🗺️ Discover the Best Airbnb Deals in Chicago, Illinois 🗺️

Looking for unbeatable discounts on Airbnbs in Chicago, Illinois? Find listings with the biggest price drops this month compared to last month.

Chicago, Illinois, United States

5.0 ★

Standard Double Hotel Room at Magnificent Mile

$173 / night

46% Cheaper than normal

1 beds

1 bathrooms

4 guests

5.0 ★

Near Lake Michigan & Wrigley Field

$220 / night

14% Cheaper than normal

2 beds

2 bathrooms

4 guests

5.0 ★

Lincoln Park Studio, Great Value!

$63 / night

41% Cheaper than normal

1 beds

1 bathrooms

2 guests

5.0 ★

Festive Graffiti Pop-Art | 1PBR | Wicker Park

$38 / night

25% Cheaper than normal

1 beds

1 bathrooms

1 guests

5.0 ★

Festive Graffiti Pop-Art | 1PBR | Wicker Park

$38 / night

32% Cheaper than normal

1 beds

1 bathrooms

2 guests

5.0 ★

Lake View | Wrigley Designer House w/Patio

$410 / night

34% Cheaper than normal

4 beds

3 bathrooms

12 guests

5.0 ★

Festive Graffiti Pop-Art | 1PBR | Wicker Park

$40 / night

27% Cheaper than normal

1 beds

1 bathrooms

2 guests

5.0 ★

Chicago Airbnb Newly Remodeled 2-Unit Apartment!

$138 / night

3% Cheaper than normal

2 beds

1 bathrooms

4 guests

5.0 ★

Chicago Speakeasy-Style Loft Suite (Room 1B)

$129 / night

15% Cheaper than normal

1 beds

1 bathrooms

2 guests

5.0 ★

Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!

$231 / night

7% Cheaper than normal

5 beds

3 bathrooms

10 guests

5.0 ★

Relaxed Bucktown/Wicker Park 1B Apt

$104 / night

36% Cheaper than normal

1 beds

1 bathrooms

3 guests

5.0 ★

Entire House/United Center /Garage-Walk to Train

$153 / night

5% Cheaper than normal

3 beds

2 bathrooms

8 guests

5.0 ★

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

$188 / night

12% Cheaper than normal

2 beds

1 bathrooms

10 guests

5.0 ★

Vibrant studio at Uptown by Red Line (02)

$100 / night

16% Cheaper than normal

Studio beds

1 bathrooms

2 guests

5.0 ★

Ukrainian Village Garden Retreat

$153 / night

15% Cheaper than normal

1 beds

1 bathrooms

2 guests

5.0 ★

Cozy 2BR Garden Apt, Steps from Train

$151 / night

29% Cheaper than normal

2 beds

1 bathrooms

4 guests

5.0 ★

Logan Square living at its best w/ bright 2 bdrm

$146 / night

13% Cheaper than normal

2 beds

1 bathrooms

4 guests

5.0 ★

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

$217 / night

13% Cheaper than normal

1 beds

1 bathrooms

4 guests

5.0 ★

South Loop 2BR Apt Near Lakefront & McCormick

$235 / night

16% Cheaper than normal

2 beds

2 bathrooms

8 guests

5.0 ★

Sounds Of The City

$135 / night

22% Cheaper than normal

1 beds

1 bathrooms

4 guests

5.0 ★

Stunning Retro Apartment in Andersonville

$172 / night

4% Cheaper than normal

2 beds

1 bathrooms

4 guests

5.0 ★

Delightful 3 bed 2 bath with Free On-Site Parking!

$165 / night

3% Cheaper than normal

3 beds

2 bathrooms

6 guests

5.0 ★

Spacious private room/ private bath in modern home

$143 / night

39% Cheaper than normal

1 beds

1 bathrooms

2 guests

4.5 ★

Modern studio at Uptown by Red line (02)

$94 / night

18% Cheaper than normal

Studio beds

1 bathrooms

2 guests

5.0 ★

Secret Garden @ The Noble Farmhouse | Wicker Park

$150 / night

23% Cheaper than normal

Studio beds

1 bathrooms

3 guests

5.0 ★

Contemporary Apartment Near Wrigley Field w/ Yard

$251 / night

10% Cheaper than normal

3 beds

2 bathrooms

7 guests

5.0 ★

Spectacular Corner 3BR Loft In Fulton Market | Fea

$544 / night

21% Cheaper than normal

3 beds

2 bathrooms

12 guests

5.0 ★

52nd Floor, VIEWS, Pool, Balcony, Pool, Gym

$299 / night

31% Cheaper than normal

1 beds

1 bathrooms

4 guests

5.0 ★

Gorgeous 1 Bedroom Condo In Chicago

$101 / night

18% Cheaper than normal

1 beds

1 bathrooms

4 guests

5.0 ★

Cozy 420-Friendly 3BR City Retreat Near McCormick

$203 / night

38% Cheaper than normal

3 beds

1 bathrooms

8 guests

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