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 passages, and forgotten basements that once served illicit liquor during the 1920s. These tours blend storytelling, architecture, cocktail culture, and historical intrigue into unforgettable evenings. 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 an understanding of the city’s unique underground scene. Whether you’re a history buff, a cocktail enthusiast, or simply seeking an unforgettable night out, knowing how to book a speakeasy tour in Chicago can transform a casual trip into a memorable adventure. This guide walks you through every step, from researching reputable operators to securing your spot during peak season, ensuring you experience the city’s hidden underworld the right way.

Step-by-Step Guide

Research Reputable Speakeasy Tour Operators

The first step in booking a speakeasy tour in Chicago is identifying legitimate, well-reviewed operators. Unlike traditional sightseeing buses, speakeasy tours are often run by small, independent companies with limited capacity and high demand. Start by searching for “Chicago speakeasy tour” on Google, but don’t rely solely on top results. Look beyond the first page and examine reviews on platforms like TripAdvisor, Yelp, and Google Reviews. Pay attention to recent feedback—ideally from the last six months—to gauge consistency in quality and customer experience.

Some operators specialize in historical accuracy, with guides dressed in period attire and using archival photographs to narrate stories of bootleggers and mobsters. Others focus on the cocktail experience, offering tastings at multiple hidden bars along the route. Determine your priority: is it the history, the drinks, or the thrill of discovery? Once you’ve narrowed your preferences, create a shortlist of three to five operators. Check their websites for transparency—do they list tour durations, pricing, meeting points, and cancellation policies? Avoid companies that offer vague descriptions or no contact information.

Understand Tour Types and Formats

Not all speakeasy tours are the same. Chicago offers several formats, each catering to different interests:

• Walking Tours – These are the most common and typically last 2–3 hours. Participants walk between 3–5 hidden bars, often in neighborhoods like River North, the Loop, or Wicker Park. Guides provide historical context at each stop and may unlock secret doors or reveal hidden rooms.
• Private Group Tours – Ideal for birthdays, bachelor parties, or corporate events. These are customizable in terms of route, duration, and even menu. They usually require advance booking and higher minimum group sizes.
• Themed Tours – Some operators offer tours centered around specific themes: “Women of the Underground,” “Mobsters and Molls,” or “Cocktails Through the Decades.” These often include rare cocktail recipes and period-specific music.
• Hybrid Experiences – A few companies combine the speakeasy tour with a dinner or live jazz performance. These are premium experiences and typically cost more but offer a fuller evening.

Be clear on what you’re signing up for. A tour that promises “five secret bars” might include one actual speakeasy and four regular bars with dim lighting. Ask for the names of the venues on the route before booking.

Check Availability and Book in Advance

Speakeasy tours in Chicago are limited in capacity—most operate with groups of 8 to 15 people per slot. Popular operators often sell out weeks in advance, especially during peak seasons (spring, summer, and holidays). Never assume you can walk in or book last-minute. Set a calendar reminder to check availability at least 4–6 weeks before your intended date.

Most operators use online booking platforms like Resy, Eventbrite, or their own custom booking systems. Navigate to the operator’s website and locate their “Book Now” or “Tours” page. Select your preferred date and time. Some tours are offered only on weekends; others run nightly. Note whether the tour is weather-dependent or requires a minimum number of participants. If a tour is marked “sold out,” don’t give up. Many companies maintain waitlists. Sign up immediately, as cancellations do occur.

Confirm Booking Details and Requirements

After completing your reservation, you’ll receive a confirmation email. Review it carefully. Look for:

• The exact meeting location (often a nondescript doorway or alley entrance)
• Start time and duration
• What’s included (e.g., 3–4 drinks, historical booklet, tips)
• What’s not included (e.g., food, gratuity, transportation between stops)
• Age restrictions (most tours require participants to be 21+ with valid ID)
• Dress code (many venues require smart casual; no flip-flops or athletic wear)

Some tours require you to bring a printed or digital copy of your ticket. Others use a name check-in system. If you’re unsure, email the operator directly for clarification. Do not rely on third-party booking platforms for confirmation details—they may not have updated information.

Prepare for the Experience

Once booked, preparation enhances your experience. Familiarize yourself with Chicago’s layout. Many speakeasy tours begin in the Loop or River North and involve walking through well-lit streets to reach hidden entrances. Wear comfortable shoes—expect 1–2 miles of walking. Bring a light jacket; indoor venues can be cool, and outdoor segments may be chilly in spring or fall.

Consider your alcohol tolerance. Most tours include 3–4 cocktail samples, each roughly 3–4 oz. Pace yourself. Some operators offer non-alcoholic alternatives upon request—mention dietary needs or preferences when booking. If you’re traveling with others, coordinate transportation. Taxis and rideshares may be hard to find late at night in certain neighborhoods, so plan your return route ahead of time.

Arrive Early and Follow Instructions

Arrive at least 10–15 minutes before the scheduled start time. The meeting point is often discreet—a back entrance, a brick archway, or a door with no signage. If you arrive late, you may miss the tour entirely. Operators do not wait for latecomers due to the nature of the venues and the need to maintain secrecy.

Follow all instructions from your guide. Do not take photos inside the speakeasies unless permitted. Many venues operate under strict confidentiality agreements to preserve their “hidden” status. Violating these rules can result in being asked to leave or even being banned from future events. Respect the atmosphere: speak softly, avoid loud behavior, and let the story unfold naturally.

Best Practices

Book During Off-Peak Times for Better Availability

While weekends are popular, weekdays—especially Tuesday and Wednesday evenings—offer better availability and often lower prices. Fewer tourists mean a more intimate experience, and guides may have more time to share anecdotes. If your schedule allows, consider booking a weekday tour. You’ll also avoid the crowds that gather near popular tourist hubs after dark.

Read the Fine Print on Cancellations and Refunds

Most speakeasy tour operators have strict cancellation policies due to fixed costs and limited capacity. Many require 72-hour notice for full refunds. Some offer credit toward a future date instead of cash refunds. Others do not allow changes once booked. Always read the terms before purchasing. If you’re uncertain about your travel plans, consider booking a tour with a flexible policy or purchasing travel insurance that covers activity cancellations.

Tip Your Guide Appropriately

Speakeasy tour guides are often historians, actors, or mixologists with deep knowledge of Chicago’s underground past. Their expertise enhances the experience significantly. While gratuity is not mandatory, it is customary to leave 15–20% of the tour price if you enjoyed the experience. Cash is preferred, as many operators do not process tips through digital payment systems. A small token of appreciation goes a long way in encouraging high-quality service.

Engage With Your Guide and Ask Questions

The best tours are interactive. Don’t be shy to ask questions. Was this bar really used by Al Capone? How did they hide the liquor? What happened to the bartender who got caught? Curiosity transforms a passive walk into an immersive journey. Guides appreciate engaged guests and often share stories not included in the standard script.

Respect the Privacy of Hidden Venues

Many speakeasies still operate today as legitimate businesses that rely on discretion. Their secrecy is part of their appeal. Do not post exact addresses, photos of entryways, or names of venues on social media. If you’re unsure whether photography is allowed, ask. Even if others are taking pictures, it doesn’t mean it’s permitted. Violating privacy can lead to venues closing their doors to public tours entirely.

Combine 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, a dinner at a classic steakhouse like The Signature Room, or a jazz night at Green Mill Cocktail Lounge—the actual haunt of Al Capone. Planning your evening around the tour creates a richer, more cohesive experience.

Stay Aware of Seasonal Changes

Some speakeasy tours operate seasonally. Winter months may see reduced schedules due to weather and lower demand. Summer tours may include outdoor patios or rooftop access. Check the operator’s website or social media for updates. Some companies offer “winter-only” tours with fireplace lounges and warm cocktails—perfect for colder months.

Tools and Resources

Recommended Booking Platforms

While many operators manage bookings directly, these platforms are trusted sources for verified speakeasy tours in Chicago:

• Viator – Offers curated tours with user reviews and flexible cancellation policies.
• GetYourGuide – Features detailed itineraries and photo previews of venues.
• Eventbrite – Often used by local historians and small businesses for ticketed events.
• Resy – Used by upscale speakeasies for reservation-based experiences.

Always cross-check these platforms with the operator’s official website. Third-party listings may charge additional fees or lack critical details.

Use Google Maps for Pre-Tour Navigation

Before your tour, open Google Maps and search for the meeting point. Zoom in to street view to familiarize yourself with the surroundings. Note nearby landmarks: a distinctive awning, a red fire escape, a neon sign two blocks away. Many meeting points are intentionally unmarked, so visual recognition is key.

Download Offline Maps and Notes

Cell service can be spotty in basements and alleyways. Download offline maps of Chicago’s downtown using Google Maps or Apple Maps. Save the tour operator’s contact number in your phone. If you have a smartwatch, set a reminder for your start time. Print or screenshot your confirmation email and store it in your wallet.

Follow Speakeasy Tour Operators on Social Media

Instagram and Facebook are primary channels for speakeasy tour companies to announce last-minute openings, seasonal themes, and special events. Follow accounts like @ChicagoSpeakeasyTours, @HiddenBarsChi, or @ProhibitionChicago. Many operators post behind-the-scenes content, historical photos, and cocktail recipes that enhance your appreciation of the tour.

Read Chicago History Books and Documentaries

Deepen your experience by learning beforehand. Recommended reads:

• Chicago’s Underground: The Rise of the Speakeasy by Robert J. Sweeney
• Al Capone’s Chicago: The Mob’s Secret City by Joseph G. Rizzo
• Prohibition: A Concise History by Daniel Okrent

Documentaries like “Prohibition” by Ken Burns (available on PBS) provide context on national trends that shaped Chicago’s underworld. This background turns a fun night out into an educational journey.

Use Cocktail Apps to Identify Drinks

Many tours serve classic Prohibition-era cocktails: Old Fashioned, Sidecar, Bee’s Knees, or French 75. Use apps like Cocktail Coach or Difford’s Guide to learn about the ingredients and history of each drink before your tour. This allows you to appreciate the craftsmanship and authenticity behind each pour.

Real Examples

Example 1: The “Whiskey & Warnings” Tour by Chicago Underground

One of Chicago’s most acclaimed operators, Chicago Underground, offers a 2.5-hour walking tour called “Whiskey & Warnings.” The tour begins at a nondescript alley behind the Chicago Theatre and includes stops at three authentic speakeasies: The Office, The Hawthorne, and The Aviary’s secret lounge. Each location features a signature cocktail paired with a true story—like how a bartender once hid liquor in hollowed-out books or how police were bribed to look the other way.

A guest, Sarah M., booked this tour two months in advance for her 30th birthday. She shared on Yelp: “The guide, Mike, knew every detail—from the exact year the mob took over the building to the brand of gin they smuggled in. We didn’t just taste drinks; we tasted history. I’ve been to dozens of bars in Chicago, but this was the only one that felt like stepping into a movie.”

Example 2: Private Group Tour for a Corporate Team

A marketing firm from Minneapolis booked a private speakeasy tour for their annual retreat. They chose “The Mob’s Manhattan” tour by Chicago Prohibition Experience, which included a custom route through five venues, a curated menu of Prohibition-era cocktails, and a post-tour trivia game with prizes. The company paid $1,200 for a group of 12. The tour ended at a rooftop bar with live jazz, where they enjoyed a final drink under the stars.

“We didn’t just bond over drinks,” said team lead David R. “We bonded over secrets. It was the most unique team-building activity we’ve ever done.”

Example 3: The “Women of the Underground” Tour

Offered seasonally by Chicago Speakeasy Society, this 90-minute tour highlights the often-overlooked female figures of Prohibition: bootleggers, bar owners, and undercover agents. Participants visit a former brothel turned speakeasy, a hidden basement where women distributed moonshine, and a bar that employed only female bartenders to avoid police scrutiny.

One visitor, Dr. Elena Torres, a professor of gender studies, wrote: “I’ve taught about Prohibition for 15 years, but I didn’t know about the women who ran these operations. This tour didn’t just show me history—it redefined it.”

Example 4: A Last-Minute Booking That Almost Didn’t Happen

Travel blogger James L. arrived in Chicago on a Friday evening with no plans. He searched “speakeasy tour Chicago” at 7 p.m. and found one available slot at 8:30 p.m. He booked immediately. The tour, led by a retired Chicago police officer, took him through a former bank vault turned cocktail lounge. He later posted a video: “I thought I was just getting a drink. I got a history lesson wrapped in mystery. Don’t wait until the last minute—but if you do, it’s still worth it.”

FAQs

Can I book a speakeasy tour without a reservation?

No. Speakeasy tours in Chicago require advance booking. Due to limited capacity and the need for coordination with private venues, walk-ins are not permitted. Even if a venue appears open to the public, the tour portion is exclusive to registered guests.

Are speakeasy tours safe?

Yes. All reputable operators follow local safety regulations. Venues are licensed, guides are trained, and routes are well-lit and public until the final hidden entrances. The “secret” aspect is about ambiance and storytelling—not danger. Always choose operators with positive reviews and clear contact information.

Do I need to be 21 to join a speakeasy tour?

Yes. All tours involve alcohol consumption, and all venues enforce a strict 21+ policy. Valid government-issued photo ID is required upon entry. No exceptions are made.

How much walking is involved?

Most tours involve 1–2 miles of walking over 2–3 hours, mostly on flat, paved sidewalks. Some venues require descending stairs or navigating narrow alleys. If you have mobility concerns, contact the operator in advance to confirm accessibility.

Are children allowed on speakeasy tours?

No. All tours are strictly for adults 21 and over due to the nature of the venues and content. There are no family-friendly or non-alcoholic versions available.

What if it rains?

Most tours operate rain or shine. Guides provide umbrellas or adjust routes slightly to minimize exposure. Indoor venues remain accessible. Cancellations due to weather are rare and only occur in extreme conditions like blizzards or flooding.

Can I bring a camera?

Photography is usually permitted in public areas and at the meeting point. However, inside speakeasies, cameras and phones are often restricted to preserve the venue’s secrecy and ambiance. Always ask your guide before taking photos. Some operators offer professional photos as a paid add-on.

How much do speakeasy tours cost?

Prices range from $45 to $120 per person, depending on duration, inclusions, and exclusivity. Basic walking tours with 3 drinks start around $55. Premium tours with food pairings or private groups can exceed $100. Be wary of tours priced significantly lower—they may not include actual speakeasy access.

Do I need to tip my guide?

Tipping is not required but is customary. A 15–20% gratuity is appropriate if you enjoyed the experience. Cash is preferred.

Can I book a tour for a large group?

Yes. Many operators offer private group bookings for 10–25 people. Contact them directly to arrange custom dates, routes, and menus. Group discounts may apply for parties of 10 or more.

Conclusion

Booking a speakeasy tour in Chicago is more than a tourist activity—it’s a portal into a hidden chapter of American history. The thrill of discovering a secret door, the taste of a century-old cocktail, and the stories whispered by knowledgeable guides create an experience that lingers long after the last sip. But this experience doesn’t happen by accident. It requires intention: researching operators, understanding formats, booking early, and respecting the traditions of the spaces you visit.

By following this guide, you’re not just securing a reservation—you’re becoming part of a legacy. The speakeasies of Chicago were once places of rebellion, resilience, and ingenuity. Today, they’re preserved not as relics, but as living tributes to a time when the law was defied, and culture was crafted in shadows. When you walk through that hidden entrance, you’re not just a guest—you’re a witness.

Plan wisely. Book early. Ask questions. Savor the secrets. And remember: the best stories aren’t told in museums. They’re whispered behind closed doors.