CHICAGo MUSt Do Hidden GEm SPEAKeasy’s

If you’re visiting Chicago and craving a night out that’s a little different from the usual bar crawl, a guided tour of the city’s secretive, speakeasy-style bars might be just what you need. We haven’t personally taken this specific experience, but based on what’s shared, it sounds like an engaging way to get a taste of the city’s lively nightlife, with a little history and a lot of atmosphere thrown in.

What really catches our eye are the small-group setting, which promises an intimate experience, and the chance to explore some of Chicago’s best-kept secrets in the Ukrainian Village neighborhood. Plus, the price point—around $45 per person—seems reasonable for a guided exploration of three unique bars, especially considering the storytelling and local insights you’ll gain.

One thing to keep in mind is that drinks and food are not included, so it’s best to eat beforehand and come prepared for a primarily drinking experience. This tour is clearly designed for those who enjoy discovering hidden spots and savoring craft cocktails rather than a casual pub crawl.

If you’re someone who loves learning about local neighborhoods, appreciates well-made craft drinks, and wants a night that mixes fun with a touch of Chicago’s secretive past, this tour could be a great choice. It’s suitable for all ages and experience levels—no alcohol required if preferred—and it offers a relaxed but immersive way to spend an evening.

Key Points

• Intimate Group Size: Limited to 16 travelers, making it feel personal and relaxed.
• Hidden Chicago Gems: Focused on discovering lesser-known bars in Ukrainian Village.
• Diverse Venues: From cozy neighborhood taverns to a lively, vintage-style jazz bar.
• Storytelling and Guidance: Learn about the area’s history and the bars’ unique stories.
• Cost-Effective: For $45, you get access and cover charges, plus water and insights.
• Flexible and Informal: No strict dress code or experience needed; all are welcome.

Exploring Chicago’s Hidden Bar Scene: What to Expect

Chicago isn’t short on bars, but if you’re into the idea of discovering places that aren’t just on the beaten path, this tour offers a curated experience. You’ll start at a cozy, welcoming spot, then move on to a neighborhood tavern with a focus on spirit-forward cocktails, craft beer, and wine. The last stop brings you into a landmark funky cocktail bar that oozes 1930s charm and features live music — perfect if you’re into vintage vibes and a bit of jazz.

The tour lasts about 1 hour and 30 minutes, which is a good length—long enough to soak in the atmosphere but not so long that it feels exhausting. The meeting point is at 921 N Western Ave, and the tour kicks off at 8:00 pm. It’s a walkable distance between venues, with the last bar about an 8-minute walk from the starting point.

The First Stop: Cozy Local Bar

We love the idea of kicking off in a cozy, intimate space that offers local beers and affordable cocktails. This sets a relaxed tone and allows for casual conversation and getting a feel for the neighborhood vibe. The emphasis on local drinks is a thoughtful touch—highlighting Chicago’s craft beer scene and giving you a taste of what’s fresh and interesting.

The Second Venue: Neighborhood Tavern

Next up is a neighborhood tavern characterized by its interesting wall objects and welcoming outdoor space (weather permitting). This spot aims to evoke a sense of local community and history, with a focus on spirits and craft beverages. It’s the kind of place where you might find yourself chatting with locals or the bartender, learning about the bar’s background or the neighborhood’s story.

The Final Stop: Funky Cocktail Bar with Live Music

What really makes this tour stand out is the final destination—a landmark bar that transports you back to the 1930s. Think vintage decor, jazz or blues filling the air, and an atmosphere that makes you feel like you’ve stepped into another era. It’s an ideal way to wind down and enjoy some live entertainment, especially if you’re into the history of cocktails or vintage music scenes.

The cover charge at this final bar is included in the tour price, which adds to the sense of value. It’s worth noting that food isn’t included, so grabbing a snack before the tour is advisable if you plan to spend some time here.

Authenticity and Local Insights: What Travelers Say

One reviewer, Stacey B, describes the experience as “really cool bars and a really great host,” emphasizing the host’s knowledge of the neighborhood and his friendly, accommodating attitude. She also notes that the tour felt tailored and comfortable, making her recommend it to others. This suggests that the guiding aspect is a highlight, adding context and personality to the visit.

Is It Worth the Price?

At $45, this tour offers a good value for anyone interested in Chicago’s underground bar scene. You’re paying for the experience, storytelling, and access to places that are usually hard to find on your own. Keep in mind that drinks are extra, but the tour provides water, which is essential to stay hydrated—especially if you plan to indulge.

Practical Tips for Participants

• Eat beforehand: Drinking on an empty stomach isn’t advisable.
• Wear comfortable shoes: The last bar involves about an 8-minute walk.
• No age restrictions: Everyone is welcome, but since drinks aren’t included, it’s suitable for all visitors.
• Book in advance: The tour is popular, often booked about 3 weeks ahead.
• Bring cash or cards: Drinks aren’t included, so you’ll need to pay for your own beverages.

The Group and Booking Details

The tour is capped at 16 travelers, ensuring a friendly, unhurried experience. It’s perfect for anyone wanting an insider view of Chicago’s hidden nightlife without feeling rushed.

Who Should Consider This Tour?

This speakeasy tour is ideal for those who enjoy discovering local gems, sampling craft cocktails, and learning about neighborhood histories. It’s a flexible experience that suits solo travelers, couples, or small groups of friends. If you’re into jazz, vintage vibes, or just want a different way to spend your evening, it’s a worthwhile adventure.

Those looking for an all-inclusive night with food and drinks included might want to consider other options, but for an authentic, guided exploration of Chicago’s secret bars, this one hits the mark.

Final Words

This Chicago speakeasy tour offers an engaging, affordable way to get a feel for the city’s nightlife beyond the typical tourist spots. You’ll enjoy cozy atmospheres, well-crafted drinks, and interesting stories—especially if you’re into vintage vibes and hidden places. While it’s not a pub crawl with free drinks, the value lies in the guidance, ambiance, and exclusive access to a few of Chicago’s coolest spots.

It’s a good pick for curious travelers who appreciate local charm and are happy to spend an evening exploring with a small, friendly group. If you’re in Chicago and want to add some secretive, stylish bars to your trip, this tour is a solid choice.

FAQ

Is transportation included?
No, private transportation isn’t part of this tour. You’ll walk between the venues, which is about an 8-minute stroll from the start to the last bar.

What time does the tour start?
It begins at 8:00 pm at 921 N Western Ave, Chicago.

Are drinks and food included?
No, drinks and food are not included. You can buy your own at each location, but water is provided.

Is the tour suitable for all ages?
Yes, everyone is welcome. Just remember, drinks are available for those who wish to purchase.

How long does the tour last?
Approximately 1 hour and 30 minutes.

How many people will be on the tour?
A maximum of 16 travelers, ensuring a friendly and personal experience.

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

What’s the vibe of the final bar?
It’s a landmark, funky cocktail bar with an ambiance reminiscent of the 1930s, complete with live music that transports you to another era.

Is this a good tour for first-time visitors to Chicago?
Absolutely. It offers a unique look into Chicago’s local bar scene and a chance to learn about the neighborhood’s history, which can be a fun and authentic addition to your trip.

Whether you’re into cocktails, history, or just looking for a memorable night out, this guided speakeasy experience might be exactly what you need. It combines discovery, storytelling, and great atmospheres — all within a cozy, manageable adventure through Chicago’s lesser-known nightlife.