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34 properties
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    Sunny Triple Room in Excellent Location - W. Lyndale, Chicago Sunny Triple Room in Excellent Location - W. Lyndale, Chicago

    Sunny Triple Room in Excellent Location

    Chicago, United States
    10 Excellent(1 review)
    Private room (3 guests / 1 bedroom / 25 m²)
    4 previous guests
    from $103US
    per night
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  • Great Modern Room with Bike - N Leavitt St, Chicago Great Modern Room with Bike - N Leavitt St, Chicago

    Great Modern Room with Bike

    Chicago, United States
    9 Great(8 reviews)
    Private room (2 guests / 1 bedroom / 195 m²)
    This 1-bedroom room in Lake View offers 195m² of space. Amenities include Wi-Fi, a TV and a dishwasher.
    10 people are interested in this property
    from $100US
    per night
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  • Modern Vintage Garden Apartment - N. Francisco Ave, Chicago Modern Vintage Garden Apartment - N. Francisco Ave, Chicago

    Modern Vintage Garden Apartment

    Chicago, United States
    Apartment (3 guests / 2 bedrooms / 70 m²)
    2 previous guests
    7 people are interested in this property
    from $153US
    per night
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  • Lake Michigan Apartment - W Margate Terrace, Chicago Lake Michigan Apartment - W Margate Terrace, Chicago

    Lake Michigan Apartment

    Chicago, United States
    9.3 Excellent(8 reviews)
    Apartment (2 guests / 1 bedroom / 45 m²)
    Offering Wi-Fi and a kitchen, this 45m² apartment has 1 bedroom. It is located in Chicago and has air conditioning.
    8 people are interested in this property
    from $68US
    per night
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  • LUXURY & HUGE DISCOUNTS GREAT REVIEWS HOT TUB. 1 FL. Close to Everything & safe - W 37th St, Chicago LUXURY & HUGE DISCOUNTS GREAT REVIEWS HOT TUB. 1 FL. Close to Everything & safe - W 37th St, Chicago

    LUXURY & HUGE DISCOUNTS GREAT REVIEWS HOT TUB. 1 FL. Close to Everything & safe

    Chicago, United States
    Apartment (6 guests / 3 bedrooms / 1300 ft²)
    Located in Chicago, this 1300m² apartment offers 3 bedrooms and parking - a hot tub and a kitchen are also provided.
    11 people are interested in this property
    from $137US
    per night
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  • Florence Comfy Room! Retreat to RELAX!!! (Women Only) - S Spaulding Ave, Chicago Florence Comfy Room! Retreat to RELAX!!! (Women Only) - S Spaulding Ave, Chicago

    Florence Comfy Room! Retreat to RELAX!!! (Women Only)

    Chicago, United States
    Private room (2 guests / 3 bedrooms / 450 ft²)
    Located in Chicago, this 42m² room offers 3 bedrooms and a TV - parking and Wi-Fi are also provided.
    8 people are interested in this property
    from $58US
    per night
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  • LUXURY & HUGE DISCOUNTS GREAT REVIEWS HOT TUB 2. City & McCormick Place & safe - W 37th St, Chicago LUXURY & HUGE DISCOUNTS GREAT REVIEWS HOT TUB 2. City & McCormick Place & safe - W 37th St, Chicago

    LUXURY & HUGE DISCOUNTS GREAT REVIEWS HOT TUB 2. City & McCormick Place & safe

    Chicago, United States
    Apartment (6 guests / 2 bedrooms / 1300 ft²)
    This 2-bedroom apartment in Chicago offers 121m² of space. Amenities include air conditioning, a TV and parking.
    9 people are interested in this property
    from $126US
    per night
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  • All-Inclusive Modern Furnished Flat - W. Washington St, Chicago All-Inclusive Modern Furnished Flat - W. Washington St, Chicago

    All-Inclusive Modern Furnished Flat

    Chicago, United States
    Apartment (2 guests / 1 bedroom / 547 m²)
    10 people are interested in this property
    from $140US
    per night
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  • Flexible Cancellation
    Space+privacy:couples, families, groups! - S Wabash Avenue, Chicago Space+privacy:couples, families, groups! - S Wabash Avenue, Chicago

    Space+privacy:couples, families, groups!

    Chicago, United States
    10 Excellent(1 review)
    House (4 guests / 2 bedrooms / 900 m²)
    4 previous guests
    from $74US
    per night
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    Comfortable Modern Duplex with Amenities (3Br,3Ba) - N Albany Ave, Chicago Comfortable Modern Duplex with Amenities (3Br,3Ba) - N Albany Ave, Chicago

    Comfortable Modern Duplex with Amenities (3Br,3Ba)

    Chicago, United States
    8 Very good(1 review)
    Apartment (10 guests / 3 bedrooms / 2000 ft²)
    This Chicago apartment with 3 bedrooms offers guests air conditioning and a dishwasher. 186m² in size, it also provides a kitchen.
    8 people are interested in this property
    from $200US
    per night
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  • Cozy and Modern Unit Available (2Br,1Ba) - North Newland Avenue, Chicago Cozy and Modern Unit Available (2Br,1Ba) - North Newland Avenue, Chicago

    Cozy and Modern Unit Available (2Br,1Ba)

    Chicago, United States
    Apartment (5 guests / 2 bedrooms / 70 m²)
    With 2 bedrooms and a kitchen, this 70m² apartment is located in Chicago. Other facilities include Wi-Fi and air conditioning.
    10 people are interested in this property
    from $121US
    per night
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  • Flexible Cancellation
    Pleasing and Comfy Unit Available (2Br,1Ba) - N Newland, Chicago Pleasing and Comfy Unit Available (2Br,1Ba) - N Newland, Chicago

    Pleasing and Comfy Unit Available (2Br,1Ba)

    Chicago, United States
    8.5 Great(4 reviews)
    Apartment (5 guests / 2 bedrooms / 70 m²)
    Offering breakfast and parking, this 70m² apartment has 2 bedrooms. It is located in Chicago and has Wi-Fi.
    7 people are interested in this property
    from $126US
    per night
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  • Flexible Cancellation
    Chicago Garden Apartment in Fun, Relaxed Neighborhood - West Cullom Ave, Chicago Chicago Garden Apartment in Fun, Relaxed Neighborhood - West Cullom Ave, Chicago

    Chicago Garden Apartment in Fun, Relaxed Neighborhood

    Chicago, United States
    10 Excellent(3 reviews)
    Apartment (4 guests / 1 bedroom / 55 m²)
    Chicago - vacation apartment for 3 people with a kitchen.
    7 people are interested in this property
    from $137US
    per night
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  • Flexible Cancellation
    Lakeview Condo on Chicago's beautiful lake front - N Lake Shore Dr, Chicago Lakeview Condo on Chicago's beautiful lake front - N Lake Shore Dr, Chicago

    Lakeview Condo on Chicago's beautiful lake front

    Chicago, United States
    Apartment (4 guests / 1 bedroom)
    This apartment in Lake View for 4 people with a kitchen offers a great vacation.
    6 people are interested in this property
    from $383US
    per night
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  • Flexible Cancellation
    Beautiful Vintage Flat with Yard - N Sacramento Ave, Chicago Beautiful Vintage Flat with Yard - N Sacramento Ave, Chicago

    Beautiful Vintage Flat with Yard

    Chicago, United States
    10 Excellent(3 reviews)
    Apartment (5 guests / 2 bedrooms / 60 m²)
    This 60m² property in Chicago offers a kitchen and a balcony. The 2-bedroom apartment also offers guests a babycot.
    11 people are interested in this property
    from $158US
    per night
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  • Amazing and Stylish Studio - North Dearborn, Chicago Amazing and Stylish Studio - North Dearborn, Chicago

    Amazing and Stylish Studio

    Chicago, United States
    Apartment (3 guests / 1 bedroom / 35 m²)
    6 people are interested in this property
    from $150US
    per night
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  • Art Filled Loft with WiFi - n wood street, Chicago Art Filled Loft with WiFi - n wood street, Chicago

    Art Filled Loft with WiFi

    Chicago, United States
    Apartment (3 guests / 2 bedrooms / 1300 ft²)
    With 2 bedrooms and a TV, this 121m² apartment is located in Chicago. Other facilities include air conditioning and breakfast.
    5 people are interested in this property
    from $153US
    per night
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    • Book now
  • Flexible Cancellation
    Cozy Room In Great Location - S. Carpenter St, Chicago Cozy Room In Great Location - S. Carpenter St, Chicago

    Cozy Room In Great Location

    Chicago, United States
    Private room (2 guests / 1 bedroom / 1500 ft²)
    from $68US
    per night
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    • Book now
  • Private Room with Garden - Maple Ave, Chicago Private Room with Garden - Maple Ave, Chicago

    Private Room with Garden

    Chicago, United States
    Private room (2 guests / 1 bedroom / 18 m²)
    Amenities such as breakfast, a balcony and a kitchen can be found at this Chicago room. It offers 1 bedroom and 18m² of space.
    5 people are interested in this property
    from $132US
    per night
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  • Amazing Bedroom in Eclectic Home - Hinman Ave, Chicago Amazing Bedroom in Eclectic Home - Hinman Ave, Chicago

    Amazing Bedroom in Eclectic Home

    Chicago, United States
    Private room (2 guests / 3 bedrooms / 20 m²)
    Breakfast, a balcony and a dishwasher can be found at this Chicago room. It offers 3 bedrooms and 20m² of space
    7 people are interested in this property
    from $105US
    per night
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  • Historic Pullman Art Studio 2-Flat Entire Apartment 2nd Floor (CHICAGO) - S St Lawrence Ave, Chicago Historic Pullman Art Studio 2-Flat Entire Apartment 2nd Floor (CHICAGO) - S St Lawrence Ave, Chicago

    Historic Pullman Art Studio 2-Flat Entire Apartment 2nd Floor (CHICAGO)

    Chicago, United States
    10 Excellent(4 reviews)
    Apartment (3 guests / 2 bedrooms / 850 ft²)
    This Chicago apartment with 1 bedroom offers guests breakfast and a kitchen. 79m² in size, it also provides Wi-Fi.
    11 people are interested in this property
    from $132US
    per night
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  • Amazing Loft Private Room - Hinman Ave, Chicago Amazing Loft Private Room - Hinman Ave, Chicago

    Amazing Loft Private Room

    Chicago, United States
    Private room (4 guests / 1 bedroom / 800 ft²)
    Amenities such as a balcony, Wi-Fi and breakfast can be found at this Chicago room. It offers 1 bedroom and 74m² of space.
    5 people are interested in this property
    from $111US
    per night
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  • Private Double Lovely Room - Maple Ave, Chicago Private Double Lovely Room - Maple Ave, Chicago

    Private Double Lovely Room

    Chicago, United States
    Private room (2 guests / 1 bedroom / 18 m²)
    Amenities such as a balcony, breakfast and a TV can be found at this Chicago room. It offers 1 bedroom and 18m² of space.
    2 people are interested in this property
    from $132US
    per night
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    • Book now
  • Lovely Bedroom by Golf Course - N. Caldwell Avenue, Chicago Lovely Bedroom by Golf Course - N. Caldwell Avenue, Chicago

    Lovely Bedroom by Golf Course

    Chicago, United States
    9.8 Excellent(10 reviews)
    Private room (2 guests / 1 bedroom / 20 m²)
    Offering parking and air conditioning, this 20m² room has 1 bedroom. It is located in Chicago and has a kitchen.
    10 people are interested in this property
    from $63US
    per night
    • Favorite
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    • Book now
  • Spacious Bedroom in Eclectic Home - Hinman Ave, Chicago Spacious Bedroom in Eclectic Home - Hinman Ave, Chicago

    Spacious Bedroom in Eclectic Home

    Chicago, United States
    Private room (2 guests / 1 bedroom / 20 m²)
    This Chicago room with 1 bedroom offers guests Wi-Fi and air conditioning. 20m² in size, it also provides breakfast.
    3 people are interested in this property
    from $105US
    per night
    • Favorite
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    • Book now
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Chicago Apartments, Vacation Rentals, and Bed and Breakfast

Great view of downtown Chicago from your penthouse rental on Wimdu Welcome to Chicago, the third-largest city in the United States and veritable headquarters of the American Midwest. Chicago, also referred to as Chicagoland, The White City, and the Windy City, tends to be known for its deep dish pizza, tradition of jazz music, food and hard industries, and 1920s gangsterism and ‘bootlegging’ . Chicago is also the birthplace of the modern skyscraper and has over 1,200 complete skyscrapers grazing against its Lake Michigan horizon. The Chicago World’s Fair of 1893 put Chicago on the international playing field and dazzled the world with its brilliant architecture and display of traditional American values . Famous Chicagoans include Al Capone, Bill Murray, and Barack Obama. In this day and age, Chicago is also well known for its summer concert series Lollapalooza and it’s world-class art museums and collections, many with better collections than even the best Parisian exhibitions. Accommodation in Chicago comes in the form of vacation rentals, apartments for rent, and high-quality bed and breakfast options.

Chicago was once notable for its rampant ‘boosterism’, which is a promotional tactic used by politicians to wildly promote their city to encourage settlement and thereby inflate the cost of local real estate. These boastful, pompous attitudes in the press earned the city the infamous nickname of ‘The Windy City’ from newspapers across the Midwest, especially Cincinnati, Cleveland, and Detroit.

Deciding on a Chicago apartment, rental, or bed and breakfast for your Windy City trip

In making plans to visit the Midwest’s 'City That Just Works', it’s important to consider where you want to stay and how you want to experience the city. If you’re just in town for business or a conference, then it’s more advisable to find an economical, well-connected apartment rental in Chicago instead of a full-fledged vacation rental or bed and breakfast option. When coming in larger groups, getting a big rental in some of the more lively regions such as Wicker Park or North Side is certainly a better idea. Or why not try out staying in an apartment in North Lincoln, a more laid back and authentic area with fantastic old and ‘greystone’ architecture. Even an extravagant rooftop apartment in Chicago with a fantastic view of its famous skyline would not be a terrible idea; again, all depending on your trip needs.

What To Do and See: Art Museums, The Skyline, Local Insider Tips

So many visitors to Chicago from across the globe never really venture away from the downtown attractions, such as Grant Park, Michigan Avenue, or the various art museums. For a more local, ‘indie’ experience, head out to either Wicker Park or Bucktown. Check out one of the many ‘hipster’ cafés and restaurants, catering to all walks of life, including offering many exclusively vegan and vegetarian options. Chicago is also famous for its record and comic book stores, so make sure to check out some of these while in town!

Whether you are a sports fan, art lover, foodie, music junkie, looking to shop, or all of the above, you will find all kinds of options for anything that tickles your fancy. The world renowned Art Institute of Chicago houses several famous works as well as an incredibly vast collection of art of all styles. Also worth a look is the Adler Planetarium, the Field Museum of Natural History, and the Shedd Aquarium. Admire art without even entering a museum at all by checking out the city’s wonderfully diverse architecture. Chicago was home to the world’s first skyscrapers and still has some of the tallest buildings. There are numerous Frank Lloyd Wright buildings in the city as well. Take a walking architecture tour and wander past buildings designed by Daniel Burnham, Louis Sullivan, and Mies van der Rohe. Chicago also has lots of beautiful public art installations as well, such as the famous Cloud Gate at Millenium Park, also known as ‘The Bean’. We also recommend paying a visit to the famous Wrigley Field, home of Chicago baseball legends the Chicago Cubs.

Chicagoan Cuisine: From Kielbasa to Deep Dish Pizza

Look, Chicago is one of the United States’ premier destinations for amazing cuisine. The state of Illinois is the fourth largest when it comes to Mexican immigrant communities, and their cuisine is some of the best in the nation. No trip to Chicago is complete with having those spicy, local, Latin American tacos or tamales! We recommend finding a taco food truck and enjoying some of the more down-to-earth Latino cuisine. Along with the Mexican and Latino communities, there are strong Polish and German traditions in Chicago as well. For traditional Polish ‘kielbasa’ sausage, drop on by Kurowski’s Butcher Shop, a Polish supermarket with the best Polish sausage in town. For the best Polish ‘sit-down’ restaurant, go to Staropolska along North Milwaukee Avenue in Logan Square. For German fare, try out the Chicago Brauhaus, located in the popular Lincoln Square neighborhood. Or why not just sample the famous Chicago Hot Dog? This one differentiates itself from the rest of the nation’s hot dog varieties in its garnish of an entire pickle and liberal use of celery salt.

For traditional Chicago deep dish pizza, the best locale hands-down is Burt’s Place in Morton Grove, which is a smaller suburb a bit north of Chicago proper. It’s a traditional pizza joint with arguably the city’s best slice of deep dish.

Getting Around ‘Chi Town’

The best way to get around Chicago is by taking what’s locally known as ‘The L’. The L is Chicago’s subway system and is one of the best in the entire country. Going both above and below ground, the L will get you to any section of the city for a meager $2.25, including dedicated train fare in The Loop, a circular section of the train service providing faster fare between the central downtown areas. Most tourists to Chicago end up staying inside the Loop during their trip, as this vicinity provides enough access to museums, bars, restaurants, and other shopping opportunities.