Chicago
Outdoor Activities

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Our most recommended Chicago Outdoor Activities

Chicago: Hop-on Hop-off Open Top Bus Tour

1. Chicago: Hop-on Hop-off Open Top Bus Tour

From your vantage point on the double-decker sightseeing bus you'll enjoy panoramic views of Chicago’s finest skyscrapers, including the 875 N Michigan, the Willis Tower and the Wrigley Building. Take in the city's impressive landmarks as your tour guide provides entertaining commentary and insight into Chicago's history. Enjoy exploring this dynamic city with the freedom to hop-on and hop-off as many times as you wish to visit attractions such as the Shedd Aquarium and the Field Museum. You’ll travel down the famous Magnificent Mile, considered one of the great avenues of the world, and continue across the Michigan Avenue Bridge over the Chicago River. The bridge connects the north and south sides of the city. This hop-on, hop-off bus tour of Chicago makes it easy for you to explore the city's sights at your own pace. There are 13 stops, where you can hop-off to visit attractions and explore places of interest. The stops are conveniently located to make navigating your way around the city easy, and with a choice of Classic, Premium or Deluxe tickets, you can take your time discovering Chicago. Be sure to take advantage of admission to the Chicago Architecture Center, included with the Premium and Deluxe tickets, to dive deeper into the city that invented the skyscraper. So don't wait, just hop-on an exciting journey through Chicago.

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Chicago River Architecture Cruise: Skip-the-Ticket-Office

2. Chicago River Architecture Cruise: Skip-the-Ticket-Office

Skip the lines at the ticket office and climb aboard a state-of-the-art cruise for a 60- or 75-minute cruise of all 3 branches of the Chicago River, and marvel at the architecture that has made the city so legendary. Get an insight into the buildings and engineering of a city that gave birth to the skyscraper and is the spiritual home of modern American architecture. Your expert guide will lead you down the Chicago River to uncover hidden gems, as well the city’s most renowned landmarks, such as the John Hancock building, Trump Tower, Marina City, Willis Tower, and more. Relax with a glass of something cold from the cash bar, as you cruise the Windy City’s waterway, and learn its status as a modern metropolis and one of the world’s most beautiful cities. End your tour in the same place where you boarded the boat.

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Chicago: Gangsters and Ghosts 2-Hour Walking Tour

3. Chicago: Gangsters and Ghosts 2-Hour Walking Tour

See a different side of Chicago on a family-friendly guided tour and hear the tales of the ghosts that haunt the city. Explore the famous Chicago Loop district with interesting stories hidden behind each turn. Embark along the Chicago Loop, known as the vice district during the 1920s and 30s. See the places where gangsters such as Al Capone used to party, make deals, and carry out business. Visit haunted locations and old crime scenes led by historians. Stop at the Congress Hotel, Death Alley, and the Palmer House. Enjoy a refreshment along with way, with frequent stops and a restroom break.

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Amazing Lakefront Segway Tour of Chicago

4. Amazing Lakefront Segway Tour of Chicago

Glide around the streets and parks of Chicago on a leisurely 2.5-hour guided Segway tour. Perfect for Chicago newbies and veterans alike, the tour uncovers quirky facts about one of America’s most energetic destinations. Start your Segway experience at Millennium Park and continue to Grant Park to stop and admire the famous Buckingham Fountain. Ride to Museum Campus to soak up spectacular views of the Chicago skyline and beautiful lakefront. The tour includes a training session to become familiar with the unique self-balancing Segways, before exploring the Windy City in a fun and futuristic fashion. Smart, entertaining tour guides work hard to provide you with the experience of a lifetime, and reward you with expansive views of the sea-like Lake Michigan.

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Chicago Lakefront: Half-Hour Seadog Speedboat Ride

5. Chicago Lakefront: Half-Hour Seadog Speedboat Ride

This half-hour Seadog Speedboat ride along Chicago’s lakefront is one of the best ways to view the city’s skyline while learning about the city. Combine an exciting speedboat ride with informative and amusing stories about the world-famous Windy City! As you depart Chicago's Navy Pier, your captain will tell you interesting facts about the pier and the lakefront as he cranks up the music and races to key lakefront landmarks. Stop near the picturesque lakefront park of the Chicago Museum campus, where you’ll learn about the architecture and history of Chicago. Admire views of the Magnificent Mile neighborhood, including the Buckingham Fountain, Sears Tower, Grant Park, and Chicago's largest shopping district. Listen to the thrilling sound of the turbo engines as you race around the Lake Michigan waterfront and back to the Navy Pier. Upgrade to the Extreme Thrill Ride Option and experience exhilarating speeds and full 360° spins. This jet-propelled ride blasts off to start and splashes down to stop. Experience full-throttle slalom runs, sharp twists and turns, and the raw power of Seadog Extreme's 1400 HP engines.

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Chicago: Bikes, Bites, and Brews Biking Tour

6. Chicago: Bikes, Bites, and Brews Biking Tour

Working up an appetite won’t be a problem on this signature bike tour combing city sightseeing with the best foods and brews in Chicago.Sample Chicago’s 4 favorite food groups – pizza, hot dogs, brownies, and beer. You’ll learn the history behind the iconic foods and also get a taste of some of Chicago’s most popular neighborhoods. On the daytime version of the tour, cruise through Wrigleyville, Gold Coast, Old Town, Lakeview, and Lincoln Park. On the nighttime version of the tour, bike through the skyscrapers and bars of downtown Chicago and see Millennium Park and Buckingham Fountain at night. On either route, enjoy the beautiful lakefront trail as well. This tour is 13 miles with perfect breaks along the way for sampling. Your experienced guide will keep you safe, in-the-know, and well-fed. Bikes provided.

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Chicago: 75-Minute Architecture Cruise by Speedboat

7. Chicago: 75-Minute Architecture Cruise by Speedboat

Climb aboard a speedboat for a thrilling 75-minute river and lake cruise of Chicago’s architectural gems. Depart from the former Navy training center of Navy Pier on the shores of Lake Michigan on the only tour to take you from the lakefront. Sail through the locks and along the Chicago River, all the way to the famous Willis Tower (formerly Sears Tower). Get up-close to Chicago’s most famous buildings and unique architecture, and enjoy amazing views and an entertaining narration as part of the exciting ride. Learn the fascinating history of buildings such as the neo-Gothic Tribune Tower, the former Sears Tower (now Willis Tower) - the second tallest building in the USA - and the Lyric Opera of Chicago. Cruise the lakefront of Lake Michigan to see monuments and attractions such as Buckingham Fountain, Grant Park, Chicago Harbor, and the Chicago Museum Campus.

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Other Sightseeing Options in Chicago

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What people are saying about Chicago

The tour was great. Lots of interesting facts. Our host couldn’t make it and they had a recording of her sessions. I recommend they record a new, better one because theirs is bad quality and could barely be heard. Either way, beautiful view. I’m guessing it’s a lot better when the host is in person.

Kevin was great!! The trip was a little chilly but we were able to warm up with a hot chocolate with Baileys! We did a bus city tour also and it was great to be able to see the city from both the water and the streets. I highly recommend this tour!

Ask for Alicia -- best Segway tour guide in Chicago! She also provided an excellent tutorial on use of the Segway before we began our tour. Highly recommend!

A great way to figure out where you want to spend additional time. Canopy on the roof keeps you warm, even when chilly.

the 5'-4" tour guide did a really good job introducing Chicago Riverside architecture. Definitely recommend y'all!