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Search results; Over 1,000 homes in Chicago

Top guest favourite

Flat in Chicago

Gym, Garage Parking, Balcony, Sleeps 4

2 bedrooms, 2 beds, 2 private bathrooms

14–19 Aug

$3,527 SGD for 5 nights

,

5.0 out of 5 average rating, 34 reviews

Apartment in Chicago

The Langley Luxe modern style unit

2 bedrooms3 beds, 1 bathroom,

28 Jun – 3 Jul

$1,211 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 3 reviews

Guest favourite

Flat in Chicago

2BR Avondale Apt: Free Parking + Steps to Blueline

2 bedrooms3 beds, 1 bathroom,

8–13 Aug

$1,229 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Home in Chicago

Historic Spacious Chicago Home • Free Parking

2 bedrooms3 queen beds, 2 bathrooms,

16–21 Aug

$1,445 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 6 reviews

Flat in Chicago

Garden Retreat Pilsen Chicago Apartment

2 bedrooms3 beds, 2 bathrooms,

29 Jun – 4 Jul

$1,296 SGD for 5 nights

New place to stay

Top guest favourite

Home in Chicago

New Home | O'Hare Airport

4 bedrooms4 beds, 3 bathrooms,

5–10 Jul

$3,021 SGD for 5 nights

5.0 out of 5 average rating, 13 reviews

Superhost

Flat in Chicago

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

2 bedrooms3 beds, 1 bathroom,

19–24 Jul

$1,947 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 3 reviews

Superhost

Apartment in Chicago

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

2 bedrooms2 beds, 2 bathrooms,

5–10 Jul

Pay $0 today

Free cancellation

4.95 out of 5 average rating, 155 reviews

Top guest favourite

Flat in Oak Park

Serene 1-Bedroom Suite in Oak Park (Free Parking!)

1 bedroom1 king bed, 1 bathroom,

20–25 Oct

$685 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 49 reviews

Top guest favourite

Flat in Chicago

Luxury Living in Bronzeville with Massive Roofdeck

3 bedrooms3 beds, 2 bathrooms,

30 Aug – 4 Sept

$2,271 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 12 reviews

Top guest favourite

Flat in Chicago

Boho City Escape | Parking + Balcony

2 bedrooms3 beds, 2 bathrooms,

28 Jun – 3 Jul

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 14 reviews

Top guest favourite

Flat in Chicago

Designer Garden Unit in Bridgeport

2 bedrooms2 queen beds, 1 bathroom,

9–14 Aug

$1,363 SGD for 5 nights

Pay $0 today

Free cancellation

4.97 out of 5 average rating, 61 reviews

Superhost

Flat in Chicago

Stunning Apt, walk to NEU, “The Bernard”

4 bedrooms3 beds, 1 bathroom,

26–31 Jul

$2,259 SGD for 5 nights

Pay $0 today

Free cancellation

Top guest favourite

Apartment in Chicago

Modern stay in lively Wicker Park neighborhood!

2 bedrooms3 beds, 1 bathroom,

31 Aug – 5 Sept

Book early to save

5.0 out of 5 average rating, 103 reviews

Top guest favourite

Home in Brookfield

Cozy Home in Brookfield

2 bedrooms2 beds, 1 bathroom,

16–21 Aug

$1,703 SGD for 5 nights

4.99 out of 5 average rating, 86 reviews

Guest favourite

Flat in Chicago

LIVN Millennium Park Downtown Chicago 1 BR

1 bedroom1 queen bed, 1 bathroom,

3–8 Aug

$3,384 SGD for 5 nights

Pay $0 today

Free cancellation

4.98 out of 5 average rating, 56 reviews

Top guest favourite

Home in Chicago

Big house in the BEST Location!

3 bedrooms3 beds, 2.5 bathrooms,

24–29 Aug

$2,102 SGD for 5 nights

4.98 out of 5 average rating, 57 reviews

Home in Chicago

Steps to Lake & Beach! Multi-Level Oakland Haven

4 bedrooms5 beds, 4.5 bathrooms,

29 Jun – 4 Jul

$3,784 SGD for 5 nights

New place to stay

Flat in Chicago

West Ridge 2BR Retreat with Laundry | Near Loyola

2 bedrooms2 beds, 2 bathrooms,

5–10 Jul

$1,250 SGD for 5 nights

New place to stay