Exploring Chicago just got more interactive with the Private Chicago Scavenger Hunts City Adventure. This is a unique way to experience the city, blending sightseeing with game-like challenges that turn exploring into a playful activity. Offered by Lets Roam, this self-guided hunt invites you to uncover Chicago’s hidden gems, iconic sights, and quirky details at your own pace. Whether you’re visiting with friends, family, or colleagues, it promises a fun, engaging way to see the city beyond typical tourist routes.
What we especially like about this experience is how it combines technology with outdoor exploration. First, the app-led format means no need for a tour guide or reservations — you can start whenever suits you. Second, the interactive role-playing and photo challenges make it engaging for groups, encouraging collaboration and a bit of friendly competition. But, a possible downside is that this activity requires a moderate level of physical activity and comfort with smartphones, so it’s not ideal for everyone.
This scavenger hunt is ideal if you enjoy self-guided adventures and want to see Chicago in a different way. It’s particularly suited for groups who like puzzles, trivia, or simply want to make their city exploration more memorable and fun. If you prefer structured tours with a guide or prefer less interactive sightseeing, this might not be your best pick. Still, for those seeking an active, playful experience, it’s worth considering.
Key Points

- Flexible start times mean you can do the hunt on your schedule, making it ideal for personalized plans.
- Cost-effective at $14.99 per person, offering good value for a playful, interactive tour.
- The activity lasts about 1.5 hours, perfect for fitting into a busy itinerary or as a standalone outing.
- Photo challenges and trivia add a fun twist, encouraging creativity and engagement.
- Self-guided format means no group size restrictions or need for reservations, giving you autonomy.
- Moderate physical activity is needed, so it’s suitable for most but not all travelers.
A Detailed Look at the Chicago Scavenger Hunt Experience
When considering this scavenger hunt, it’s important to understand what makes it tick. For starters, it’s a self-guided tour that relies on the Let’s Roam app, which means you get to control when and where you start. The start point is conveniently located at 1416 W 18th St, and from there, you’re free to explore at your own pace. The app guides you through a series of challenges, questions, and photo activities, all designed to make you look closer at the city’s sights and lesser-known spots.
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How the Tour Works
The process is straightforward. Once you purchase your tickets, you download the app from the Play Store or App Store, register, and redeem your tickets. The app then acts as your personal guide, providing clues, questions, and challenges along the route. Because the activity is completely self-guided, you can start whenever you like, which adds a layer of flexibility many travelers appreciate. The entire experience lasts around 1.5 hours, but you could stretch it out if you want to take more time exploring or snapping photos.
What You Explore
The hunt takes you through some of Chicago’s best sights, but what sets this apart is that the questions and challenges are often hidden in the details—plaques, statues, murals, and art pieces. You won’t just be looking at landmarks; you’ll be actively engaging with the city’s stories and symbols. The photo challenges are a highlight, encouraging everyone to get creative and capture fun moments with their group.
The Challenges and Activities
Each participant gets an interactive role, adding a layer of personalization to the experience. You’ll receive texted photo challenges and fun activities that can be enjoyed with the group. These challenges often involve capturing funny or interesting photos, which makes the activity more lively and less like a standard sightseeing tour. The points earned through these challenges can add a competitive element, which keeps everyone engaged and motivated.
Practical Details
The activity is private, meaning only your group participates — no strangers mixed in. It’s suitable for those with a moderate physical fitness level, as you’ll be walking around the city, possibly on uneven surfaces or through crowded areas. Public transportation nearby makes it easier to access the starting point, and service animals are allowed if needed.
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What the Reviews Say
While the tour currently has no reviews yet, the structure and features suggest a positive experience for those who enjoy interactive outings. The price point is reasonable, especially given the features and flexibility. Some users might find the app-based format a bit casual or less structured than guided tours, but for many, this is part of the appeal.
What Makes It Worth Considering

This scavenger hunt offers great value—at just $14.99 per person, you’re paying for an engaging, personalized experience rather than a standard sightseeing pass. It’s a fun way to turn a typical city walk into an adventure, especially for those who thrive on puzzles, trivia, or group activities. The fact that it’s completely self-guided means you can tailor your pace and avoid the constraints of scheduled tours.
On the downside, the activity does depend on your comfort with smartphones and walking. If you’re someone who prefers a guided commentary or a more relaxed sightseeing experience, you might find this a bit too interactive or physically demanding. Also, because the tour is relatively short, it’s best suited as part of a broader exploration of Chicago rather than a comprehensive city tour.
Who Should Consider This Tour?

If you’re visiting Chicago with friends, family, or colleagues and want a memorable, lively way to explore, this scavenger hunt could be a perfect fit. It’s also excellent for those who enjoy puzzles, trivia, or creative photo challenges. It works well for spontaneous plans or as a fun activity between other tours. However, those who prefer structured tours with a guide or are less mobile might want to look for other options.
Private Chicago Scavenger Hunts City Adventure
FAQs

How do I start the scavenger hunt?
You simply download the Let’s Roam app, register, and redeem your tickets. There’s no need for a reservation—you can start whenever you’re ready.
Can I do this tour at any time?
Yes, the tour is self-guided, so you choose your start time — just within the opening hours (8AM-5PM, daily).
Is this suitable for children?
While the activity involves walking and smartphone use, it’s generally suitable for most people with moderate physical fitness. No specific age restrictions are mentioned, but children comfortable with smartphones and walking should be fine.
What is the duration of the tour?
It lasts approximately 1.5 hours, but you can take longer if you want to enjoy the photo challenges or explore additional sights.
Are there any group size restrictions?
Since it’s a private activity for your group, there are no restrictions beyond your group size—great for small family outings or larger groups.
What if I need help during the tour?
Customer service from Lets Roam is available to assist if you encounter issues or have questions while navigating the app.
Is this activity family-friendly?
Yes, given the photo challenges and walking involved, it can be suitable for families, but always consider the group’s mobility and comfort with screen use.
In the end, if you’re after an engaging way to see Chicago that combines sightseeing, puzzle-solving, and some friendly competition, this private scavenger hunt is worth considering. It’s flexible, affordable, and offers a different perspective on the city’s landmarks and stories. Just be prepared for some walking and the use of your phone — and you’re likely to walk away with some fun memories and great photos.
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