Chicago Scavenger Hunts, Team Building Events and Tours

Discover a whole new side of Chicago with a team building scavenger hunt activity. If you’re planning a weekend getaway, hosting out of town friends, planning a school field trip or a company outing, our scavenger hunts are for you.

How it Works
Our Chicago Scavenger Hunts
The Loop Scavenger Hunt

Navigate Chicago's deepest urban canyons, as you explore the city's most iconic and interesting spots. From the Chicago Board of Trade to the Federal Reserve Bank, discover La Salle Street's "rich" history like so many titans of industry before you. On State Street and other great streets, get schooled on some of Chicago's most captivating architecture. Find Picassos and Chagalls along the storied sidewalks then peer through world's largest Tiffany stained-glass window. Search for valuables along Jeweler's Row and get dramatic at the Chicago Theater. From skyscrapers to sculptures, old churches to elegant hotels, the Loop will wow you with its bravado and its beauty.

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Magnificent Mile Scavenger Hunt

Designed to rival New York's 5th Avenue and Paris's Champs Elysees, the Mile is big on history and haute couture. From the Drake to the Allerton, you'll check into some of Chicago's swankiest hotels like so many celebs and statesmen before you. Then saunter down Chicago's best street of shopping and marvel at some of its most magnificent architecture.

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Art Institute Chicago Scavenger Hunt

A new scavenger hunt is under construction...

Contact us for more information.

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Coming Soon...

A new scavenger hunt is under construction... Stay tuned!



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Chicago Team Building Scavenger Hunts

Create an unforgettable company outing in the top neighborhoods and museums that the Windy City has to offer!
In our Chicago team building scavenger hunts, group members will work together to solve clever challenges that will take them to sites all over the neighborhood, from 'must-see' places to undiscovered local favorites.

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Our Customers

Chicago School Field Trips with Scavenger Hunts

As one of the country’s oldest cities, Chicago has both a complex and colorful history. We want to help bring that history to life for you. Whether you’re trying to plan the perfect field trip for your class or want to learn more about the city where you’ll be spending some of your most formative years (shout out to our college students!), our scavenger hunts are the perfect choice for you.

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What People are Saying

Chicago Scavenger Hunts and Tours

Hoping to make your time in Chicago extra special? Check out our group scavenger hunts. Whether you are looking to plan a great family activity, plan something totally unique for a group of visiting guests, or do something a little different in the city you call home, we have a competitive scavenger hunt for you.

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For more information on your next team building activity, call us at 877-787-2929 or fill out the form below

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How Strayboots Works

Where, When,
& How Many?

Pick the date, location and group size and we'll create a personalized team building package for your group

Create Teams
& Get Started

Split your group up into teams and have them meet at the predesignated starting points in your city of choice

View Clues on
Your Mobile

Each team "captain" receives a link and instructions on their smartphone to lead their teammates to each clue

Solve Challenges

Participants work together and learn new things about their city and each other, while racing to the finish