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Search results; Over 1,000 homes in Chicago

Top guest favourite

Flat in Chicago

Cozy loft in Chicago's Uptown

1 bedroom, 2 beds, 1 private bathroom

4–9 Jul

$1,094 SGD for 5 nights

,

4.97 out of 5 average rating, 331 reviews

Home in Chicago

Newly Renovated Home 4BD/3BTH with garage!

4 bedrooms5 beds, 3 bathrooms,

28 Jun – 3 Jul

$2,466 SGD for 5 nights

New place to stay

Guest favourite

Flat in Chicago

Luxury Loft Collection 01 - Terrace - River North

3 bedrooms8 beds, 3 bathrooms,

23–28 Aug

$6,429 SGD for 5 nights

4.91 out of 5 average rating, 117 reviews

Top guest favourite

Home in Chicago

Beautifully Renovated Loft-Style Coach House

3 bedrooms3 beds, 2 bathrooms,

3–8 Jul

$2,580 SGD for 5 nights

5.0 out of 5 average rating, 14 reviews

Flat in Chicago

2BR Avondale Apt: Free Parking + Steps to Blueline

2 bedrooms3 beds, 1 bathroom,

14–19 Jun

$1,184 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Flat in Chicago

Pilsen Modern Chic Retreat

2 bedrooms3 beds, 1.5 bathrooms,

12–17 Oct

$1,595 SGD for 5 nights

4.95 out of 5 average rating, 113 reviews

Guest favourite

Apartment in Chicago

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

2 bedrooms2 beds, 2 bathrooms,

5–10 Jul

$1,663 SGD for 5 nights

4.95 out of 5 average rating, 155 reviews

Top guest favourite

Flat in Chicago

Luxe Wrigley Estate: Pool Table + Parking + Patio

4 bedrooms7 beds, 2 bathrooms,

7–12 Jun

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Home in Chicago

Big house in the BEST Location!

3 bedrooms3 beds, 2.5 bathrooms,

17–22 Aug

$1,983 SGD for 5 nights

4.98 out of 5 average rating, 56 reviews

Top guest favourite

Home in Brookfield

Cozy Home in Brookfield

2 bedrooms2 beds, 1 bathroom,

14–19 Jun

$1,553 SGD for 5 nights

4.99 out of 5 average rating, 85 reviews

Top guest favourite

Home in Chicago

Chicago Row House Garden Apartmt

1 bedroom1 bed, 1 bathroom,

29 Aug – 3 Sept

$1,185 SGD for 5 nights

4.96 out of 5 average rating, 48 reviews

Top guest favourite

Flat in Chicago

Designer Garden Unit in Bridgeport

2 bedrooms2 queen beds, 1 bathroom,

9–14 Aug

$1,367 SGD for 5 nights

4.97 out of 5 average rating, 59 reviews

Guest favourite

Flat in Chicago

Downtown Penthouse Huge Patio with Great View

3 bedrooms5 beds, 2 bathrooms,

7–12 Jun

$6,480 SGD for 5 nights

4.99 out of 5 average rating, 70 reviews

Top guest favourite

Home in Villa Park

Cozy 5BD Home with Scandinavian Vibes

5 bedrooms5 beds, 2 bathrooms,

16–21 Aug

4.97 out of 5 average rating, 33 reviews

Top guest favourite

Home in Chicago

New Home | O'Hare Airport

4 bedrooms4 beds, 3 bathrooms,

5–10 Jul

5.0 out of 5 average rating, 13 reviews

Flat in Chicago

Plymouth Collection: 3BD 2BA with Gym & Rooftop

3 bedrooms3 beds, 2 bathrooms,

2–7 Jul

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Flat in Chicago

Historic oasis in the middle of everything.

3 bedrooms4 beds, 1 bathroom,

21–26 Jun

4.96 out of 5 average rating, 309 reviews

Superhost

Flat in Chicago

Luxe 4BR Brick & Stone by Douglass Park + Med Dist

4 bedrooms4 beds, 2 bathrooms,

7–12 Jun

Guest favourite

Room in Chicago

Private Room in Norwood Park

1 bed1 bathroom,

14–19 Jun

4.97 out of 5 average rating, 37 reviews