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Toast of the Town-Seasonal Cocktail Tour

Chicagoeasy

Difficulty

easy

Duration

2–3 hours

Fitness Level

Suitable for most fitness levels, as walking distances between bars are moderate and at a comfortable pace.

Overview

Explore the rich history behind the city’s most iconic cocktails on Bulldog Tours’ Toast of the Town-Seasonal Cocktail Tour. Sip your way through seasonal flavors while discovering captivating stories and hidden local gems.

Details

Experience the perfect fusion of history and flavor on Bulldog Tours’ Toast of the Town-Seasonal Cocktail Tour. This private history tour offers a unique chance to explore the cultural roots and tales behind some of the city's most iconic cocktail bars. Each stop highlights seasonal ingredients, local mixology craftsmanship, and historical anecdotes that enrich the experience beyond just a drink. Guests get to sip expertly crafted cocktails inspired by the city's past while strolling through vibrant neighborhoods teeming with stories. This intimate tour is ideal for those who appreciate both heritage and unique flavors, making it a must-try for history buffs and cocktail enthusiasts alike. Walking from one venue to another allows you to absorb the local atmosphere, meet passionate bartenders, and discover hidden gems that don’t often appear in typical guides. Whether it’s learning about prohibition-era secrets or how specific recipes evolved over time, the tour brings the city’s past to life in a lively, tasteful way. From the casual sipper to the seasoned cocktail lover, everyone finds something memorable here. Bulldog Tours’ expert guides ensure a personalized experience with attention to safety, comfort, and enjoyment in every step and sip.

Adventure Tips

Stay Hydrated

Drink water between cocktail tastings to stay refreshed and enjoy the entire tour safely.

Wear Comfortable Shoes

Expect light walking between venues, so wear shoes that support prolonged standing and strolling.

Bring a Valid ID

You must be 21+ to participate and enjoy alcoholic beverages on this tour.

Keep an Open Mind

Try seasonal cocktails and flavors you might not usually choose to fully embrace the experience.

Local Insights

Hidden Gems

  • A historic speakeasy with original 1920s decor
  • A small craft distillery producing unique seasonal spirits

Wildlife

  • Urban peregrine falcons
  • Squirrels in nearby parks

History

The tour explores cocktail culture influenced by Prohibition-era history and the city's role in shaping modern mixology.

Conservation

Bulldog Tours emphasizes supporting local businesses and encourages minimizing waste by using reusable glasses and sustainable ingredients.

Frequently Asked Questions

Photography Tips

Best Times

Golden hour
Early evening
Late afternoon

Best Viewpoints

  • Historic bar interiors with vintage decor
  • City streets with vibrant murals
  • Outdoor patios with skyline views

What to Photograph

Signature cocktails
Architectural details
Local bartenders in action

Recommended Gear

Comfortable Walking Shoes

Essential

Supportive footwear helps you enjoy the strolls between cocktail stops without discomfort.

Light Jacket or Sweater

Spring evenings can get cool, so an extra layer ensures comfort.

spring specific

Sunscreen

Protect your skin during outdoor patio stops on sunny summer days.

summer specific

Valid Photo ID

Essential

Required for alcohol service verification at all venues.

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