Top Chicago Sightseeing Tours

Chicago is an absolute tourism paradise, a gorgeous, historic, and culturally influential Midwestern city that boasts amazing Lake Michigan views, impressively dizzying skylines around every corner, and an outstanding series of eateries that attract guests from far and wide.

While you may be overwhelmed with choosing from such amazing attractions as the world-class museums, spectacular public parks, and skyscrapers with the best views, the same may be said of your sightseeing tour options! In Chicago, you can see the city on foot, bike, boat, bus, trolley, kayak, or segway! There are so many different touring options it is practically impossible to not find something you like!

So don your camera-strap necklace, binoculars, bright shirt, and fanny pack and get ready to take in some of the Midwest's most outstanding scenery, architecture, culture, history, and food!

  • Lakefront Neighborhoods Tour -
    Bike - See all the sights of the Lakefront Neighborhood with this fun, active, and exciting three-hour bike tour. During the ride, you will see the Lincoln Park Zoo, the old Playboy Mansion, and fancy Gold Coast mansions. Explore North Avenue Beach as well, and enjoy the seven miles of sightseeing bliss on Lakeshore Avenue!
  • Chicago Architecture Foundation River Cruise -
    Boat - This tour is the favorite of many, an absolute must in Chicago if you have time. On this tour, you will cruise along the Chicago River all the way from River City North to Goose Island aboard Chicago's beloved First Lady. Enjoy 90 minutes of valuable city info narrated to you as well as amazing unimpeded skyline views, the entire tour exploring three different branches of the river and over 50 skyscraping sites!
  • Absolutely Chicago Segway Tours -
    Segway - This option is one of the most fun, unique, and exhilarating on our list, a safe and easy to learn the way to glide through some of the city's absolute best views and neighborhoods. On this tour you will see museum campus and Lake Michigan’s shoreline, though you can choose between such customized tours as Art and Architecture, Gangster, Haunted, Fireworks, or even private!
  • Untouchable Tours -
    Bus - Start on North Clark Street and travel back in time as you explore a Prohibition-era Chicago, a land filled with gangsters and hoodlums! See secret dens, shootouts, and brothels along the way as you listen to the costumed guides tell harrowing legends of Johnny Torrio and "Machine Gun" Jack McGurn! This is the ultimate history and culture tour!
  • Chicago Hop On Hop Off Tours-
    Trolley - Hop on to the double-decker bus that provides the most open sightseeing tour in the whole city, allowing guests to board or exit whenever they please. This is an excellent model of transportation in the city, plus you get to tour at your own pace! There are onboard narration and a daily downtown tour offered, not to mention the seasonal, neighborhood, and night tours possible!
  • Chicago Food Planet Tours - 
    Walking - If you love food like we do you’ll love this tour, a classic food tasting and cultural walking tour that shows you all of the most delicious, hidden, and locally popular eateries throughout the Windy City. Tour and taste Gold Coast and Old Town, Chinatown, or Bucktown and Wicker Park, each providing one of a kind glimpses at the city, pleasing both your cultural sense of adventure and your stomachs!
  • Chicago Film Tour -
    Bus - Did you know that Chicago has served as the vibrant backdrop of several Hollywood blockbusters such as The Fugitive, Blues Brothers, The Dark Knight, Spiderman, and of course the iconic scene at the Chicago Institute of Art in Ferris Bueller's Day Off? Well with this super fun bus tour you will see over 30 different filming locations that have seen over 80 movies, the tour complete with behind the scenes trivia and current filming information
  • Chicago Helicopter Experience -
    Helicopter - Talk about an adrenaline rush! This quick but unforgettable 15-minute helicopter tour will give you an aerial view of Chi-town’s skyline, taking you from Bridgeport to Montrose Harbor, all along the coast of Lake Michigan. Though the price may seem steep, the photo opportunities and views along the way will make it fully worth it.
  • Chicago Brew Bus -
    Bus [21+] - This is an excellent and super fun option for the over 21 crowds, taking your group to some of the absolute best local breweries such as Lagunitas, Atlas, and Lake Effect and showing you a different side of the history of the Prohibition cultured city. You will be able to drink on the bus, as well as receive 4-6 samples at three different breweries along the way! Try to keep your wits about you though, you don’t want to miss anything along the way.
  • Wright Around Oak Park Tour -
    Walking - If you love Frank Lloyd Wright's architecture, you’re going to love this tour, culture and history-filled look at the Frank Lloyd Wright Historic District in Oak Park. This tour allows you to explore the world’s largest collection of Wright’s architecture, as well as his own home and studio, an amazingly informational three-hour journey!

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