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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
Cozy loft in Chicago's Uptown
1 bedroom
,
·
2 beds
,
·
1 private bathroom
9–14 Nov
9–14 Nov
$1,058 SGD
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for 5 nights
$1,058 SGD for 5 nights
,
·
4.97 out of 5 average rating, 331 reviews
4.97 (331)
Top guest favourite
Guest favourite
Home in Chicago
New Home | O'Hare Airport
4 bedrooms
4 bedrooms
4 beds
,
·
4 beds
3 bathrooms
,
·
3 bathrooms
5–10 Jul
5–10 Jul
$3,116 SGD
$2,512 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Flat in Chicago
3BR Vintage Apt • Patio • Walk to McKinley Park
3 bedrooms
3 bedrooms
3 queen beds
,
·
3 queen beds
1 bathroom
,
·
1 bathroom
21–26 Jun
21–26 Jun
$1,526 SGD
Show price breakdown
for 5 nights
$1,526 SGD for 5 nights
Free cancellation
New place to stay
New
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
$2,825 SGD
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for 5 nights
$2,825 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 15 reviews
5.0 (15)
Superhost
Superhost
Flat in Chicago
Stunning Apt, walk to NEU, “The Bernard”
4 bedrooms
4 bedrooms
3 beds
,
·
3 beds
1 bathroom
,
·
1 bathroom
26–31 Jul
26–31 Jul
$2,301 SGD
Show price breakdown
for 5 nights
$2,301 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms
3 bedrooms
3 beds
,
·
3 beds
2 bathrooms
,
·
2 bathrooms
30 Aug – 4 Sept
30 Aug – 4 Sept
$2,266 SGD
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for 5 nights
$2,266 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 12 reviews
5.0 (12)
Top guest favourite
Guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms
2 bedrooms
2 queen beds
,
·
2 queen beds
1 bathroom
,
·
1 bathroom
9–14 Aug
9–14 Aug
$1,360 SGD
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for 5 nights
$1,360 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 62 reviews
4.97 (62)
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
18–23 Oct
18–23 Oct
$1,426 SGD
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for 5 nights
$1,426 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 115 reviews
4.95 (115)
Flat in Chicago
Retro Logan Square Retreat • Blue Line
1 bedroom
1 bedroom
1 bunk bed
,
·
1 bunk bed
1 bathroom
,
·
1 bathroom
15–20 Aug
15–20 Aug
$911 SGD
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for 5 nights
$911 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Flat in Chicago
Modern 2 BR Retreat Steps From Family Park
2 bedrooms
2 bedrooms
3 beds
,
·
3 beds
1 bathroom
,
·
1 bathroom
12–17 Jul
12–17 Jul
$1,662 SGD
Show price breakdown
for 5 nights
$1,662 SGD for 5 nights
Free cancellation
New place to stay
New
Home in Chicago
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms
3 bedrooms
6 beds
,
·
6 beds
2 bathrooms
,
·
2 bathrooms
21–26 Jun
21–26 Jun
$2,919 SGD
$2,634 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Top guest favourite
Guest favourite
Flat in Chicago
Boho City Escape | Parking + Balcony
2 bedrooms
2 bedrooms
3 beds
,
·
3 beds
2 bathrooms
,
·
2 bathrooms
24–29 Jul
24–29 Jul
$3,177 SGD
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for 5 nights
$3,177 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 14 reviews
5.0 (14)
Guest favourite
Guest favourite
Flat in Evanston
"Melody of Evanston 3bd, 2 Bath UrbanLux"
3 bedrooms
3 bedrooms
6 beds
,
·
6 beds
2 bathrooms
,
·
2 bathrooms
20–25 Jun
20–25 Jun
$5,474 SGD
$3,983 SGD
Show price breakdown
for 5 nights
Free cancellation
4.94 out of 5 average rating, 36 reviews
4.94 (36)
Top guest favourite
Guest favourite
Flat in Chicago
CityLine Views • Rooftop • Free EV Garage Parking
2 bedrooms
2 bedrooms
8 beds
,
·
8 beds
2 bathrooms
,
·
2 bathrooms
15–21 Jun
15–21 Jun
$5,671 SGD
Show price breakdown
for 6 nights
$5,671 SGD for 6 nights
Free cancellation
4.96 out of 5 average rating, 70 reviews
4.96 (70)
Townhouse in Chicago
Walk to United Center 9 mins-Downtown FreeParking
3 bedrooms
3 bedrooms
3 beds
,
·
3 beds
3 bathrooms
,
·
3 bathrooms
30 Jun – 5 Jul
30 Jun – 5 Jul
$2,975 SGD
$2,646 SGD
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for 5 nights
Free cancellation
4.67 out of 5 average rating, 6 reviews
4.67 (6)
Top guest favourite
Guest favourite
Flat in Chicago
Luxe Wrigley Estate: Pool Table + Parking + Patio
4 bedrooms
4 bedrooms
7 beds
,
·
7 beds
2 bathrooms
,
·
2 bathrooms
22–27 Jun
22–27 Jun
$5,242 SGD
$4,092 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Guest favourite
Guest favourite
Flat in Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
2 bedrooms
2 bedrooms
2 bathrooms
,
·
2 bathrooms
30 Aug – 4 Sept
30 Aug – 4 Sept
$2,571 SGD
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for 5 nights
$2,571 SGD for 5 nights
Free cancellation
4.93 out of 5 average rating, 14 reviews
4.93 (14)
Guest favourite
Guest favourite
Home in Oak Park
Spacious Oak Park 4bd/3.5ba and Parking
4 bedrooms
4 bedrooms
5 beds
,
·
5 beds
3.5 bathrooms
,
·
3.5 bathrooms
28 Jun – 3 Jul
28 Jun – 3 Jul
$3,049 SGD
$2,624 SGD
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for 5 nights
Free cancellation
4.87 out of 5 average rating, 67 reviews
4.87 (67)
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
25–30 Aug
25–30 Aug
$2,288 SGD
Show price breakdown
for 5 nights
$2,288 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 7 reviews
5.0 (7)
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