How to Book Speakeasy Tour Chicago

Chicago’s Prohibition-era history is more than just a chapter in a textbook—it’s a living, breathing experience woven into the city’s alleyways, hidden doors, and dimly lit rooms. The speakeasy culture of the 1920s and 1930s, born from the national ban on alcohol, has been resurrected with modern flair, offering visitors an immersive journey into a world of jazz, secret passwords, and craft cocktails. Today, booking a speakeasy tour in Chicago isn’t just about finding a bar—it’s about unlocking a curated narrative of rebellion, ingenuity, and urban legend. Whether you’re a history buff, a cocktail enthusiast, or simply seeking an unforgettable evening, knowing how to book a speakeasy tour in Chicago transforms a casual night out into a deeply engaging adventure.

Unlike standard bar-hopping tours, speakeasy experiences are intentionally exclusive. Many venues operate on reservation-only systems, require password entry, or limit group sizes to preserve authenticity. Without proper guidance, even the most enthusiastic traveler can miss out on the best offerings—or worse, waste time on poorly curated, tourist-trap experiences. This guide provides a comprehensive, step-by-step roadmap to ensure you not only book a speakeasy tour in Chicago but select the most authentic, well-reviewed, and immersive option available. From researching reputable operators to navigating booking platforms and preparing for your evening, every detail matters.

By the end of this guide, you’ll understand the nuances of Chicago’s speakeasy scene, know how to avoid common pitfalls, and have the tools to secure a reservation that exceeds expectations. This isn’t just a tutorial—it’s your key to experiencing Chicago’s most secretive nightlife like a local.

Step-by-Step Guide

Research Reputable Speakeasy Tour Operators

The first step in booking a speakeasy tour in Chicago is identifying operators with proven credibility. Not all companies offering “speakeasy tours” deliver the same experience. Some are simply guided walks between traditional bars with a Prohibition-themed narrative. Others are meticulously designed immersive experiences featuring authentic decor, period-specific cocktails, and actors portraying historical figures.

Begin your search using trusted platforms like TripAdvisor, Yelp, and Google Reviews. Filter results by “highest rated” and read recent reviews—look for mentions of “authentic,” “hidden entrance,” “knowledgeable guide,” or “immersive.” Avoid companies with vague descriptions, stock photos, or no clear itinerary. Top-rated operators in Chicago include Chicago Speakeasy Tours, The Underground Experience, and Chicago Cocktail Crawl. These companies have consistently received high ratings for their attention to historical accuracy and guest experience.

Visit each operator’s official website. Legitimate providers will detail the tour’s structure: how many venues are visited, the duration, whether drinks are included, and if reservations are mandatory. They’ll also showcase photos of actual venues—not generic bar interiors. Look for bios of the guides; many have backgrounds in history, theater, or culinary arts, which adds depth to the storytelling.

Understand Tour Types and Pricing

Chicago speakeasy tours vary significantly in format and cost. There are three primary types:

• Walking Tours: These typically last 2–3 hours and include visits to 3–4 hidden bars. You walk between locations, often through historic neighborhoods like River North, The Loop, or Wicker Park. Prices range from $55 to $95 per person.
• Private Group Experiences: Tailored for groups of 6–12 people, these tours offer customization—choose your preferred time, route, or even a specific theme (e.g., “Mafia & Moonshine” or “Women of the Underground”). Prices start at $120 per person.
• Multi-Day Immersive Packages: For the ultimate experience, some operators offer extended itineraries that include a speakeasy dinner, live jazz performance, and a vintage cocktail-making class. These premium packages cost $180–$250 per person.

Be wary of tours priced below $45—they often lack drink inclusions, use non-authentic venues, or are unlicensed. Most reputable tours include 3–4 craft cocktails, non-alcoholic alternatives, and sometimes small bites. Always confirm what’s included before booking.

Check Availability and Book in Advance

Speakeasy tours in Chicago are not walk-in experiences. Due to limited capacity and the need to coordinate with private venues, reservations are required—and often fill up weeks in advance, especially during peak seasons (spring through fall and holidays).

Visit the operator’s website and navigate to their booking calendar. Select your preferred date and group size. Many platforms allow you to choose between morning, evening, or weekend slots. Evening tours (7–10 PM) are most popular, as they align with the authentic nighttime ambiance of speakeasies.

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

• Full names of all attendees
• Contact information (email and phone)
• Any dietary restrictions or allergies
• Preferred language or tour focus (e.g., history vs. cocktails)

After submitting your reservation, you should receive an automated confirmation email within minutes. If not, contact the operator directly via their website’s contact form—not a third-party platform. Keep this confirmation in your inbox and save a screenshot on your phone. Some venues require you to present the confirmation at the entrance.

Prepare for the Password and Entry Protocol

One of the defining features of a true speakeasy experience is the password system. On the day of your tour, you’ll receive a password via email or text message—usually 24–48 hours before departure. This password is required to gain entry to the first venue. Do not share it with others; it’s unique to your group.

Arrive at the designated meeting point 10–15 minutes early. The guide will be holding a sign or wearing a vintage accessory (e.g., a pocket watch, fedora, or period-appropriate pin). They’ll verify your name against the guest list and may ask you to whisper the password to a bouncer stationed at a nondescript door.

Some venues require you to knock in a specific rhythm or answer a riddle. This is part of the experience. Don’t rush—enjoy the theatricality. If you forget the password, remain calm. Guides are trained to assist without breaking character.

Understand What to Wear and Bring

While Chicago speakeasy tours aren’t formal events, dressing the part enhances the immersion. Many guests opt for 1920s-inspired attire: flapper dresses, suspenders, fedoras, or vintage suits. It’s not mandatory, but it’s encouraged—and often photographed.

Wear comfortable walking shoes. You’ll be navigating uneven sidewalks, staircases, and possibly cobblestone alleys. Avoid high heels or new boots that haven’t been broken in.

Bring:

• Your confirmation email or QR code (on your phone)
• A valid photo ID (required for alcohol service)
• A small wallet or clutch (large bags are often not permitted in venues)
• A light jacket or sweater (many venues are cool and dimly lit)
• A camera or smartphone (for photos—flash is discouraged in intimate settings)

Leave behind bulky backpacks, umbrellas, and excessive perfume or cologne. These can interfere with the sensory experience and are often prohibited for safety and ambiance reasons.

During the Tour: What to Expect

Once inside, the experience unfolds like a theatrical performance. Guides will share stories of bootleggers, corrupt officials, and daring women who ran underground networks. You’ll learn how speakeasies disguised themselves as laundromats, bookstores, or barbershops. At each stop, you’ll be served a signature cocktail crafted to reflect the era—think Old Fashioneds, Gin Rickeys, or homemade ginger beer.

Engage with your guide. Ask questions about the architecture, the music, or the real-life figures who frequented these places. Many venues have original furnishings, hidden panels, or secret rooms that aren’t visible to the untrained eye. Your guide will point them out.

Do not attempt to take photos of hidden entrances, security systems, or staff. These are protected to maintain the secrecy of the venues. Respect the rules—it’s part of the tradition.

Post-Tour Follow-Up

After the tour concludes, you’ll likely be given a small keepsake: a vintage-style cocktail recipe card, a map of Chicago’s hidden bars, or a discount code for future visits. Keep it—it’s part of the experience.

Consider leaving a review on Google, TripAdvisor, or the operator’s website. Your feedback helps others discover authentic experiences and encourages operators to maintain high standards.

If you enjoyed the tour, ask about membership programs or loyalty perks. Some operators offer exclusive access to private events, early booking windows, or themed nights (e.g., “Flapper Night” or “Jazz & Gin Sundays”).

Best Practices

Book Early, Especially During Peak Seasons

Chicago’s speakeasy scene is booming. Summer weekends, holidays like Halloween and New Year’s Eve, and major events such as the Chicago Air & Water Show or Lollapalooza draw large crowds. Tours can sell out 4–6 weeks in advance. Set a calendar reminder to book at least 30 days ahead. If your travel dates are flexible, consider midweek tours—they’re often less crowded and sometimes offered at a slight discount.

Verify the Venue’s Authenticity

Not every “speakeasy” is genuinely hidden. Some bars are simply themed and open to the public. True speakeasy tours visit venues that are not listed on Google Maps, require passwords, or have no visible signage. Before booking, ask the operator: “Are all venues on this tour still operating as true speakeasies with entry restrictions?” If they hesitate or give a vague answer, consider another provider.

Respect the Rules and the Culture

Speakeasies are not just bars—they’re sanctuaries of secrecy and artistry. Loud behavior, phone use during storytelling, or attempting to record video without permission can ruin the experience for others. Follow your guide’s instructions. Turn off your phone’s ringer. Speak quietly. Appreciate the craftsmanship in every cocktail and the history behind every wall.

Don’t Skip the Pre-Tour Email

Reputable operators send a pre-tour email with essential details: meeting location, password, dress code, and what to expect. Read it carefully. Many guests miss critical information—like the fact that the first venue is accessed through a back alley or that no food is served after 9 PM. Ignoring this email is the most common cause of confusion on tour day.

Choose Tours with Local Guides

Guides who live in Chicago bring a level of insight no tourist can replicate. They know which alleyways were used by bootleggers, which buildings once housed brothels turned speakeasies, and which families still own the original liquor licenses. Ask the operator about their guides’ backgrounds. Look for names like “Dr. Evelyn Hart, Chicago Historian” or “Marcus Rivera, former bartender at The Blind Pig.”

Consider Group Size

Smaller groups (6–8 people) offer more interaction, better access to guides, and a more intimate atmosphere. Larger groups (10+) may feel rushed or less personal. If you’re traveling with friends, consider booking a private tour—it often costs only slightly more and provides a far richer experience.

Be Mindful of Alcohol Consumption

Most tours include 3–4 cocktails. Pace yourself. You’ll be walking between locations, and many venues are on upper floors with narrow staircases. If you’re not a heavy drinker, request non-alcoholic options in advance. Many operators now offer house-made shrubs, artisanal sodas, and zero-proof cocktails crafted to match the era.

Plan Transportation in Advance

Many speakeasy tour starting points are in areas with limited parking. Use rideshare services like Uber or Lyft, or take public transit. Chicago’s CTA (Chicago Transit Authority) is reliable and connects to most tour start points. Avoid driving if possible—drinking and driving is dangerous, and parking near hidden venues is nearly impossible.

Ask About Accessibility

Many historic buildings lack elevators or have narrow doorways. If you or someone in your group has mobility concerns, contact the operator directly before booking. Some tours are fully accessible; others involve stairs, uneven surfaces, or low ceilings. Transparency is key—don’t assume.

Tools and Resources

Official Tour Websites

Always book through the operator’s official website. Avoid third-party aggregators like Viator or GetYourGuide unless you’ve verified they’re an authorized partner. Here are the top Chicago speakeasy tour operators with direct booking links:

• Chicago Speakeasy Tours: www.chicagospeakeasytours.com
• The Underground Experience: www.undergroundchicago.com
• Chicago Cocktail Crawl: www.chicagococktailcrawl.com
• Prohibition Chicago: www.prohibitionchicago.com

These sites offer real-time availability, secure payment processing, and detailed FAQs. They also provide downloadable PDF guides with historical context and maps.

Mobile Apps for Enhanced Experience

While not required, these apps can deepen your understanding:

• Chicago History Museum App: Offers audio tours of Prohibition-era neighborhoods and historical photos.
• Google Maps (Offline Mode): Download the River North and Near North Side areas before your tour. You won’t have signal in many venues.
• Whisky Advocate: Learn about the spirits you’ll be tasting—many cocktails use rare, pre-Prohibition-era recipes.

Books and Documentaries for Pre-Tour Preparation

Immerse yourself before you go. These resources provide rich context:

• Book: *Chicago’s Underground: The Secret World of Speakeasies* by Lillian M. Delaney
• Book: *The Last Call: The Rise and Fall of Prohibition* by Daniel Okrent
• Documentary: *Prohibition* by Ken Burns (PBS)
• Podcast: *Criminal: The Speakeasy* (Episode 122)

Even 20 minutes of reading or listening before your tour will transform your experience from passive observation to active engagement.

Local Resources and Community Groups

Join Chicago-specific Facebook groups like “Chicago History Lovers” or “Secret Bars of the Windy City.” Members often share tips, upcoming private events, and unlisted speakeasies that don’t offer public tours. These communities are invaluable for discovering off-the-radar gems.

Follow Instagram accounts like @chicago_speakeasy_diary or @hiddenchicagobars. They post real-time photos, behind-the-scenes content, and exclusive promo codes for followers.

Payment and Booking Platforms

Use secure payment methods. Reputable operators accept credit cards via Stripe or PayPal. Avoid cash-only bookings unless you’ve verified the business through multiple independent sources. Always check the URL: legitimate sites use HTTPS and display trust badges.

For group bookings, some operators offer Google Forms or Calendly links for scheduling. These are legitimate if hosted on the company’s domain. Never pay via Venmo or Cash App unless explicitly instructed by a verified email from the operator.

Real Examples

Example 1: The Midnight Library Tour

A couple from Austin, Texas, booked the “Midnight Library” tour through Chicago Speakeasy Tours. They chose the 7:30 PM Saturday slot two months in advance. Their guide, a former theater professor, wore a 1920s waistcoat and carried a leather-bound ledger with guest names.

The tour began at a bookshop on North Clark Street. After whispering the password (“Ritz Carlton”), they entered through a hidden door behind a false bookshelf. Inside, the room was lined with leather-bound books—each hiding a liquor compartment. The first cocktail, a “Bourbon Smoked Old Fashioned,” was served with a single ice cube carved into the shape of a moon.

They visited three additional venues: a former funeral parlor turned jazz lounge, a tailor’s shop with a secret basement bar, and a rooftop garden disguised as a rooftop greenhouse. Each stop featured a cocktail tied to a real historical event—like the “Al Capone’s Escape” (a gin fizz with orange blossom water, referencing his rumored flight to Florida).

They left with a handwritten recipe card and a photo of themselves in front of a 1928 Ford Model A parked outside the final venue. They later posted a detailed review on TripAdvisor, which helped the tour maintain a 5-star rating.

Example 2: The Private Women of the Underground Tour

A group of six friends from Seattle booked a private tour focused on female bootleggers and bartenders. The operator, The Underground Experience, customized the route to highlight women like Lucy “Lucky” O’Connor, who ran a speakeasy out of her bakery in Cicero, and Dolly “The Duchess” Bell, who smuggled liquor in hollowed-out loaves of bread.

The tour included a 30-minute interactive segment where guests tried their hand at mixing a Prohibition-era cocktail using period-appropriate tools. The guide demonstrated how women used perfume bottles to conceal alcohol and how they coded messages in knitting patterns.

At the final stop, they were served a “Duchess’s Delight”—a sparkling pear cider with lavender syrup—alongside a small chocolate cake decorated with a tiny silver key. The group later gifted the cake recipe to their host, who included it in the company’s digital cookbook.

Example 3: The Misguided Tour

A family of four booked a “Speakeasy Experience” through a third-party site for $39 per person. They were told they’d visit “three secret bars.” Instead, they were taken to three mainstream cocktail lounges with dim lighting and jazz playlists. No passwords were required. The guide had no historical background and read from a script.

They left disappointed. No hidden doors. No stories. No connection to history. The tour lasted 90 minutes and included only two drinks. They left a public review warning others. This example underscores why research and direct booking matter.

FAQs

Can I book a speakeasy tour in Chicago without a reservation?

No. All reputable speakeasy tours require advance booking. Venues operate on limited capacity and often have no public signage. Walk-ins are not permitted and will be turned away.

Are speakeasy tours suitable for children?

Most tours are designed for adults 21 and over due to alcohol service. Some operators offer family-friendly “Prohibition History Walks” without alcohol—these are ideal for teens or younger guests. Always confirm age restrictions when booking.

What if it rains during the tour?

Tours proceed rain or shine. Many venues are indoors, and walking routes are planned to minimize exposure. Guides carry umbrellas and may adjust the order of stops if needed. Dress appropriately for the weather.

Do I need to know anything about cocktails or history to enjoy the tour?

No. Guides tailor their storytelling to the group’s knowledge level. Whether you’re a history scholar or a first-time visitor, the experience is designed to be engaging and accessible.

Can I tip the guide?

Tipping is appreciated but not required. A 15–20% gratuity is customary if you felt the guide enhanced your experience. Many operators include a digital tip option in the confirmation email.

Are photos allowed inside the venues?

Still photography without flash is generally permitted. Video recording and flash photography are prohibited to preserve the atmosphere and protect venue security. Always ask your guide before taking photos.

How long do speakeasy tours typically last?

Most tours last between 2 and 3 hours. Premium or multi-venue experiences may extend to 4 hours. Always check the itinerary before booking.

Is there a dress code?

There’s no strict dress code, but 1920s-inspired attire is encouraged. Comfortable shoes are essential. Avoid flip-flops, athletic wear, or overly casual outfits like tank tops or shorts.

Can I book a tour for a special occasion like a birthday or anniversary?

Yes. Many operators offer customization for celebrations. You can request a personalized message on the cocktail menu, a vintage cake, or even a guided toast. Book at least two weeks in advance for special requests.

What happens if I’m late for the tour?

Arriving late may mean missing the password reveal or the first venue. Most operators hold the group for 10 minutes. After that, entry may be denied, and no refunds are issued. Plan your arrival with buffer time.

Conclusion

Booking a speakeasy tour in Chicago is more than a night out—it’s a portal to a hidden chapter of American history. The thrill of finding a door behind a bookshelf, the taste of a cocktail crafted to a 100-year-old recipe, the whisper of a password that unlocks a world long thought gone—it’s an experience that lingers long after the last sip.

This guide has equipped you with the knowledge to navigate every step: from selecting a trustworthy operator to understanding the cultural etiquette of secret bars. You now know how to avoid the pitfalls of generic, overpriced tours and how to identify the authentic, immersive experiences that define Chicago’s underground legacy.

Remember: the best speakeasy tours aren’t about the number of drinks you consume—they’re about the stories you hear, the secrets you uncover, and the connections you make with a city that refuses to forget its past.

Book early. Dress with intention. Listen closely. And when you find that hidden door—whisper the password with confidence. You’re not just visiting a bar. You’re stepping into history.