CHICAGo MUSt Do Hidden GEm SPEAKeasy’s

If you’re looking for a way to truly experience Chicago’s vibrant nightlife beyond the typical bar scene, this guided tour of hidden speakeasies offers an authentic taste of the city’s secret drinking spots. Spanning about 1 hour and 30 minutes, it’s a compact yet rich journey through some of the trendiest, lesser-known bars in the Ukrainian Village neighborhood. What makes this tour special is its focus on craft cocktails, local beers, and live music, all within atmospheric spaces that echo the glamour and grit of the 1930s.

One of the things we really appreciate is how this tour combines storytelling with the chance to explore three distinct venues. From cozy neighborhood taverns to a landmark cocktail bar, each stop offers a different vibe and unique character. Plus, the tour guide’s knowledge about the neighborhood and the history behind each bar adds a layer of depth that elevates the experience from just going out for drinks to a true cultural exploration.

A potential consideration is that drinks or food are not included—except water—so you’ll want to eat beforehand or be prepared for some additional costs. Also, the tour is suitable for most travelers, with no age restrictions, making it a flexible choice for groups or solo adventurers alike. If you’re after an evening combining good drinks, engaging stories, and a dash of Chicago’s secret bar culture, this tour is an excellent pick.

Key Points

• Authentic Neighborhood Experience: Focuses on the trendy Ukrainian Village, away from tourist traps.
• Variety of Venues: Includes a cozy local bar, a craft spirit-forward tavern, and a vintage-style landmark bar.
• Expert Guidance: The host is praised for being friendly, knowledgeable, and accommodating.
• Cost and Value: At $45, the tour offers a well-rounded experience with cover charges included at the final stop.
• No Food or Drinks Included: Only water is provided, so plan to eat beforehand.
• Flexible and Accessible: Open to most travelers, with the tour ending close to the starting point.

An In-Depth Look at the Chicago Hidden Speakeasies Tour

What to Expect from the Itinerary

This tour begins promptly at 8:00 pm at 921 N Western Ave, setting the stage for an evening immersed in Chicago’s clandestine bar scene. After the meet-up, the guide will lead you to the first venue— a charming, cozy bar that offers local beers and affordable cocktails. This spot provides a warm, welcoming atmosphere that immediately eases you into the night’s theme of vintage Chicago charm. It’s an ideal place to settle in with a drink and start soaking in the neighborhood’s vibe.

Next, the group moves to a neighborhood tavern. Here, the focus shifts to spirit-forward cocktails, craft beers, and wine, with interesting wall objects and an outdoor space where weather permits. This venue’s mix of craft beverages and eclectic decor offers a glimpse into the local bar scene, making it a favorite among those who appreciate good craftsmanship in their drinks.

The final stop is a landmark, funky cocktail bar and intimate live music venue that transports visitors to a different era—think jazz, vintage decor, and an ambiance reminiscent of the 1930s. The guide will share stories behind the space, enhancing the experience. The cover charge at this bar is included, but drinks are not—you’ll want to have your wallet ready for additional purchases.

The Atmosphere and Experience

The host’s storytelling ability shines as they share insights into each location’s history and character, making the visit more than just about drinking. One reviewer highlighted how the host’s knowledge of the neighborhood made the experience memorable: “He really knows the neighborhood, super friendly and very accommodating.”

The visual appeal of each bar varies—from the cozy, intimate setting of the first spot to the more lively, artsy vibe of the last. Expect interesting wall objects and vintage decor that evoke a 1930s lounge, especially at the final bar which is designed to feel like stepping into a bygone era. The outdoor space in the second venue, weather permitting, adds a fresh element to your experience.

Drinking and Tips

Since only water is provided, we recommend eating before the tour begins—drinking on an empty stomach is never a good look. The prices for drinks will vary depending on what you choose, but the inclusion of cover charges at the final bar means you won’t have to worry about extra entry fees. The tour offers a chance to sample a range of craft cocktails, beers, and non-alcoholic drinks, allowing you to tailor your experience to your taste.

Why Reviewers Love It

Guests have praised the tour for its cool bars and friendly guide. Stacey_B describes it as “really great,” noting that the host did “the most to make us comfortable and happy.” That personal touch and the authentic, eclectic venues are what set this experience apart.

Practical Details

• Duration: About 1 hour and 30 minutes.
• Price: $45 per person, which includes cover charges at the last venue.
• Group Size: Limited to 16 travelers, maintaining an intimate atmosphere.
• Accessibility: Near public transportation, and most travelers can participate.
• Booking: Usually booked 21 days in advance, so plan ahead.

Additional Info and Flexibility

The tour operates rain or shine, so check the weather forecast if you’re planning outdoor stops. It’s non-refundable, but if the minimum number of travelers isn’t met, a full refund or alternative date will be offered.

Who Will Love This Tour?

This tour is perfect for night owls who appreciate a good story along with their drinks. It’s ideal for travelers wanting to see Chicago’s hidden bar scene without the stress of navigating unfamiliar neighborhoods alone. Craft cocktail lovers, fans of vintage aesthetics, and those interested in local culture and history will find it especially engaging.

If you prefer a lively, music-filled atmosphere and enjoy discovering off-the-beaten-path venues, you’ll love the last stop’s live music and funky decor. It’s also a fantastic fit for groups, couples, or solo travelers who enjoy socializing and learning about Chicago’s lesser-known side.

The Sum Up

This guided tour of Chicago’s hidden speakeasies offers a unique blend of history, craft drinks, and lively ambiance that’s hard to beat for an evening out. It’s a thoughtfully curated experience that balances storytelling with the enjoyment of the city’s best-kept secrets. For just $45, you gain access to exclusive bars, learn about their history, and enjoy the atmosphere of a bygone era—all with the guidance of an enthusiastic, knowledgeable host.

While drinks are not included, the cover charges are, which adds great value. The tour’s intimate size and friendly atmosphere make it a superb choice for anyone looking to see a different side of Chicago, especially those who love good cocktails, local beers, and a dose of vintage charm.

If you’re eager to explore beyond the standard tourist spots and dive into Chicago’s underground bar scene, this tour delivers an engaging, authentic, and fun night out.

FAQs

Is this tour suitable for all ages?
Yes, there are no age restrictions, so most travelers are welcome. Just keep in mind that alcohol is involved, so minors should be accompanied by an adult.

Are drinks included in the tour price?
No, drinks are not included—only water is provided. You’ll want to bring some extra money for additional beverages at each stop.

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

Do I need to book in advance?
It’s recommended to book at least 3 weeks ahead, as the tour is popular and spaces are limited to 16 travelers.

What should I wear?
Casual, comfortable attire is fine. Since some venues may have vintage decor, smart casual is always a safe choice.

Is transportation provided?
No, private transportation isn’t included. The tour begins and ends at the same location near public transit, and the last bar is about an 8-minute walk from the meeting point.

Can I customize the date if I don’t see my preferred day listed?
Absolutely. If you’re in a group of at least two and your preferred date isn’t available, just send a message to the organizer—additional dates can often be arranged.

This guided tour offers a fantastic way to uncover Chicago’s secret drinking spots, enjoy craft cocktails, and soak up some vintage vibes—all with the comfort of a knowledgeable guide leading the way. Perfect for those craving an authentic, off-the-beaten-path night out.