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Search results; Over 1,000 homes in Chicago
Over 1,000 homes in Chicago
Top guest favourite
Guest favourite
Guest suite in Chicago
Great location, private entry and patio!
1 bedroom
,
·
3 beds
,
·
1 private bathroom
30 Aug – 4 Sept
30 Aug – 4 Sept
$1,151 SGD
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for 5 nights
$1,151 SGD for 5 nights
,
·
4.96 out of 5 average rating, 347 reviews
4.96 (347)
Guest favourite
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
20–25 Sept
20–25 Sept
$3,451 SGD
$3,040 SGD
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for 5 nights
Book early to save
Pay $0 today
Free cancellation
4.95 out of 5 average rating, 22 reviews
4.95 (22)
Top guest favourite
Guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
2–7 Aug
2–7 Aug
$2,614 SGD
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for 5 nights
$2,614 SGD for 5 nights
5.0 out of 5 average rating, 12 reviews
5.0 (12)
Top guest favourite
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
12–17 Oct
12–17 Oct
$1,792 SGD
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for 5 nights
$1,792 SGD for 5 nights
Pay $0 today
Free cancellation
4.95 out of 5 average rating, 120 reviews
4.95 (120)
Guest favourite
Guest favourite
Flat in Chicago
Easy Downtown Access from Cozy Pilsen Nest
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
18–23 Aug
18–23 Aug
$1,960 SGD
$1,664 SGD
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for 5 nights
Pay $0 today
Free cancellation
4.94 out of 5 average rating, 66 reviews
4.94 (66)
Home in Forest Park
Renovated 2 bedroom - 1.5 bath Coach House
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
6–11 Aug
6–11 Aug
$1,965 SGD
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for 5 nights
$1,965 SGD for 5 nights
Pay $0 today
Free cancellation
New place to stay
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Guest favourite
Guest favourite
Flat in Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
2 bedrooms
2 bedrooms
16–21 Aug
16–21 Aug
$2,664 SGD
$1,867 SGD
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for 5 nights
4.95 out of 5 average rating, 19 reviews
4.95 (19)
Apartment in Chicago
Ukrainian Village 2 Bd/2ba - Steps from Division!
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
22–27 Aug
22–27 Aug
$1,717 SGD
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for 5 nights
$1,717 SGD for 5 nights
Pay $0 today
Free cancellation
New place to stay
New
Guest favourite
Guest favourite
Apartment in Chicago
Ultimate Group Experience Entire Building Chicago
9 bedrooms
9 bedrooms
,
·
15 beds
15 beds
29 Aug – 3 Sept
29 Aug – 3 Sept
$7,304 SGD
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for 5 nights
$7,304 SGD for 5 nights
Pay $0 today
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
2–7 Aug
2–7 Aug
$6,205 SGD
$5,584 SGD
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for 5 nights
Pay $0 today
Free cancellation
4.95 out of 5 average rating, 41 reviews
4.95 (41)
Top guest favourite
Guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
13–18 Aug
13–18 Aug
$2,664 SGD
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for 5 nights
$2,664 SGD for 5 nights
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Guest favourite
Guest favourite
Flat in Chicago
Bronzeville Hidden Oasis
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
22–27 Sept
22–27 Sept
$2,203 SGD
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for 5 nights
$2,203 SGD for 5 nights
4.98 out of 5 average rating, 183 reviews
4.98 (183)
Guest favourite
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
16–21 Aug
16–21 Aug
$1,753 SGD
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for 5 nights
$1,753 SGD for 5 nights
Pay $0 today
Free cancellation
4.96 out of 5 average rating, 81 reviews
4.96 (81)
Guest favourite
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms
3 bedrooms
,
·
3 queen beds
3 queen beds
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,465 SGD
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for 5 nights
$1,465 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 22 reviews
5.0 (22)
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
2–7 Aug
2–7 Aug
$2,105 SGD
$1,693 SGD
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for 5 nights
Pay $0 today
Free cancellation
4.91 out of 5 average rating, 74 reviews
4.91 (74)
Home in Chicago
Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
29 Aug – 3 Sept
29 Aug – 3 Sept
$1,675 SGD
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for 5 nights
$1,675 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms
3 bedrooms
,
·
3 queen beds
3 queen beds
30 Aug – 4 Sept
30 Aug – 4 Sept
$2,101 SGD
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for 5 nights
$2,101 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 17 reviews
5.0 (17)
Top guest favourite
Guest favourite
Flat in Chicago
NorthSide Chicago duplex 5-BD,2King size-free park
5 bedrooms
5 bedrooms
,
·
6 beds
6 beds
29 Aug – 3 Sept
29 Aug – 3 Sept
$2,586 SGD
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for 5 nights
$2,586 SGD for 5 nights
Pay $0 today
Free cancellation
4.97 out of 5 average rating, 199 reviews
4.97 (199)
Guest favourite
Guest favourite
Flat in Chicago
Modern 2 BR Retreat Steps From Family Park
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
30 Aug – 4 Sept
30 Aug – 4 Sept
$2,058 SGD
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for 5 nights
$2,058 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 7 reviews
5.0 (7)
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