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Search results; Over 1,000 homes in Chicago

Guest favourite

Apartment in Chicago

The Upscale Getaway Near Downtown

2 bedrooms, 3 beds, 2 private bathrooms

27 Jul – 1 Aug

$2,883 SGD for 5 nights

,

4.93 out of 5 average rating, 290 reviews

Flat in Chicago

3BR Vintage Apt • Patio • Walk to McKinley Park

3 bedrooms3 queen beds, 1 bathroom,

21–26 Jun

$1,896 SGD for 5 nights

Pay $0 today

Free cancellation

New place to stay

Guest favourite

Flat in Chicago

2BR Avondale Apt: Free Parking + Steps to Blueline

2 bedrooms3 beds, 1 bathroom,

8–13 Aug

$1,219 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 6 reviews

Top guest favourite

Flat in Oak Park

Treetop Oasis With Parking Walkable To Town+Train

2 bedrooms4 beds, 1 bathroom,

28 Jun – 3 Jul

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Free cancellation

4.97 out of 5 average rating, 79 reviews

Superhost

Flat in Chicago

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

2 bedrooms3 beds, 1 bathroom,

19–24 Jul

$1,918 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Home in Chicago

New Home | O'Hare Airport

4 bedrooms4 beds, 3 bathrooms,

5–10 Jul

$2,941 SGD for 5 nights

5.0 out of 5 average rating, 13 reviews

Superhost

Flat in Chicago

Stunning Apt, walk to NEU, “The Bernard”

4 bedrooms3 beds, 1 bathroom,

26–31 Jul

$2,306 SGD for 5 nights

Pay $0 today

Free cancellation

Flat in Chicago

Pilsen Prism: Sun-Drenched 3BR + Parking

3 bedrooms3 beds, 2.5 bathrooms,

22–27 Jun

$3,129 SGD for 5 nights

5.0 out of 5 average rating, 3 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

Flat in Oak Park

Spacious & Stylish Duplex Parking & Walkability

3 bedrooms5 beds, 2.5 bathrooms,

12–17 Jul

$2,597 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 81 reviews

Home in Chicago

Steps to Lake & Beach! Multi-Level Oakland Haven

4 bedrooms5 beds, 4.5 bathrooms,

29 Jun – 4 Jul

$3,776 SGD for 5 nights

New place to stay

Home in Chicago

Boho Luxe Retreat | Garage Parking | Sleeps 13

3 bedrooms6 beds, 2 bathrooms,

21–26 Jun

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Free cancellation

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Flat in Chicago

Boho City Escape | Parking + Balcony

2 bedrooms3 beds, 2 bathrooms,

24–29 Jul

$3,173 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 14 reviews

Top guest favourite

Flat in Chicago

Luxe Wrigley Estate: Pool Table + Parking + Patio

4 bedrooms7 beds, 2 bathrooms,

22–27 Jun

Free cancellation

5.0 out of 5 average rating, 6 reviews

Guest favourite

Home in Oak Park

Spacious Oak Park 4bd/3.5ba and Parking

4 bedrooms5 beds, 3.5 bathrooms,

28 Jun – 3 Jul

Pay $0 today

Free cancellation

4.88 out of 5 average rating, 66 reviews

Guest favourite

Home in Norridge

Modern Ranch | 5 Min to O'Hare, 25 to Chicago

3 bedrooms3 beds, 1.5 bathrooms,

9–14 Aug

$2,454 SGD for 5 nights

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Free cancellation

4.89 out of 5 average rating, 9 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

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Free cancellation

4.97 out of 5 average rating, 61 reviews

Flat in Chicago

Retro Logan Square Retreat • Blue Line

1 bedroom1 bunk bed, 1 bathroom,

15–20 Aug

$913 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Flat in Chicago

Luxury Living in Bronzeville with Massive Roofdeck

3 bedrooms3 beds, 2 bathrooms,

30 Aug – 4 Sept

$2,272 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 12 reviews