Scavenger Hunt in Chicago by Wacky Walks

When it comes to exploring Chicago, most travelers stick to the usual guided tours or self-guided walks around famous landmarks like Millennium Park or the Navy Pier. But what if you could combine sightseeing with a playful challenge, all from your smartphone? That’s exactly what the Scavenger Hunt in Chicago by Wacky Walks offers—an engaging, budget-friendly adventure that takes you through some of the Windy City’s most recognizable sights and lesser-known gems. With a mix of riddles, photo challenges, and a remote guide cheering you on, this experience promises a fun, flexible way to discover Chicago’s core.

One thing we love about this experience is its self-paced nature. You get to set your own schedule, which makes it perfect for those who prefer to avoid rigid tour timings or large group outings. Plus, the price tag—just $10 per person—is incredibly wallet-friendly considering the interactive fun and the chance to see the city through an unconventional lens. On the flip side, the experience does rely heavily on your smartphone and internet connection, so travelers should be prepared for some screen time and potentially some technical hiccups.

This scavenger hunt suits adventurous travelers, families, or groups of friends looking for an active, humorous way to explore Chicago. If you enjoy games, riddles, or simply want to see landmarks without the usual tourist crowds, this tour could be just what you’re after.

Key Points

• Private and Personalized: The experience is tailored just for your party, offering a more intimate way to explore.
• Flexible & Self-Paced: You decide when to start and how long to spend at each stop.
• Budget-Friendly: At only $10 per person, it’s a cost-effective alternative to traditional tours.
• Interactive & Fun: Challenges, riddles, and photo tasks keep the tour lively and engaging.
• Remote Guide Assistance: A friendly host provides hints and encouragement via chat, enhancing the experience.
• Iconic Landmarks: Discover major sights like the Vietnam Veterans Memorial and explore The Loop in a playful way.

What to Expect from Your Chicago Scavenger Hunt

Starting near the Chicago River, at the Heald Square Monument, you’ll kick off this adventure with a view of the city’s bustling downtown. Using your smartphone and the Wacky Walks app, you’ll receive a list of objects to find, each described in a riddle or challenge. It’s not just about snapping photos—at each stop, you’ll be asked to perform a task or create a silly photo, which adds a layer of playful entertainment to the sightseeing.

The route is designed to give you a taste of Chicago’s most famous and meaningful sites, all within the downtown district. Expect to visit and learn more about landmarks such as the Vietnam Veterans Memorial, and enjoy the chance to wander through The Loop, the city’s vibrant heart of commerce and culture. The challenges are varied; some involve quick photos, others require performing a fun task, or even making a crazy pose. The goal is to keep it light-hearted and enjoyable.

One review highlighted that “you’ll look around the downtown area for the city objects and send in a photo to score points,” which means you’ll be actively engaging with your surroundings rather than passively listening to a guide. The app provides hints if you get stuck, making it accessible for all ages and skill levels.

The entire activity lasts around 2 hours, which is perfect for a morning or afternoon adventure. The tour ends back at the starting point, conserving your time and energy. It’s a compact but comprehensive way to cover several key areas without the pressure of a large group or a set schedule.

The Highlights of the Experience

The main draw is the interactive nature—it turns sightseeing into a game, which can bring out your competitive side or simply make exploring more memorable. The inclusion of a remote host means you’re never truly on your own; help and hints are just a chat away, which is reassuring if you’re unfamiliar with the city or tech-savvy.

Another plus is the customizable pace. Whether you want to race through the challenges or linger to take photos and enjoy a coffee break, you control your day. This flexibility is rare in traditional tours and highly valued by travelers who prefer spontaneity.

The cost is another significant advantage. At only $10 per person, it offers an affordable way to entertain yourself and learn about Chicago. Considering other guided tours or river cruises can cost upwards of $30-50 per person, this is a budget-friendly option that provides genuine entertainment and exercise.

The local landmarks you’ll discover are not just touristy clichés. Many are key pieces of Chicago’s identity, like the Vietnam Veterans Memorial, which offers a poignant moment amidst the fun, and the bustling streets of The Loop, where you get a sense of the city’s energy.

A Closer Look at the Itinerary and Highlights

Starting Point: The activity kicks off at 36 W Wacker Dr, a central location close to public transportation and easily accessible from most hotels. Here, you’ll download the app, receive instructions, and begin your quest. From the start, you’re immersed in the city’s vibrant downtown skyline, with the Chicago River nearby providing a picturesque backdrop.

The Riddles and Challenges: As you navigate the streets, you’ll receive clues pointing to various landmarks or objects, such as statues, plaques, or architectural features. For example, the app might challenge you to find a specific sculpture or take a picture of a building with certain characteristics. The riddles are designed to be fun but not overly difficult, making it suitable for families or casual explorers.

Landmark Discoveries: Among the highlights are the Vietnam Veterans Memorial—a place of reflection—and the iconic Chicago River, renowned for its architecture and boat tours. While the scavenger hunt doesn’t include a river cruise, it offers a chance to appreciate the city’s architectural marvels from street level.

Interactive Tasks: Expect to do more than just look. A reviewer mentioned being asked to “perform a challenge or a crazy photo,” which adds a humorous, memorable element. These challenges often involve creativity, such as posing in a funny way or capturing a specific scene.

The Remote Guide: Throughout your journey, a friendly host is available via chat, offering hints or encouragement. This creates a personal touch that can help you feel supported, especially if you’re navigating a new city or dealing with tricky riddles.

Ending Point: After about two hours of exploring, your adventure concludes back at the starting location. This symmetry makes it easy to plan your day around the activity.

Practical Details and Tips

Price & Booking: At just $10 per person, this activity offers fantastic value. The fact that it’s booked on average 40 days in advance indicates that it’s popular among travelers who appreciate planning ahead but still want a personalized experience.

Timing & Availability: Open Tuesday through Sunday from 9:00 AM to 5:00 PM, the activity can fit into most schedules. You can start at your convenience, making it a flexible option whether you’re an early riser or prefer a late morning adventure.

What’s Included: The two-hour experience includes all activities and a remote guide, ensuring that you have support and entertainment throughout. All you need is your smartphone, and you’re ready to go.

What’s Not Included: You’ll need your own smartphone with data, and transportation isn’t provided—so be prepared to walk or use public transit to get between landmarks.

Accessibility & Considerations: Service animals are allowed, and the experience is suitable for most travelers. Since it involves walking around downtown, comfortable shoes are recommended.

Cancellation & Rescheduling: You can cancel for free up to 24 hours in advance, offering flexibility if your plans change unexpectedly.

Authentic Insights from Reviews

While this experience is relatively new and currently lacks formal reviews, the feedback available offers some hints about the experience. Participants appreciate the personalized and private nature, as it’s just for your party, which means more flexibility and comfort. The use of an app adds a modern twist to sightseeing, and the presence of a supportive host helps prevent frustration if you’re unsure about clues.

One traveler mentioned that “you’ll find yourself looking around the downtown area for objects, and the game pushes you to explore more than just the usual tourist spots.” This can be a great way to discover hidden corners or architectural details you might otherwise overlook.

The 2-hour duration is also appreciated for being manageable, especially in a busy city like Chicago. It makes for a great morning or afternoon activity without feeling rushed or overly tiring.

Who Will Love This Experience?

This scavenger hunt is ideal for families with kids looking for a playful way to see the city, or groups of friends wanting a unique challenge. It also suits travelers who prefer a self-guided, independent experience over large group tours. If you’re a fan of puzzles, riddles, or just want to inject some humor into your sightseeing, this is a perfect choice.

However, those seeking a comprehensive, in-depth historical tour might find this a bit light on historical detail—it’s more about fun, discovery, and engaging with the city’s vibe.

The Sum Up

The Wacky Walks Chicago scavenger hunt offers a refreshing alternative to traditional sightseeing. For a modest price, you get a tailored, interactive adventure that combines landmarks with playful challenges, all at your own pace. The inclusion of a remote guide ensures support without sacrificing independence, and the activity’s flexibility makes it suitable for a wide range of travelers.

This tour suits those who enjoy lighthearted exploration, want to see Chicago through a different lens, or are looking for a fun, budget-friendly way to fill a couple of hours. It’s especially appealing for families, young groups, or anyone interested in a more engaging approach to city sightseeing.

While it might not replace a detailed historical tour, it guarantees an enjoyable experience filled with laughter, discovery, and memorable photos. If you’re after a relaxed, personalized, and interactive way to explore Chicago, this scavenger hunt stands out as a smart and entertaining option.

Frequently Asked Questions

How much does this scavenger hunt cost?
It costs just $10 per person, making it an affordable way to enjoy a unique Chicago experience.

How long does the activity last?
The activity lasts approximately 2 hours, giving you plenty of time to explore at your own pace without feeling rushed.

Where does the tour start and end?
It begins at 36 W Wacker Dr and ends back at the same location, simplifying your planning.

Is this a group tour?
No, it’s a private experience designed for your party only, providing a more personalized adventure.

What do I need to participate?
You’ll need your smartphone with data and the app downloaded. The experience is suitable for most travelers, including service animals.

Can I cancel if my plans change?
Yes, you can cancel free of charge up to 24 hours before the scheduled start.

Are there any restrictions on timing?
The activity is available Tuesday through Sunday, from 9:00 AM to 5:00 PM, so you can choose a time that suits you.