Bike and Roll Chicago

(9 activities)
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    Bike and Brewery Tour

    Something fun is brewing in Chicago, and this frothy bike outing is your chance to find out. Cruise a lakeside bike path with a local guide that will take you alongside some of the city’s most historic neighborhoods: Prairie Mansion District, Chinatown, and Pilsen. As you roll, enjoy anecdotes about the city and its love of beer. Plus, stop at various local establishments for local bites to keep you fueled. Then, end the tour with a walkthrough of Lagunitas Brewery to see the magic of how it’s made. Bet you can’t wait to drink it all in, huh?
    Bike and Brewery Tour

    239 E Randolph St, Chicago

    • Explore several historic districts during a leisurely cycling tour
    • Stop at various eateries for samples, and tour Lagunitas Brewery
    • Enjoy anecdotes about the city’s history and beer scene
    • Treat yourself to a fun, social exploration of Chicago
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    Night Bicycle Tour

    What’s more breathtaking than Chicago’s illuminated beauty, with moonlight and dwindling city shadows reflecting on the water? See it all! This awesome bike tour takes you to some of Chicago’s best attractions in the twilight. Enjoy a bike ride through the city followed by a skyline boat tour ending with sparkling fireworks. During the bike ride, you’ll visit glowing sights like the Magnificent Mile, the skyline, Crown Fountain, Buckingham Fountain, and ending at Navy Pier. When you find yourself gasping for air, remember that was just the beauty of Chicago taking over.
    Night Bicycle Tour

    239 E Randolph St, Chicago

    • Bike through the Chicago cityscape under the moonlight and illuminated skyline
    • Enjoy some of the most popular attractions in the city
    • Take a skyline boat tour ending with sparkling fireworks
    • Visit Magnificent Mile, Crown Fountain, Buckingham Fountain, and Navy Pier
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    Chicago's Famous Foods Tour

    Does biking still count as exercise if you’re eating a slice of pizza as you peddle? Find out the answer to this question and more on this bike tour for foodies. You’ll be cruising the streets on the back of a brand new comfort bike, while being guided by a friendly tour guide that knows exactly where to find the best food. Featured foods include Chicago-style deep dish pizza, hot dogs, and Italian beef. With each bite, your guide will tell you the story of the foods you’re sampling, so you can get fitter, fuller, and smarter all at the same time!
    Chicago's Famous Foods Tour

    316 N Wabash Ave, Chicago

    • Enjoy a bike tour of Chicago as you sample some of the city’s best foods
    • Learn about the history of the city from a knowledgeable and friendly tour guide
    • Gain insight into the history of chocolate and the art of crafting sweets
    • Satisfy your stomach while working it off on the bike in one tour
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    Segways at Sunset Tour

    What better way to celebrate the day than a romantic sunset … enjoyed from the back of a segway! During this guided tour, you’ll be taking a sunset excursion into the parks of Chicago’s waterfront area, including Grant and Millenium Park. You’ll be led by an entertaining guide that knows the terrain and history like only a local could, and find numerous photo opportunities along the way, including shots of Buckingham Fountain, Soldier Field, and the Chicago skyline. This is a great way to save your legs, but still have a little fun after a long day, and you’re sure to be the envy of all the pedestrians you cruise past. What a perfect segue from day to night!
    Segways at Sunset 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 at sunset while the wind blows through your hair
    • See the amazing lakefront and picturesque parks that make the area so beautiful
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    Bikes, Blues, And BBQ Tour

    Doesn’t the tour title say it all? For those who don’t know, Hyde Park is one of Chicago’s best kept secrets, and it’s saturated with culture, history, music, and great food! Here, you’ll bike through the gorgeous neighborhood and surrounding parks, stopping at the best eateries in the area. Is your mouth watering yet? If that’s not enough, the top sights include the Obama residence, University of Chicago, Midway Plaisance, Museum of Science and Industry, Osaka Garden, Rockefeller Chapel, and Frank Lloyd Wright’s Robie House. With this amazing food and history, Hyde Park won’t be a secret much longer...
    Bikes, Blues, And BBQ Tour

    1558 E 53rd St, Chicago

    • Ride a bicycle around Chicago's Hyde Park to the best eateries
    • Uncover the culture, history, music, and food that this area has to offer
    • Visit world-famous sights, including the Obama residence, University of Chicago, Midway Plaisance, Museum of Science and Industry, Osaka Garden, and Frank Lloyd Wright’s Robie House
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    2 positive reviews
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    Lincoln Park Bike Adventure

    Bike, Lincoln Park, Lake Michigan? This is perfect for any tourist or Chicagoan. This is Chicago’s beauty demonstrated in a single adventure. On this tour, you’ll enjoy the car-free lakefront trail and explore Chicago’s beaches, parks, lagoons, and gorgeous Lincoln Park Zoo (free admission!). You’ll encounter a diverse mix of nature and attractions, including top sights: The Chicago Lakefront, Navy Pier, North Avenue Beach, Lincoln Park Zoo, and the Conservatory. This is easy-riding and great fun for any age!
    Lincoln Park Bike Adventure

    600 E Grand Ave, Chicago

    • Enjoy a car-free lakefront trail and explore Chicago’s beaches, parks, and lagoons
    • Encounter a diverse mix of nature and Chicago attractions
    • See The Chicago Lakefront, Navy Pier, North Avenue Beach, Lincoln Park Zoo, and the Conservatory
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    2 positive reviews
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    Millennium Park Segway Tour

    Roll up to Cloud Gate in style… on a segway! During this tour of Chicago’s famous Millennium Park, you won’t have to worry about tiring yourself out by walking everywhere. Keep snazzy and sweat-free as you glide around the grounds of the park, seeing all the sights from Crown Fountain to Lurie Garden. You’ll marvel at the diversity of the attractions in the park, all of which are such an architectural contrast to the surrounding skyscrapers and bustling noise of the city. This is a tour you certainly won’t forget! Plus, with this two-wheel drive, you never have to worry about lack of parking.
    Millennium Park Segway Tour

    239 E Randolph St, Chicago

    • Hop on a segway and take a tour of the famous Millennium Park in Chicago
    • Get a crash-course on how to safely operate your segway
    • See famous sights like Cloud Gate at AT&T Plaza or Crown Fountain
    • Take unforgettable pictures on your snazzy” two-wheel drive”
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    Lakefront Segway Tour

    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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    Friendly Neighborhoods Bike Tour

    Like any worldly city, Chicago’s a city of neighborhoods: North Side, South Side, the Loop, Old Town. It’s all here. On this tour, you’ll explore some of Chicago’s favorite neighborhoods. The Gold Coast offers world-class shopping and dining, and luxurious residences including the Playboy Mansion. Old Town is home to the distinctive Chicago architecture and features narrow streets, cobblestone sidewalks, and charming homes. From there, you’ll hit up Lincoln Park, with its tree-lined residences, parks, and nature. No neighborhood tour is complete without lakefront views. See Chicago’s many diverse sides in a single bike ride.
    Friendly Neighborhoods Bike Tour

    316 N Wabash Ave, Chicago

    • Uncover Chicago’s diversity through a neighborhood tour of the city
    • Visit the Gold Coast, Old Town, Lincoln Park, and several other locations
    • See Chicago’s sights atop a bike traveling through the bustling cityscape
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