Chicago
Solo travelers' tours

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Our most recommended Chicago Solo travelers' tours

Chicago Lakefront: Seadog Speedboat Ride

1. 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 Seadog Speedboat Fireworks Cruise on Lake Michigan

2. Chicago Seadog Speedboat Fireworks Cruise on Lake Michigan

Enjoy a summer or autumn evening on this Chicago Seadog Speedboat Fireworks Cruise on Lake Michigan. This popular 60-minute narrated tour ensures you have the best views of this magnificent fireworks display. Every seat on the Seadog Speedboat Fireworks Cruise has amazing panoramic views of Chicago's historical skyline. Whether you are looking for a romantic evening, a night out with friends, or simply appreciate the art of pyrotechnics, this tour will have everyone of all ages leaving with a smile. Come and visit all of the possibilities that Chicago has to offer by enjoying a magical Fireworks Cruise on Lake Michigan. These memories are made to last a lifetime!

Chicago: 90-Minute River and Lakefront Cruise at Night

3. 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: 1.5-Hour Open-Top Double-Decker Night Tour

4. Chicago: 1.5-Hour Open-Top Double-Decker Night Tour

From the top deck of a double-decker bus, experience Chicago at night. Enjoy a 75-minute, live-guided panoramic tour and take in unique views of the Chicago Skyline, comprised of world-famous skyscrapers and revolutionary architecture. Take a photo overlooking downtown from the Museum Campus in front of the Adler Planetarium. Be amazed by the beautiful water and light display of The Buckingham Fountain as you discover the bustling nightlife of Chicago. Marvel at the magical light show of the one-of-a-kind Art on the Mart, displayed on the facade of the Merchandise Mart. See the city reflect off of The Bean (Cloud Gate) at the famous Millennium Park. Experience the city that built the skyscraper and see architectural marvels like 875 N Michigan Ave (formally the John Hancock Building), the Wrigley Building, the Chicago Tribune Building, and the Willis Tower. End the tour at the Chicago Riverwalk, with the knowledge that you can continue exploring the city with confidence. From the pioneering skyscrapers, to the Great Chicago Fire, this night tour will take you on a journey you won't soon forget. Be sure to soak up the exciting atmosphere that makes the Windy City such a fascinating and dynamic place.

Chicago: Family Fun Urban Adventure River and Lake Cruise

5. 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.

Amazing Lakefront Segway Tour of Chicago

6. 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 Crimes Night Tour

7. Chicago Crimes Night Tour

Uncover how some of the world’s most famous criminals, mobsters, and gangsters conned their way through the Windy City. Ride in luxury on a climate-controlled bus, as you explore famous Chicago crime scenes ranging from the 19th century through to modern times. Learn about Al Capone, the Untouchables, the Chicago Mob, John Dillinger, The Lady in Red, Captain George Streeter, Frank "The Enforcer" Nitti, Bugs Moran, Johnny Torrio and more. Grab your camera for a drive-by shooting of historic and architectural landmarks, and stake out crime scenes like the Biograph Theatre, Holy Name Cathedral and St. Valentine's Day Massacre, one of Chicago's most notorious murder sites. Walk the path that notorious Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths. Travel into the criminal past of Chicago's River North, Gold Coast, Lincoln Park, Old Town, Loop, and Magnificent Mile neighborhoods.

Chicago: Treasures of the Golden Age Walking Tour

8. Chicago: Treasures of the Golden Age Walking Tour

This Historic Treasures of Chicago tour covers the most significant historic architectural landmarks in Chicago’s Loop. Your expert guide, trained by the Chicago Architecture Center, will focus on great cultural buildings from the late 19th and early 20th centuries, which harkened back to earlier time periods and were designed in revival styles such as Beaux Arts, neo-Georgian and neo-Gothic. Marvel at exteriors and interiors of dazzling beauty and startling originality, and get a glimpse inside some of the city's most beloved buildings.    The highlights of this walking tour will include the Chicago Cultural Center, home to the world's largest Tiffany dome; the iconic Marshall Field's department store, now Macy's on State; and the Palmer House, a beautifully restored hotel from the 1920s. 

Chicago: History, Culture and Architecture Walking Tour

9. Chicago: History, Culture and Architecture Walking Tour

Start your tour under the dazzling marquee of the Chicago Theater (which you might recognize from the movie-musical Chicago) before heading off into the bustling city. Your first stop is inside one of the best-preserved spaces built for shopping in Chicago, featuring an unforgettable atrium at its core. Then head towards the Chicago Pedway, a uniquely Chicago feature used by locals and commuters daily to move about the city in a network of underground tunnels. Afterward, head back above-ground near City Hall and head inside to see the classic interior design and architecture. Next, enjoy a sweet treat, and local tradition: Chicago-style popcorn. Weather permitting, take a stroll along the Chicago Riverwalk while taking in views of several soaring buildings, including Marina Towers, the Britannica Building, and the Willis Tower. From there, make your way to another delicious destination. Along the way, enjoy views of the world-famous Wrigley Building and the incredible Chicago Tribune building, the heart of Chicago’s thriving and historic journalism industry. Your second tasty confection is locally made chocolate from a Chicago staple. Finally, take a stroll through the beautiful lakefront parks along Michigan Avenue. Round up your tour in the picturesque Millennium Park, home to the iconic Bean sculpture. Here, your guide will conclude your tour and point you in the right direction toward more amazing sights, great lunch spots, or drink recommendations.

Chicago Lakefront Bike Tour of Lincoln Park

10. Chicago Lakefront Bike Tour of Lincoln Park

The parks, skyline and lakefront of the Windy City are beautiful from any point of view. But they come alive when you can feel the wind in your hair. Bicycling along the Lakefront Trail and past beaches, lagoons and city landmarks is exhilarating, even at a casual pace. And our informative, entertaining tour guides make sure you have a good time. The route we follow starts at Millennium Park and includes the Lincoln Park Zoo and Conservatory, the Navy pier, Notebaert Nature Museum and North Avenue Beach. It is an easy 8-mile ride that takes about 3 hours. Our tour is designed for maximum enjoyment, not speed, so it makes a great outdoor activity for friends, families, couples or anyone who wants to see popular Chicago sights up close and personal.

Frequently asked questions about Chicago Solo travelers' tours

What are other things to do than Solo travelers' tours that are worth visiting in Chicago?

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Other Sightseeing Options in Chicago

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What people are saying about Chicago

Overall rating

4.5 / 5

based on 991 reviews

Very informative, everything worked out wonderfully from pick up to the end. Very nice and very good guide, also nice and courteous driver, comfortable car. The tour itself has a strong focus on Lloyd Wright, but that's fitting in a city where he started, has been active, and where many of his homes stand. Overall excellent tour with insights we would never have had otherwise.

Our guide, Dash, was very knowledgeable about all aspects of the city, from the food to the history to all sorts of hidden gems to visit on our trip after the tour, and the whole experience was both fun and informative.

Chicago has som beautiful architctural treasures with very interesting histories. This tour brings alive those factors We got to see some fabulous interiors also. This tour will make your day !

Wonderful overview of some interesting buildings. Well paced and the guide Ross, told lots of interesting stories. You don't have to love architecture to enjoy this tour.

VERY VERY INTERESTING THE WHOLE TIME!!! AWESOME!!! Def Recommend!!! book early!!