Chicago: Prohibition Speakeasies Bus Tour or Walking Tour

If you’re curious about Chicago’s colorful past during Prohibition and want to see some of the city’s secret drinking spots, this tour offers a fascinating glimpse into the era. Whether you prefer walking through downtown or exploring neighborhoods from a bus, it’s a laid-back way to combine history, architecture, and a few drinks.

What we love about this experience is the chance to visit multiple historic speakeasies, each with its own unique vibe, and the stories shared by guides who really know their stuff. Plus, the option to buy drinks along the way makes it more engaging than just a walk or ride without any perks.

A possible drawback is that the tours are adult-only, so if you’re traveling with younger kids or looking for family-friendly activities, this won’t be suitable. Also, some might feel the ticket price is a bit high if you’re not planning to purchase drinks or aren’t a fan of guided tours.

All in all, this tour is perfect for history buffs, nightlife enthusiasts, or anyone wanting a different perspective on Chicago’s lively past. It offers a good mix of storytelling, sightseeing, and socializing — ideal for solo travelers, couples, or groups of friends.

Key Points

• Two options to choose from: Downtown walking tour or neighborhood bus tour, depending on your preference for pace and comfort.
• Visited speakeasies are iconic: Each venue has its own character, from hidden gems to elegant hotels.
• Learn about the era: Guides are praised for their knowledge and storytelling skills.
• Enjoy era-appropriate drinks: You can buy cocktails at each stop, adding to the experience.
• Small group sizes: Tours are capped at 20 people, making it more personal and engaging.
• Operates rain or shine: Be prepared for any weather, especially if you opt for the walking tour.

You can check availability for your dates here:

A Closer Look at the Tour Options

The Downtown Walking Tour: Hidden in Plain Sight

This option is perfect if you love wandering through city streets and getting a closer look at Chicago’s architecture and neighborhoods. Starting in the Loop and River North, you’ll visit three iconic speakeasies that played key roles during Prohibition.

What’s great here is the chance to see some of Chicago’s best-loved historic venues — some from the outside, some inside, depending on access. Guides often include stories about how alcohol flowed through different social layers, from gangsters to high society, making it feel like stepping back in time.

The less than one-mile walk makes this manageable even for those who prefer a relaxed pace. Reviewers rave about guides like Jonathan, who bring the city’s stories alive with humor and insight. One reviewer noted, “Our guide was extremely knowledgeable and entertaining,” which is common praise.

The Original Chicago Prohibition Bus Tour

If you prefer to cover more ground without walking, the bus version is a good pick. It visits four neighborhood speakeasies spread across Gold Coast, Lincoln Park, Wicker Park, and River North.

This option allows you to cover a larger area, seeing different parts of Chicago’s historic districts. The bus provides a comfortable, relaxing way to learn about the full scope of Prohibition’s impact on the city’s social scene. You’ll get to see some places you might not stumble upon on your own, with the added benefit of a guide narrating the history along the way.

What to Expect at Each Venue

At each speakeasy, you’ll learn about its significance in the Prohibition era. Many of these places have histories tied to gangsters and high society, which makes the visits more than just a cocktail stop.

Guests often mention the quality of guides, like Jonathan or John, who provide detailed, engaging stories. One review noted, “Jonathan was super knowledgeable and enthusiastic,” making the experience more memorable. Some venues are described as stunning, with beautiful interiors and historic charm, giving you a real feel for the era.

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Drinking and Food Options

While the tour price covers entry to the venues, drinks and food are available for purchase. Expect cocktail recommendations that reflect the period — so you might find yourself sipping a classic gin Rickey or a whiskey sour. Several reviews highlight how the drinks enhance the immersion, with one person noting, “We had great drinks along the way from three very different places.”

Group Size and Atmosphere

With groups limited to 20 people, it’s just the right size to keep things intimate and conversational. This makes it easier to ask questions, chat with guides, and connect with fellow travelers. Guides are often praised for their approachability and storytelling skills, making the whole experience feel like a lively history lesson with friends.

Accessibility and Practical Info

• Tours run for about 3-4 hours, generally in the afternoon.
• You’ll need to bring your ID or passport, especially if you plan to buy alcohol.
• Payment can be made via credit or cash at venues.
• No hotel pickup or drop-off is included, so plan to meet at the designated spot.
• Tours operate rain or shine, so dress accordingly—comfortable shoes for walking or layers for weather changes.

Authentic Experiences and Traveler Feedback

Many reviewers emphasize the quality of the guides. One reviewer said, “Jonathon was so knowledgeable, super enthusiastic, and very funny,” which appears to be a common theme. Guests also appreciate the authenticity of the venues, with some noting that the interiors are stunning and full of history.

Others mention how the tour brings Chicago’s past to life, with comments like, “It was like taking a 3-hour university lecture that was fun,” and “The places he took us to were superb.” Some found the stories captivating, and a few remarked on the atmosphere that transports you back to an era when Chicago was a hub of gangster activity and secret speakeasies.

The value for money is generally seen as good, especially considering you get access to four venues and a knowledgeable guide. Many say the experience exceeded their expectations, with one reviewer claiming it was their favorite in Chicago.

However, a few noted that if drinks aren’t included or discounted, the overall value might feel less appealing, especially given the tour price. One comment suggested that offering drink specials could improve perceived value.

The Sum Up

This Chicago Prohibition Speakeasies tour is a great way to spend an afternoon exploring the city’s clandestine past while enjoying some era-inspired cocktails. The combination of expert storytelling, beautiful venues, and the chance to learn about Chicago’s gangster days makes it stand out. Whether you choose the walking route or a bus trip, you’re in for a lively, informative, and fun experience.

It’s best suited for those interested in history, architecture, and nightlife, or anyone who appreciates a good story with their drinks. The small group size and enthusiastic guides help the experience feel personal and engaging, making it more than just a bar crawl.

If you’re curious about Chicago’s hidden past and want to sip cocktails at historic venues, this tour offers a memorable and authentic look at one of the city’s most intriguing eras.

FAQ

Is this tour suitable for people under 21?
No, this is an adults-only experience due to adult themes and alcohol consumption policies.

How long does the tour last?
The tour runs for about 3 to 4 hours, usually in the afternoon, giving you plenty of time to enjoy the venues and stories.

Can I buy drinks at the speakeasies?
Yes, drinks are available for purchase at each venue. The guide will recommend some era-appropriate cocktails.

Is transportation provided between venues?
If you choose the walking tour, you’ll move on foot; for the bus tour, transportation between locations is included.

What should I bring?
Bring your ID or passport, and cash or credit card for drinks and tips.

Are the venues accessible?
This depends on each venue’s layout, but the tour is designed to be manageable within a short walk or ride.

What happens if it rains?
The tours operate rain or shine. Dress appropriately and be prepared for weather conditions.

Is the group size large?
No, groups are capped at 20 people, ensuring a more personal experience.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund, making it flexible if your schedule shifts.

Whether you’re a history buff, a cocktail lover, or just looking for a fun way to see Chicago differently, this tour offers a lively peek into the city’s underground past — with plenty to enjoy along the way.

You can check availability for your dates here: