Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

Chicago’s old speakeasies come with more than a password and a cocktail. This private evening tour takes you through secret entrances to three or four working bars tied to the city’s Prohibition-era past, with stories of bootlegging, racketeering, gangsters, and bank robbers along the way.

I like two things here: you get a private guide who can adapt the history to your interests, and a chauffeur handles the ride between venues. The chance to enter through hidden passages and see bars preserved in their original condition adds a sense of place that a lecture or themed cocktail lounge cannot match.

The main consideration is cost. At $950 for up to five people, the tour makes the most sense for a full group, and drinks are extra. It is also not suitable for anyone under 21 or for people with mobility impairments.

• Three to four working speakeasies: Expect real venues, not just a history talk or a single themed bar.
• Secret entrances: The tour includes entry through hidden passages, a fitting way to meet the city’s Prohibition past.
• A guide who can adjust the focus: Kai shifted the balance toward gangster and Chicago history when asked.
• Private chauffeured transport: A luxury sedan, SUV, Sprinter, or mini coach may be used, depending on group size.
• Drinks are pay-as-you-go: Your guide can recommend period-inspired cocktails, but the cost of alcohol is not included.
• A set time window: Three hours covers transport, stories, and visits to several venues, so the pace will keep moving.

A secret entrance into Chicago’s Prohibition years

The tour’s central appeal is the chance to visit working speakeasies through secret entrances. These are not simply bars dressed up with a few old-fashioned props: some have been preserved in their original condition, and the tour connects their atmosphere to Chicago’s Prohibition years.

You’ll hear about bootlegging and racketeering, along with the gangsters and bank robbers associated with the era. The history gives context to the drinks and rooms, rather than leaving you to guess why a hidden doorway matters. If you enjoy a city story with its cocktail, this is a more engaging way to spend an evening than moving from bar to bar without a guide.

The stops are not named in the tour details, and the exact venues may vary. You should expect three or four speakeasies, but don’t book with one particular bar or a specific gangster connection in mind. The appeal is the combination of several working venues, hidden entrances, and a guide who links them to Chicago’s past.

Three or four stops, with time to listen and look around

Over three hours, your group visits three to four speakeasies. The stops are the heart of the evening, but this is also a guided history tour, so expect the guide to spend time explaining the Prohibition-era stories behind the places and cocktails.

At each venue, you can buy drinks and ask for recommendations drawn from the period. The cocktails are not included in the price, so factor in extra spending if you plan to order at every stop. You are there to hear about the drinks and the people who ordered them, not to receive a tasting flight as part of the ticket.

The tour does not provide a minute-by-minute schedule or specify how long you’ll stay at each bar. With several stops and transportation between them, the pace is likely to be purposeful. If you prefer a long, unhurried evening at one venue, this format may feel too brief. If you want to see several places and get the city’s story along the way, the variety is a plus.

Some venues are described as preserved in their original condition. That can make the setting feel more connected to the past than a modern bar with a Prohibition theme, though the tour does not promise that every room or feature is original. Go for the combination of historic atmosphere and guided context, not a museum-style examination of period interiors.

Ask for the history you want to hear

The guide can shape the evening around your interests. Kai, one of the guides who has led the tour, adjusted the balance when a group asked for more Chicago and gangster history instead of focusing mainly on the speakeasy stops. That is a useful point for anyone who wants context rather than a quick succession of cocktail bars.

You can make your preference clear early. Tell your guide if you’re especially interested in gangsters, bootlegging, or the city’s wider history. The tour includes a historian, and the guide’s recommendations are part of the experience, so a little direction from you can help set the tone.

Alan has also led the tour. He was described as kind, funny, and good at making the evening enjoyable for a group. Those names give you a sense of the guides who have hosted it, but they are not a promise that either person will lead your departure. The available information lists English and Chinese as tour languages.

A private ride keeps the evening together

Hotel pickup and drop-off are included anywhere within Chicago city limits. You travel between stops with a chauffeur, rather than having to arrange separate rides or keep your group together on public transit. That is particularly handy when the evening includes several drinks and unfamiliar addresses.

The vehicle depends on group size. Options include a Mercedes S 550 sedan, Cadillac Escalade, Mercedes Sprinter, or mini coach bus. The experience is described as luxury transportation, but the exact vehicle is not guaranteed in advance. For a group of five, the larger vehicle options may be more comfortable than a sedan, depending on what is assigned.

The chauffeur’s gratuity is included. The tour guide’s gratuity is not, so budget separately if you choose to tip your guide. It is a small distinction worth knowing before you book.

What $950 buys your group

The price is $950 for a private group of up to five. At the maximum group size, that works out to $190 per person before drinks and any guide tip. If fewer people join, the total price stays the same, so the per-person cost rises. For two people, for example, you are paying for a private experience rather than a shared group tour.

That price covers three hours with a guide, entry to three or four working speakeasies, luxury transport, and hotel pickup and drop-off within city limits. The chauffeur’s gratuity is included as well. Alcohol is available for purchase at the venues but is not included, so the final cost depends partly on what you order.

I’d judge the value by how much you want the private format. You are paying for your own guide and vehicle, the ability to request a different historical emphasis, and a coordinated evening across several venues. If you mainly want a cheap drink in an old bar, this is an expensive way to get one. If you’re sharing the cost with a full group and want transport and storytelling built in, the price is easier to justify.

Practical details before you book

Bring a passport or ID card, as well as a driver’s license. Sleeveless shirts are not allowed, so choose a top with sleeves rather than finding out at the door. The tour is for people 21 and older and is not suitable for people with mobility impairments.

The pickup area is limited to Chicago city limits. If you are staying outside the city, confirm that your address qualifies before counting on hotel pickup. The tour lasts three hours, and starting times depend on availability.

The operator offers free cancellation up to 24 hours in advance and a reserve-now, pay-later option. Those terms can help if your plans are still shifting, but check the current details when choosing a date.

Who will enjoy this private speakeasy tour

This tour is a strong fit for a group of friends, a couple celebrating a special occasion, or anyone who wants Chicago history served with a drink. It suits people who enjoy listening to stories and visiting several bars in one evening. The private format is especially useful if your group has a shared interest, since you can ask the guide to give more attention to the subjects you care about.

It is less appealing if you want an inexpensive night out, dislike moving between venues, or would rather spend the whole evening in one bar. You should also look elsewhere if anyone in your party is under 21, has a mobility impairment, or would be uncomfortable with the dress restriction.

Should you book it?

Book this tour if you can fill most of the five-person group, value private transport, and want a guide to connect Chicago’s speakeasies with the Prohibition-era stories behind them. The hidden entrances and working venues make it more than a standard history walk, while the private guide gives you room to ask for more gangster history or a different emphasis.

Skip it if your priority is low cost, included cocktails, or a slow evening at a single bar. For the right group, though, the mix of secret entrances, local history, and chauffeured travel makes a memorable way to spend three hours in Chicago.

FAQ

How long is the tour?

The tour lasts three hours.

How many speakeasies does the tour visit?

The tour includes entry to three or four working Chicago speakeasies.

Are drinks included in the price?

No. Alcohol is available for purchase at the venues, but drinks are not included.

What is the price for a group?

The price is $950 per group of up to five people.

Is the tour private?

Yes. It is a private group experience.

Is transportation included?

Yes. Luxury transportation is included, with a chauffeur between stops.

Can I be picked up at my hotel?

Pickup and drop-off are included anywhere within Chicago city limits.

What languages are available?

The tour is offered in English and Chinese.

What should I bring?

Bring a passport or ID card and a driver’s license.

Is the tour suitable for children or people with mobility impairments?

No. It is not suitable for people under 21 or people with mobility impairments.