Chicago
Interactive Tours & Incentive Events

Enter your dates to find available activities

Our most recommended Chicago Interactive Tours & Incentive Events

Chicago: 90-Minute Mob and Crime Bus Tour

1. Chicago: 90-Minute Mob and Crime Bus Tour

Experience Chicago’s underworld of criminals and gangsters on a luxury 90-minute bus tour. Find out how some of the world’s most famous criminals, mobsters, and gangsters conned their way through the city. Ride comfortably in luxury, on a climate-controlled bus, as you see famous Chicago crime scenes that range from the 19th century through modern times. Unlike Chicago walking tours, this Mob and Crime Tour isn’t affected by the Windy City weather. Learn from a local expert tour guide giving interactive live commentary about Al Capone, the Untouchables, the Chicago Mob, John Dillinger, Terrible Tommy O'Connor, H. H. Holmes, the Chicago Black Sox, Leopold and Loeb, bank heists, Cap George Streeter, and more. Grab your camera for a drive-by shooting of the historic criminal courthouse, a Chicago architectural landmark where some of Chicago's most notorious cases were tried. You'll also view historic video footage, receive an informative pamphlet with photos, and can even take part in a crime quiz. Stake out crime scenes like the Biograph Theatre, Holy Name Cathedral, Clark Street Bridge, and other Chicago landmarks. See the site of the St. Valentine's Day Massacre, one of Chicago's most notorious murder scenes. Get off the bus and 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.

...
Eastside Chicago: Exploration Game

2. Eastside Chicago: Exploration Game

Start the adventure at The Art Institute of Chicago. It will take you between 1.5 to 2 hours to complete and you can also explore at your own pace. Pause the game and resume anytime from the location where you paused it. You will finish at the Fountain of the Great Lakes. As you solve challenges, the story unfolds and exact directions on your phone will guide you to the next location. So, are you up for an exciting city game? After your booking, you will receive an email on how to download the game to your phone. You can play on your own, in a large group, or in several smaller groups that compete against each other and meet at the final stop of the game. For larger groups, one person can purchase access for the entire group by selecting the number of people in the group. All group members will be able to download and play the city game on their phones. Alternatively, each person can make their own purchase.

...
Chicago: Millennium Park Self-Guided Walking Tour

3. Chicago: Millennium Park Self-Guided Walking Tour

On this self-guided walking tour where your phone is your personal guide, explore Millennium Park’s best sights and dive into some of Chicago’s little-known history along the way. This tour has been developed by local guides, creative writers, and professional voice artists. Begin your tour at the park’s north end, by Harris Theater for Music and Dance. From there, simply follow the audio instructions and the route via the app that will be your guide, narrator, and map in one. Head south toward the Pritzker Pavilion while learning some background on how the park came into existence. As an added perk, most stops along the tour have animated videos allowing you to visualize what you cannot see, such as snapshots from different centuries or interior rooms. Once at the impressive pavilion, learn about the vast array of performances held here and the high-tech design which makes it all possible, as well as the man behind it: Jay Pritzker. Get the full story on this precocious kid who went from building model cities out of his grandfather’s scrap wood to designing some of the most famous structures in the country. As you continue, you’ll come to the park’s so-called Secret Garden. Take a stroll along a peaceful boardwalk surrounded by plant life and listen to the little-known symbolism behind the garden’s design. Pause for a fantastic look at Chicago’s skyline before heading past the Art Institute of Chicago and ending up at the astonishing Crown Fountain. Get familiar with the intricately detailed face towers of the fountain, then head north toward Chicago’s most famous sculpture. At last, arrive at Cloud Gate, known by the locals as The Bean. Learn about the artist behind it as well as the technique he used to create such a huge, smooth surface. At the end of your tour, don’t forget to snap some surreal pictures of your reflection.

...
Chicago: 2.5-Hour Amazing Scavenger Hunt Adventure

4. Chicago: 2.5-Hour Amazing Scavenger Hunt Adventure

Turn downtown Chicago into your own personal giant game board with Urban Adventure Quest, an interactive Amazing Race-style scavenger hunt that allows you to do just that. On this 2.5-hour sightseeing tour of Chicago, you’ll be guided from your smartphone through the city on a fun, team-building journey. This is the perfect tour for groups – large or small – looking to make their way to the most well-known sites, as well as to those often-overlooked hidden gems the city keeps secret. Race to be the first to finish the game, or take as much time as you need, solving clues, completing challenges, and learning about local history along the way. The adventure will start riverside among the historic buildings and will take you along a game route that will show you the rich history, strong focus on public art, and indelible culture of this great city.   Points of interest on your quest: Riverfront Hard Rock The Bean Art Institute of Chicago Palmer House

...

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

Overall rating

4.5 / 5

based on 176 reviews

John, guide, and Wayne, driver, were both excellent at their jobs. Chicago is a beautiful city and your 40+ person bus was clean and comfortable ( only 15 participants). We saw the outside of the theater where Dillinger spent his last night, the alley where he was shot, and the Harry Caray Restaurant where there was a lot of historical news articles and photographs to look at. Everything else was “the building used to be here where... “ or “see that McDonalds, that used to be...” Again, John did an excellent job painting the historical background and telling the stories of the north side and south side gangs. I just wished that Chicago had the foresight to keep/rebuild/remodel some of the 1920s/1930s historical places that defined that era.

It just so happened that 1 of the days I was in town called for rain & this was perfect. There are 2 stops where you can get off the bus & we were able to do both of those despite a few rain drops. Leah was super knowledgeable on all areas of Chicago crime. I felt like the whole tour flowed very well from start to finish.

Was a terrific way to get out and see a little bit of the city and learn about some gangsters.

Our guide was great and very informative. His dad jokes were pretty on point too.

Caleb was a very cool, informative, & humorous guide, made the tour fun