There are many ways to strengthen team bonds in a company. However, if you’re looking for a fun and engaging team-building activity that fosters healthy competition and collaborative spirit, a scavenger hunt is the best way to go.
Chicago is one of the best cities to arrange scavenger hunts. The city is steeped in history, rich in beautiful architectural wonders, and, lest we forget, scrumptious local food. There’s no shortage of wonderful things your team can explore and bond over.
Here are 15 scavenger hunt ideas in Chicago, complete with local venues, sample clues, and practical tips to make your scavenging more exciting.
1. cityHUNT’s Loop & Millennium Park Hunt
If you’re to discover the City of Big Boulders up close, there’s no place else to start but the landmarks that showcase the heart of the metropolis: the Loop and Millennium Park.
Kick off your quest at the Millennium Monument, which features a near full-scale replica of the Roman Doric-style columnades. Witness the city’s sprawling skyline reflected in the polished surface of the Cloud Gate.
Wander through the historic Route 66, immersing in its timeless charm that inspired countless journeys. From there, ascend 1,353 feet up on the Willis Tower, and walk on the glass floors of The Ledge.
A scavenger hunt around the Loop is ideal for about two hours of exploration through the city’s architecture, cuisine, and wondrous history. Customize your Chicago experience with cityHUNT!
Other notable sights to visit in the Loop & Millennium Park:
- Millennium Park’s Crown Fountain
- The official start sign of Route 66 at 122 Street, Michigan Avenue
- Tiffany Dome at the Chicago Cultural Center
- Chicago Board of Trade and the Rookery Building
- Wrigley Square and the Seated Lincoln sculpture
Sample Clue:
“Mother of all roads they call me, and fittingly so. Find the sign where every journey starts and pose for a photo.”
2. The Magnificent Mile
This 13-block stretch of North Michigan Avenue is another area worth checking out with an outdoor scavenger hunt. Famed for its vibrant commerce and culture, the Magnificent Mile lives up to its name with its many offerings.
The Old Water Tower is a must-visit here. As one of the few buildings that survived the Great Chicago Fire of 1871, there’s no other piece of architecture that encapsulates the city’s resilience.
Be in awe of the Gothic inspirations of the Tribune Tower, where priceless artifacts from across the world gather. Make your way along the Chicago River to locate the World War I Memorial and honor our fallen heroes.
To better appreciate the pilgrimage, finish at the Old Fort Dearborn, where you’ll learn its history and reimagine the Windy City in its earlier days.
Other notable attractions to visit in the Magnificent Mile:
- Site of the Eastland Disaster
- Bataan-Corregidor Memorial Bridge
- Chicago’s skyline-defining 875 N. Michigan (John Hancock Center)
- The Drake Hotel’s historic Palm Court
- Tony Award-winning Lookingglass Theatre Company
Sample Clue:
“I’ve been through fire and flames, yet tall I stood remain. I’m ancient, and history will mark my place. Find the plaque and take a selfie at my base.”
3. Old Historic Landmarks and Hidden Plaques
Experience the Wind City’s history firsthand by incorporating ancient landmarks and plaques into the hunt. Invite your team to dig into the past by completing plaque inscriptions of historic sites and buildings before time runs out.
Think of the Wooden Alley, the only remaining wooden-paved street in the city, found between Astor and State Streets. Examine the Old Water Tower and spot the scorch marks that tell its story.
Other notable historic landmarks to check out:
- 1836 Clarke-Ford House Museum on Indiana Avenue
- Soldier Field (Chicago Bears stadium)
- Washington Square Park
- The Museum of Science and Industry
- Old St. Patrick’s Church (the oldest church in the city)
Sample Clue:
“Locate the city’s oldest standing church. Take a group photo with the church in the background and complete the inscription with the date when the church’s cornerstone was laid.”
4. Mystery Hunt at the Art Institute of Chicago
There’s a reason why the Art Institute of Chicago is among the top museums in the world. It has something to offer everyone, whether you enjoy exploring ancient relics, priceless art, or Western history.
Stroll through the museum’s galleries and be transported to a different time, where you need to solve riddles and identify artworks to complete the quest.
Here, you can find the famous Illinois-born Parisian dancer, Miss Loïe Fuller, famed for her mesmerizing “Serpentine Dance.” Or the notorious snoozer, Rip Van Winkle, freshly awoken from his 20-year nap.
For those who prefer a thrilling twist, why not arrange an “escape the museum,” scattering hair-raising clues throughout the museum’s bizarre collections?
Think of the multi-armed Buddhist goddess, lost in a dance, wearing skulls as necklaces. Or the uncanny picture of A Witches’ Sabbath, featuring a goat-riding witch, broom in hand, chasing a horde of unearthly creatures.
Overlaying a mystery narrative over the hunt would make for an exciting twist that your teammates would certainly enjoy.
Other notable sights to visit in the Art Institute:
- Aztec Stone of the Five Suns
- Rembrandt’s Old Man with a Gold Chain
- The Assumption of the Virgin by El Greco
- Paris Street Rainy Day by French artist Gustave Caillebotte
- Head of a Guillotined Man by Théodore Géricault
Sample clue:
“Meet the goddess with skulls for jewels and arms for might, and behold your path under her watchful sight.”
5. Food and Flavor Trail
Sample Chicago’s diverse cuisines with a scrumptious foodie adventure. Let your crew hunt with their taste buds. For this challenge, you want to craft exciting food-related missions by teaming up with local vendors.
Enjoy Chi-Town’s unique staples, such as deep-dish pizza, Italian beef sandwich, Polish sausage, and Chicago-style hot dogs, loved for their all-beef frank and “dragged through the garden” toppings.
There’s a wealth of local restaurants and cafes you can pick as official stops, whether you’re craving Chinese, Mexican, or Italian grub. End the trail with a feast, offering a chance to share your day’s yummy tales.
Other notable dining spots to try:
- River North for cozy dining
- West Loop, at the former meatpacking district
- Chicago’s historic Chinatown
- Eclectic dining experience at the Logan Square
- Classic recipes in Lincoln Park
Sample Clue:
“Walk through the farmer’s market, in front of a stall with a blue awning. Order the mystery jam and take a selfie as a receipt.”
6. University Campus Challenge
College campuses are often brimming with local myths, histories, and legends. Guide your squad through a series of puzzles and fascinating trivia across olden academic halls and courtyards.
The University of Chicago is a treasure trove of historical sites and landmarks. You’ll find structures like the Joseph Bond Chapel, flaunting awe-inspiring stained glass windows, intricate stone carvings, and an ornate organ.
Don’t forget to admire the Cobb Gate and its grotesque architectural designs. This gargoyle-laden archway has guarded the campus since 1897!
Other notable campus landmarks to check out:
- The Cobb Lecture Hall (1892)
- John Crerar Library (1984)
- William Rainey Harper Memorial Library (1912)
- Ida Noyes Hall (1916)
- Institute for the Study of Ancient Cultures (1931)
Sample Clue:
“Head to the historic stone archway, under the gargoyle’s gaze, and snap a photo with your team. Make sure to include one gargoyle in your photo.”
7. Seasonal Pop-Up Hunt
Align your hunt with Chicago’s local events to weave in holiday magic. Between October and December, there are plenty of town traditions to infuse in your challenges.
Halloween season calls for a night of haunting challenges. Through cryptic texts and macabre riddles, steer your fellow hunters into a wild ghost-chase through Wind City’s most haunted buildings.
Winter is for a totally different set of snowy twists and puzzles. Decorated storefronts, ice sculptures, Christmas treats, and festive displays take the spotlight here.
Other seasonal events to check out:
- The Arts in the Dark Parade (October 18)
- Upside Down Halloween Parade (October 25)
- Haunted Halsted Halloween Parade (October 31)
- The Wintrust Magnificent Mile Lights Festival (November 22)
- Christmas Around the World and Holidays of Light (November 16)
Sample Clue:
“Tonight, the veil between the worlds is thin. Join the cursed procession and collect three pictures of three different ghostly floats.”
8. Riverwalk and Bridge Architecture
If you’re a resident of the city, you may have already seen the Chicago River countless times. But if you look closely enough, you may yet discover new, interesting fragments of Chicago’s long history.
In this hunt, invite your participants to look up, read plaques, count spans, and interpret architectural styles.
Start from the Congress Parkway Passage at the southern end of the Loop. Head west and check out the River Theater, a shaded area known for its geometric elements and breathtaking river views.
The Rush Street bridge is a 10-minute walk from the River Theater. This historic bascule bridge offers panoramic views of the local boats and the city skyline. The DuSable (Michigan Avenue) Bridge, with its Beaux-Arts architectural theme, is nearby.
Other notable sights to visit in the Chicago Riverwalk:
- The Marina (State to Dearborn), where local boats dock
- Water Plaza from LaSalle Street to Wells Street
- Floating wetland gardens in the Jetti
- The Cove
- See the Chicago River’s three branches from The Boardwalk
Sample Clue:
“Stone and steel lifts with grace, giving passage to weary sailors aboard. Find the plaque with my story embossed, and your next stop will be exposed.”
9. Public Arts and Sculptures
You can find great artworks on every corner in the art mecca that is Chicago. They make for a memorable and educational checkpoint for a team bonding scavenger hunt.
Encourage your group to discover artworks from unsung artists and masters, beginning with Pablo Picasso’s 160-ton masterpiece at the Institute of Art. That 42-inch-tall sculpture model is hard to miss!
Within walking distance of Picasso’s is the Flying Dragon by Alexander Calder. The Bright Flamingo is also nearby, at the Federal Plaza, with its scarlet steel body and massive, curved lines contrasting with gray concrete all around.
Amp up the fun by hiding letters at each checkpoint. Have them assemble a word or a phrase to raise the stakes and encourage friendly competition.
Other notable arts and sculptures to check out:
- Monument with Standing Beast by Jean Dubuffet
- Muddy Waters mural by Eduardo Kobra
- The Sun, the Moon, and One Star by Joan Miró
- Rushmore, an epic mural by Kerry James Marshall
- The Agora by Polish artist Magdalena Abakanowicz.
Sample Clue:
“Walk among the headless giants, unmoving and voiceless in the crowds. Step among their massive strides, there your next clue you will find.”
10. Hunt Film and TV Show Sets
Movie buffs will love a scavenger hunt through real-life locations featured in popular films and TV shows. Challenge your crew to identify still frames or descriptions, and visit their spots to take creative snaps.
For fans of Christopher Nolan’s The Dark Knight (2008), you can step inside the actual Wayne Enterprises, which was filmed in the former IBM building at 330 N. Wabash Ave. Better yet, scope the cityscape like Batman atop the Willis Tower!
The third installment of the blockbuster, The Transformers: Dark of the Moon, also showcased downtown Chicago, which heavily featured the Jewelers Building and Trump International Hotel & Tower.
Other notable film sets and sites to check out:
- The Biograph Theater in Lincoln Park, where Johnny Depp died in Public Enemies (2009)
- Soul Food Cafe and Ray’s Music Exchange in The Blues Brothers (1980)
- The Art Institute of Chicago in Ferris Bueller’s Day Off (1986)
- The Picasso statue in Daley Plaza featured in The Fugitive (1993) with Harrison Ford
- Navy Pier’s Grand Ballroom in The Color of Money (1986)
Sample Clue:
“The Dark Knight surveyed Gotham from atop this building. Ascend the tower and take a snapshot with Chicago’s skyline in clear view—bonus points for creative superhero poses.”
11. Adventure Aboard the Transit Line
Involving public rides as part of the game is a great way to take in more of the Windy City’s attractions.
Aboard the L train, you can discover Chicago from one end to another, and hop off wherever you desire. You can use each station, platform, tilework, signage, or nearby landmark as a clue to the next stage of the hunt.
Different lines offer different views (and hints) of the city.
The Red Line passes through Cermak-Chinatown, where the oldest Chinese communities reside. At Berwyn, you can find Andersonville with its Swedish-inspired culture.
The Green Line passes close to many visit-worthy sites, including the Garfield Park Conservatory, the Field Museum, and Bronzeville.
Other key attractions to check out:
- The Nine Dragon Mural Wall in Cermak
- Heritage Museum of Asian Art
- Chinese-American Museum of Chicago
- The Chicago Architecture Center
- African and Caribbean art at Gallery Guichard
Sample Clue:
“Board the south-bound Red Line toward Cermak-Chinatown. Exit at the stop and keep your eyes peeled for the fearsome nine dragons for your next instructions.”
12. Nature Quest in Lincoln Park
Meet the city’s furry residents in an exciting scavenger hunt at Lincoln Park’s zoo and conservatory. Guide your nature-lover group to discovering the oddest of animals and the strangest of facts through one of Chicago’s most picturesque neighborhoods.
Whip up fun and tricky questions about the fantastical creatures in the zoo; design tasks to challenge participants to identify rare plant species. Let the plaques and botanical labels be your guide.
Photo challenges add another layer of excitement. Pose with howling gibbons, clicking alpacas, snorting twigas, silent axolotls, and rare pythons. If you’re lucky, you may find yourself face-to-face with a cheetah.
Other notable attractions to check out:
- Armitage and Halsted
- Cafe Ba-Ba-Reeba!
- J. Parker rooftop
- Kingston Mines
- Alfred Caldwell Lily Pool
Sample Clue:
“Head to the primate enclosure where the white-cheek gibbons lie. Take a quick video of your squad imitating a gibbon call.”
13. Indoor Market or Mall Hunt
Turn Chicago’s famed malls and markets into a massive game board. This way, regardless of the weather, your colleagues can have their fair share of fun.
The Water Tower Place and the Merchandise Mart are both excellent venues for a hunt. Send your teams to an errand race, where they must collect supplies of your choosing. The first group to gather everything wins.
Schedule your team building activities scavenger hunt on a Sunday to catch the lively Maxwell Street Market. If you visit in June, you can support the local DIY community at the Renegade Craft Fair in Logan Square.
Other notable venues and events to check out:
- Block 37
- Mallers Building
- Andersonville Vintage Market
- Vintage House Chicago
- The Shops at North Bridge
Sample Clue:
“Bring ten unusual Chicago-themed souvenirs from different shops. Provide receipts for each item. The first team to return wins.”
14. Neighborhood Murals Hunt
Highlight Chicago’s street mural culture with team building scavenger hunts. Uncover a different side of the Windy City, through alleys, viaducts, and neighborhood walls.
Participants follow limited hints about the murals they must find. This can be a riddle, a reference to their location, or an incomplete image. Assigning points for each artwork is a superb opportunity to foster a collaborative spirit.
Throughout the city, neighborhoods are alive with eye-catching murals.
Pilsen, the heart of Chicago’s mural movement, boasts countless stunning street colors, including Gulliver en el país de las Maravillas, Increíbles las cosas a se ven, and Quetzalcoatl and the Stork.
Logan Square and Wicker Park/Bucktown have over 50 breathtaking urban arts—an open-air gallery you can enjoy free of charge. Among our favorites are Greetings From Chicago by Victor Ving and Lisa Beggs, and Nike Running by Hebru Brantley.
Other notable neighborhoods to check out:
- Humboldt Park on the West Side
- Rogers Park along Lake Michigan
- Wabash Arts Corridor in the South Loop
Sample Clue:
“On a wall near the 16th street, a giant from classic tales lies in rest. Capture the titan’s towering body for 10 points.”
15. Chilling Hunt at Chicago History Museum
Unveil the Windy City’s darkest secrets in a Chicago History Museum challenge. Step back in time, meet Chicago’s first settlers, witness the Great Fire, and take a glimpse of the major events that shaped the region.
A cunning killer is on the loose. The task is to save yourself and your companions from certain death and identify the sinister villain before time runs out. Gather evidence of the suspect’s identity by solving puzzles and answering trivia questions scattered in exhibits.
The Chicago History Museum has plenty of great exhibits matching a chilling hunt’s theme.
Think of The Trial for the Murder of Emmett Till, which sheds light on the gruesome murder of Emmett Till, sparking the Civil Rights Movement in the 1950s. Or the City on Fire, presenting the devastating events of the 1871 fire.
Other notable exhibits to check out:
- Al Capone and the Prohibition Era
- Facing Freedom in America Exhibition
- Designing For Change: Chicago Protest Art of the 1960s–70s
- Crossroads of America
- Costume and Textiles Collection
Sample Clue:
“Survey the trial room to find the victim’s photograph before the tragedy. Take note of the date the image is taken—it’s a key to your investigation.”
Scavenger Hunts With cityHUNT
Team bonding scavenger hunts are a fantastic option for boosting employee engagement. They encourage communication, teamwork, leadership skills, and out-of-the-box thinking, all vital qualities needed in the workplace.
Not to mention, they foster a deeper sense of camaraderie, which is essential for building lasting relationships.
cityHUNT understands this and offers a one-of-a-kind city-wide scavenger hunt for everyone. With over 20 years of experience, our team of expert organizers will craft unique and immersive hunts you can customize based on your preferences.
Message us for a quote and talk with our adventure consultants today!
