Chicago Loop
Solo travelers' tours

Enter your dates to find available activities

Our most recommended Chicago Loop Solo travelers' tours

Chicago Crimes Night Tour

1. 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

2. 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: Art Deco Skyscrapers Walking Tour

3. Chicago: Art Deco Skyscrapers Walking Tour

Tour the lobbies of five opulent Art Deco skyscrapers built near the banks of the Chicago River during the business boom of the Roaring '20s. Art Deco abounds in Chicago. The style made its way to the city in the 1920s, after it was showcased at an international art exposition in Paris. It was widely seen at the 1933-1934 Century of Progress Exposition in Chicago as well. Influenced by Cubism and the art and architecture of the ancient Middle East, Art Deco can be found in popular motifs like zigzags, octagons, sunbursts and flowers. Art Deco reflects the era’s fun-loving optimism with lavish materials and geometric ornaments. Discover the origins of Art Deco while admiring buildings like the Carbide and Carbon Building (now the St. Jane Hotel), the Chicago Motor Club Building (now the Hampton Inn), the colorful, but often overlooked, Trustees System Service Building (now the Century Tower) and the Engineering Building—all of which are designated Chicago landmarks. This tour ends at the Merchandise Mart.

The Chicago Theatre Marquee Tour

4. The Chicago Theatre Marquee Tour

Explore the grandeur of The Chicago Theatre, which opened in 1921, on a 1-hour guided tour. Your guide will accompany you through the elegant lobby, sweeping staircase and the majestic auditorium, which is complete with murals above the stage and on the ceiling. During your visit, you will get access to various sections of the seven-story, 3,600-seat auditorium and an intimate view of the 29-rank Wurlitzer theatre pipe organ, the first musical instrument having attained a city landmark status.  Next, view artist signatures on the dressing room walls, including Frank Sinatra, Dean Martin, Dolly Parton and many more. You will finish your tour on a high and feeling like a star as you get the chance to stand on the famous Chicago Theatre stage. Once called “the Wonder Theatre of the World”, the Chicago Theatre hosts over 175 events a year, bringing together the world’s brightest stars and greatest productions.

Frequently asked questions about Chicago Loop Solo travelers' tours

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

The other unmissable things to do in Chicago Loop are:

What are the best Chicago Loop Solo travelers' tours?

Which Chicago Loop Solo travelers' tours are taking additional COVID-19 precautions?

Other Sightseeing Options in Chicago Loop

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

What people are saying about Chicago Loop

Overall rating

4.4 / 5

based on 279 reviews

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 !

John was our guide and he was so much fun to have leading us through the whole thing! He’s very knowledgeable and made the whole experience fun & interesting! Highly recommend trying this out!

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.

Our guide was great and made for a very interesting and informative tour. I would highly recommend!

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