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Chicago Sightseeing Tours

Posted by maren on September 7, 2018

Chicago Sightseeing Tours


Sightseeing tours in Chicago by Gray Line include bus tours, historical tours and riverboat architectural tours where you can get a good overview of the city’s attractions so that you can plan a more detailed itinerary. You can experience the vacation of a lifetime exploring gangster hidey holes, glittering shopping destinations, historic sites and magnificent attractions like the Gold Coast. The first step is booking a Chicago tour.

It’s tough to choose what to see in Chicago because the city has it all--miles of beaches, historic buildings, famous restaurants, stunning architecture and world-class museums. Gray Line offers Chicago tours that help you plan the rest of your vacation. Our Company has a history almost as storied as Chicago--Gray Lines was founded in 1910 and has helped millions of travelers in hundreds of offices. Our Chicago tour experts are ready to help you plan the most memorable vacation of a lifetime.

Chicago Architecture Tour by Riverboat


There are many Chicago tours designed to capture the flavor of Chicago, but our most popular tours are the architectural tours by riverboat. You can capture stunning photographs of Chicago's most beautiful and historic buildings, bascule bridges and audacious spires such as The Trump Tower. Wet your whistle with these samples of our tour options:

  • South Side Land and River Architecture Tour
    The tour includes the Art Institute of Chicago, President Obama’s home and Jackson Park, location of the Museum of Science and Industry. The tour includes travel by bus and riverboat where you’ll enjoy a 90-minute Architecture River Cruise. Chicago is the birthplace of the skyscraper. After the Chicago fire cleared the way for modern development, skyscrapers quickly rose from the minds of world-famous architects. You can view these historic buildings and the newest buildings by boat.

  • North Side Land and River Architecture Tour
    Chicago’s Scenic North Side features the Magnificent Mile, a 13-block area where Chicago showcases spectacular shopping, dining and entertainment destinations. Our North Side sightseeing tours in Chicago pass by more than 275 restaurants, 460 stores, 60 hotels and many other indulgences. You’ll get to see historic buildings such as the Wrigley Building, Wrigley Field, Chicago Water Tower and Pumping Station, Tribune Tower and Fort Dearborn.

  • INSIDE CHICAGO Land and River Architecture Tour
    This comprehensive land and river tour showcases everything Chicago offers including Chicago’s Lakefront Museum Campus, beautiful parks, breathtaking architecture and historic neighborhoods.

  • INSIDE CHICAGO Grand Tour and Chicago Style Pizza
    This comprehensive tour gives you a fine overview of the attractions Chicago offers, and you get a personal Chicago Style Pizza to enjoy.

  • INSIDE CHICAGO Grand Tour and 360 CHICAGO Observation Deck
    Enjoy the sights and attractions of both North and South Sides of Chicago. You can get the best views of Lake Michigan and the city’s soaring skyscrapers with the inclusive visit to the 360 CHICAGO Observation Deck.

  • Dovetail Brewery Trolley Tour
    Guided tours in Chicago are famous for visiting breweries, and the Dovetail Trolley Tour follows Lake Shore Drive with stunning views of Lake Michigan and Chicago’s North Side. The tour includes a one-hour tour of the brewery with tasting opportunities. The tour is only for those 21 years old or older.

  • HISTORIC CHICAGO South Side Tour Plus Chicago Style Pizza
    Guided tours in Chicago include the South Side where your bus heads down Michigan Avenue past the famous Art Institute of Chicago to the site of Chess Records, where the iconic Route 66 begins. The tour includes the site of the 1893 World's Fair, Adler Planetarium and other historic sites. Each guest receives a personal 8-inch Chicago Style Pizza.

  • HISTORIC CHICAGO North Side Tour Plus 360 CHICAGO Observation Deck
    The North Side bus tour starts at the Palmer House Hilton and includes the Magnificent Miler, Fort Dearborn, Millenium Park, the Gold Coast and Chicago’s El Train Theatre Neighborhoods. Each tour guest receives a free ticket to the 360 CHICAGO Observation Deck.

  • HISTORIC CHICAGO North Side Tour Plus Chicago Style Pizza
    This tour takes guests along Chicago’s North Side where the Chicago River,m Wrigley Building, Elo Train and Chicago Theater. Each guest gets a thin-crust or deep-dish Chicago Style Pizza.

  • HISTORIC CHICAGO South Side Tour Plus 360 CHICAGO Observation Deck
    Enjoy 2 hours of sightseeing in Chicago’s famous South Side, which is forever immortalized in many songs such as those by singer Jim Croce. The tour includes admission to the 360 CHICAGO Observation Deck, which offers stunning views of Lake Michigan and the Chicago skyline.

  • HISTORIC CHICAGO Land and River Architecture Tour Grand Tour
    The Grand Tour takes you INSIDE CHICAGO for a more detailed of Chicago’s Lakefront Museum Campus where there are multiple sports venues, Adler Planetarium and museums. The tour also includes Chicago’s eclectic neighborhoods such as Chinatown, the Gold Coast, Wrigleyville and Lincoln Park.



Booking a tour with Gray Line means no worries because the name has been a trusted brand for more than 100 years. Schedule a Chicago Architecture Tour or historic tour today to explore Chicago’s famous past and glittering present

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