Chicago Downtown Scavenger Hunt: Made Men and the Magnificent Mile
Over 1000 people completed this hunt
- Valid for up to 2 years
- Usable in 3000+ cities
- Perfect holiday gift
Two hours. One epic Chicago adventure. Your team will solve puzzles, complete challenges, and explore historic landmarks. On this modern day treasure hunt in Chicago you will compete for the top spot in your city. You can start your scavenger hunt any time your group is ready. Learn how it works.
This scavenger hunt will help you explore Chicago. This top rated Chicago Downtown Scavenger Hunt scavenger hunt is 14.24 miles and has 8 stops.
About this hunt
Duration 1.5-2 Hours
Distance 22.91 KM (14.24 Mi)
Go anytime
Over 1000 people completed this hunt
About this hunt
Duration 1.5-2 Hours
Distance 22.91 KM (14.24 Mi)
Go anytime
Two hours. One epic Chicago adventure. Your team will solve puzzles, complete challenges, and explore historic landmarks. On this modern day treasure hunt in Chicago you will compete for the top spot in your city. You can start your scavenger hunt any time your group is ready. Learn how it works.
This scavenger hunt will help you explore Chicago. This top rated Chicago Downtown Scavenger Hunt scavenger hunt is 14.24 miles and has 8 stops.
Stops on this hunt
Holy Name Cathedral
Bullet holes from an unsolved 1920s shooting, believed to be mob-related, can still be seen in the wooden doors.
Exchequer Restaurant & Pub
Once a popular hangout for Al Capone and his crew, it's now a local dining favorite.
The Green Mill
Once owned by "Machine Gun" Jack McGurn, an associate of Al Capone, this iconic jazz club was a Prohibition-era hotspot for mobsters.
The Pump Room
A glamorous eatery in the Ambassador Chicago hotel, rumored to have been visited by mobsters during its heyday.
Biograph Theater
The infamous location where John Dillinger, an American gangster, was gunned down by federal agents in 1934.
The Redhead Piano Bar
A throwback to the speakeasy era, this classic Chicago bar captures the essence of the Prohibition days.
Three Arts Club Cafe
Housed in a historic building, this cafe captures the elegance of bygone eras, making it a serene spot amidst the city hustle.
The Drake Hotel
Known for its opulence, the hotel had many dealings with mob figures; its Cape Cod Room was a favorite of notorious gangster Frank Nitti.
More details
Activity Type: Anytime Scavenger Hunt
Starting Area: 4802 N Broadway, Chicago, IL 60640, USA
Travel Method: Walking
Walking Distance: 14.24 Mi (22.91 KM)
Time:1.5 - 2 Hours
Skill Level:Friend & Family Fun
Extra Admissions: None
Discount applied below
Promo Applied
- Valid for one scavenger hunt in any of our 3,000+ locations.
- Perfect for couples, families, or friends to explore and have fun together.
- Solve challenges, discover landmarks, and create unforgettable memories.
- Includes printable gift card options.
Promo Applied
- Valid for one year for up to 6 players in each activity. Year starts after the first redemption. Primary ticketholder must always be present (but can bring different people); this ticket cannot be split.
- Unlimited scavenger hunts, bar crawls, audio tours, and ghost tours with ANY theme.
- Use in any of our 3,000+ cities, including options in the U.S., Europe, Australia, and Asia. Many cities have multiple activities.
- Includes printable gift card options.
Promo Applied
- Valid for one scavenger hunt in any of our 3,000+ locations.
- Perfect for couples, families, or friends to explore and have fun together.
- Solve challenges, discover landmarks, and create unforgettable memories.
- Includes printable gift card options.
Promo Applied
- Valid for one year for up to 2 players in each activity. Year starts after the first redemption. Primary ticketholder must always be present (but can bring different people); this ticket cannot be split.
- Unlimited scavenger hunts, bar crawls, audio tours, and ghost tours with ANY theme.
- Use in any of our 3,000+ cities, including options in the U.S., Europe, Australia, and Asia. Many cities have multiple activities.
- Includes printable gift card options.
Proceed to checkout
How the Chicago Downtown Scavenger Hunt works
Explore Chicago like never before. All you need is a phone and some free time! Our cross-platform mobile app (available on iOS and Android) uses GPS and AI photo scanning to help you navigate from stop to stop as you uncover hidden art, history, and culture all around you.
Solve riddles at each stop, complete hilarious photo challenges, and compete with your team to score the most points and top our city-wide leaderboard.
Reviews for Chicago Downtown Scavenger Hunt: Made Men and the Magnificent Mile
This was so much fun!!! My husband and I had a great time exploring. A great way to spend a day. Highly recommended!!
Carol Hild
Loved it! Great experience and challenging as well. Highly recommend!
Aaron Doman
Had so much fun today with my team spice girls for Laura Bachelorette party
Pam Fox
Easy and fun adventure. Good way to tour the city
Scot Branham
Super fun! Great team building for a great company function
Maggie Silliman
Lots of fun, and a great activity with a group! We took the light rail down for some extra adventure. We learned a few fun facts.
Terri Hensen
So much fun and not pricey at all. Did it with a group including kids. They had fun too. We will for sure do more hunts in the future.
Tania Paddock
It was good family fun. Great that you can pause to have lunch etc. was fairly easy but didn’t initially realise clues had time limits - hence missed out! Would definitely do another elsewhere.
Joanne Clements
Had lots of fun. Would definitely recommend this as a fun day.
Megan Prenc
Great time with family and friends would definitely do another tour!
Mike Vigil
Had an enjoyable time and visited a place I've not been before.
Stephanie Yencer
Awesome fun! You should try this. Great competition.
Ben Rathbone
Super fun experience reconnecting with my city and work team!
Sabrina Foster
Awesome way to learn more about our beautiful city! Great date night!
Laura Taylor
SO Fun!! It’s a great team bonding experience & fun to learn about the town you’re in. And an added bonus of exercise!
Monica Thomas
That’s a fun way to see the city and it’s history!
Howard Usher
Awesome game -it rocked!!
James Macie
FAQs.
Why Do A Scavenger Hunt With Us?
How Outdoor Scavenger Hunts Work
Are Your Outdoor Scavenger Hunts Covid Safe?
How Do In-Home Scavenger Hunts Work?
Why It's The Perfect Gift
How Long is a Scavenger Hunt?
When Can I Do The Hunt?
Does everyone need an interactive role?
What is the full list of all the scavenger hunts and activities that I can do in Chicago
Gifting FAQs.
How Do I Gift a Scavenger Hunt?
Can I Gift Tickets or Annual Passes?
When and Where Do I Receive The Gift Certificate?
Who Becomes the Primary Member — Me or The Gift Recipient?
Why It's The Perfect Gift
Is Anything Shipped Physically?
What is the full list of all the scavenger hunts and activities that I can do in Chicago
Other great activities
© 2016-2025 Let's Roam, LLC. Let’s Roam® is a registered trademark. All Rights Reserved.
Hey! Sorry to interrupt.
We’re Charlie and Mike, founders of ScavengerHunt.com
Want an extra 10% Off Your Order?
NO, CONTINUE SHOPPING
Unlock your extra 10% off your first order!
Final step to get your extra 10% off!
MAYBE LATER
