CHICAGo MUSt Do Hidden GEm SPEAKeasy's - First Stop: A Cozy Bar with Local Beers and Affordable Cocktails

CHICAGo MUSt Do Hidden GEm SPEAKeasy’s

Discover Chicago's hidden speakeasies with this 1.5-hour guided tour through cozy bars, craft cocktails, local beers, and live music in Ukrainian Village.

Explore Chicago’s Hidden Speakeasies with a Guided Tour for Just $45

CHICAGo MUSt Do Hidden GEm SPEAKeasy's - Explore Chicago’s Hidden Speakeasies with a Guided Tour for Just $45

The CHICAGo MUSt Do Hidden GEm SPEAKeasy’s tour offers a unique way to experience Chicago’s vibrant bar scene. For $45 per person, this 1 hour 30 minutes journey takes you through three carefully selected, hidden-away bars in the trendy Ukrainian Village neighborhood. The tour is perfect for anyone interested in craft cocktails, local beers, and live music in a cozy, intimate setting.

Starting at 921 N Western Ave, the tour begins at 8:00 pm, making it an ideal evening activity. The tour is designed to appeal to small groups of up to 16 people and is suitable for most travelers, with most participants able to join. While drinks or food aren’t included, water is provided to keep everyone hydrated as the guide shares stories about each location.

This experience is especially recommended for those who enjoy bar hopping with a local expert guiding the way. It’s a chance to discover Chicago’s underground bar culture and enjoy a nostalgic atmosphere that transports you to another era.

Key Points

  • Affordable Price: Only $45 per person for a fun, guided bar crawl.
  • Duration: 1 hour 30 minutes exploring three different bars.
  • Locations: Starts at 921 N Western Ave, ends back at the same spot.
  • Includes Cover Charge: Cover charge at the last bar is included.
  • Focus on Storytelling: Guides share stories and insights about each bar and neighborhood.
  • No food or drinks included: Only water is provided; eat beforehand.

Meet at the First Location on Western Avenue

CHICAGo MUSt Do Hidden GEm SPEAKeasy's - Meet at the First Location on Western Avenue

The tour kicks off at 921 N Western Ave, where all guests gather at 8:00 pm. The meeting point is conveniently close to public transportation, making arrival straightforward. The group size is capped at 16 travelers, allowing for an intimate experience with plenty of personal attention from the guide.

From here, the guide leads the group through a carefully curated selection of hidden bars. Each spot offers its own unique vibe, from cozy local taverns to landmark cocktail venues. The tour concludes back at the starting point, making for easy planning afterward.

First Stop: A Cozy Bar with Local Beers and Affordable Cocktails

CHICAGo MUSt Do Hidden GEm SPEAKeasy's - First Stop: A Cozy Bar with Local Beers and Affordable Cocktails

The first bar welcomes guests into a comfortable, inviting space that showcases Chicago’s local beer scene and affordable cocktails. The ambiance is relaxed, with friendly staff ready to serve a variety of locally brewed beers and crafted drinks. The focus here is on getting a feel for the neighborhood while enjoying a drink in a friendly atmosphere.

Guests can expect to see interesting wall objects that add to the bar’s character, making it a great spot for conversation and relaxation. Since food and drinks are not included, it’s recommended to eat beforehand to maximize enjoyment throughout the evening.

Second Stop: Neighborhood Tavern with Spirit-Forward Cocktails

CHICAGo MUSt Do Hidden GEm SPEAKeasy's - Second Stop: Neighborhood Tavern with Spirit-Forward Cocktails

The second venue is a neighborhood tavern that specializes in spirit-forward cocktails, craft beer, and wine. When weather permits, the outdoor space becomes a charming spot to linger and soak in the neighborhood vibe. The decor features interesting wall objects, creating a quirky, artsy atmosphere.

Here, the guide offers insights into craft cocktail creation, giving guests a chance to understand the art behind the drinks. This bar provides a more refined experience, perfect for those who appreciate well-made cocktails and an authentic neighborhood feel.

Third Stop: Landmark Funky Cocktail Bar with Live Music

CHICAGo MUSt Do Hidden GEm SPEAKeasy's - Third Stop: Landmark Funky Cocktail Bar with Live Music

The final venue is a famous, funky cocktail bar that doubles as an intimate live music venue. The atmosphere transports guests to another era, reminiscent of the 1930s lounge scene. The bar features fabulous, intricate cocktail creations and a lively ambiance suitable for enjoying live music.

This spot is a highlight of the tour, blending excellent drinks with entertaining live performances. It’s an ideal place to relax and reflect on the evening’s adventures, with a distinctive vibe that’s rare to find in typical city bars.

The Guide’s Role in Creating a Memorable Night

CHICAGo MUSt Do Hidden GEm SPEAKeasy's - The Guide’s Role in Creating a Memorable Night

The tour is led by a friendly and knowledgeable guide who shares storytelling about each location and the surrounding neighborhood. This insight adds depth to the experience, making it more than just bar hopping. The guide’s enthusiasm and local knowledge help create an engaging, comfortable atmosphere, ensuring everyone feels welcome and informed.

Guests often appreciate the guidance in discovering hard-to-find bars, making this tour ideal for those wanting to see Chicago’s secret nightlife spots. The tour’s small group size enhances interaction, allowing for personalized attention.

Practical Tips for a Great Experience

CHICAGo MUSt Do Hidden GEm SPEAKeasy's - Practical Tips for a Great Experience

Since drinks and food are not included, it’s wise to eat beforehand to enjoy the cocktails and beers without concerns. The last bar is about an 8-minute walk from the starting point, so comfortable shoes are recommended. Also, water is provided, but staying hydrated is important during the evening.

While the tour is accessible to most, it’s important to note that the entire experience is about 90 minutes, so it’s suitable for those comfortable with standing and walking. The non-refundable policy means booking with certainty is wise, especially as the tour needs a minimum number of travelers to run.

Who Will Enjoy This Tour?

CHICAGo MUSt Do Hidden GEm SPEAKeasy's - Who Will Enjoy This Tour?

This guided tour is perfect for adults who appreciate craft cocktails and local beers and enjoy discovering hidden gems in a city. It’s well-suited for small groups, couples, friends, or anyone interested in Chicago’s bar scene without paying steep cover charges individually. Fans of live music and retro atmospheres will find the final bar particularly captivating.

Why This Tour Offers Good Value

With a cover charge included at the last bar, plus storytelling and guidance, the $45 price provides a cost-effective way to experience some of Chicago’s most interesting and hard-to-find bars. The tour’s focus on local neighborhood spots means visitors get an authentic taste of Chicago’s nightlife culture.

Limitations and Considerations

While the tour offers a great overview of secret spots, it does not include drinks or food, so guests should plan accordingly. The experience is focused on the bar scene—not meals—so arriving prepared is key. Also, the tour’s scheduled start time at 8:00 pm means it’s best suited for those available in the evening and comfortable with walking.

Final Thoughts on the Chicago Speakeasy Tour

The CHICAGo MUSt Do Hidden GEm SPEAKeasy’s tour stands out for its careful selection of bars, engaging storytelling, and small-group intimacy. It offers a fun, relaxed way to explore Chicago’s hidden nightlife and enjoy craft cocktails in unique settings.

Ideal for night owls and adventure seekers, this tour delivers a nostalgic, lively experience that highlights the city’s creative bar culture. While drinks are not included, the cover charge at the final bar ensures you gain access to a fabulous venue with live music.

If you’re eager to uncover Chicago’s secret bars and enjoy an authentic neighborhood vibe, this guided tour provides a memorable, affordable evening tailored for small groups and curious explorers.

✨ Book This Experience

CHICAGo MUSt Do Hidden GEm SPEAKeasy’s



5.0

100% 5-star

“Really cool bars and a really great host. He really knows the neighborhood super friendly and very accommodating. He did the most to make us comfo…”

— Stacey B, Apr 2025

Frequently Asked Questions

Is there an age limit for this tour?
Most travelers can participate, and no specific age restrictions are mentioned, but it’s intended for adults enjoying cocktails and nightlife.

Are drinks included in the price?
No, drinks and food are not included; only water is provided for hydration.

Where does the tour start and end?
It begins and ends at 921 N Western Ave in Chicago.

How long does the tour last?
The tour lasts approximately 1 hour 30 minutes.

Do I need to book in advance?
Yes, this tour is typically booked about 21 days in advance and requires a minimum number of travelers.

Is transportation provided between stops?
No, the last stop is about an 8-minute walk from the starting point.

What is the group size?
Groups are limited to 16 travelers for a more personal experience.

Can I schedule this tour for a special date?
Yes, if the listed dates don’t fit your schedule, you can contact the provider for custom arrangements for groups of 2 or more.

What should I bring?
Comfortable shoes and an appetite to explore Chicago’s hidden bar scene. It’s also wise to eat beforehand.

What makes this tour stand out?
The tour’s focus on hidden, hard-to-find bars with storytelling and local insights makes it a unique way to experience Chicago’s nightlife.