Cultural & Sightseeing · Tomorrow

(15 activities)
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    Classic Skyline Lake Tour

    (51)
    What's the one thing everyone must do in Chicago? Besides eating pizza, you need to see that breathtaking skyline! Traveling along the great Lake Michigan on a cruise vessel, learn about Chicago's colorful history and famous landmarks. You'll enjoy the panorama of Chicago's famous skyline, showcasing all the notable skyscrapers, such as the John Hancock, Trump Tower, and Willis Tower. As you progress down the lake, bare witness to the scenic downtown areas like Gold Coast and Buckingham Fountain. For those of you looking for a quick trip that makes the ultimate punch, there's nothing better than heading out on the lake and seeing that irresistible skyline.
    Classic Skyline Lake Tour

    600 E Grand Ave, Chicago

    • Take in the breathtaking views of Chicago's skyline from the calm tides of Lake Michigan
    • Photograph the towering buildings like the John Hancock, Trump Tower, and Willis Tower
    • Travel down Lake Michigan, along the city front, and see bustling downtown areas like Gold Coast and Buckingham Fountain
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    50 positive reviews
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    Mini Bus and Boat Tour

    (6)
    On this tour you'll see Chicago's world renowned architecture and learn about the city's colorful history, including gangsters like Al Capone, and John Dillinger. Drink in the beautiful views of a lake that looks more like an ocean, and a river that now runs backwards! Downtown, you'll see Millennium Park, The Loop, Museum Campus, Soldier Field, The Willis (Sears) Tower and more. Then it's up north, to the fashionable Gold Coast (including the original Playboy Mansion), Lincoln Park and Wrigley Field (legendary home of baseball's Chicago Cubs since 1916). Of course, you'll stop a few times along the way, so that you can get out, stretch your legs and take some pictures of Chicago's many fantastic sights. At the conclusion of your Chicago mini-bus tour, you'll visit Navy Pier. From there, you'll enjoy a 75 minute cruise along the scenic Chicago River, while learning a thing or twenty about architecture, Chicago history, and even how to reverse the direction of a river!
    Mini Bus and Boat Tour

    300 East Ohio St, Chicago

    • Enjoy Chicago sights and sounds on a mini-bus tour and a River Cruise
    • See all of the famous downtown sights, as well as some of Chicago's distinct neighborhoods
    • Explore the sights and sounds of Chicago in style, onboard a climate controlled, large-windowed mini bus
    • Relax and enjoy the city's world-renowned architecture, on the Chicago River
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    6 positive reviews
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    Architectural Tour

    (31)
    Part adventure, part history lesson. If only school had been this fun! This tour will have you paddling through the heart of Chicago as you take on the urban canyon that is the downtown Chicago River. Along the way, your guide will fill you in on the history of the area, pointing out architectural points of interest and other oddities that will make this journey almost as intellectually satisfying as it is visually riveting. All told, you'll spend several leisurely hours on the water, getting a light upper body workout that will leave you feeling rejuvenated and limber. Whether you've never kayaked before or you're an experienced pro, you'll love this intimate introduction to the city's history.
    Architectural Tour

    1220 W LeMoyne Ave, Chicago

    • Kayak across the city on the Chicago River during this energizing adventure tour
    • Learn about the history and architecture of Chicago as you paddle by several famous sites
    • Let a certified instructor show you the ropes during a safe row
    • Feel adrenaline of adventure consume your senses and fuel your sense of wonder
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    31 positive reviews
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    Mini Bus Tour

    (6)
    On this tour you'll see Chicago's world renowned architecture and learn about the city's colorful history, including gangsters like Al Capone and John Dillinger. Drink in the beautiful views of a lake that looks more like an ocean, and a river that now runs backwards! Downtown, you'll see Millennium Park, The Loop, Museum Campus, Soldier Field, The Willis (Sears) Tower and more. Then it's up north, to the fashionable Gold Coast (including the original Playboy Mansion), Lincoln Park, and Wrigley Field (legendary home of baseball's Chicago Cubs since 1916). Of course, you'll stop a few times along the way, so that you can get out, stretch your legs and take some pictures of Chicago's many fantastic sights.
    Mini Bus Tour

    300 East Ohio St, Chicago

    • Explore the sights and sounds of Chicago in style, aboard a climate controlled, large-windowed mini bus
    • You'll see some of Chicago's most interesting and popular downtown sights and neighborhoods
    • Snap beautiful pictures at the photo-ops along the way
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    6 positive reviews
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    Chicago Ghost Tour

    (11)
    The Windy City is known for her food, architecture, and haunting history! Join this walking tour as the sun sets through downtown Chicago, and hear some of the most gruesome and creepy local stories recounted by your expert guide. First stop is the Congress Hotel, known as the most haunted hotel in Chicago. Walk along the streets that H. H. Holmes, Chicago's first serial killer, wandered as he stalked his prey. Then, visit Death Alley and the site of the Eastland Disaster, and catch a glimpse of Chicago's sordid past through stories of the Everleigh Club, the 1900's Red Light district, and famous downtown prison breaks. But consider yourself warned: this tour is not meant for the faint of heart, taking only those who seek a good thrill and are interested in the underbelly of Chicago.
    Chicago Ghost Tour

    520 S Michigan Ave, Chicago

    • Enjoy a spooky insider's look at the haunted history of The Windy City on this after hours walking tour
    • Visit the locations where H. H. Holmes, Chicago's first serial killer, wandered as he stalked his prey
    • Hear stories of gruesome and creepy happenings in Chicago
    • Gain a unique perspective on Chicago, and mingle with fellow tour goers
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    11 positive reviews
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    By Night Mafia and Blues Tour

    First, you will visit the chilling spot where the St. Valentine's Day Massacre murders took place and talk about the events that "lead" up to it. You'll learn about prohibition and how it still happens today in a different form and see how the music of the slaves known as the Blues became a powerful tool to help grow the Mafia in Chicago. Next you will explore some of the bars and nightlife that now dominates Chicago's north-side and will make a stop at a legendary bar previously owned by Al Capone, a Chicago Landmark. There will be some time to enjoy a drink (not included) and possibly some live music in the spirit of the 1920s. This tour will then end with a short sightseeing drive to enjoy the view of Chicago's skyline at night.
    By Night Mafia and Blues Tour

    Downtown Chicago Hotels, Chicago

    • Get inside tips from a local and expert tour guide
    • The small tour group ensures personal service for you and guests
    • This private tour is operated with just your party and a guide/driver
    • See the sights illuminated at night
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    Lakefront Segway Tour

    (12)
    Windy city not quite windy enough for you? Feel the joys of your hair blowing back as you cruise around on your very own segway! This guided tour will introduce you to Chicago's majestic lakefront area. Led by a guide whose aim is to entertain and inform, you'll explore Grant Park, Buckingham Fountain, Millennium Park, and Museum Campus. Zipping around at speeds of up to 12 mph, you'll have the chance to take in the majestic views around you, including the Chicago skyline, Soldier Field, the Shedd Aquarium, and the Adler Planetarium. You might even get a few good pictures if you can tear your hand away from the accelerator long enough to fish out your camera.
    Lakefront Segway Tour

    239 E Randolph St, Chicago

    • Enjoy a unique mobile tour of Chicago's waterfront area while you drive your own segway
    • Learn about the area from a local tour guide that's both entertaining and knowledgeable
    • Take in the scenery of the Chicago skyline while the wind blows through your hair
    • See the amazing lakefront and picturesque parks that make the area so beautiful
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    12 positive reviews
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    Tour North Shore

    On this tour you will pass by four cities, including the charming downtown Evanston, mansions, and historic American homes. You will drive by a former American Vice President's Home and the home of one of the most respectable women in the nineteenth century. Before leaving Evanston we will visit the Shakespeare Garden and drive by one the top 10 American Universities. Next, spend some time to reconnect at the Bahai temple (of which is the oldest Bahai House of Worship in the world and the only one in the United States). There are only seven Bahai temples in the world, you can't visit Chicago and miss the opportunity of seeing this breathtaking temple. Your last visit will be the Chicago Botanic Garden, where you will have free time to take the tram or walk at leisure. Your guide will drive you back to the hotel after the tour.
    Tour North Shore

    Downtown Chicago Hotels, Chicago

    • Enjoy a 4-hour scenic ride along Lake Michigan North Shore, which is one of the wealthiest in the country.
    • See the Lakefront of Uptown and Rogers Park, Loyola University, Northwestern University, Evanston Downtown, Bahai Temple, and Chicago Botanic Garden
    • The guide will pick you up and drop you off at your hotel
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    Lincoln Park and Gangster Tour

    (17)
    Before the Great Chicago Fire in 1871, Lincoln Park was home to German and Polish immigrants, but since the fire only reached the edge, it grew with the "worthy families" who had been forced out of downtown. On this guided walking tour, learn about the fascinating history of Lincoln Park, and how it has become a cultural center and youthful area with nearby DuPaul University and Notebaert Nature Center! Explore the dark side of this neighborhood beyond its beautiful scenery and collegiate history, including the bloody gang killings on Valentines Day and the capture and eventual death of the infamous Depression-era outlaw John Dillinger. Stop by at the Wise Fool's pub before ending your night with passes to the Kingston BLUES club for a fully encompassing Chi-town experience!
    Lincoln Park and Gangster Tour

    2391 N Stockton Dr, Chicago

    • Learn about the fascinating history of Lincoln Park on this informative guided walking tour
    • Explore a cultural center and youthful area of Chicago with nearby DuPaul University
    • Follow your expert guide to hear about the Valentines Day massacre and the death of the infamous John Dillinger
    • Stop by at the Wise Fool's pub, and end your night with passes to the Kingston BLUES club
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    17 positive reviews
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    River North Food Tour

    (6)
    Do you consider yourself a foodie? If so, then this food tour through River North is right up your alley. This historically affluent neighborhood is home to such hotspots as Al's Beef, Barcito, Xoco, and the Doughnut Vault, all of which you will get to visit on this tour. These highly acclaimed food-lover spots have been featured on the History Channel, Food & Wine Magazine, and even Top Chef Masters. It's no wonder the best of the best reside here. In between tastings, you'll also learn about the neighborhood's history and architecture. Bring your appetite on this tour, because you're going to need it!
    River North Food Tour

    222 W Merchandise Mart Plaza, Chicago

    • Enjoy the luxury and opulence of the Magnificent Mile and Gold Coast on this food tour through the historically affluent neighborhood of River North
    • Discover the historic architecture and public spaces that make this one of Chicago's most notable neighborhoods
    • Sample treats at various hot spots including the Doughnut Vault, Lou Malnati's, Xoco, Al's Beef, Barcito, and More Cupcakes
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    6 positive reviews

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