Outdoor Escape Room in Old Town Chicago: A Unique Urban Adventure

Imagine combining the thrill of a puzzle-solving game with the joy of exploring one of Chicago’s most charming neighborhoods. For $75 per group (up to six people), you’ll get around two hours of engaging fun that takes you through the streets, murals, sculptures, and landmarks of Old Town Chicago. Led by Escapely, this experience isn’t your typical sightseeing tour—it’s a cross between an escape room, scavenger hunt, and urban adventure.
What we really like about this tour is how it turns the city into your game board. You’re not just walking past sights—you’re actively hunting for clues, deciphering puzzles, and following a lively storyline involving a fortune teller, star-crossed lovers, and mystical quests. Plus, with the option to receive your kit in the mail for bookings made a week or more ahead, it’s flexible enough to fit into different travel plans.
A potential consideration is that this experience is non-refundable and can’t be rescheduled, so you’ll want to make sure your schedule is firm. Also, it’s designed for small groups, so if you’re traveling with larger parties, you’d need to split into multiple groups.
This adventure suits families, friends, and couples who enjoy puzzles, exploring, and a little bit of storytelling magic. If you love discovering neighborhoods through interactive activities rather than just walking past landmarks, this is a fun way to see Old Town from a different perspective.
Key Points

- Interactive adventure that combines outdoor exploration with puzzle-solving.
- Affordable price point for up to six participants, offering great value.
- Flexible booking options, with mail delivery available for advance bookings.
- Full immersion in Old Town’s sights, murals, and landmarks, making sightseeing more engaging.
- Adjustable difficulty level with hints available, suitable for all skill levels.
- Non-refundable policy means planning ahead is key.
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A Closer Look at the Outdoor Escape Room Experience

If you’re looking for a way to spice up your visit to Chicago’s Old Town, this outdoor escape game offers a fresh spin on sightseeing. Instead of just looking at buildings and statues, you’re actively involved in a story that winds through the neighborhood’s streets, alleyways, and hidden corners. The experience begins at the Village Cycle Center on North Wells Street, where you’ll pick up your game kit—either mailed ahead of time or on-site if booking last minute.
From there, the real fun begins. You follow clues that could be anywhere—from murals and statues to landmarks you might recognize. The clues are part puzzle, part treasure hunt, part story, designed to keep you guessing and exploring. We loved the way the storyline unfolds through QR codes and puzzles, adding a modern twist to the outdoor adventure. The puzzles are flexible, with an option to use hints if you get stuck, making it accessible for all ages and experience levels.
A highlight is how the game encourages discovery of hidden gems and iconic sites. You might find yourself at a statue or mural that you’d normally pass by, but now you’re looking at it through a detective’s lens. This makes the neighborhood feel alive and personally engaging—you’re not just observing, you’re solving.
The game’s physical component includes a lockbox and clues you physically find around you, which adds a tactile element missing from digital-only apps. The app interface is intuitive, allowing you to input solutions and get hints seamlessly, keeping the flow smooth and enjoyable.
According to reviews, players appreciate the balance of puzzle difficulty and storytelling. One quote highlights the feeling of being part of a story: “It’s a scavenger hunt with a story, you really feel like you’re part of a city adventure.” Others mention how it’s a fantastic way to discover old-town Chicago’s architecture, murals, and landmarks while having fun.
The experience wraps up back at the starting point, so you’re not left wandering or unsure of where you began. If you’re pressed for time, this organized route ensures you see a lot without feeling lost or overwhelmed.
What Makes This Tour Stand Out?
The story-driven gameplay makes this experience more memorable than a typical walk or self-guided tour. The storyline involving mystics and star-crossed lovers adds a layer of intrigue, making it suitable for those who love a narrative twist. It also caters well to groups, with one ticket covering up to six people, promoting teamwork and shared discovery.
The flexibility in difficulty levels is a plus. Whether your group consists of puzzle enthusiasts or casual explorers, you can opt for more hints or challenge yourselves further. This adaptability means it’s suitable for families with kids, couples, or groups of friends.
Another thing we appreciate is the value for money. For $75, you’re getting a two-hour outdoor activity that combines sightseeing, puzzle-solving, and storytelling, making it a more engaging alternative to standard tour options. Plus, discovering hidden parts of Old Town adds to the overall experience, turning a simple neighborhood walk into a memorable adventure.
Possible Drawbacks and Considerations

While many will find this experience delightful, it’s worth noting that the non-refundable policy requires you to be certain of your plans beforehand. If your schedule changes or weather turns bad, rescheduling isn’t an option. The activity also requires walking around Old Town, so comfortable shoes are a must.
Plus, since the puzzles are part of a story, they might be more challenging for those unfamiliar with QR code scanning or smartphone-based puzzles. But with hints available, most groups should find their way comfortably.
Who Would Enjoy This?

This experience is perfect for families wanting a fun, interactive way to explore Chicago’s neighborhoods; groups of friends looking for a unique activity; or couples seeking a playful date idea. It’s especially appealing if you enjoy puzzles, storytelling, and discovering city sights through an active and engaging lens.
If you’re tired of traditional sightseeing or looking for an activity that combines exploration with a narrative, this outdoor escape game offers a wonderful way to experience Old Town more personally and memorably.
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FAQ

How long does the activity take?
Plan for about two hours, depending on how much time you spend exploring and solving puzzles along the way.
What is included in the price?
Your fee covers one game box with puzzles and clues, a 2-3 hour adventure, and access to QR codes for hints, storyline, and navigation.
Can I participate if I don’t live in Chicago?
Yes. The experience is designed for visitors and locals alike. Just make sure to meet at the Village Cycle Center to start your adventure.
What if I need assistance during the game?
The app allows you to get hints when needed, so you can choose to use as many or as few as you like.
Are there any age restrictions?
The experience is suitable for most travelers, and most participants can participate. For very young children, you might find the puzzles challenging, but the outdoor exploration can still be fun.
Where do I pick up the kit if I book last minute?
Last-minute bookings can be picked up at the start point on the day of your adventure. The exact location will be sent to you after booking.
Final Thoughts

For anyone with a curiosity for Chicago’s neighborhoods and a love of puzzles and stories, this outdoor escape room in Old Town offers a distinctive twist on sightseeing. It encourages active exploration, engages your brain, and reveals both famous and hidden sights around one of Chicago’s most vibrant areas. The blend of storytelling, puzzle-solving, and neighborhood discovery makes it a compelling choice for groups seeking a memorable, interactive outing.
While it might not be suitable for travelers seeking a traditional tour or those with tight schedules (due to its non-refundable policy), those who love a good challenge and discovering a city with a story will find this adventure well worth the $75. It’s a playful, authentic way to see Old Town through a different lens—and create some fun memories along the way.
More Tour Reviews in Chicago
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- Cooking Class with Celebrity Chef Tony Hu
- Downtown Chicago Walking Tour – Semi-Private 12ppl Max
- Chicago Architecture Walking Tour: What’s New
- Illinois Holocaust Museum presents Experience360 Ticket
- A Storied Neighborhood: A Self-Guided Audio Tour with Bill Ayers
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