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Search results; Over 1,000 homes in Chicago
Over 1,000 homes in Chicago
Guest favourite
Guest favourite
Flat in Chicago
Elegant Suite in Gold Coast
1 bedroom
,
·
2 beds
,
·
1.5 private bathrooms
28 Aug – 2 Sept
28 Aug – 2 Sept
$3,316 SGD
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for 5 nights
$3,316 SGD for 5 nights
,
·
4.98 out of 5 average rating, 206 reviews
4.98 (206)
Guest favourite
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
1–6 Jul
1–6 Jul
$2,743 SGD
$1,380 SGD
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for 5 nights
4.97 out of 5 average rating, 76 reviews
4.97 (76)
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
$1,384 SGD
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for 5 nights
$1,384 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 119 reviews
4.95 (119)
Superhost
Superhost
Apartment in Chicago
Elegant Historic Duplex | Old Town • Lincoln Park
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2.5 bathrooms
2.5 bathrooms
23–28 Aug
23–28 Aug
$2,413 SGD
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for 5 nights
$2,413 SGD for 5 nights
Free cancellation
New place to stay
New
Guest favourite
Guest favourite
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
$1,455 SGD
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for 5 nights
$1,455 SGD for 5 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Home in Chicago
Designer Home | Steps to the Obama Center & Beach
5 bedrooms
5 bedrooms
,
·
10 beds
10 beds
,
·
3.5 bathrooms
3.5 bathrooms
1–6 Jul
1–6 Jul
$6,162 SGD
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for 5 nights
$6,162 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
3–8 Jul
3–8 Jul
$2,351 SGD
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for 5 nights
$2,351 SGD for 5 nights
5.0 out of 5 average rating, 12 reviews
5.0 (12)
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
$2,854 SGD
$2,335 SGD
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for 5 nights
5.0 out of 5 average rating, 52 reviews
5.0 (52)
Top guest favourite
Guest favourite
Room in Chicago
NEW,Roscoe Village,Cubs, Pvt Bath, Pvt Entrance
3 beds
3 beds
,
·
1 bathroom
1 bathroom
25–30 Oct
25–30 Oct
$790 SGD
$683 SGD
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for 5 nights
Free cancellation
4.95 out of 5 average rating, 678 reviews
4.95 (678)
Flat in Chicago
Northside Chicago Apartment
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
7–12 Sept
7–12 Sept
$741 SGD
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for 5 nights
$741 SGD for 5 nights
Free cancellation
New place to stay
New
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
$1,845 SGD
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for 5 nights
$1,845 SGD for 5 nights
5.0 out of 5 average rating, 8 reviews
5.0 (8)
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
$1,880 SGD
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for 5 nights
$1,880 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 10 reviews
5.0 (10)
Home in Chicago
Comfortable welcoming stay for business or leisure
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
1–6 Jul
1–6 Jul
$3,590 SGD
$3,002 SGD
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for 5 nights
New home discount
Free cancellation
New place to stay
New
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
,
·
2 bathrooms
2 bathrooms
5–10 Jul
5–10 Jul
$2,288 SGD
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for 5 nights
$2,288 SGD for 5 nights
5.0 out of 5 average rating, 15 reviews
5.0 (15)
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
5–10 Jul
5–10 Jul
$1,993 SGD
$1,570 SGD
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for 5 nights
4.91 out of 5 average rating, 188 reviews
4.91 (188)
Guest house in Chicago
Upscale Wicker Park Retreat
4 bedrooms
4 bedrooms
,
·
8 beds
8 beds
,
·
3 bathrooms
3 bathrooms
12–17 Jul
12–17 Jul
$4,597 SGD
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for 5 nights
$4,597 SGD for 5 nights
New place to stay
New
Place to stay in Chicago
Happy Homes U&I – Quiet Basement Retreat
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
2 bathrooms
2 bathrooms
1–6 Jul
1–6 Jul
$400 SGD
Show price breakdown
for 5 nights
$400 SGD for 5 nights
Free cancellation
New place to stay
New
Top guest favourite
Guest favourite
Flat in Chicago
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
21–26 Sept
21–26 Sept
$1,168 SGD
$1,082 SGD
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for 5 nights
4.98 out of 5 average rating, 129 reviews
4.98 (129)
Luxe
Luxe
Flat in Chicago
Luxury PH: Panoramic Views + Prime Location
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3.5 bathrooms
3.5 bathrooms
6–12 Jul
6–12 Jul
$16,105 SGD
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for 6 nights
$16,105 SGD for 6 nights
New place to stay
New
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