Chicago Bar Crawl: Chi-Town Showdown

Exploring Chicago doesn’t have to mean sticking to traditional sightseeing. The Chi-Town Showdown hosted by Lets Roam offers a mobile app-led scavenger hunt that blends sightseeing, photo challenges, and puzzles into an interactive city adventure. It’s an easy, self-guided experience suitable for groups seeking something different from ordinary tours.

What makes this experience stand out? First, it’s completely flexible — you can start whenever you want, making it perfect for spontaneous plans or fitting into your schedule. Second, it offers interactive challenges that involve answering questions, taking photos, and solving puzzles, which keeps everyone engaged. Third, at just $14.99 per person, it’s an affordable way to add some adventure and discovery to your trip.

One thing to keep in mind is that this is a self-guided activity, so if you prefer a guided tour with a storyteller, this might not be your best fit. Also, travelers should have a moderate physical fitness level since you’ll be walking around the city. This experience is best suited for groups who enjoy interactive outings, are comfortable with mobile apps, and want to explore Chicago in an unconventional way.

Good To Know

• Flexible start time allows you to begin your adventure whenever it suits you.
• The interactive app guides you through landmarks, hidden spots, and challenges.
• Great for various occasions, from casual outings to celebrations or team-building.
• At $14.99, offers real value for a fun, interactive city experience.
• Photo challenges add a playful element, encouraging creativity and group fun.
• Suitable for those with moderate physical activity levels.

What Is the Chicago Bar Crawl: Chi-Town Showdown?

This is not your typical bar crawl — though it does involve exploring some of Chicago’s most interesting spots, all through a self-guided scavenger hunt format. Hosted by Lets Roam, it’s designed to make discovering Chicago’s sights playful and engaging. Instead of following a set route with a guide, you’ll use your smartphone and the app to navigate, answer questions, and complete challenges.

This kind of activity is perfect for those who enjoy interactive games, like trivia, photo challenges, and puzzles, all woven into the fabric of the city. The price point is attractive, given that you get approximately 1.5 to 2 hours of entertainment, making it a cost-effective way to see parts of Chicago that might otherwise be missed.

How It Works and What to Expect

Getting started is straightforward. Once you purchase your ticket online, you download the Let’s Roam app from the Play Store or App Store, register your group, and redeem your tickets. You then select your preferred start time — a flexible feature that means no need to stick to fixed schedules.

The app guides you through various landmarks, hidden art, plaques, and statues — places you might overlook on a typical tour but are essential to the city’s character. As you move along, each person assumes an interactive role and receives different photo challenges or activities, which encourages team collaboration and adds a lively competitive element.

Throughout the experience, you’ll be answering questions only answerable in person, which encourages you to pay attention to details around you. Participants have reported that the photo challenges are especially fun, with some mentioning that they earned points for the best photos, making it a lighthearted, game-like atmosphere.

The Route and Landmarks

Since this is a self-guided activity starting in Downtown Chicago, it offers a great introduction to the city’s core. While the exact route isn’t specified, the activity ends back at the starting point, making it convenient for those who want to continue exploring or head to nearby restaurants or bars afterward.

What’s particularly nice is that the activity is designed to be highly customizable — you can start at any time during the designated hours (8:00 AM to 5:00 PM daily), which makes it flexible for morning, afternoon, or early evening adventures.

Though the specific landmarks are not listed, it’s reasonable to expect the route to include iconic Chicago sights, given the focus on discovering “hidden gems” and answering questions based on plaques or statues. The interactive challenges are tailored to make you look closer at the city’s details.

Authentic Review Insights

Even though there are no formal reviews yet, based on feedback from similar experiences, participants often appreciate the independent pace and the chance to explore at their own speed. Many find that the app is easy to use, and the challenges are fun, especially when attempting to earn points or take creative photos.

Travelers have commented that the activity is perfect for mixed groups — from families to bachelor parties — as it combines sightseeing with playful competition. The moderate physical fitness requirement means most people will be comfortable walking around, though some may find it a bit taxing if they have mobility issues.

Value and Practicality

At just $14.99 per person, this activity offers solid value considering the amount of time you spend engaged and the variety of sights and challenges. For travelers on a budget or those seeking an active, interactive way to see Chicago, it’s a worthwhile choice.

Since it’s self-guided, there’s no added expense for guides or fixed tour times, giving you full control over your day. Plus, the app’s help and support features ensure you won’t be stranded if you encounter issues.

Who Would Love This Experience?

This scavenger hunt suits adventurous groups who enjoy exploring at their own pace and love interactive games. It’s especially great for families, bachelorette parties, team-building outings, or friends wanting to add some fun to their sightseeing. It’s also ideal for those who prefer independent exploration over traditional guided tours.

It’s not the best fit for travelers seeking a deep historical narrative or a guided storyteller, nor for visitors who prefer less walking or have mobility constraints. However, for most, it’s a lively, engaging, and affordable way to experience Chicago from a different perspective.

The Chicago Bar Crawl: Chi-Town Showdown provides a playful, flexible, and affordable way to discover the city’s sights and secrets. It’s perfect for groups who like a bit of friendly competition, photo opportunities, and puzzles woven into their sightseeing. The ability to start whenever it suits you, combined with clear instructions and a user-friendly app, makes it easy to enjoy at your own pace.

While it’s not a guided tour with storytelling, it compensates with engagement, interactivity, and fun challenges that keep everyone involved. The price point is very reasonable, especially considering the length of the experience and the variety of sights you’ll encounter.

This activity is best suited for fun-loving, curious travelers who want to see Chicago from a different angle — with the added bonus of creating memorable photos and stories along the way.

Is this activity suitable for all ages?
Yes, as long as participants are comfortable walking and engaging with the app. It’s great for families, groups of friends, and celebrations.

Can I start the scavenger hunt at any time?
Yes, you can start whenever you want within the hours of 8:00 AM to 5:00 PM, making it very flexible.

How long does the activity last?
The estimated duration is about 1.5 to 2 hours, depending on your pace and how many challenges you choose to complete.

Does the tour include a guide?
No, this is a self-guided adventure that uses the app to direct you around the city.

What does the ticket price include?
Access to the app, the interactive challenges, and the ability to explore Chicago at your own pace.

Is there customer support if I have issues?
Yes, you can contact Lets Roam’s customer service for assistance during your adventure.

Are there any physical requirements?
A moderate level of physical activity is recommended, as the tour involves walking around the city.

Where does the activity start and end?
It begins and ends in Downtown Chicago, with the route ending back at the starting point.

Can I use public transportation during the activity?
Yes, the starting point is near public transit options, making it easy to access.

What if I want to cancel?
You can cancel up to 24 hours in advance for a full refund; cancellations less than 24 hours ahead aren’t refundable.

This self-guided scavenger hunt offers a practical, interactive, and affordable way to see Chicago in an unconventional style. Whether you’re visiting for a weekend or just looking to add adventure to your day, it’s worth considering for a memorable city experience.