Chicago Speakeasy Tour Limo | Hidden Bar Chauffeur Routes

Chicago has a real speakeasy scene — actual hidden entrances, password-required reservations, and prohibition-era cocktail bars that take their craft as seriously as their secrecy. Royal Carriage Limo runs custom speakeasy tour itineraries for date nights, anniversary celebrations, bachelorette and bachelor parties, and corporate offsites looking for something more interesting than the Loop sports-bar standard.

Chicago Speakeasy Tour Pricing

Vehicle	Capacity	4-Hour Rate	6-Hour Rate
Cadillac Escalade SUV	1-6	$560	$800
Mercedes Sprinter	14	$760	$1,080
Stretch Limousine	8-10	$695	$895
30-Passenger Party Bus	30	$1,395	$1,795

Includes chauffeur, fuel, tolls, water, and 20% gratuity. Cocktails are paid separately at each bar.

Top Chicago Speakeasies

The Library at the Drake

Ground-floor of the Drake Hotel (Gold Coast). Old-school clubby room, classic cocktails, fireplace.

The Office at The Aviary

Hidden behind a panel inside The Aviary (Fulton Market). Reservation-only, the most ambitious cocktail program in the city.

The Drifter

Below Green Door Tavern in River North. Vaudeville-themed; tarot-card menu (yes, really).

Untitled Supper Club

Hidden basement in River North. Three rooms, jazz Tuesdays, 400+ whiskey bottles.

The Violet Hour

Wicker Park. Velvet drapes, no sign, strict cocktail-respect rules. The OG craft-cocktail bar in Chicago.

Room 13

Hidden inside Old Crow Smokehouse in River North. Prohibition decor, jazz on Friday nights.

The Berkshire Room

Inside the Acme Hotel (River North). Classic cocktails, hotel-bar atmosphere with a hidden-room feel.

Watershed

Lincoln Park, behind a brewery. Cocktails plus a strong wine list.

Sample Speakeasy Tour Itinerary

Time	Stop
7:00 PM	Pickup at home
7:30 PM	The Violet Hour (Wicker Park) — start with a classic Sazerac
9:00 PM	The Drifter (River North) — tarot-card menu, vaudeville room
10:30 PM	The Office at The Aviary — reservation-only fine-dining cocktails
12:00 AM	Untitled Supper Club — late-night jazz, 400 whiskeys
1:30 AM	Drop-off home

We customize entirely — sub Watershed for The Drifter, finish at Room 13 instead of Untitled, build a date-night two-stop instead of a four-stop crawl.

Why a Limo for Speakeasy Night

• Reservations are tight — chauffeur drops at the front door, no parking-circle delays
• Hidden entrances are easier with directions — chauffeur knows where every door actually is
• Multiple cocktails over 4-5 hours means responsible transport is mandatory
• No coat-check juggling — coats stay on the limo
• Privacy — the ride between bars is part of the night

What Royal Carriage Provides

• Reservation help — we know which speakeasies need 2 weeks lead time
• Discreet drop-off — chauffeur stops where the entrance actually is, even when there's no sign
• Climate-controlled wait — chauffeur stays curbside between bars
• Late-night chauffeurs — no early cutoff; we run until 2 AM and beyond if booked

Booking Lead Times

• The Aviary / The Office: 30-60 days advance reservation
• The Violet Hour: 7-14 days for a Friday/Saturday booking
• Limo booking: 7-14 days for Saturday nights
• Bachelor / bachelorette weekend: 30+ days

Why Royal Carriage for Speakeasy Tours

• Local nightlife knowledge — we know which bars are actually quality vs. tourist-trap
• Patient chauffeurs — willing to wait through long cocktail-mixing
• Reliable late-night — we don't end the booking at midnight
• Insured for late-night urban driving

Pair with our bourbon tour Chicago limo and bachelor party transportation coverage for combined cocktail-themed weekends.

Reserve Your Speakeasy Tour

Call (224) 801-3090 with the date, group size, and 3-5 speakeasies of interest. We build the route, suggest reservation timing, and lock the chauffeur. Saturday nights book first.