Best Solo travelers' tours in Chicago

Local Recommendations from our My Guide Chicago team

Book Top Experiences and Tours in Chicago:

If youʻre booking your trip to Chicago last minute, we have you covered. Below are some of the top tours and experiences!

Filter Solo travelers' tours in Chicago

Chicago: 90-Minute River and Lakefront Cruise at Night

204 Reviews

Chicago: 90-Minute River and Lakefront Cruise at Night

Glide along the Chicago River and Lakefront as you're dazzled by the sparkle of the city at night. Enjoy breathtaking views of the dramatic skyscrapers and Buckingham Fountain's spectacular light display while listening to lively commentary.

$42.00

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Amazing Lakefront Segway Tour of Chicago

93 Reviews

Amazing Lakefront Segway Tour of Chicago

Glide around the Chicago lakefront on a Segway tour. Zip past the cascading fountains of Millenium Park, admire the city's towering skyline, and swoop through Grant Park’s manicured gardens.

$79.00

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Chicago: Sunset Tour by Open-top Bus with Live Guide

42 Reviews

Chicago: Sunset Tour by Open-top Bus with Live Guide

Experience the Windy City’s dazzling skyscrapers lit up at night. Set off on a panoramic night tour from Navy Pier to the Magnificent Mile, passing by the Chicago Theatre and Buckingham Fountain.

$44.55

~~From $49.50~~

Chicago Lakefront: Seadog Speedboat Ride

322 Reviews

Chicago Lakefront: Seadog Speedboat Ride

Enjoy Chicago's iconic skyline with a speedboat tour of Lake Michigan. Depart from Navy Pier and feel an adrenaline rush as you take in views of the city from a different perspective.

$41.59

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Chicago: Ultimate Food Walking Tour with Tastings

42 Reviews

Chicago: Ultimate Food Walking Tour with Tastings

Join the ultimate foodie adventure in Chicago with a food and tasting walking tour. Explore from deep-dish pizza to Chicago-style hot dogs and get the insider's take on the city’s culinary history.

$63.75

~~From $75.00~~

Chicago: Private Architecture Tour - 3 or 6 Hours

5 Reviews

Chicago: Private Architecture Tour - 3 or 6 Hours

Discover a city known for its architectural creativity and ingenuity. Explore some of Chicago's most iconic buildings, with the option to visit Oak Park and the homes of Frank Lloyd Wright.

$780.00

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Chicago: Magnificent Mile Walking Tour

6 Reviews

Chicago: Magnificent Mile Walking Tour

Learn how the Magnificent Mile developed from a warehouse district into the Champs Elysee of Chicago. Admire a wide range of architectural styles including Parisian, Gothic, Neoclassical, Art Deco, Mid-20th Century Modern, and 21st-Century Contemporary.

$30.00

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Chicago: Seadog Speedboat Fireworks Cruise on Lake Michigan

72 Reviews

Chicago: Seadog Speedboat Fireworks Cruise on Lake Michigan

Watch the fireworks dance over Chicago's skyline on this popular 60-minute speedboat tour. Enjoy panoramic views of a magnificent fireworks display from the waters of Lake Michigan. Perfect for a romantic evening or a memorable night out with friends.

$59.44

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Must-See in Chicago: Architecture, History & Culture Tour

66 Reviews

Must-See in Chicago: Architecture, History & Culture Tour

Take a private or shared group walking tour of some of Chicago’s greatest hits: incredible architecture both old and new, delicious local treats, stunning river views, and much more.

$50.15

~~From $59.00~~

Chicago: Evolution of the Skyscraper Walking Tour

8 Reviews

Chicago: Evolution of the Skyscraper Walking Tour

Chicago built some of the world’s first skyscrapers, with changing designs and technologies over time. Explore how these major developments came about, with examples from classic buildings to super-tall highrises from 1872 to the present.

$30.00

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Chicago: Family Fun Urban Adventure River and Lake Cruise

172 Reviews

Chicago: Family Fun Urban Adventure River and Lake Cruise

This popular 90-minute, fully narrated daytime river and lake tour delights families with incredible views of Chicago's famous architecture, stunning skyline and stories about the city's rich history.

$42.00

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Chicago Crimes Night Tour

71 Reviews

Chicago Crimes Night Tour

Explore Chicago's criminal history on this 2-hour night time tour. Discover the history of Chicago’s most famous criminals, gangsters and mobsters, such as the famous Al Capone and John Dillinger.

$55.00

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