CHICAGo MUSt Do Hidden GEm SPEAKeasy’s

Introduction

This review covers a spirited adventure through some of Chicago’s best-kept secret bars—perfect for anyone looking to enjoy a night filled with flavor, history, and a touch of nostalgia. The Chicago Must Do Hidden Gem Speakeasys Tour offers a taste of the city’s clandestine cocktail culture, all within the vibrant Ukrainian Village neighborhood. If you’re curious about discovering spots that aren’t on the typical tourist map, this tour provides a fun, authentic way to explore Chicago’s lively bar scene.

What we really appreciate about this experience is how it combines storytelling with visits to hidden bars that are often overlooked. Plus, the tour’s focus on craft cocktails and local beers means you’re getting more than just a drink—you’re diving into the artistry behind each sip. A potential consideration is that drinks and food are not included, so it’s best to eat beforehand and be prepared to pay for your own beverages.

This tour is perfect for night owls, history buffs, and cocktail enthusiasts who enjoy discovering authentic local spots without the hassle of wandering aimlessly. Whether you’re traveling solo or with friends, it offers a friendly, inclusive atmosphere—no experience necessary.

Key Points

• Authentic Hidden Bars: Explore some of Chicago’s most intriguing speakeasies that are hard to find without guidance.
• Craft Cocktail Focus: Experience expertly made drinks, from spirit-forward cocktails to craft beers and non-alcoholic options.
• Local Neighborhood Flavor: The Ukrainian Village setting offers a trendy, historic vibe with picturesque outdoor spaces.
• Engaging Storytelling: Learn about each bar’s history and unique character from a knowledgeable guide.
• Music & Ambiance: The last bar features live music and a vintage ambiance that transports you to the 1930s.
• Value for Money: At $45 per person, cover charges are included, but drinks are extra—so come prepared.

A Deep Dive into the Experience

The Beginning: Meeting Point and First Impressions

The tour kicks off at 921 N Western Ave, a lively hub in Chicago’s Ukrainian Village. The meeting is relaxed, with the guide introducing a bit of local history and setting a friendly tone. As a small group (max 16 people), you’ll quickly feel at ease—an important aspect when exploring secretive spots.

Cozy Bars with Local Flavor

The first stop is a charming, cozy bar that offers local beers and affordable cocktails. It’s the kind of place where the warm lighting and friendly staff make you feel like you’re visiting a friend’s basement lounge. Here, you get your first taste of Chicago’s craft spirit, and your guide shares stories about the neighborhood’s history and how these hidden gems came to be.

Neighborhood Tavern: Spirit-Forward and Fun

Next, you’ll walk about 8 minutes to a neighborhood tavern filled with interesting wall objects and a vibrant outdoor space when weather permits. This bar specializes in spirit-forward cocktails, craft beers, and wine, making it ideal for those who appreciate thoughtfully crafted drinks. The ambiance is lively yet intimate, perfect for conversations or just soaking in the local vibe.

Guests often comment on the interesting wall objects that create a sense of history and personality. The outdoor area is a bonus during good weather, offering a relaxed setting to enjoy your drinks.

The Landmark Funky Cocktail Bar & Live Music

The tour culminates at a landmark bar that feels like stepping back into a different era. With a vintage decor echoing the 1930s, this spot combines funky cocktails with intimate live music. You might find yourself transported to a speakeasy from the Prohibition era, with jazz or blues softly filling the background. The cover charge at this final destination is included, adding good value to the overall experience.

Guests rave about the atmosphere that echoes another era, saying it’s a highlight that makes the whole tour stand out. The live music and funky vibe create a memorable, authentic experience.

What to Expect Throughout

Throughout the tour, your guide shares fascinating stories about each location and the history of Chicago’s clandestine bar scene. There’s an emphasis on storytelling, helping you understand the cultural significance of these hidden spots. This makes the experience more meaningful than simply ticking off bar visits.

Keep in mind that drinks and food are not included, so it’s wise to eat before the tour or bring some extra cash. Water is provided, which is crucial for staying hydrated during a night of alcohol tasting.

Group Size and Practical Details

The tour is capped at 16 travelers, ensuring an intimate atmosphere and personalized attention. It begins at 8:00 pm, making it ideal for an evening out after a day of exploring the city. The entire experience lasts approximately 1 hour 30 minutes, making it a perfect short, yet enriching, outing.

Transportation between bars is walkable, with the last stop a leisurely 8-minute stroll from the first. This allows for a more relaxed pace and some sightseeing en route.

Price and Value

At $45 per person, this tour is a good value for the unique access it provides. The cover charge at the final bar is included, but remember that drinks are extra. Considering the quality of the cocktails, the engaging stories, and the authentic ambiance, many find the price reasonable—especially when compared to the cost of similar private or guided bar experiences.

Authenticity and Guest Feedback

The one available review is glowing, praising the “really cool bars” and a host who is “super friendly and very accommodating.” The reviewer felt well taken care of and enjoyed the neighborhood exploration, reinforcing the tour’s value for those seeking genuine local flavor.

Who Is This Tour Best For?

This experience suits travelers eager to see Chicago beyond its iconic skyscrapers. If you enjoy craft cocktails, history, and hidden gems, you’ll find this tour rewarding. It’s especially great for those who like small group outings with personalized storytelling and a relaxed pace.

It’s also ideal for anyone interested in nightlife and music, given the live performances at the final stop. However, be prepared for some walking and to pay for your own drinks. It’s not suitable for those looking for a party-focused night with free drinks or a quick bar crawl.

The Sum Up

This Chicago Must Do Hidden Gem Speakeasys Tour offers a distinctive way to experience the city’s vibrant bar culture. You’ll visit thoughtfully selected spots that balance local charm, history, and delicious drinks. The small group setting, engaging storytelling, and atmospheric venues make it a standout choice for anyone wanting a memorable night out.

It’s especially well-suited for travelers who appreciate a mix of authentic ambiance and insider knowledge. The fact that the last bar features live music and a vintage vibe makes this tour a comprehensive glimpse into Chicago’s lively, hidden nightlife.

While drinks aren’t included, the value lies in the access to unique locations and the stories behind them. Bring some cash for drinks, eat beforehand, and enjoy a well-curated evening exploring Chicago’s secret bar scene.

FAQ

Are drinks included in the tour?
No, drinks and food are not included. Water is provided, but you’ll need to pay for your own beverages throughout the tour.

How long does the tour last?
The tour is approximately 1 hour 30 minutes, making it a manageable evening activity.

Where does the tour start and end?
It starts at 921 N Western Ave in Chicago’s Ukrainian Village and ends back at the same location after visiting three hidden bars.

Is transportation provided between locations?
No, the locations are within walking distance, with the last bar about an 8-minute walk from the start point.

What is the group size?
The tour hosts a maximum of 16 travelers, providing an intimate experience.

Is this tour suitable for everyone?
Most travelers can participate, and there are no restrictions on orientation or experience level. Just be ready for some walking and to buy drinks separately.

Can I schedule a specific date?
Yes, if you don’t see your preferred date, you can contact the organizer for a custom booking with a minimum of 2 people.

What if I need to cancel or change the booking?
This experience is non-refundable and cannot be changed once booked. Be sure of your plans before booking.

Interested in more Chicago experiences?
Check out other tours like the Chicago River Architecture Tour or the Skydeck Chicago Observatory for a full picture of what the city offers.