
2–7 Aug
$2,108 SGD
$1,695 SGD
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for 5 nights
4.91 out of 5 average rating, 74 reviews
4.91 (74)
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
12–17 Oct
12–17 Oct
$1,795 SGD
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for 5 nights
$1,795 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 121 reviews
4.95 (121)
Guest favourite
Guest favourite
Apartment in Chicago
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
$1,566 SGD
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for 5 nights
$1,566 SGD for 5 nights
4.96 out of 5 average rating, 161 reviews
4.96 (161)
Top guest favourite
Guest favourite
Home in Chicago
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
19–24 Jul
19–24 Jul
$2,768 SGD
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for 5 nights
$2,768 SGD for 5 nights
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Guest favourite
Guest favourite
Flat in Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
2 bedrooms
2 bedrooms
,
·
2 bathrooms
2 bathrooms
16–21 Aug
16–21 Aug
$2,668 SGD
$1,869 SGD
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for 5 nights
4.95 out of 5 average rating, 19 reviews
4.95 (19)
Home in Chicago
Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
29 Aug – 3 Sept
29 Aug – 3 Sept
$1,677 SGD
Show price breakdown
for 5 nights
$1,677 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Flat in Oak Park
Spacious & Stylish Duplex Near Downtown w/Parking
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
29 Aug – 3 Sept
29 Aug – 3 Sept
$2,606 SGD
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for 5 nights
$2,606 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 86 reviews
5.0 (86)
Guest favourite
Guest favourite
Flat in Evanston
New 3bd/1.5 bth Apt w/private prkg
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
17–22 Sept
17–22 Sept
$2,218 SGD
$2,009 SGD
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for 5 nights
Book early to save
4.92 out of 5 average rating, 191 reviews
4.92 (191)
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