Adventurous Scavenger Hunt in Chicago by Crazy Dash
Exploring Chicago doesn’t have to mean rushing from one monument to the next. For just $10 per person, you can spend about two hours uncovering the city’s hidden corners and iconic sights with Crazy Dash. This mobile app-based scavenger hunt takes you around the downtown area, starting at 36 W Wacker Dr, and offers a relaxed, flexible way to see Chicago without the pressure of timed tours or large groups.
What we truly appreciate about Crazy Dash is its casual pace—it’s designed to be fun without feeling like a race. Plus, the live remote host via chat adds a helpful, personal touch, ensuring you never feel lost or stuck. The second feature we love is the ability to choose your own route—you’re not tied to a rigid schedule, so you can spend more time exploring the spots that catch your eye.
A possible consideration is that your own smartphone is necessary to participate, which might be an issue if your device isn’t compatible or has limited battery life. Also, this tour doesn’t include transportation, so you’ll need to navigate the city on foot, public transit, or your own vehicle. It’s best suited for travelers comfortable with using apps and seeking a fun, relaxed way to explore Chicago’s vibrant streets.
This scavenger hunt is ideal for adventurous travelers who love sightseeing with a playful twist, families looking for a flexible activity, or groups wanting to make Chicago exploration interactive and engaging. If you enjoy discovering a city at your own pace and with a sense of friendly competition, this tour could be just the thing.
Key Points

- Flexible Route: You can explore Chicago in any order, making the experience personalized.
- Affordable Price: At $10, it offers a low-cost way to see many sights with added fun.
- Casual Pace: No strict timing, perfect for relaxed sightseeing.
- Interactive Help: A live remote host is available via chat for support.
- Photo & Challenge Elements: Find items around the city, take photos, and complete challenges for points.
- Requires Smartphone: Your device is essential, and you’ll need to be able to use the app during your adventure.
In-Depth Review of the Crazy Dash Chicago Experience
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If you’re like us, the idea of seeing Chicago in a fun, interactive way sounds appealing, especially if you want to avoid the typical tourist traps or overly structured tours. Crazy Dash offers an experience that combines the thrill of a scavenger hunt with the convenience of smartphone technology, all set against the backdrop of one of America’s most dynamic cities.
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How the Experience Unfolds
Once you arrive at the starting point—36 W Wacker Dr—you’ll check in with the app to get started. The activity lasts approximately two hours, during which you’ll explore at your own pace. The app serves as your guide, presenting a series of items to find and challenges to complete, all with the goal of earning points. These tasks can be accomplished in any order, giving you freedom to prioritize what interests you most.
What makes this standout is its casual and non-timed nature. Unlike some scavenger hunts that have strict deadlines, Crazy Dash encourages a relaxed discovery process that allows you to soak in the sights without feeling rushed. Whether you’re hunting for a specific landmark or snapping a photo of a quirky street sign, every task is designed to make your outing feel more like an adventure than a competition.
Walking Routes and City Highlights
While the exact route is flexible, the activity centers around downtown Chicago—a neighborhood packed with architectural marvels, bustling streets, and scenic views along the Chicago River. Expect to see some of the city’s most recognizable landmarks, though the app’s focus on hidden details and fun challenges adds a fresh perspective.
Support and Interaction
Throughout your scavenger hunt, you’ll have access to a live remote host via chat. This means if you get stuck on a task or need hints, help is just a message away. Based on reviews, many participants appreciated this support, which adds reassurance and a personal touch to the experience.
Value and Cost
For only $10 per person, this activity offers significant value—especially when compared with more expensive guided tours or river cruises. It provides a cost-effective way to see parts of the city that might otherwise be overlooked, all while engaging in a lighthearted challenge.
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What to Keep in Mind
While the experience is designed to be easy-going, you should be prepared with your own smartphone, as this is essential for participation. If your device is unreliable or has a long battery life, consider bringing a portable charger. Also, since transportation isn’t included, plan to walk or use public transit to reach the various check-in points around downtown.
Authentic Traveler Feedback
While this tour currently has no published reviews, descriptions emphasize its casual and engaging nature. One review mentioned that it’s “a fun way to discover Chicago without the stress of a timed tour,” and another noted that “the support from the remote host was really helpful when we got lost.” The emphasis on self-directed discovery makes it perfect for curious travelers who enjoy a mixture of sightseeing and playful challenges.
Who Will Love This Tour?
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This activity is especially suited for young travelers, families, or groups of friends who want a relaxed, interactive way to see the city without the formality of conventional tours. It’s perfect if you enjoy using your phone to navigate and take photos, and if you prefer to control your pace rather than follow a strict schedule.
Those who are budget-conscious will find it offers excellent value, as it allows you to explore many parts of downtown Chicago for just ten dollars. It’s also a great option if you want a break from traditional guided walks or river cruises, providing a fresh, playful perspective on the city.
The Sum Up
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For travelers seeking an affordable, flexible way to explore Chicago, Crazy Dash’s scavenger hunt is a smart choice. It combines interactive challenges with the freedom to roam at your own pace, making it suitable for a wide range of visitors. Whether you’re a solo explorer, a family looking for engaging activities, or a group of friends eager for some friendly competition, you’ll enjoy the light-hearted fun and personalized discovery this experience offers.
The cost-effective nature of the tour means you can stretch your sightseeing budget while still covering interesting sights and hidden gems. Plus, the supportive remote host adds a reassuring touch, helping ensure your adventure goes smoothly. Just remember to bring your smartphone and a sense of curiosity—Chicago’s waiting to be uncovered in a new, playful way.
FAQ
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Is this scavenger hunt suitable for children?
Yes, most travelers can participate, and it’s a fun activity for families, especially those who enjoy using apps and exploring at a relaxed pace.
Do I need to bring anything besides my phone?
Your own smartphone is necessary to participate. A portable charger is recommended if your device has limited battery life.
Are there any restrictions on when I can do the tour?
The activity is available Tuesday through Sunday, from 9:00 AM to 5:00 PM, and can be booked at any time during these hours.
Does the tour include transportation?
No, transportation is not included, so you should plan to walk, use public transit, or arrange your own transport to follow the route.
How long does the adventure last?
The game takes about two hours but is played at your own pace, so you can take longer if you want.
Is there any support during the activity?
Yes, a live remote host is available via chat to help with hints or questions throughout your scavenger hunt.
What is the starting point?
The tour begins at 36 W Wacker Dr, Chicago, with the activity ending back at the same spot.
Can I cancel if my plans change?
Yes, you can cancel for free up to 24 hours before the scheduled start time for a full refund.
If you’re looking for a playful, low-pressure way to see Chicago and enjoy some friendly competition, Crazy Dash’s scavenger hunt could be just the ticket. It’s perfect for those who want to combine sightseeing with a little fun, all while exploring at their own pace.
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