CHICAGo MUSt Do Hidden GEm SPEAKeasy’s

Experience Chicago’s Hidden Speakeasies: A Guide to the Must-Do Night Tour

In Chicago, the night isn’t complete without exploring its secret bar scene. For just $45 per person, you’ll spend about one and a half hours wandering through three of the city’s most quirky, hidden gems in the trendy Ukrainian Village neighborhood. Led by a knowledgeable guide, this tour offers a chance to step back into the Roaring Twenties, sampling craft cocktails, local beers, and even non-alcoholic drinks. It’s a well-rounded experience that mixes history, ambiance, and a good dose of fun.

What we love most about this tour is how it combines authentic local flavor with charming atmospheres. Each bar has its own unique vibe: from cozy neighborhood taverns to a lively spot with live music that transports you to another era. Another highlight is the guidance and storytelling, which enriches the experience by sharing the stories behind each place and the neighborhood’s history.

A possible consideration is that drinks or food are not included, so it’s wise to eat beforehand and stay hydrated. Also, since the last stop is about an 8-minute walk from the starting point, comfortable shoes will make your evening smoother.

This tour suits those who enjoy craft cocktails, discovering hidden locales, and listening to live music. It’s perfect for adventurous travelers, nightlife enthusiasts, or anyone keen to experience Chicago’s authentic, off-the-beaten-path drinking scene.

Key Points

• Authentic Hidden Bars: You’ll visit three carefully selected, lesser-known bars in Ukrainian Village that are hard to find on your own.
• Rich Stories & Guidance: The guide offers engaging storytelling about the neighborhood and bar history, making each stop more meaningful.
• Diverse Vibe: From cozy neighborhood taverns to lively music venues, each spot offers a different flavor.
• Affordable and Value-Driven: For $45, you get access to cover charges at the final bar, plus water and expert guidance.
• No Drinks Included: Remember, drinks are not part of the package, so plan to eat beforehand.
• Group Size: Limited to 16 travelers, creating a friendly, intimate atmosphere.

A Closer Look at the Chicago Hidden Gem Speakeasy Tour

Starting Point and Overall Layout

The tour kicks off at 921 N Western Ave at 8:00 pm, a lively part of Chicago’s Ukrainian Village. Here, your guide greets you and provides a quick rundown of what’s to come. The meeting point’s accessibility to public transit makes it convenient for most travelers, and the small group size (up to 16 people) ensures a personalized experience.

First Stop: Cozy Local Bar

The initial venue is a welcoming, stylish bar offering local beers and affordable cocktails. It’s the perfect place to start, offering a relaxed environment with a friendly atmosphere. Here, you’ll have the chance to chat with your guide, learn about the neighborhood’s history, and get comfortable with your surroundings. The emphasis on craft beers and simple, well-made drinks makes it an excellent introduction to Chicago’s bar scene.

Second Stop: Neighborhood Tavern

Next, you’ll walk to a neighborhood tavern that specializes in spirit-forward cocktails, craft beer, and wine. Its walls are decorated with interesting objects, adding charm and character. When weather permits, the outdoor space is a delightful spot to soak up the neighborhood vibe. This bar is known for its authentic ambiance and attention to cocktail craft, making it a favorite among locals.

Final Stop: Funky Cocktail Bar & Live Music Venue

The last leg takes you to a landmark, funky cocktail bar renowned for its intimate live music and retro atmosphere, reminiscent of a 1930s lounge. Here, the cover charge is included, so you can enjoy the enthralling ambiance without any extra expense. The music and decor transport you to a different era, making it a memorable conclusion to your evening.

What Makes This Tour Special?

The true magic of this experience lies in discovering places you might never stumble upon on your own. The guide’s stories bring life to each bar, revealing the hidden history of the neighborhood and its secret spots. It’s not just about drinks; it’s about understanding Chicago’s vibrant nightlife culture and connecting with local history.

Authenticity and Atmosphere

Reviewers consistently praise the authenticity of these bars. Stacey_B notes, “Really cool bars and a really great host—he knows the neighborhood and makes everyone comfortable.” That personal touch makes a significant difference, especially in small-group settings.

Practical Tips and Considerations

Since drinks aren’t included, it’s wise to eat beforehand to ensure you’re not drinking on an empty stomach. The last bar’s walking distance is about 8 minutes—so wear comfortable shoes. The tour’s duration is roughly 90 minutes, making it a perfect evening activity without feeling rushed.

Why This Tour Offers Great Value

For just $45, the experience includes guided storytelling, the cover charge at the final venue, and access to a carefully curated selection of hidden bars. Considering the cost of drinks in Chicago, this tour offers excellent value—you’re paying for access, insight, and an exclusive peek into the city’s secret nightlife spots. Plus, the small group size ensures a more personalized and engaging experience.

Who Should Book This Tour?

This experience is ideal for night owls who enjoy discovering less touristy venues, appreciating craft cocktails, and listening to music. It appeals to those interested in local history and hidden gems, and those who want a fun, relaxed evening with a knowledgeable guide. If you’re traveling with friends or a partner, it’s a great way to share an authentic Chicago experience that’s both social and intimate.

Final Thoughts

This Chicago speakeasy tour offers a fun, enriching way to explore the city’s hidden bar scene in a cozy neighborhood. The guidance and storytelling add depth and context, making each stop more than just a drink. If you’re after an authentic night out that combines history, ambiance, and local flavor, this tour hits the mark.

The combination of charming venues, expert guidance, and a walkable route through Ukrainian Village makes it a memorable way to spend an evening. Just remember to eat beforehand, stay hydrated, and enjoy the journey into Chicago’s secret nightlife.

FAQ

Is this tour suitable for non-drinkers?
Yes. While drinks aren’t included, non-alcoholic beverages are available, and the tour focuses on the atmosphere and stories—it’s inclusive for all.

How long does the tour last?
Approximately 1 hour and 30 minutes, covering three bars with about 8 minutes of walking between the last two.

Are drinks included?
No, drinks are not included. You’ll purchase your own drinks at each location, but the cover charge at the final bar is covered.

Is there a minimum age to participate?
Most travelers can participate, but since alcohol is involved, age restrictions likely apply—generally 21 and over.

What should I bring?
Comfortable shoes for walking, and it’s wise to eat beforehand. Water is provided to stay hydrated.

Can I book this tour for a specific date?
Yes, you can request a different date if the minimum number of 2 travelers is met. Just message the organizer.

Is the tour family-friendly?
It’s mainly geared toward adults interested in nightlife, but there’s no age restriction specified. It’s best for those over 21.

Where does the tour end?
Back at the starting point, after the final bar, approximately 8 minutes walk from the initial meeting spot.

How can I learn more or book?
Visit the provider’s page via the link for additional details and booking options.

This tour offers a lively, authentic peek into Chicago’s hidden bar culture, perfect for those wanting a unique night out with a knowledgeable guide and a lively atmosphere. Whether you’re a local eager for new spots or a visitor keen to see the city’s secret side, it’s a fun, affordable way to spend an evening.