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Search results; Over 1,000 homes in Chicago

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Apartment in Chicago

Lovely top floor 2BR/2BA, steps from everything!

2 bedrooms, 2 beds, 2 bathrooms

2–7 Nov

$1,224 SGD for 5 nights

,

4.95 out of 5 average rating, 175 reviews

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Hotel in Chicago

Sports Illustrated Resorts Chicago, Studio king

1 bedroom, 1 king bed, 1 bathroom

1–6 Oct

$2,903 SGD for 5 nights

New place to stay

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Flat in Chicago

Luxury Loft Collection 01 - Terrace - River North

3 bedrooms, 8 beds, 3 bathrooms

8–13 Nov

$2,815 SGD for 5 nights

4.9 out of 5 average rating, 126 reviews

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Home in Chicago

Beautifully Renovated Loft-Style Coach House

3 bedrooms, 3 beds, 2 bathrooms

8–13 Nov

$1,984 SGD for 5 nights

5.0 out of 5 average rating, 37 reviews

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Flat in Chicago

Designer Loft 3E | Heart of Gold Coast/River North

3 bedrooms, 6 beds, 2.5 bathrooms

16–21 Oct

$3,264 SGD for 5 nights

New place to stay

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Apartment in Chicago

The Modern Woodlawn 2 Bed 2 Bath

2 bedrooms, 2 beds, 2 bathrooms

19–24 Oct

$1,617 SGD for 5 nights

4.96 out of 5 average rating, 93 reviews

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Flat in Chicago

Kasa Lake Shore Chicago | Two Bedroom Double Queen

2 bedrooms, 3 beds, 1 bathroom

4–9 Oct

$3,955 SGD for 5 nights

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Flat in Chicago

Pilsen Modern Chic Retreat

2 bedrooms, 3 beds, 1.5 bathrooms

24–29 Jan

$964 SGD for 5 nights

4.95 out of 5 average rating, 136 reviews

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Apartment in Chicago

3-bedroom exposed brick in Chicago's Wicker Park

3 bedrooms, 4 beds, 2 bathrooms

25–30 Oct

$2,358 SGD for 5 nights

4.97 out of 5 average rating, 172 reviews

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Rooms in Chicago

Spacious Sun-Lit Suite in Chicago

2 bedrooms, 2 beds, 1 bathroom

1–6 Oct

$951 SGD for 5 nights

4.96 out of 5 average rating, 26 reviews

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Home in Forest Park

Ferdinand Rear Home

2 bedrooms, 2 queen beds, 1 bathroom

2–7 Jan

$514 SGD for 5 nights

4.75 out of 5 average rating, 4 reviews

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Flat in Chicago

ChiCasa Wicker Park Paradise

3 bedrooms, 5 beds, 2.5 bathrooms

15–20 Nov

$2,231 SGD for 5 nights

5.0 out of 5 average rating, 65 reviews

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Flat in Chicago

Luxury penthouse with city views

3 bedrooms, 4 beds, 2.5 bathrooms

4–9 Oct

$2,272 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

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Flat in Chicago

Designer CuratedVintage Condo in Popular West Town

2 bedrooms, 3 beds, 1 bathroom

2–7 Jan

$712 SGD for 5 nights

4.94 out of 5 average rating, 263 reviews

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Apartment in Chicago

Apartment in Logan Square | Walker's Paradise!

2 bedrooms, 2 beds, 1 bathroom

28 Nov – 3 Dec

$1,326 SGD for 5 nights

4.94 out of 5 average rating, 16 reviews

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Flat in Oak Park

Oak Park Space+Style Duplex Parking+Walk to Train

3 bedrooms, 6 beds, 2.5 bathrooms

1–6 Oct

$2,728 SGD for 5 nights

5.0 out of 5 average rating, 104 reviews

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Flat in Oak Park

Treetop Oasis Spacious & Modern King Bed + Parking

2 bedrooms, 4 beds, 1 bathroom

1–6 Nov

4.98 out of 5 average rating, 102 reviews

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Bungalow in Chicago

Beverly Hills of Chicago Luxury Guest Favorites xx

5 bedrooms, 8 beds, 3.5 bathrooms

4–9 Oct

$6,586 SGD for 5 nights

4.96 out of 5 average rating, 48 reviews

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Flat in Chicago

A Stylish, sundrenched Chicago Ravenswood Flat

3 bedrooms, 4 beds, 1 bathroom

15–20 Nov

$1,393 SGD for 5 nights

4.99 out of 5 average rating, 363 reviews