Chicago’s streets buzz with energy, history, and endless discovery opportunities, and a walking scavenger hunt can transform the Windy City into your personal playground. There’s a myriad of iconic landmarks, hidden gems, and neighborhoods bursting with character.
Whether you’re planning team activities or exploring with work friends, Chicago delivers unforgettable adventures. Plus, the city’s walkable layout makes it perfect for outdoor walk scavenger hunts.
Are you ready to see Chicago in a whole new way? Pack for the hunt, and let’s get to it!
1. cityHUNT’s Customized Scavenger Hunt in Chicago
Looking for a walking scavenger hunt that actually fits your team? cityHUNT builds experiences around what your group needs (i.e., better communication, stronger trust, or just a great day out together).
Your crew might tackle trivia about the 1893 World’s Fair or hunt for tiny details in Chicago’s famous public art. How about creative photo ops along the Riverwalk? Each challenge pushes your team to observe, collaborate, and think on its feet.
Here’s the best part: We adapt the route to you. Smaller groups can dive into Lincoln Park or the West Loop’s food scene. Larger teams can conquer iconic spots like Navy Pier or Millennium Park.
This outdoor walk scavenger hunt blends exploration with real teamwork. We offer customized adventures that turn familiar Chicago streets into discovery zones.
2. Millennium Park
Cloud Gate, or the bean, offers endless photo challenge possibilities. Have teams capture reflections, find specific architectural details, or recreate famous poses.
But don’t stop at the bean. The Crown Fountain’s digital faces change throughout the day, creating unique observation tasks. Can your team spot patterns or even identify which Chicago residents appear on screen?
The Lurie Garden hides seasonal surprises worth hunting for. Native prairie plants, hidden pathways, and rotating blooms give organizers fresh material year-round. Plus, the Frank Gehry-designed Jay Pritzker Pavilion’s steel ribbons create a stunning backdrop for group photos.
What makes this spot golden, you ask? It’s compact, pedestrian-friendly, and packed with Instagram-worthy moments. Your walking scavenger hunt for adults can cover tons of ground without anyone getting lost.
3. Magnificent Mile
This stretch of Michigan Avenue combines luxury shopping, historic buildings, and public art into one walkable corridor.
Starting with architectural hunts, teams can identify Art Deco details, count gargoyles for clues, or photograph building cornerstones. The mix of old and new creates perfect comparison challenges.
Additionally, public sculptures dot the streetscape. Have participants locate specific pieces or match artwork to artists. The Chicago Avenue Pumping Station, with its castle-like limestone exterior, makes an excellent landmark checkpoint.
Window displays also constantly change, offering seasonal scavenger hunt materials. Challenge teams to find specific colors, themes, or products. It keeps the outdoor walk scavenger hunt fresh even for repeat visitors.
The Mile’s energy is unmatched. Sidewalks buzz with locals and tourists alike, adding spontaneous people-watching elements to your hunt. Plus, countless photo ops mean every team returns with unique shots.
4. Art Institute of Chicago
The Art Institute transforms any walking scavenger hunt into a culture-packed adventure. Those iconic bronze lions guarding the entrance? Perfect starting point for team photos or creative challenges.
Inside, the collection spans centuries and continents. Organizers can craft hunts around finding specific paintings, matching artists to movements, or locating hidden symbols in famous works.
Hint: Grant Wood’s “American Gothic” and Georges Seurat’s “A Sunday on La Grande Jatte” seem to be crowd favorites.
The Modern Wing’s architecture deserves attention, too. Renzo Piano’s design features a flying carpet roof and stunning natural light, both of which work to incorporate observation challenges.
Here’s what makes it work: The museum layout encourages exploration without overwhelming participants. Create checkpoints across different galleries or focus on a single collection.
Pro tip for organizers: Outdoor spaces, such as the garden and terrace, offer breathing room between indoor challenges. Want more tips as an organizer? Read our guide on how to make a city scavenger hunt.
5. Chinatown
Chinatown explodes with color, flavors, and cultural details that make scavenger hunts unforgettable. The neighborhood’s vibrant energy starts at the Chinatown Gate on Wentworth Avenue—an ornate red entrance perfect for kicking off challenges.
Dragons appear everywhere here. Teams can count dragon sculptures, photograph different dragon styles, or find the hidden dragons woven into building details. Trust us; it’s harder than it sounds.
Food becomes part of the adventure, too. Challenge participants to identify ingredients in shop windows, find specific types of tea, or locate traditional bakeries. The aromatic streets add sensory elements that most walking scavenger hunts for adults miss.
Ping Tom Memorial Park offers riverside views and modern Chinese garden design. The pagoda, red lanterns, and Lake Michigan backdrop create stunning photo opportunities.
Finally, what sets Chinatown apart is the authentic cultural immersion without ever leaving the city. Plus, the compact layout keeps teams together while offering endless discovery moments.
6. Chicago Riverwalk
The Chicago Riverwalk stretches 1.25 miles along the Chicago River’s south bank—and it’s packed with scavenger hunt gold. This pedestrian pathway winds through the heart of downtown, connecting six distinct sections called “rooms.”
The Marina Plaza features floating gardens and boat docks. Teams can count vessel types, identify architectural reflections in the water, or photograph bridges from unique angles.
Speaking of bridges, Chicago’s got 38 movable bridges, many visible from the Riverwalk. Why not challenge participants to sketch bridge mechanisms or time bridge lifts?
The Cover also offers kayak rentals and waterfront dining. Create challenges around spotting specific boats, finding public art installations, or capturing the perfect river sunset shot. The Vietnam Veterans Memorial Plaza adds historical significance with its contemplative water feature and inscribed names.
Further, architectural towers are overhead everywhere you look. Teams can identify buildings by their distinctive features: The corncob-shaped Marina City, the white terra cotta Wrigley Building, or the neo-Gothic Tribune Tower.
7. Chicago Water Tower
The Chicago Water Tower stands as one of the few structures surviving the Great Fire of 1871. The Gothic Revival limestone tower on North Michigan Avenue practically screams historical scavenger hunt material.
Teams can hunt for architectural details, for instance. Those include the tower’s castellated crown, decorative stonework, or the attached pumping station across the street.
We suggest challenging participants to count turrets, photograph gargoyles, or identify the tower’s unique architectural style. The surrounding parklet includes bronze plaques detailing the fire’s history as well.
Create trivia challenges about the fire’s origin, its path through the city, or reconstruction efforts. How many city blocks burned? What percentage of Chicago’s population lost their homes? The answers are right there.
Inside the pumping station, City Gallery hosts rotating photography exhibitions. Time your walking scavenger hunt to include current exhibits for bonus art appreciation challenges. Even more, the Lookingglass Theatre Company operates there.
All in all, this location works beautifully because it’s compact yet information-rich. Teams can spend quality time in one spot while uncovering layers of Chicago history. Plus, the closeness to the Magnificent Mile means easy connection to other hunt stops.
8. Wrigley Field & Wrigleyville
Wrigley Field isn’t just a ballpark. It’s a 110-year-old Chicago institution that makes any scavenger hunt walk legendary. Have the teams take photos of the ivy-covered outfield walls, hand-operated scoreboard, and vintage marquee.
Even without game-day access, teams can photograph the iconic red marquee, count the number of championship flags, or hunt for Harry Caray’s statue outside the main gate. You can also check our guide on how to organize a photo scavenger hunt here.
Rooftop buildings across from Wrigley can be unique vantage points. Challenge teams to identify which buildings have rooftop seating or count the total rooftops visible from Waveland Avenue. These famous rooftops have hosted fans since the 1910s.
Murphy’s Bleachers, The Cubby Bear, and other legendary watering holes line Clark Street. Each establishment has its own Cubs history worth incorporating into trivia. For example, what year did Murphy’s open? Which famous musicians played at The Cubby Bear?
Game day or not, Wrigleyville’s energy is infectious! The neighborhood’s residential streets feature vintage greystones and colorful team flags. This walking scavenger hunt for adults blends sports culture and Chicago history—what more could you want?
9. DuSable Museum of African American History
The DuSable Museum anchors Washington Park on the South Side. It’s essential for culturally rich outdoor walk scavenger hunts. Named after Jean Baptiste Point DuSable, Chicago’s first non-indigenous settler, the museum celebrates African American history, culture, and art.
Outside, Washington Park itself offers 372 acres of green space. The park features lagoons, walking paths, and the Fountain of Time sculpture (a 126-foot-long monument depicting 100 figures passing before Father Time).
For this location, challenge teams to count figures, identify symbolic elements, or photograph the sculpture from different angles. Here you can create challenges about finding specific historical figures, matching quotes to leaders, or identifying art movements.
What organizers love about this location is that your team gets to learn fascinating facts during their scavenger hunt walk. And if you’re planning your own museum scavenger hunt, read our guide for helpful insights.
10. Navy Pier
Navy Pier stretches 3,300 feet into Lake Michigan, which makes it Chicago’s ultimate playground for walking scavenger hunts. It’s an entertainment hub that combines lakefront views, attractions, restaurants, and public art into one massive outdoor walk scavenger hunt.
Take The Centennial Wheel. It towers 200 feet high with climate-controlled gondolas. Teams can estimate the wheel’s height, count gondolas, or photograph it from various pier angles. You can also challenge participants to capture the wheel framed by the Chicago skyline.
Then there’s the Shakespeare Theater, the Chicago Children’s Museum, and the Crystal Gardens conservatory. Organizers can turn these spots into indoor checkpoints. Teams might identify plant species in the Gardens or solve riddles related to Shakespeare plays.
11. Chicago Cultural Center
The Chicago Cultural Center might be the city’s best-kept scavenger hunt secret. This 1897 Beaux-Arts landmark on Michigan Avenue houses the world’s largest Tiffany stained-glass dome—and that’s just the beginning!
Preston Bradley Hall’s dome spans 38 feet across with an estimated 30,000 pieces of glass. Have teams identify colors, count radial sections, or estimate the dome’s size. Plus, the Renaissance court features a smaller but equally stunning Tiffany dome.
Did you know that marble covers nearly every surface there? There’s Italian Carrara marble, rare green marble from Greece, and mosaics crafted from colored stone and glass. Teams can perhaps photograph the mosaic patterns or sketch the architectural details.
The building originally served as Chicago’s first public library. As such, you can create trivia about the building’s transformation or challenge teams to find specific historical quotes carved into the stonework.
And the best part is that this scavenger hunt walk serves as a year-round location, regardless of the weather. Plus, it’s free, making it a budget-friendly spot for any group size.
12. Neighborhood Murals
It’s no secret that Chicago’s neighborhoods explode with street art that transforms any outdoor walk scavenger hunt into a mobile gallery. For instance, Pilsen’s 16th Street corridor alone features dozens of murals celebrating Mexican heritage, social justice, and community pride.
Teams can hunt for specific murals, such as “Gulliver in Wonderland” or “La Virgen de Guadalupe.” Additionally, challenge participants to identify artists and decode symbolic elements.
For a different vibe, check out Logan Square and Wicker Park. The mural at Milwaukee and Diversey featuring Chicago’s skyline is where all the fun should be. How many buildings do you think your teams can identify? What’s missing from the skyline that’s actually there?
13. University of Chicago
The University of Chicago campus in Hyde Park delivers Gothic Revival architecture that could pass for Hogwarts. Built in the 1890s, these limestone buildings and quadrangles create an atmospheric setting for academic-themed scavenger hunts.
The Main Quadrangle features six interconnected quads surrounded by ivy-covered buildings. Teams can spot and identify gargoyles perched on building corners; many depict professors, mythical creatures, or academic symbols.
Fun fact: Henry Moore’s “Nuclear Energy” sculpture marks where Enrico Fermi achieved the first controlled nuclear reaction in 1942. Trivia about the Manhattan Project, scientific breakthroughs, or the sculpture’s symbolism all work perfectly.
At this location, some of your team can revisit their glory college days while the others watch students bustling between classes. Check out how else a scavenger hunt can help boost teambuilding.
14. Lincoln Park and Lincoln Park Zoo
Lincoln Park spans 1,208 acres along Lake Michigan. It’s considered Chicago’s largest public park and is perfect for outdoor walk scavenger hunts. The free zoo there houses over 200 species. Animal-spotting challenges anyone?
Teams can photograph specific animals, identify habitats, or count species from different continents. Your checkpoints can be the historic Kovler Lion House, Farm-in-the-Zoo, and Regenstein African Journey.
Besides animals, the park’s conservatory features tropical plants and seasonal displays. The urban wildlife in the North Pond Nature Sanctuary is another haven worth exploring.
Organizers love the variety here that keeps everyone engaged. Nature lovers, history buffs, and architecture fans all find something compelling. As a plus, the lakefront location means stunning skyline views!
15. Old St. Patrick’s Church
Old St. Patrick’s Church survived the Great Fire of 1871, which makes it Chicago’s oldest public building. This West Loop gem on Adams Street features stunning Celtic stained glass and Romanesque Revival architecture worth hunting for.
The interior showcases fifteen stained-glass windows designed by none other than Thomas O’Shaughnessy. Each window depicts Celtic crosses, Irish saints, and intricate patterns.
Ask the teams to identify specific saints, count window panels, or photograph particular color combinations. They can assemble later for group photos at the Celtic cross garden and courtyard.
All in all, this location is perfect for teams wanting substance alongside adventure. They get to enjoy walking around a breathtakingly beautiful and culturally significant spot.
16. Wabash Arts Corridor
The Wabash Arts Corridor transforms South Loop’s Wabash Avenue between Van Buren and Cermak into a street-level gallery. Look out for twenty-plus murals covering building facades. Together, they create Chicago’s most concentrated outdoor art collection.
Massive works by renowned artists dominate entire buildings. “Resist” by Shepard Fairey spans multiple stories. As such, teams can count faces depicted or identify symbolic elements. Jeff Zimmermann’s geometric abstractions create additional color-matching challenges.
You can also organize challenges where teams identify which murals are newest. Even more challenging, ask them to photograph three distinct art styles or find specific artists’ signatures hidden within pieces.
17. Chicago Old Town
Nothing beats the charm of Old Town’s Victorian-era architecture and bohemian history! Being one of Chicago’s oldest neighborhoods, it’s centered around Wells Street and North Avenue. Similarly, this area survived the Great Fire relatively intact.
Here, the teams can hunt for historic homes dating to the 1870s. They’ll identify architectural styles, such as Queen Anne, Italianate, and Second Empire.
Participants can also count turrets or find the older building cornerstone. Instagram-worthy backdrops include the colorful painted ladies on Crilly Court and the decorative cornices.
For entertainment, teams can afterward visit Second City comedy on Wells Street. Have some trivia ready about famous alumni (i.e., Tina Fey, Bill Murray, and Stephen Colbert).
18. Washington Square Park
Washington Square Park sits in the Gold Coast neighborhood. The latter is a leafy urban oasis nicknamed “Bughouse Square” for its free-speech forum history. This National Historic Landmark hosted soapbox speakers, debates, and protests throughout the early 1900s.
The park’s trees, benches, and walking paths create a peaceful setting that’s perfect for observation challenges. Your teams will write down tree species, count historic lampposts, and take photos of the Newberry Library.
Be sure to put together trivia about the Dil Pickle Club and famous speakers who held court there. Plan an additional architectural hunt through the surrounding Gold Coast. Both are quiet activities compared to other downtown spots on our list.
19. Museum Campus
Museum Campus consolidates three world-class museums on 57 lakefront acres: the Field Museum, Shedd Aquarium, and Adler Planetarium.
For starters, the Field Museum houses SUE, the T. rex, ancient Egyptian artifacts, and gemstone collections. There, teams can photograph specific dinosaurs, name the cultures represented in exhibits, or solve natural history trivia.
Alternatively, Shedd Aquarium features Art Deco ornamentation and aquatic motifs. Teams may count carved fish or name the marine species in the facade. Inside the aquarium, there are 32,000 animals that your teams can spot as a challenge.
Finally, the Adler Planetarium sits on Northerly Island’s tip, providing 360-degree views. And if you’re planning an astronomy-focused hunt, then the Doane Observatory’s copper dome and zodiac-themed architecture is the perfect spot for one!
20. Tribune Tower
The Tribune Tower on Michigan Avenue showcases Gothic Revival architecture and one of Chicago’s quirkiest collections. This 1925 skyscraper makes any walking scavenger hunt internationally adventurous without leaving the city!
The hunt here is simple. Teams search for pieces from the Great Wall of China, the Parthenon, Westminster Abbey, the Taj Mahal, or the Berlin Wall. Additionally, they can photograph specific stones or collect as many countries as possible.
We believe this place is magical because all of the world’s history is condensed into one building’s facade. Your corporate walk scavenger hunt becomes a global treasure hunt.
Explore Chicago with cityHUNT
Ready to turn Chicago’s streets into your team’s next adventure? At cityHUNT, we plan walking scavenger hunts that work on more than basic team building. We focus more on creating experiences your crew will actually remember.
Every challenge gets customized around your group’s goals. Maybe you’re working on communication. Perhaps team morale needs some strengthening. Or maybe everyone needs a fantastic day exploring together.
Whatever drives your company, cityHUNT builds the hunt around it. Your route adapts to your group size and interests. You’ll be solving puzzles, spotting details, and laughing together while discovering what makes Chicago unforgettable.
We guarantee that your team will walk away with shared stories and genuinely stronger connections. Check out our top 15 team-building scavenger hunt ideas in Chicago for more inspiration!
.jpg){kind=link}