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Search results; Over 1,000 homes in Chicago

Superhost

Apartment in Chicago

Near McCormick Place and Minutes from Downtown!

1 bedroom, 1 bed, 1 private bathroom

29 Aug – 3 Sept

$1,196 SGD for 5 nights

,

4.86 out of 5 average rating, 399 reviews

Room in Chicago

Iconic City | Riverwalk. Free Breakfast*

2 beds

23–28 Aug

$1,455 SGD for 5 nights

New place to stay

Room in Chicago

Iconic Journey | Navy Pier. Free Breakfast*

2 beds

7–12 Sept

$1,204 SGD for 5 nights

New place to stay

Guest favourite

Flat in Chicago

LIVN Millennium Park Downtown Chicago 1 BR

1 bedroom, 1 queen bed

28 Aug – 2 Sept

4.88 out of 5 average rating, 139 reviews

Home in Chicago

Charming Historic Row Home | Lincoln Park

3 bedrooms, 3 beds

15–20 Nov

$1,692 SGD for 5 nights

New place to stay

Top guest favourite

Guest house in Chicago

Horner Park Coach House

1 bedroom, 1 bed

27 Oct – 1 Nov

$733 SGD for 5 nights

5.0 out of 5 average rating, 5 reviews

Guest favourite

Apartment in Chicago

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

2 bedrooms, 2 beds

2–7 Nov

$1,277 SGD for 5 nights

4.95 out of 5 average rating, 169 reviews

Guest favourite

Guest suite in Chicago

2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking

2 bedrooms, 3 beds

28 Sept – 3 Oct

$788 SGD for 5 nights

4.88 out of 5 average rating, 441 reviews

Guest favourite

Flat in Chicago

Spacious 1BR | Washer/Dryer | Near Lincoln Square

1 bedroom, 1 bed

30 Aug – 4 Sept

4.89 out of 5 average rating, 9 reviews

Top guest favourite

Flat in Chicago

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

1 bedroom, 2 beds

24–29 Nov

$922 SGD for 5 nights

4.99 out of 5 average rating, 109 reviews

Top guest favourite

Home in Lombard

Modern Boho house in Lombard 7 min to Metra

2 bedrooms, 3 beds

4–9 Oct

$1,383 SGD for 5 nights

4.99 out of 5 average rating, 154 reviews

Top guest favourite

Flat in Chicago

Quiet & Modern Avondale Apartment

2 bedrooms, 2 queen beds

27 Sept – 2 Oct

$1,154 SGD for 5 nights

5.0 out of 5 average rating, 19 reviews

Guest favourite

Flat in Chicago

Sunny Penthouse - Oakwood Beach

2 bedrooms, 3 beds

27 Sept – 2 Oct

$2,053 SGD for 5 nights

4.96 out of 5 average rating, 71 reviews

Room in Chicago

Charming Room in Historic Ukrainian Village!

1 queen bed

6–11 Sept

$622 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Flat in Oak Park

Premier Luxe Retreat | Free Parking

1 bedroom, 4 beds

7–12 Sept

$830 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Guest favourite

Apartment in Chicago

UChicago Condo | 2 Baths, Private Parking & Entry

1 bedroom, 1 queen bed

23–28 Aug

4.94 out of 5 average rating, 67 reviews

Top guest favourite

Flat in Forest Park

Walk to Oak Park from Our Sunny Turn of the Century Apt

2 bedrooms, 3 beds

23–28 Oct

$1,095 SGD for 5 nights

4.98 out of 5 average rating, 417 reviews

Room in Chicago

Near Magnificent Mile | Gym. Free Breakfast.

2 queen beds

22–27 Aug

$1,919 SGD for 5 nights

New place to stay

Top guest favourite

Home in Chicago

Peaceful Modern Full House in Trendy Bridgeport

2 bedrooms, 2 queen beds

2–7 Nov

$831 SGD for 5 nights

4.96 out of 5 average rating, 310 reviews