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Search results; Over 1,000 homes in Chicago
Over 1,000 homes in Chicago
Guest favourite
Guest favourite
Apartment in Wrigleyville
Dream Condo steps from Wrigley Field!
2 bedrooms
,
·
2 beds
,
·
1 private bathroom
6–11 Jul
6–11 Jul
$1,493 SGD
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for 5 nights
$1,493 SGD for 5 nights
,
·
4.82 out of 5 average rating, 387 reviews
4.82 (387)
Guest favourite
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
7–12 Jul
7–12 Jul
$2,514 SGD
$1,702 SGD
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for 5 nights
4.98 out of 5 average rating, 83 reviews
4.98 (83)
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
26 Sept – 1 Oct
26 Sept – 1 Oct
$3,814 SGD
$3,355 SGD
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for 5 nights
Book early to save
5.0 out of 5 average rating, 21 reviews
5.0 (21)
Top guest favourite
Guest favourite
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
16–21 Aug
16–21 Aug
$1,670 SGD
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for 5 nights
$1,670 SGD for 5 nights
5.0 out of 5 average rating, 12 reviews
5.0 (12)
Guest favourite
Guest favourite
Flat in Downtown Chicago
Luxury Loft Collection 03 - Terrace - River North
3 bedrooms
3 bedrooms
,
·
7 beds
7 beds
16–21 Aug
16–21 Aug
$5,992 SGD
$4,043 SGD
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for 5 nights
4.95 out of 5 average rating, 107 reviews
4.95 (107)
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
9–14 Aug
9–14 Aug
$3,182 SGD
$2,931 SGD
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for 5 nights
New place to stay
New
Home in Chicago
Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
10–15 Aug
10–15 Aug
$1,764 SGD
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for 5 nights
$1,764 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Flat in South Side
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
16–21 Aug
16–21 Aug
$1,332 SGD
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for 5 nights
$1,332 SGD for 5 nights
5.0 out of 5 average rating, 18 reviews
5.0 (18)
Guest favourite
Guest favourite
Home in Ukrainian Village
West Town Gem: 2BR w/ Patio, W/D + Free Parking
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
15–20 Aug
15–20 Aug
$2,200 SGD
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for 5 nights
$2,200 SGD for 5 nights
5.0 out of 5 average rating, 11 reviews
5.0 (11)
Guest favourite
Guest favourite
Flat in Belmont Cragin
Modern 2 BR Retreat Steps From Family Park
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
30 Aug – 4 Sept
30 Aug – 4 Sept
$1,675 SGD
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for 5 nights
$1,675 SGD for 5 nights
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Apartment in Wicker Park
Luxury Oasis in the Heart of the City w Roof Deck
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
5–10 Jul
5–10 Jul
$4,333 SGD
$3,960 SGD
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for 5 nights
New place to stay
New
Guest house in West Town
Upscale Wicker Park Retreat
4 bedrooms
4 bedrooms
,
·
8 beds
8 beds
12–17 Jul
12–17 Jul
$3,900 SGD
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for 5 nights
$3,900 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Flat in Lake View
A Whimsical Fairy-tale Loft in Ravenswood Chicago
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
5–10 Jul
5–10 Jul
$1,213 SGD
$1,066 SGD
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for 5 nights
4.99 out of 5 average rating, 346 reviews
4.99 (346)
Top guest favourite
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
25–30 Oct
25–30 Oct
$1,359 SGD
$1,212 SGD
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for 5 nights
4.95 out of 5 average rating, 119 reviews
4.95 (119)
Guest favourite
Guest favourite
Flat in Downtown Chicago
Luxury Designer Loft 402 | River North
3 bedrooms
3 bedrooms
,
·
3 queen beds
3 queen beds
4–9 Aug
4–9 Aug
$5,941 SGD
$4,211 SGD
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for 5 nights
4.95 out of 5 average rating, 21 reviews
4.95 (21)
Superhost
Superhost
Flat in South Loop
Paradise Lounge South loop 3br W/ Balcony
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
9–14 Aug
9–14 Aug
$2,191 SGD
$1,883 SGD
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for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Apartment in Wrigleyville
Wrigleyville Updated Condo with Free Parking
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
27 Sept – 2 Oct
27 Sept – 2 Oct
$2,667 SGD
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for 5 nights
$2,667 SGD for 5 nights
5.0 out of 5 average rating, 101 reviews
5.0 (101)
Guest favourite
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms
2 bedrooms
,
·
3 queen beds
3 queen beds
23–28 Aug
23–28 Aug
$1,855 SGD
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for 5 nights
$1,855 SGD for 5 nights
5.0 out of 5 average rating, 12 reviews
5.0 (12)
Superhost
Superhost
Apartment in North Side
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
15–20 Aug
15–20 Aug
$1,707 SGD
$1,567 SGD
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for 5 nights
4.96 out of 5 average rating, 160 reviews
4.96 (160)
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