219 properties in Chicago
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    Our Kind of Town

    Standing proud beside Lake Michigan, Chicago is down-to-earth, friendly, and full of culture. It has outdoor art by famous artists including Chagall and Picasso, and there are some fascinating architectural works from the Art Institute of Chicago.

    Home to blues and house music, Chicago has an eclectic music scene that reflects its spirit. The Windy City is also a pioneer in a variety of Americanized dishes from it's European immigrant roots like deep-dish pizza and the Chicago hot dog.

    The world’s first skyscraper and Ferris wheel were erected in Chicago. The latter, on Navy Pier, is one of the Midwest’s most visited sights. Also famed is the ‘L’ transport system, whose raised trains circle The Loop, the main business district. Check out its skyline reflection in the shiny bean sculpture in huge Millennium Park.

    Home of the Bulls and Bears, Chicago is a stronghold of sport and has teams playing baseball, basketball, American football and hockey, to name a few. If you get a chance, try to catch a game.

    Chicago Midway and Chicago O’Hare Airport are both on the outskirts of this vast city, so make sure to leave enough time for travel from your Booking.com hotel, apartment or hostel. And all that jazz.

    Popular in the States

    • San Francisco, CA

      Vintage cable cars rattle up San Francisco’s steep hillsides for picture-perfect views of the Golden Gate Bridge and Alcatraz Island.

    • Washington, DC

      From the White House and Lincoln Memorial to the Smithsonian’s world-class museums, Washington, DC is nothing if not monumental.

    • Fort Lauderdale, FL

      Soak up the sun on Fort Lauderdale, Florida’s laid-back beaches, palm-fringed canals and vibrant oceanfront Strip.

    • Houston, TX

      The largest city in Texas, Houston packs a punch with its glittering high-rise skyline, gigantic Galleria Mall and NASA Space Center.

    • Seattle, WA

      The towering Space Needle surveys Seattle’s contrasts, from vibrant Pike Place Market to the serene beauty of the Puget Sound.

    Discover the Best Hotels, B&Bs, Inns and Vacation Rentals in Chicago – Based on 73,919 Real Reviews from Actual Guests