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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 Rogers Park Township
Your Chicago Retreat
3 bedrooms
,
·
3 beds
,
·
1.5 private bathrooms
9–14 Aug
9–14 Aug
$2,274 SGD
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for 5 nights
$2,274 SGD for 5 nights
,
·
4.99 out of 5 average rating, 300 reviews
4.99 (300)
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
$1,661 SGD
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for 5 nights
$1,661 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 12 reviews
5.0 (12)
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
$1,349 SGD
$1,139 SGD
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for 5 nights
Pay $0 today
Free cancellation
4.95 out of 5 average rating, 119 reviews
4.95 (119)
Flat in Little Italy
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
$3,183 SGD
$2,932 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Guest favourite
Guest favourite
Apartment in Bronzeville
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
$7,562 SGD
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for 5 nights
$7,562 SGD for 5 nights
Pay $0 today
Free cancellation
4.89 out of 5 average rating, 9 reviews
4.89 (9)
Guest favourite
Guest favourite
Flat in Downtown Chicago
Modern 3BR Apartment Near North Ave Shops
3 bedrooms
3 bedrooms
,
·
3 double beds
3 double beds
,
·
2 bathrooms
2 bathrooms
21–26 Jul
21–26 Jul
$4,698 SGD
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for 5 nights
$4,698 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Top guest favourite
Guest favourite
Home in South Side
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
$3,563 SGD
$3,137 SGD
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for 5 nights
Book early to save
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 21 reviews
5.0 (21)
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
9–14 Aug
9–14 Aug
$1,633 SGD
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for 5 nights
$1,633 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Top guest favourite
Guest favourite
Bungalow in Beverly
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
$6,312 SGD
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for 5 nights
$6,312 SGD 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
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
$1,859 SGD
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for 5 nights
$1,859 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 12 reviews
5.0 (12)
Guest favourite
Guest favourite
Flat in South Side
Bronzeville Hidden Oasis
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
22–27 Sept
22–27 Sept
$2,303 SGD
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for 5 nights
$2,303 SGD for 5 nights
Pay $0 today
Free cancellation
4.98 out of 5 average rating, 183 reviews
4.98 (183)
Guest favourite
Guest favourite
Guest suite in Norwood Park
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
16–21 Aug
16–21 Aug
$769 SGD
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for 5 nights
$769 SGD for 5 nights
Pay $0 today
Free cancellation
4.88 out of 5 average rating, 433 reviews
4.88 (433)
Top guest favourite
Guest favourite
Apartment in Wicker Park
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
6–11 Aug
6–11 Aug
$5,136 SGD
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for 5 nights
$5,136 SGD for 5 nights
Pay $0 today
Free cancellation
4.97 out of 5 average rating, 156 reviews
4.97 (156)
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
30 Aug – 4 Sept
30 Aug – 4 Sept
$2,290 SGD
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for 5 nights
$2,290 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 Ukrainian Village
Stylish & Spacious Multi-Level Apt in Wicker Park
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
30 Aug – 4 Sept
30 Aug – 4 Sept
$2,326 SGD
$2,119 SGD
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for 5 nights
Free cancellation
4.96 out of 5 average rating, 26 reviews
4.96 (26)
Top guest favourite
Guest favourite
Flat in North Side
Quiet & Modern Avondale Apartment
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
6–11 Sept
6–11 Sept
$1,243 SGD
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for 5 nights
$1,243 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Guest favourite
Guest favourite
Flat in Belmont Cragin
Modern 2 BR Retreat Steps From Family Park
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
30 Aug – 4 Sept
30 Aug – 4 Sept
$2,056 SGD
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for 5 nights
$2,056 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Flat in West Side
Cozy Apartment in Pilsen | 2BR 2B | 15 Min to Town
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
2 bathrooms
2 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,394 SGD
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for 5 nights
$1,394 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
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
$742 SGD
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for 5 nights
$742 SGD for 5 nights
Pay $0 today
Free cancellation
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