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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Our Chicago Scavenger Hunts
NEW ACTIVITY!!!
Strayboots Strategy Game

Can you beat the clock and our new Strategy Scavenger Hunt?
You have not hunted until you have tried Strayboot's new Strategy Based Scavenger Hunt.
This new spin on our original hunt embraces teamwork and strategic communication in a brand new way.

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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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INDOOR HUNT - Chicago Navy Pier Scavenger Hunt

Beat the weather with an exploration of Chicago's Navy Pier! This 50 Acre playground is full of entertainment, restaurants, and shops, perfect for two hours of fun.

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MUSEUM HUNT - The Art Institute of Chicago Scavenger Hunt

Fun team building activity, in one of the oldest and largest art museums in the United States! Explore the permanent collection of the Art Institute of Chicago which includes
over 300,000 works of arts — ranging from ancient art through contemporary art.

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Custom Team Building Event

Time to let your imagination go wild!
Create a custom event for your team, with the help of our talented event planners.

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Custom Team Building Event

Time to let your imagination go wild!
Create a custom event for your team, with the help of our talented event planners.

Highlights

At Strayboots, your wish is our command. Cater to your company's values, practices, and more with an activity that allows you to explore your surroundings and your co-workers’ competitive sides!

PRICE - From $40 /person
LENGTH – 2-5 hours
AVAILABILITY – Anytime
CAPACITY – 10-10,000 participants

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Our Customers
NYU Team building
Harvard University Team building
Pace University Team building
Stevenson Team building
MIT Team building

Part Student Tour, Part Game

Sign up for one of our carefully crafted scavenger hunts and we guarantee that you’ll see the city in a whole new way.
On our scavenger hunts, you'll wind through some of the city’s most popular neighborhoods and famed sights.
Not only will you see the main tourist attractions in the Windy City, but you’ll also discover local haunts that would otherwise go unnoticed.
Pose with Abe in Lincoln Park, learn about the famed Chicago architecture at the John Hancock building on Magic Mile, or spend your day at the Institute of Art.

If you’re interested in a neighborhood in particular, let us know! We're always looking to learn about new places to add to our hunts so we will do our best to make a hunt for it.

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What People are Saying

How the Scavenger Hunts Work

Split students into teams, giving them only a cell phone as an aid.
Teams will solve challenges and riddles, using the phone as a guide to the next question. Every correct answer means points and fun trivia for your team.
Take fun pictures along the way.
Select a central spot to meet at the end of the hunt, declare a winner and share your stories.

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Plan Your School Travel Activity Today!

Let us help you! Whether you’re a teacher, faculty member or student, we know that things get busy. Drop us a line or call us up (877-787-2929 ext 2) today and we’ll plan your scavenger hunt!

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Help us build you the best offer
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Feel free to select more than one, we can handle it...

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Help us build you the best offer
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Feel free to select more than one, we can handle it...

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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
Together

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