Airbnb and Apartments in Chicago

Airbnb and Apartments in Chicago

Book your Airbnb in Chicago for your next vacation

3,725 accommodations in Chicago

Book your Chicago vacation rental from 3,725 short-term rentals listings. Compare top rentals sites such as Vrbo, Booking.com, Housing Anywhere and more on Likibu, the world’s largest rentals Meta search.

  1. Apartment 1 bedroom, with gym
    Apartment 1 bedroom, with gym

    Oak Park, Illinois

    • 85m²
    • 3
    • 1
    • 1

     

    From

    $297

    / night

  2. Bed and breakfast 5 guests, with garden
    Bed and breakfast 5 guests, with garden

    Chicago, Illinois

    • 5

    4.8 209 Reviews

     

    $$$

  3. Bed and breakfast 3 guests, with air conditioning
    Bed and breakfast 3 guests, with air conditioning

    Chicago, Illinois

    • 3

    4.8 276 Reviews

     

    $$$$

  4. Apartment 3 bedrooms, with air conditioning
    Apartment 3 bedrooms, with air conditioning

    Chicago, Illinois

    • 93m²
    • 6
    • 3
    • 2

    5.0 37 Reviews

  5. Ad
    Ad - Kayak
    Choose hotel comfort

    Chicago, United States

    Search on Kayak - Chicago

  6. Apartment 3 bedrooms, with air conditioning
    Apartment 3 bedrooms, with air conditioning

    Chicago, Illinois

    • 111m²
    • 6
    • 3
    • 1

    4.9 43 Reviews

     

    $$$

  7. Bed and breakfast 2 guests, with air conditioning
    Bed and breakfast 2 guests, with air conditioning

    Chicago, Illinois

    • 2

    4.8 46 Reviews

     

    $$$$

  8. Apartment 3 bedrooms, with air conditioning
    Apartment 3 bedrooms, with air conditioning

    Chicago, Illinois

    • 148m²
    • 8
    • 3
    • 2

    10.0 34 Reviews

    From

    $663

    / night

  9. Apartment 3 bedrooms, with air conditioning
    Apartment 3 bedrooms, with air conditioning

    Chicago, Illinois

    • 125m²
    • 6
    • 3
    • 2

    4.9 35 Reviews

  10. Room 7 guests, with wifi
    Room 7 guests, with wifi

    Chicago, Illinois

    • 7
    • 4
    • 1

    5.0 51 Reviews

    From

    $35

    / night

  11. House 4 bedrooms, with gym
    House 4 bedrooms, with gym

    Chicago, Illinois

    • 278m²
    • 18
    • 4
    • 4

    9.6 68 Reviews

    From

    $672

    / night

  12. House 3 bedrooms, with garden
    House 3 bedrooms, with garden

    Chicago, Illinois

    • 167m²
    • 8
    • 3
    • 1

    4.7 120 Reviews

     

    $

More results in Chicago

Top tips to check out before booking a vacation rental in Chicago


Vacation rentals prices and availability in Chicago

Average price per night in Chicago

  • $344Jun
  • $343Jul
  • $369Aug
  • $365Sep
  • $430Oct
  • $292Nov

Airbnbs and vacation rentals that are available in Chicago (%)

  • 94%Jun
  • 94%Jul
  • 94%Aug
  • 94%Sep
  • 94%Oct
  • 94%Nov

Frequently Asked Questions about Chicago vacation rentals


Chicago, a bustling metropolis nestled by Lake Michigan, is renowned for its stunning architecture, vibrant arts scene and culinary excellence. With a wide range of apartment rentals available throughout the city, visitors can choose from luxurious high-rise apartments with panoramic views of the skyline, cozy homes in quiet, leafy neighborhoods or trendy lofts in the heart of the bustling downtown. Staying in an Airbnb in Chicago allows guests to immerse themselves in the local culture, whether it’s exploring the city’s world-class museums, enjoying jazz or blues in a historic club or indulging in deep-dish pizza and other local delicacies. Chicago's diverse neighborhoods each offer their own unique experiences, making it an ideal destination for travelers seeking both the excitement of a big city and the warmth of a welcoming community.


Best vacation accommodations in Chicago

Airbnb, apartments and houses with terrace or balcony in Chicago

Apartment 2 bedrooms, with jacuzzi
Apartment 2 bedrooms, with jacuzzi

Chicago, Illinois

  • 9
  • 2
  • 3

5.0 139 Reviews

From

$364

/ night

House 4 bedrooms, with garden
House 4 bedrooms, with garden

Chicago, Illinois

  • 149m²
  • 9
  • 4
  • 2

4.9 22 Reviews

Apartment 2 bedrooms, with air conditioning
Apartment 2 bedrooms, with air conditioning

Chicago, Illinois

  • 102m²
  • 5
  • 2
  • 2

4.8 23 Reviews

Bed and breakfast 2 bedrooms, with garden
Bed and breakfast 2 bedrooms, with garden

Chicago, Illinois

  • 102m²
  • 6
  • 2
  • 1

4.9 122 Reviews

From

$264

/ night

Apartments and vacation homes with fireplace in Chicago

Apartment 2 bedrooms, with pool
Apartment 2 bedrooms, with pool

Chicago, Illinois

  • 117m²
  • 4
  • 2
  • 2

10.0 11 Reviews

From

$193

/ night

Aparthotel 1 bedroom, with pool
Aparthotel 1 bedroom, with pool

Chicago, Illinois

  • 97m²
  • 4
  • 1
  • 1

5.0 383 Reviews

From

$341

/ night

Aparthotel 3 bedrooms, with pool
Aparthotel 3 bedrooms, with pool

Chicago, Illinois

  • 209m²
  • 8
  • 3
  • 2

5.0 266 Reviews

From

$915

/ night

Aparthotel 2 bedrooms, with jacuzzi
Aparthotel 2 bedrooms, with jacuzzi

Chicago, Illinois

  • 214m²
  • 8
  • 2
  • 3

5.0 228 Reviews

From

$623

/ night

Houses, apartments and airbnb with wifi in Chicago to stay connected

Apartment 1 bedroom, with air conditioning
Apartment 1 bedroom, with air conditioning

  • 61m²
  • 2
  • 1

 

From

$160

/ night

Room 10 guests, with garden
Room 10 guests, with garden

Chicago, Illinois

  • 10
  • 4
  • 1

5.0 14 Reviews

From

$119

/ night

Bed and breakfast 9 guests, with air conditioning
Bed and breakfast 9 guests, with air conditioning

Chicago, Illinois

  • 9

4.7 67 Reviews

 

$$$$

Apartment 4 bedrooms, with air conditioning
Apartment 4 bedrooms, with air conditioning

Chicago, Illinois

  • 93m²
  • 8
  • 4
  • 2

4.7 64 Reviews

Condos and holiday apartment rentals in Chicago

Apartment 2 bedrooms, with air conditioning
Apartment 2 bedrooms, with air conditioning

Chicago, Illinois

  • 130m²
  • 8
  • 2
  • 1

4.7 87 Reviews

 

$

Apartment 2 bedrooms, with air conditioning
Apartment 2 bedrooms, with air conditioning

Chicago, Illinois

  • 111m²
  • 4
  • 2
  • 1

4.7 34 Reviews

Apartment 1 bedroom, with air conditioning
Apartment 1 bedroom, with air conditioning

Chicago, Illinois

  • 4
  • 1
  • 1

9.4 14 Reviews

From

$364

/ night

Apartment 1 bedroom, with air conditioning
Apartment 1 bedroom, with air conditioning

Chicago, Illinois

  • 93m²
  • 4
  • 1
  • 1

4.5 97 Reviews

 

$


Vacation rentals in the United States


Recommendations of activities and areas to visit or stay at in Chicago

Spending a vacation in Chicago offers a unique blend of architectural grandeur, rich cultural experiences, and expansive green spaces. From exploring world-class museums like The Art Institute of Chicago to enjoying panoramic city views from the Willis Tower Skydeck, there’s an abundance of activities to fill your itinerary. The city's diverse culinary scene, ranging from deep-dish pizza to gourmet dining, promises a treat for every palate. Chicago’s vibrant neighborhoods and friendly atmosphere make it an ideal destination for travelers seeking both adventure and relaxation.

Must-visit places and attractions in Chicago

The Art Institute of Chicago

Located in Grant Park, The Art Institute of Chicago is one of the oldest and largest art museums in the United States. Known for its curatorial efforts and impressive range of permanent collections, it houses famous works such as Grant Wood's American Gothic and Georges Seurat’s A Sunday Afternoon on the Island of La Grande Jatte. The museum's Modern Wing, designed by Renzo Piano, displays works from the 20th and 21st centuries, offering art lovers a comprehensive view of Western art history.

Millennium Park

Adjacent to the Art Institute, Millennium Park is a modern social hub of Chicago, famous for its innovative public art installations like Anish Kapoor’s reflective sculpture Cloud Gate (commonly known as "The Bean"). The park also features Frank Gehry’s Jay Pritzker Pavilion, which hosts free concerts and events, and the Lurie Garden, which provides a peaceful escape with its beautifully designed plant arrangements. This vibrant area is a must-visit for anyone looking to experience Chicago’s commitment to modern urban park design.

Navy Pier

Extending into Lake Michigan, Navy Pier is one of Chicago’s most popular tourist attractions. It features a Ferris wheel, theaters, museums and a variety of dining and shopping options. Originally opened in 1916 as a shipping facility and amusement area, it has evolved into a family-friendly destination that offers stunning views of the city skyline and lake, and hosts numerous festivals and fireworks displays throughout the year.

Willis Tower Skydeck

For breathtaking panoramic views of Chicago, the Willis Tower Skydeck offers visitors the chance to step onto The Ledge—a series of glass bays extending four feet from the 103rd floor. At 1,353 feet above ground, it provides a unique perspective of the city’s architectural marvels and is a thrilling experience for those daring enough to look straight down.

The Museum of Science and Industry

Located in the Hyde Park neighborhood, the Museum of Science and Industry is one of the largest science museums in the world. Its interactive exhibits, including a replica coal mine, a German submarine (U-505) captured during World War II, and a working model railroad, capture the imagination of children and adults alike. This museum provides a fascinating insight into the industrial and technological advances that have shaped the modern world.

Best areas to stay at if you are willing to book an Airbnb in Chicago

The Loop

The heart of Chicago’s business district, known as The Loop, is also a central point for many cultural institutions, shopping streets and stunning high-rises. Staying here puts visitors within walking distance of the Art Institute, Millennium Park and the theaters of State Street. The area is also well connected by Chicago’s subway system, making it easy to explore other parts of the city.

Lincoln Park

A neighborhood known for its namesake park, Lincoln Park is a desirable area for families and young professionals alike. The park itself hosts the free Lincoln Park Zoo, one of the oldest zoos in the country, and the Chicago History Museum. The neighborhood’s tree-lined streets feature beautiful Victorian homes, fashionable boutiques and some of the city’s finest dining, all contributing to its reputation as one of Chicago’s most charming areas.

Wicker Park and Bucktown

For those interested in a more bohemian vibe, Wicker Park and Bucktown are known for their artsy residents, live music scenes and vibrant nightlife. These adjacent neighborhoods boast an eclectic mix of bookshops, coffeehouses, fashionable boutiques and innovative restaurants. The area also hosts numerous art festivals and gallery nights, making it a haven for creative spirits.

River North

River North is Chicago’s premier art district, home to countless art galleries, design studios and the decorative Merchandise Mart. Known for its dynamic nightlife, the neighborhood also hosts many of the city’s trendiest clubs and cocktail bars. River North offers luxurious hotel alternatives in converted warehouse lofts and high-end apartments, making it a stylish option for staying in the city.

Hyde Park

Hyde Park, home to the University of Chicago and the aforementioned Museum of Science and Industry, is one of Chicago’s most intellectually vibrant neighborhoods. With its blend of historic architecture, innovative cultural institutions and academic atmosphere, Hyde Park offers a unique Chicago experience. The neighborhood’s diverse community and proximity to both downtown and quieter suburbs make it an attractive choice for visitors.

Chicago's rich tapestry of neighborhoods provides a broad spectrum of experiences, from the architectural grandeur of The Loop to the historic tranquility of Hyde Park. Whether you are looking for the arts, dining or just a great place to stay, Chicago offers a dynamic environment that is sure to enrich your travel experience.


Browsing on our website implies that you authorize us to install cookies on your computer or mobile device. More information