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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Our Chicago Scavenger Hunts
Strayboots Strategy Game

Can you beat the clock and our new Chicago 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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Your place, Your employees, Your rules!

Make a great first impression with Strayboots to welcome new hires, while helping them get to know the office and the area. Create interactions with other employees, add custom challenges to increase brand awareness, teach them about the company culture and history, all in a fun, unique, and competitive 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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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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Downtown Chicago Scavenger Hunt

Chicago is not only known for its famous deep dish pizza, but also its interesting architecture, museums and beautiful parks along Lake Shore Drive.
Come and hunt with us from Buckingham Fountain to Printer's Row as you experience the south end of the business district of Chicago.
Walk the streets with the locals, run into true sports fans or Columbia students while you answer riddles and complete challenges. The race is on, who will meet us at the starting line?

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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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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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Scavenger Hunt Anywhere

Looking for an amazing scavenger hunt in a new location, Museum, or a top neighborhood? Our explorers are here to help you build it!

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Scavenger Hunt Anywhere

Looking for an amazing scavenger hunt in a new location, Museum, or a top neighborhood? Our explorers are here to help you build it!


Just tell us where and we'll do our magic...

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Our Customers
Startup institute Team building
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Our Scavenger Hunts

Our Chicago scavenger hunts really do show you it all. With options in some of the city’s top neighborhoods, you'll hit all the top sites as well as uncover some of the hidden gems that Chicago has to offer. You can have it all -- from checking out a famous fudge shop at Navy Pier to diving into the Institute of Art, from setting up the perfect date across this very romantic city to getting wet at the Old Town Aquarium in Lincoln Park.

If there is a neighborhood that really excites you, let us know! We will try our best to make a hunt for it.

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What People are Saying

How the Group Events Work

Arrange guests on multiple teams, ensuring each has a cell phone.
Teams will solve challenges and riddles, using the phone as a guide to the next question.
For each correct answer, your team will receive points and interesting facts about the area.
There will be fun photo ups to pose at along the way.
At the end of the hunt, meet at a central spot, declare a winner and share your stories.

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Plan Your Fun Activity Today!

Let’s get going today! Drop us a line or give us a call (877-787-2929 ext 2) today and we’ll start planning your scavenger hunt!

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


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