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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

$1,098 SGD for 5 nights

,

4.97 out of 5 average rating, 331 reviews

Top guest favourite

Place to stay in Berwyn

room in family home

1 bedroom1 bed, 1 bathroom,

1–6 Dec

$346 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 9 reviews

Place to stay in Chicago

Private Room for 3 Guests By Grand Ave Blueline

1 bedroom2 beds, 2 bathrooms,

1–6 Jan

$566 SGD for 5 nights

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Free cancellation

Top guest favourite

Flat in Chicago

Ravenswood Guest House Annex

1 bedroom3 beds, 1 bathroom,

7–12 Sept

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Free cancellation

4.93 out of 5 average rating, 485 reviews

Top guest favourite

Home in Chicago

Chicago Row House Garden Apartmt

1 bedroom1 bed, 1 bathroom,

29 Aug – 3 Sept

$1,187 SGD for 5 nights

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Free cancellation

4.96 out of 5 average rating, 47 reviews

Top guest favourite

Guest suite in Chicago

Private Lincoln Square one bed+bath studio apt.

1 bedroom1 queen bed, 1 bathroom,

12–17 Oct

$1,179 SGD for 5 nights

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Free cancellation

4.99 out of 5 average rating, 419 reviews

Top guest favourite

Flat in Chicago

Stylish Hyde Park/Kenwood Brownstone Garden Apt

2 bedrooms3 beds, 1.5 bathrooms,

12–17 Jul

$1,331 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 12 reviews

Top guest favourite

Apartment in Chicago

Summer Break Incoming! Live Like an A-ville Local!

2 bedrooms2 bathrooms,

7–12 Jun

Extended stay discount

4.98 out of 5 average rating, 42 reviews

Flat in Chicago

Luxury South Loop Apt

2 bedsNo bathroom,

2–7 Jul

$2,561 SGD for 5 nights

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Free cancellation

New place to stay

Guest favourite

Rooms in Chicago

Spacious Haven in North Park

3 bedrooms4 beds, 1 bathroom,

21–26 Sept

$822 SGD for 5 nights

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Free cancellation

4.9 out of 5 average rating, 59 reviews

Flat in Chicago

Garden Retreat Pilsen Chicago Apartment

2 bedrooms3 beds, 2 bathrooms,

7–12 Jun

$1,219 SGD for 5 nights

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Free cancellation

New place to stay

Top guest favourite

Flat in Chicago

Bright & Spacious Boho Oasis: A Warm Retreat

1 bedroom2 beds, 1 bathroom,

26–31 Jul

$2,055 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 7 reviews

Featured hotel

Hotel in Chicago

Deluxe king room & rooftop bar with views

1 bedroom1 king bed, 1 bathroom,

29 Jun – 4 Jul

$1,521 SGD for 5 nights

+$200 SGD Airbnb credit

5.0 out of 5 average rating, 4 reviews

Guest favourite

Flat in Chicago

LIVN Millennium Park Downtown Chicago 1 BR

1 bedroom1 queen bed, 1 bathroom,

10–15 Jun

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Free cancellation

4.98 out of 5 average rating, 52 reviews

Flat in Chicago

Comfortable 2BR Stay Near Restaurants & Transit

2 bedrooms3 beds, 1 bathroom,

7–12 Jun

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Free cancellation

New place to stay

Top guest favourite

Flat in Chicago

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

1 bedroom2 beds, 1 bathroom,

6–11 Sept

$1,027 SGD for 5 nights

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Free cancellation

4.99 out of 5 average rating, 106 reviews

Flat in Chicago

Chicago Classic•Skyline View•1BR + Den, Train Near

1 bedroom5 beds, 1 bathroom,

28 Jun – 3 Jul

$1,073 SGD for 5 nights

Free cancellation

New place to stay

Superhost

Flat in Chicago

DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry

2 bedrooms3 beds, 1 bathroom,

5–10 Jul

$1,434 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Room in Chicago

Private room w/bath in urban canopy

1 double bed1 bathroom,

28 Jun – 3 Jul

$694 SGD for 5 nights

Pay $0 today

Free cancellation

4.96 out of 5 average rating, 546 reviews