Chicago
Outdoor Activities

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Our most recommended Chicago Outdoor Activities

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

1. 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.

Chicago: Lake Michigan Skyline Sightseeing Cruise

2. Chicago: Lake Michigan Skyline Sightseeing Cruise

Immerse yourself in the sights and learn about Chicago’s history and architecture during a cruise on Lake Michigan. Take advantage of skip-the-line entry privileges with a barcoded ticket that lets you proceed directly to the boarding line. Whether you’re a local or a visitor to the city for the first time, taking in the spectacular views of Chicago's skyline from the lake makes for a perfect outing. You’ll see the city as never before while listening to commentary on Chicago's history and architectural gems. Simply hop on board, sit back, relax, and enjoy as you admire Chicago's most significant landmarks and striking buildings that make up the city's skyline that has appeared in so many movies and TV shows.

Chicago Lakefront: Seadog Speedboat Ride

3. Chicago Lakefront: 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.

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

4. 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 12 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 24- or 48-hour tickets, you can take your time discovering Chicago. With the 48-hour ticket, enjoy a non-stop panoramic sightseeing bus tour through Chicago at night too. Admire the illuminated skyline from the Museum Campus and see River North's vibrant nightlife scene. Take one loop from Michigan Avenue to the Magnificent Mile and the Cultural Mile. In addition, be sure to take advantage of admission to the Chicago Architecture Center, included if an appropriate option is selected, to dive deeper into the city that invented the skyscraper. So don't wait, just hop on an exciting journey through Chicago.

Chicago: Gangsters and Ghosts 2-Hour Walking Tour

5. 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.

Chicago: 90-Minute River and Lakefront Cruise at Night

6. Chicago: 90-Minute River and Lakefront Cruise at Night

Experience the magic of Chicago at nighttime and watch the city's glorious skyscrapers, historic buildings and modern marvels come to life with millions of twinkling lights. Relax and unwind at the end of the day on a cruise which not only lets you enjoy the scenic Chicago River, but also takes you through the Chicago Harbor Lock and out onto Lake Michigan where you can admire epic views of the sparkling Chicago skyline and shoreline. Throughout the ride, listen to lively narration about Chicago's rich history as the onboard guides point out the many sights of the city including Buckingham Fountain, Willis Tower, Aon Center, John Hancock Building, Museum Campus, Marina City, Wrigley Building, Chicago Tribune Building, Navy Pier, the Lighthouse and more. This tour also gives you the unique experience of passing through the Chicago River Lock System, while learning about the operation and the uses of the lock from your guide. You’ll also feel the boat rise as you enter Lake Michigan and lower as you return to the river, a unique experience for any boat lover.

Chicago: Family Fun Urban Adventure River and Lake Cruise

7. Chicago: Family Fun Urban Adventure River and Lake Cruise

Discover Chicago’s stunning skyscrapers, historic buildings, and modern marvels on this fun, family friendly boat cruise. Relax and unwind as you admire scenic views from the Chicago River and the Chicago Harbor Lock. Then move out onto Lake Michigan where you can gaze upon the entire city skyline and shoreline. During the boat ride, enjoy lively narration and stories about Chicago’s rich history as your knowledgeable guides point out the many sights of the city including Willis Tower, Aon Center, John Hancock Building, Museum Campus, Marina City, Wrigley Building, Chicago Tribune Building, Navy Pier, the Lighthouse and more. The tour also gives you the opportunity to experience passing through the Chicago River Lock System. Listen to your guide explain the full workings of the lock and feel the boat rise as you enter Lake Michigan, and then lower again when returning to the Chicago River.

Chicago: 75-Minute Architecture Cruise by Speedboat

8. Chicago: 75-Minute Architecture Cruise by Speedboat

Climb aboard a speedboat for a thrilling river and lake cruise around some of Chicago’s architectural gems. Gain insights into the city's most famous landmarks from your guide. Admire sights like Willis Tower, Tribune Tower, and Buckingham Fountain. Depart from the former Navy training center of Navy Pier on the shores of Lake Michigan on a tour along the lakefront. Sail through the locks and along the Chicago River all the way to the second tallest building in the USA, Willis Tower (formerly Sears Tower). Get up close to Chicago’s most iconic buildings and unique architecture, and enjoy amazing views and an entertaining narration as part of the exciting ride. Learn the fascinating history of structures like the neo-Gothic Tribune Tower 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.

Amazing Lakefront Segway Tour of Chicago

9. Amazing Lakefront Segway Tour of Chicago

Glide around the streets and parks of Chicago on a leisurely guided Segway tour. Perfect for Chicago newbies and veterans alike, the tour uncovers quirky facts about one of America’s most energetic destinations. Begin with a training session to become familiar with the unique self-balancing Segways, before exploring the Windy City in a fun and futuristic fashion. 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. Capture pictures to share of the expansive views of the sea-like Lake Michigan. Return to your meeting point at the end of your tour.

Chicago: Bikes, Bites, and Brews Biking Tour

10. 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.

Frequently asked questions about Chicago Outdoor Activities

What are other things to do than Outdoor Activities that are worth visiting in Chicago?

The other unmissable things to do in Chicago are:

Other Sightseeing Options in Chicago

Want to discover all there is to do in Chicago? Click here for a full list.

What people are saying about Chicago

Although it was a cold and windy day it was still really neat to see the city from that angle and learn about the different forms of architecture.

Once you have your pass, you can make the day your own. A nice variety of places to learn and explore.

Sarah was an awesome guide! Very funny and knowledgeable! We really enjoyed our tour with her!

Great experience!! Best way to see and understand why Chicago is unique :)

Great tour about the history of gangsters and ghosts in Chicago!