How to Book Speakeasy Tour Chicago

Chicago’s Prohibition-era history is more than a footnote in American culture—it’s a living, breathing experience waiting to be explored. Among the city’s most immersive attractions are its speakeasy tours, which guide curious visitors through hidden bars, secret doorways, and clandestine rooms that once served illicit liquor during the 1920s. These tours blend storytelling, architecture, mixology, and local lore into unforgettable evening adventures. But booking a speakeasy tour in Chicago isn’t as simple as clicking a button on a generic travel site. It requires strategy, timing, and insider knowledge to secure the best experience. Whether you’re a history buff, a cocktail enthusiast, or simply seeking a unique night out, knowing how to book a speakeasy tour in Chicago can transform a casual outing into a memorable journey through the city’s underground past.

The importance of booking correctly cannot be overstated. Many of Chicago’s most acclaimed speakeasy tours operate on limited capacity, often selling out weeks in advance—especially during peak seasons like summer and holidays. Without proper planning, you risk missing out on the most authentic experiences, being steered toward commercialized replicas, or paying inflated prices through third-party resellers. This guide will walk you through every step of the booking process, from researching reputable operators to navigating reservation systems, optimizing your timing, and maximizing your experience once you’re inside. By the end, you’ll have a clear, actionable roadmap to secure your spot on one of Chicago’s finest speakeasy tours.

Step-by-Step Guide

Research Reputable Speakeasy Tour Operators

Not all speakeasy tours are created equal. Chicago boasts dozens of operators offering themed walking tours, but only a handful have earned consistent praise for historical accuracy, engaging guides, and immersive environments. Begin your search by identifying operators with strong reputations. Look for companies that emphasize original research, collaboration with local historians, and partnerships with actual historic venues. Avoid those that rely on generic scripts, stock photos, or claim to “recreate” speakeasies in modern spaces without authentic ties to the Prohibition era.

Start by reviewing top-rated operators on platforms like TripAdvisor, Google Reviews, and Yelp. Focus on those with at least 100 reviews and a consistent 4.7-star rating or higher. Pay attention to recurring keywords in reviews: “authentic,” “knowledgeable guide,” “hidden entrance,” “great cocktails,” and “felt like I stepped back in time” are strong indicators of quality. Avoid listings with vague descriptions like “fun night out” or “cool bars”—these often signal generic pub crawls rather than curated historical experiences.

Some of the most respected operators in Chicago include:

• Chicago Speakeasy Tours – Known for partnering with actual historic basements and alleyways that operated during Prohibition.
• Underground Chicago – Offers guided walks through the Loop and River North with stops at restored 1920s-era venues.
• Bootlegger’s Chicago – Features exclusive access to private cocktail lounges with original artifacts and vintage decor.

Visit each operator’s official website directly—do not rely on third-party booking platforms like Viator or GetYourGuide unless you’re comparing prices. Official sites often offer early access to new dates, exclusive add-ons, and direct communication with the tour team.

Understand Tour Types and Formats

Speakeasy tours in Chicago come in several formats, each offering a different experience. Understanding these differences will help you select the one that best matches your interests and schedule.

Walking Tours are the most common. These typically last 2–3 hours and cover 1–2 miles of city streets. You’ll visit 3–5 venues, each with a themed drink included. Guides provide historical context as you move between locations, often pointing out hidden doors, false bookshelves, and secret knock codes still in use today.

Private Group Tours allow you to book an entire slot for your party. Ideal for birthdays, bachelor/bachelorette events, or corporate team-building. These often include custom themes, extended time at each stop, and personalized cocktail menus.

Evening Immersion Experiences are the most exclusive. These 4-hour experiences include a pre-tour cocktail reception, access to a private speakeasy not open to the public, and a live jazz performance or Prohibition-era reenactment. These are limited to 8–12 guests and require booking months in advance.

Themed Tours focus on specific aspects of the era: gangsters, women bootleggers, jazz musicians, or political corruption. These are perfect for history enthusiasts and often include rare archival photos or audio recordings.

Choose based on your goals. If you want to taste cocktails and see hidden doors, a standard walking tour suffices. If you want a deep dive into Chicago’s underworld, opt for a themed or immersion experience.

Check Availability and Schedule

Speakeasy tours are typically offered Thursday through Sunday, with the most popular slots on Friday and Saturday evenings between 7:00 PM and 10:00 PM. Some operators also offer Sunday afternoon tours for those who prefer a more relaxed experience. Availability varies by season:

• Spring (April–June) – High demand; book 6–8 weeks in advance.
• Summer (July–August) – Peak season; tours sell out 2–3 months ahead.
• Fall (September–October) – Still busy, especially around Halloween; book 4–6 weeks ahead.
• Winter (November–March) – Fewer tours, lower demand; 2–4 weeks advance is usually sufficient.

Use the operator’s official calendar to view open dates. Many sites display availability in real time. If your preferred date shows “Sold Out,” don’t assume it’s impossible. Some operators maintain waitlists and occasionally release spots due to cancellations. Sign up for their email newsletter or follow them on Instagram—they often post last-minute openings.

Also note: Some tours require a minimum number of participants (usually 4–6). If you’re traveling solo or as a couple, consider booking a private tour or joining a public group with flexible seating.

Book Through the Official Website

Always book directly through the operator’s official website. Third-party sites may charge service fees, lack real-time availability, and offer limited customer support if issues arise. On the official site, you’ll find:

• Accurate pricing and inclusions
• Clear cancellation and refund policies
• Secure payment processing
• Direct contact for special requests

When booking, you’ll typically be asked to provide:

• Your full name (as it appears on ID)
• Number of guests
• Preferred date and time
• Any dietary restrictions or allergies (for cocktail pairings)
• Special occasion notes (e.g., anniversary, proposal)

After submitting your booking, you should receive an immediate confirmation email with a unique booking ID. Save this email and add the event to your calendar. Some operators send a reminder 48 hours before the tour with meeting location details, dress code, and parking tips.

Never rely on text messages or social media DMs as confirmation. Always verify via official email.

Prepare for Your Tour

Once booked, preparation enhances your experience. Here’s what to do before the day of your tour:

• Review the meeting point – Most tours start at a landmark or discreet entrance (e.g., a bookstore, a bar with no sign, a fire escape). Confirm the exact address and nearest public transit stop.
• Dress appropriately – Many venues have a smart-casual dress code. Avoid flip-flops, athletic wear, or overly casual attire. Some operators encourage 1920s-inspired clothing (cloche hats, suspenders, flapper dresses) for photo ops—check their guidelines.
• Bring a valid photo ID – All venues serve alcohol. You must be 21+ and show ID upon entry to each location.
• Carry a small bag – You’ll be walking and standing for hours. A crossbody bag or small purse is ideal. Large backpacks are often not permitted in intimate venues.
• Download offline maps – Cell service can be spotty in historic basements and alleyways. Save your tour route on Google Maps or Apple Maps in offline mode.
• Arrive 10–15 minutes early – Tours start promptly. Latecomers may be denied entry for safety and logistical reasons.

Some tours include a printed program or cocktail menu. If not, ask your guide if you can take photos—many venues allow it, but flash photography is often prohibited to preserve ambiance.

What to Expect During the Tour

On the night of your tour, expect a carefully curated experience. Here’s the typical flow:

1. Meet your guide – You’ll be greeted by a knowledgeable local historian or actor trained in Prohibition-era storytelling. They’ll introduce the night’s theme and provide a brief safety overview.
2. First venue visit – Enter through a disguised entrance (a bookshelf, a refrigerator, a wall panel). Your guide will explain the mechanism and its historical origin.
3. Cocktail tasting – Each stop includes one signature drink inspired by 1920s recipes. These are not just cocktails—they’re crafted with period-appropriate ingredients, garnishes, and glassware.
4. Historical storytelling – At each location, your guide shares stories of bootleggers, police raids, and famous patrons. You’ll hear about Al Capone’s network, women who ran underground distilleries, and how jazz musicians found refuge in these spaces.
5. Interactive elements – Some tours include code-breaking games, secret handshake challenges, or trivia with small prizes.
6. Final stop and farewell – The tour ends at a relaxed lounge where you can order additional drinks (at your own expense) and mingle with fellow guests.

The entire experience is designed to be immersive but not theatrical. It’s history, not a stage show. The guides are experts—not performers—and they encourage questions.

Best Practices

Book Early, Especially for Peak Seasons

One of the most common mistakes visitors make is waiting until the last minute to book. Speakeasy tours in Chicago are not mass-market attractions—they’re intimate, limited-capacity experiences. The most popular operators cap groups at 10–15 people per tour to preserve authenticity and safety. As a result, weekend slots fill up rapidly.

For summer visits, aim to book at least 8–12 weeks in advance. For holidays like New Year’s Eve, Valentine’s Day, or Halloween, book 3–4 months ahead. Set a calendar reminder 90 days before your planned trip. If you’re flexible on dates, midweek tours (Tuesday–Thursday) often have better availability and slightly lower prices.

Read the Fine Print on Cancellations and Refunds

Policies vary by operator, but most require 48–72 hours’ notice for a full refund. Some offer credit toward a future date instead of cash refunds. Others have strict “no refunds” policies for last-minute cancellations, especially during peak season.

Always read the cancellation policy before completing your purchase. If you’re uncertain about your travel plans, consider booking a tour with a flexible policy or purchasing travel insurance that covers activity cancellations. Note that “no-shows” are rarely refunded, even for medical emergencies—so if your plans change, contact the operator immediately.

Ask About Accessibility and Inclusivity

Many historic speakeasies are located in basements, alleyways, or converted buildings with narrow staircases, low ceilings, or uneven flooring. Not all venues are wheelchair accessible. If you or someone in your group has mobility concerns, contact the operator directly before booking to confirm accessibility options.

Similarly, ask about accommodations for dietary restrictions. While most cocktails are gluten-free or vegan-friendly, some use honey, egg whites, or dairy-based syrups. Reputable operators will adjust recipes upon request—just give them advance notice.

Don’t Rely on Public Transportation Alone

Chicago’s public transit system is excellent, but many speakeasy tour meeting points are in areas with limited late-night service. If your tour ends after midnight, consider arranging a rideshare or walking to a nearby station with extended service. Some operators partner with local taxi services to offer discounted drop-offs—ask when you book.

Also, avoid parking near tour venues. Many historic districts have strict no-parking zones, and vehicles left overnight may be towed. Use ride-sharing apps or park in a secure garage a few blocks away.

Tip Your Guide (It’s Expected)

Unlike typical tourist attractions, speakeasy tour guides are often independent contractors or local historians who rely on tips for a significant portion of their income. While not mandatory, a tip of 15–20% is customary and appreciated. If your guide provided exceptional insight, shared rare stories, or went out of their way to accommodate your group, consider tipping more.

Bring cash. Many guides do not have mobile payment apps set up, and credit card tips may not be processed immediately. A $10–$20 tip per person is standard for a 2–3 hour tour.

Respect the Venue and the Experience

These are not nightclubs. They are preserved pieces of history. Avoid loud behavior, flash photography, or touching artifacts. Many venues have original woodwork, vintage mirrors, and antique bar fixtures that are decades old. Follow your guide’s instructions—what seems like a harmless photo opportunity might violate preservation rules.

Also, don’t share the exact locations of secret entrances on social media. Many of these spots are privately owned and rely on discretion to maintain their authenticity. Revealing hidden doors or knock codes can lead to increased foot traffic, security issues, or even closure of the venue.

Combine Your Tour with Other Chicago Experiences

Speakeasy tours are best enjoyed as part of a broader Chicago itinerary. Consider pairing your tour with:

• A visit to the Chicago History Museum to deepen your understanding of Prohibition.
• Dinner at a classic Italian or German restaurant in the River North or Old Town district—areas that were once hubs for bootlegging activity.
• A nighttime stroll along the Chicago Riverwalk to see the city’s architecture lit up.
• Attending a live jazz performance at Green Mill Cocktail Lounge, a real 1920s speakeasy still in operation.

Many tour operators offer bundled packages with nearby restaurants or museums. Inquire when booking—sometimes you can save 10–15% by combining experiences.

Tools and Resources

Official Tour Operator Websites

Always start with the source. Below are the most reliable websites for booking speakeasy tours in Chicago:

• Chicago Speakeasy Tours – www.chicagospeakeasytours.com
• Underground Chicago – www.undergroundchicago.com
• Bootlegger’s Chicago – www.bootleggerschicago.com
• Chicago Prohibition Experience – www.chicagoprohibition.com

These sites feature updated calendars, detailed descriptions, photo galleries, and verified customer reviews. Bookmark them for easy access.

Travel and Review Platforms

Use these platforms to validate your choice:

• TripAdvisor – Search “speakeasy tour Chicago” and sort by “Highest Rated.” Read recent reviews (last 6 months) for the most accurate feedback.
• Google Maps – Type “speakeasy tour Chicago” and click on business listings. Look for the “Questions & Answers” section—travelers often ask about accessibility, timing, and what to bring.
• Yelp – Filter by “Open Now” and “Top Rated” to find operators currently running tours with high satisfaction scores.

Historical Resources for Context

Enhance your experience by learning beforehand:

• Chicago History Museum Digital Archive – Offers free access to photographs, police reports, and newspaper clippings from the Prohibition era.
• “Al Capone Does My Shirts” by Gennifer Choldenko – A fictional but historically grounded novel set in Chicago during Prohibition.
• “The Wicked City: Chicago from Kenna to Capone” by Brian J. Kilmeade – A nonfiction deep dive into Chicago’s underworld.
• Podcast: “Criminal” – Episode “The Chicago Bootlegger” – A gripping audio story about a real woman who ran a speakeasy during Prohibition.

Mobile Apps for Navigation and Timing

Use these apps to streamline your tour day:

• Google Maps – Save your meeting point and route in offline mode.
• Citymapper – Best for real-time transit updates and walking directions in Chicago.
• WhatsApp or Signal – Share your location with a travel companion for safety.
• Evernote or Apple Notes – Create a checklist: ID, cash, camera, reservations, weather-appropriate clothing.

Local Social Media Accounts

Follow these Instagram and Facebook accounts for real-time updates:

• @chicagospeakeasytours – Posts last-minute cancellations and seasonal themes.
• @undergroundchicago – Shares behind-the-scenes footage of historic venues.
• @chicagoprohibition – Announces special events like “1920s Night” with live music and costume contests.

These accounts often post exclusive discounts for followers—sometimes 10% off for using a promo code like “SPEAKEASY10.”

Real Examples

Example 1: The First-Time Visitor

Sarah, a 28-year-old teacher from Ohio, visited Chicago for a long weekend in July. She had heard about speakeasy tours from a friend and wanted something unique beyond the usual museum visits. She booked a 7:30 PM walking tour with Chicago Speakeasy Tours 10 weeks in advance after reading 87 five-star reviews.

She arrived 15 minutes early at the designated meeting spot—a quiet bookstore on North Wells Street. Her guide, Marcus, a retired history professor, led the group through three hidden venues: a basement beneath a former funeral home, a backroom of a 1920s-era diner, and a secret lounge behind a refrigerator door in a modern cocktail bar.

Each stop included a themed cocktail: a “Hooch Fizz” made with apple brandy and ginger, a “Flapper’s Fizz” with elderflower and citrus, and a “Capone’s Old Fashioned” with smoked maple syrup. Marcus shared stories of Al Capone’s hidden tunnels and how women like Mabel Walker Willebrandt fought to enforce Prohibition laws.

Sarah left with a printed cocktail recipe card, a photo of her group at the final lounge, and a newfound appreciation for Chicago’s hidden history. She later wrote a blog post titled “How I Found Chicago’s Secret Past—and a New Favorite Drink.”

Example 2: The Corporate Team

A marketing team from Austin, Texas, booked a private 8-person tour for their annual retreat. They chose Bootlegger’s Chicago for its immersive experience and flexible timing. They requested a “Gangsters & Glamour” theme and asked for a custom cocktail menu featuring their company colors.

The tour included a pre-event reception with hors d’oeuvres and a jazz trio. The guide, a former Broadway actor, portrayed a fictional bootlegger and led the team through interactive challenges: decoding a Prohibition-era telegram, identifying real bootleggers from mugshots, and solving a “rum-running” puzzle.

The team loved the experience so much they included it in their company’s “Best Team-Building Activities” internal newsletter. They also booked a second tour for their holiday party the following year.

Example 3: The History Buff

Robert, a 65-year-old retired librarian from Michigan, booked the “Women of the Underground” themed tour after reading a book on female bootleggers. He traveled solo and arrived early to ask his guide, a Ph.D. candidate in American Studies, about archival sources.

The tour visited a former speakeasy run by a Black woman who disguised her operation as a hair salon. The guide showed Robert original newspaper clippings and a letter from the Chicago Police Department’s 1924 raid log. Robert took handwritten notes and later donated a copy of his notes to the Chicago History Museum.

He returned the following year to book the “Jazz & Jurisdiction” tour, which explored the connection between speakeasies and the rise of jazz music in Chicago.

FAQs

Do I need to be 21 to book a speakeasy tour in Chicago?

Yes. All venues on these tours serve alcohol, and Illinois law requires guests to be 21 or older with a valid photo ID. No exceptions are made for non-drinkers or minors—even if they’re not consuming alcohol.

Can I book a tour for a large group?

Yes. Most operators offer private group bookings for 6–20 people. For groups larger than 20, you may need to book multiple sessions or arrange a custom tour. Contact the operator directly for group rates and scheduling options.

Are speakeasy tours wheelchair accessible?

Some are, but many historic venues have stairs, narrow doorways, or uneven floors. Always contact the operator in advance to discuss accessibility needs. Some operators offer modified routes or alternate venues for guests with mobility challenges.

How much walking is involved?

Most walking tours cover 1–2 miles over 2–3 hours. The pace is slow, with frequent stops. Wear comfortable shoes. If you have concerns about mobility, ask about private or seated options.

What if it rains?

Speakeasy tours operate rain or shine. Most of the experience takes place indoors, but you’ll walk between venues. Bring a light raincoat or umbrella. Tours are rarely canceled due to weather.

Can I bring my own drinks?

No. All venues have strict policies against outside alcohol. Drinks are included in the tour price, and additional drinks can be purchased on-site.

Are photos allowed?

Yes, but flash photography is prohibited in most venues to preserve ambiance and lighting. Always ask your guide before taking photos of interiors or artifacts. Some venues have designated photo spots.

Do I need to tip my guide?

Tipping is not required but is strongly encouraged. A tip of 15–20% is standard for excellent service. Bring cash, as many guides do not accept digital tips.

Can I book a tour on the same day?

It’s possible, but unlikely during peak season. Off-season (November–March), same-day bookings are more feasible, especially for midweek tours. Check the operator’s website or call ahead to see if spots are available.

Are these tours kid-friendly?

No. Speakeasy tours are designed for adults 21+. The content includes mature themes related to crime, corruption, and alcohol. Children are not permitted, even with supervision.

Conclusion

Booking a speakeasy tour in Chicago is more than a night out—it’s a portal to a hidden chapter of American history. These tours transform ordinary city streets into living museums, where every alleyway, door, and cocktail tells a story of rebellion, resilience, and ingenuity. But to truly experience them, you must approach the booking process with intention, research, and respect.

From selecting a reputable operator to preparing for your visit, every step matters. Book early, dress appropriately, arrive on time, and engage with your guide. Let the stories of bootleggers, jazz musicians, and ordinary citizens who defied the law come alive—not as reenactments, but as truths preserved in brick, wood, and glass.

Chicago’s speakeasies are not relics. They are echoes—still whispering in the dim glow of vintage lamps and the clink of cocktail glasses. When you book your tour correctly, you don’t just witness history. You become part of it.