We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Search results; Over 1,000 homes in Chicago

Home in Chicago

Newly Renovated Home 4BD/3BTH with garage!

4 bedrooms5 beds, 3 bathrooms,

28 Jun – 3 Jul

$2,472 SGD for 5 nights

New place to stay

Superhost

Flat in Chicago

Stunning Apt, walk to NEU, “The Bernard”

4 bedrooms3 beds, 1 bathroom,

26–31 Jul

$1,895 SGD for 5 nights

Top guest favourite

Home in Oak Park

Grove Flat

2 bedrooms2 beds, 1 bathroom,

15–20 Aug

$1,223 SGD for 5 nights

5.0 out of 5 average rating, 13 reviews

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

$2,586 SGD for 5 nights

5.0 out of 5 average rating, 14 reviews

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

Guest favourite

Apartment in Chicago

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

2 bedrooms2 beds, 2 bathrooms,

5–10 Jul

$1,667 SGD for 5 nights

4.95 out of 5 average rating, 155 reviews

Top guest favourite

Flat in Chicago

Pilsen Modern Chic Retreat

2 bedrooms3 beds, 1.5 bathrooms,

12–17 Oct

$1,598 SGD for 5 nights

4.95 out of 5 average rating, 113 reviews

Top guest favourite

Flat in Chicago

ChiCasa Wicker Park Paradise

3 bedrooms4 beds, 2.5 bathrooms,

29 Aug – 3 Sept

5.0 out of 5 average rating, 49 reviews

Guest favourite

Apartment in Chicago

The Modern Woodlawn 2 Bed 2 Bath

2 bedrooms2 beds, 2 bathrooms,

9–14 Aug

$1,675 SGD for 5 nights

4.96 out of 5 average rating, 77 reviews

Flat in Chicago

2BR Avondale Apt: Free Parking + Steps to Blueline

2 bedrooms3 beds, 1 bathroom,

14–19 Jun

$1,227 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Flat in Chicago

West Ridge 2BR Retreat with Laundry | Near Loyola

2 bedrooms2 beds, 2 bathrooms,

5–10 Jul

$1,249 SGD for 5 nights

New place to stay

Top guest favourite

Apartment in Chicago

Modern stay in lively Wicker Park neighborhood!

2 bedrooms3 beds, 1 bathroom,

31 Aug – 5 Sept

5.0 out of 5 average rating, 103 reviews

Top guest favourite

Flat in Chicago

Luxe Wrigley Estate: Pool Table + Parking + Patio

4 bedrooms7 beds, 2 bathrooms,

22–27 Jun

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Home in Brookfield

Cozy Home in Brookfield

2 bedrooms2 beds, 1 bathroom,

14–19 Jun

$1,557 SGD for 5 nights

4.99 out of 5 average rating, 85 reviews

Top guest favourite

Home in Chicago

New Home | O'Hare Airport

4 bedrooms4 beds, 3 bathrooms,

5–10 Jul

$3,322 SGD for 5 nights

5.0 out of 5 average rating, 13 reviews

Top guest favourite

Flat in Chicago

Fulton House #1 (2bd/ 1ba)

2 bedrooms2 queen beds, 1 bathroom,

14–19 Jun

4.95 out of 5 average rating, 103 reviews

Guest favourite

Flat in Chicago

LIVN Millennium Park Downtown Chicago 1 BR

1 bedroom1 queen bed, 1 bathroom,

10–15 Jun

4.98 out of 5 average rating, 54 reviews