Chicago's cocktail scene goes deep: craft bars in every neighborhood, tiki rooms with exotic ingredients, hotel bars with classic-cocktail programs, and dive bars that mix a real Old Fashioned. Meridian Fleet Chicago runs full-evening cocktail tour itineraries: 4-5 stops, chauffeur waits between bars, group of 6-30 friends rolling together without anyone driving.
Chicago Cocktail Tour Pricing
| Vehicle | Capacity | 4-Hour Rate | 6-Hour Rate |
|---|---|---|---|
| Cadillac Escalade SUV | 1-6 | $560 | $800 |
| Mercedes Sprinter | 14 | $716 | $1,080 |
| Stretch Limousine | 8-10 | $656 | $895 |
| 26-Passenger Party Bus | 26 | $1,080 | $1,620 |
Includes chauffeur, tolls, and water, with no gratuity added. Drinks paid separately at each bar.
Top Chicago Cocktail Bars
Craft Cocktail Standards
- The Violet Hour (Wicker Park), strict cocktail-focused, the OG
- Billy Sunday (Logan Square), smaller-format cocktails, top program
- The Whistler (Logan Square), cocktail-and-music venue
- Sportsman's Club (Ukrainian Village), neighborhood-cool craft bar
Hotel Cocktail Bars
- The Library at the Drake (Gold Coast), clubby, classic
- The Berkshire Room at the Acme Hotel (River North)
- Cherry Circle Room at the Chicago Athletic Association, Adams Street, classic Chicago
- Bar Allegro at the Pendry Chicago (Loop), Italian aperitivo program
Tiki and Exotic
- Lost Lake (Logan Square), top-tier tiki, reservation usually required
- Three Dots and a Dash (River North), large-format tiki, group-friendly
- The Bamboo Room at Three Dots, reservations-only smaller tiki room
Late-Night & Dive
- Delilah's (Lincoln Park), 800+ whiskey bottles, no attitude
- Map Room (Bucktown), beer + cocktail, neighborhood dive
Fine-Dining Cocktail
- The Aviary (Fulton Market), reservation-only cocktail experience
- The Office at The Aviary, hidden room inside The Aviary
Sample 5-Stop Cocktail Tour Itinerary
| Time | Stop | Order This |
|---|---|---|
| 7:00 PM | The Violet Hour | Old Fashioned |
| 8:30 PM | Three Dots and a Dash | Three Dots and a Dash (the namesake) |
| 10:00 PM | Lost Lake | Bunny's Banger |
| 11:30 PM | Billy Sunday | Whatever the bartender suggests |
| 1:00 AM | Delilah's | Bourbon flight |
| 2:00 AM | Drop-off home |
We customize completely, five tiki stops, four hotel bars, or a mix.
Why a Limo for Cocktail Touring
- Five drinks across five bars means responsible transport is mandatory
- No coat-check juggling, coats stay onboard
- No parking math, Chicago neighborhood-bar parking is a war
- Reservations are easier with door-to-door drop-off
- Group photos at each stop
What Meridian Fleet Provides
- Reservation help. We know which bars need 7-14 days advance booking
- Late-night chauffeurs, booking runs to 2 AM and beyond when needed
- Patient curbside waits, chauffeur stays at the bar entrance during your stop
- Climate-controlled cabin, cool in summer, warm in winter
- Bottled water onboard, between-cocktail hydration matters
Booking Lead Times
- The Aviary / Lost Lake: 14-30 days advance reservation
- The Violet Hour, Billy Sunday: 7-14 days for Saturday
- Limo booking: 7-14 days for Saturday nights
- Bachelorette / bachelor weekend: 30+ days
Why Meridian Fleet for Cocktail Tours
- Knows the neighborhood-bar geography, Logan Square to Wicker Park to River North is a 90-minute Uber loop without a chauffeur
- Patient and discreet. Late-night cocktail crawls run long
- Reliable, chauffeur stays the full booking; no early cutoff
- Insured for late-night urban driving
Pair with our bourbon tour Chicago limo and speakeasy tour Chicago limo for combined cocktail-and-spirits weekends.
Reserve Your Cocktail Tour
Call (224) 801-3090 with the date, group size, and 3-5 bars of interest. We send a quote, suggest the route order, and lock the chauffeur. Saturday nights book first.
Related Reading
Ready to book?
Next step: Chicago limo service · Book online · Call (224) 801-3090
Upfront fares, professional chauffeurs, 24/7 dispatch across Chicagoland.
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Meridian Fleet Editorial Team
Covering Chicago luxury transportation since 2024
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Frequently Asked Questions
How do I book a ride with Meridian Fleet?+
Book online at meridianfleetchicago.com/book-now for instant confirmation, or call (224) 801-3090. A 40% deposit (or full payment) at booking secures your reservation. Free cancellation 3+ days before pickup.
What areas do you serve?+
All of Chicago and suburbs within 60 miles, including O'Hare, Midway, North Shore, western suburbs, and Indiana border towns. Long-distance trips to Milwaukee, Indianapolis, and downstate Illinois available.
Are your rates quoted upfront or metered?+
All rates are quoted upfront and locked at booking. Weekday savings Mon–Thu, no surprise charges. Fares are upfront: tolls are not included, no gratuity added. The price you see is the price you pay.
Ready to Book Your Ride?
Chicago luxury transportation, upfront rate, available 24/7. Instant online quotes, weekday savings Mon–Thu.

