Experience the Hidden Corners of Chicago with a Private Scavenger Hunt
If you’re looking for a fresh way to explore Chicago’s bustling streets, the Private Chicago Scavenger Hunts City Adventure offered by Lets Roam might just be what you need. For $14.99 per person, you get approximately 90 minutes of interactive fun that takes you through key sights and lesser-known gems in the city. Starting at 1416 W 18th St, this activity is a modern twist on sightseeing, combining smartphone technology, trivia, and photo challenges that are perfect for both travelers and locals wanting to see their city anew.
What we love about this experience are two main things: First, the self-guided format means you can start whenever you’re ready, giving you complete flexibility—no need to coordinate schedules or wait for a group. Second, the interactive roles and photo challenges inject a playful competitive element, making it engaging for groups of friends, families, or even team-building outings. The app guides you seamlessly through the route, making it easy to follow without a tour guide hovering over your shoulder.
Of course, one thing to consider is that since this is a mobile app-led activity, your phone’s battery life becomes important—be sure to have a portable charger handy. Also, while the activity states it’s suitable for a moderate physical fitness level, be prepared for some walking and standing, especially if you want to fully enjoy all the photo challenges and puzzles.
This scavenger hunt is perfect for those who enjoy a personalized, flexible, and interactive way to see Chicago. Whether you’re here for a special occasion, a spontaneous outing, or a laid-back adventure, this experience caters to a wide range of interests—just remember it’s best suited for those comfortable using a smartphone and walking at a moderate pace.
Key Points

- Flexible Start Time: You can begin the adventure whenever it suits you, without prior reservations.
- Interactive Challenges: Includes trivia, puzzles, and photo tasks that keep everyone engaged.
- Self-Guided Tour: Guided by an app, you explore at your own pace without a physical guide.
- Cost-Effective: At under $15 per person, it offers a fun, budget-friendly way to see the city.
- Customizable: Designed for various occasions, from casual outings to group celebrations.
- Concise Duration: Around 90 minutes, making it easy to fit into a busy sightseeing day.
Exploring Chicago Through a New Lens

The Private Chicago Scavenger Hunts City Adventure offers a fresh way to see the city beyond the typical tourist spots. Instead of a static tour bus or a guided walk, you’re given the tools to discover Chicago at your own pace, guided by an intuitive app that makes navigation and participation simple and fun. This kind of activity suits travelers who love a little healthy competition, enjoy solving riddles, or are keen on capturing the city through their camera lens.
Imagine wandering through neighborhoods, discovering plaques and statues, or stumbling onto hidden murals—all while answering questions that challenge your knowledge or encourage you to look closer. The scavenger hunt’s focus on hidden gems and local points of interest really encourages you to see Chicago with fresh eyes.
The route ends back at your starting point, which makes logistics simple—no need to worry about how to get back or arrange transportation. Plus, with the activity being entirely private, only your group participates, ensuring an intimate and personalized experience. It’s a great way to make your time in Chicago memorable without the hefty price tag of a guided tour.
For broader city exploration in Chicago, we've covered these other tours
How It Works and What to Expect
Getting started is straightforward: download the Let’s Roam app from your app store, register, and redeem your tickets. Once you’re set up, the app will guide you through the challenges, presenting questions, puzzles, and photo tasks based on your location. Each participant receives a role, adding to the fun and variety—everyone gets to contribute in their own way.
The photo challenges are a highlight; you might be asked to snap a picture with a specific landmark or creatively capture a scene, earning points for the best shots. These challenges can be a great ice-breaker or a way to inject some humor into your exploration.
During the activity, you’ll visit notable sights, hidden corners, or spots that could easily be overlooked on a traditional tour. The challenges are designed to be engaging but not overly strenuous, making it suitable for most travelers with a moderate fitness level.
The Route and Highlights
While the exact stops depend on how you choose to navigate, the activity starts at a vibrant part of W 18th Street, an area known for its historic architecture and eclectic vibe. From there, the route likely includes key landmarks and quirky local sights, all revealed through your app prompts.
The route concludes back at the starting point, making it convenient for those who need to catch transportation or continue with their day plans. The entire experience is designed to be completed within 1.5 to 2 hours, making it a perfect addition to a broader sightseeing itinerary or a standalone afternoon activity.
Authentic Experiences and Authenticity
Unlike cookie-cutter tours, this scavenger hunt offers a personalized and authentic way to engage with Chicago. As one reviewer notes, “We loved the way it made us look at the city differently, noticing details we might have missed.” Another mentioned, “The challenges felt tailored and fun, and it was a great way to explore a neighborhood we didn’t know well.”
The ability to start anytime means you can choose the best time for your group—whether on a sunny morning, a lazy afternoon, or an evening stroll—maximizing your enjoyment and comfort.
Value and Practicality
At just under $15 per person, this activity provides excellent value, especially considering the personalized experience and the number of sights you’ll see. Compared to guided tours, you save both money and time, with the flexibility to tailor the pace and route to your interests.
However, keep in mind that the activity relies on your smartphone, so ensure your device is charged—and think about bringing a portable charger if you plan to extend your exploration beyond the allotted time.
Prefer personalized experiences? Here are other private options we've covered in Chicago
- Chicago: Private Architecture Tour – 3 or 6 Hours
- Chicago Downtown Highlights Private Walking Tour
- Chicago: Private Guided Tour of Chicago Suburbs Movie Sites
- Chicago Highlights Private Walking Tour With A Guide
- Echoes of Elegance: Chicago Private Architecture Tour
- Chicago: Private custom tour with a local guide
Who Will Love This Experience?
This scavenger hunt is perfect for adventurous travelers, families with kids, or groups of friends looking for a fun bonding experience. It’s well-suited for casual sightseeing or special celebrations such as birthdays or team outings. If you prefer guided commentary or extensive historical background, this might not be your ideal choice—but if you enjoy discovery and a bit of friendly competition, it’s hard to beat.
It’s especially appealing for those who like to see local neighborhoods, uncover hidden street art, or challenge themselves with trivia questions while walking through the city.
Final Thoughts

The Private Chicago Scavenger Hunts City Adventure by Lets Roam offers a dynamic and affordable way to see Chicago on your terms. It combines technology, exploration, and fun, making it perfect for travelers who want to add a sense of adventure to their city visit. Its flexibility, focus on local sights, and interactive format make it a memorable activity—especially if you enjoy solving puzzles and snapping photos along the way.
While it’s not a comprehensive historical tour, it’s a great way to discover Chicago’s vibrant neighborhoods and hidden corners, all at your own pace and with your own group. For those who like a mix of sightseeing, games, and socializing, this scavenger hunt could just be your new favorite way to explore a city.
FAQs

Can I start the scavenger hunt whenever I want?
Yes, you can begin at any time during the operating hours. There’s no need for a reservation, making it flexible for your schedule.
How long does the activity usually take?
The activity lasts about 1.5 to 2 hours, which makes it easy to fit into a broader day of sightseeing.
Do I need a tour guide or reservation?
No, this is a self-guided experience via the app, so no guide or reservation needed.
What do I need to participate?
Just download the Lets Roam app, register, and have your smartphone charged to access the challenges.
Is it suitable for all fitness levels?
Yes, the activity is designed for moderate physical activity, involving walking and standing.
Is the route customizable?
The app guides you through the route, but you have the flexibility to start at any point and explore at your own pace.
What if I need help during the activity?
Customer service is available if you encounter issues or need assistance during the hunt.
What areas does the scavenger hunt cover?
It starts on W 18th Street and includes notable sights and hidden gems in the vicinity, with the route ending back at the starting point.
Can I do this activity with a large group?
Yes, it’s a private experience for your group only, which makes it ideal for families, friends, or corporate outings.
In the end, whether you’re a first-time visitor or a local looking to rediscover Chicago, this scavenger hunt offers a playful, flexible, and affordable way to enjoy the city’s sights. Just remember to bring your phone fully charged, wear comfortable shoes, and prepare for a fun day of exploring with plenty of opportunities to learn, laugh, and take great photos.
More Private Tours in Chicago
- Art Institute of Chicago Private Expert Guided Tour
- Chicago Airport (MDW) to Chicago – Round-Trip Private Transfer
- Chicago Midway Airport (MDW) to Chicago -Arrival Private Transfer
- Private Transfer Chicago Airport to Chicago by Luxury Car or SUV
- Private Luxury 6-Pax SUV Limo Transfer from or to Chicagoland Airport and Suburb
- Private Chicago Boat Rental – Explore Chicago’s Skyline
More City Tours in Chicago
More Tour Reviews in Chicago
More Chicago experiences we've covered
- Chicago Highlights Running Tour
- Art Institute of Chicago Private Expert Guided Tour
- Chicago City Minibus Tour
- Chicago, Cloud Gate, Grant Park Full-Day City Tour
- Small Group Bike Tours From Chicago to Lake Geneva
- Chicago Airport (MDW) to Chicago – Round-Trip Private Transfer
- Chicago Walking Tour: Modern Architecture
- Fun City Scavenger Hunt in Chicago by 3Quest Challenge
- Chicago Creepy Cruise
- Chicago: Gangsters, Ghosts, and Haunted Hotels Segway Tour
- Chicago Midway Airport (MDW) to Chicago -Arrival Private Transfer
- CHICAGo MUSt Do Hidden GEm SPEAKeasy’s
