Date Night Historic Chicago Walking Bar Tour

Date Night Historic Chicago Walking Bar Tour 

Enjoy a romantic and educational date night tour near the Mag Mile on this historic Chicago pub crawl! Exploring beautiful architectural spaces together can be such an intimate experience. You and your partner will learn about prohibition, jazz, theater, vices and social clubs. This special Valentine’s Day tour includes light appetizers and a chocolate dessert making it a perfect evening for a date night.

Our afternoon or evening walking tour stays mostly indoors, making it great for any kind of weather.  This fun date night tour is specifically about Chicago’s entertainment history. In addition to learning how Chicagoans have had good times over history, our tour groups see magnificent lobbies, Gilded Age mansions, and Chicago’s underground layers. We even see a building that was an early speakeasy and jazz club. You’ll also hear about the infamous Curse of the Billy Goat over a bite of a “cheezborger.”

On this date night tour downtown, you and your special someone will be immersed in stories of the city’s history and you’ll enjoy drinks, snacks and a dessert. Drink package includes choice of wine or beer at three drink stops and server gratuities. Drinks stops are a one-of-a-kind burger joint slash dive bar, a bar in a lavish 19th-century mansion, and our third drink stop is in the exotic surrounds of an historic Michigan Avenue hotel.

This tour is more than a historic Chicago pub crawl – you’ll eat, drink, and learn about Chicago architecture, Prohibition-era history, and party culture on this educational walking tour. In addition to the tour guide’s stories, guests view historic photos and film on iPads. Plus, the convenient Mag Mile locale makes it easy to add on another romantic experience downtown for after your tour – like a ferris wheel ride or cocktails at the Signature Room.

Our date night walking tour goes well beyond a typical historic pub crawl, and this will be a particularly special event for Valentine’s Day!

This Chicago architecture walking tour is also available as a private group tour for nine or more guests during Valentine’s weekend if you’d like to bring together a group of couples!Walking Bar Tour Highlights

Highlights

• Michigan Ave, aka “Magnificent Mile”
• Tribune Tower
• Chicago’s underground layers
• The famous Billy Goat Tavern
• A former historic jazz club and speakeasy
• A 19th-century mansion

Stories and Ideas

• Architecture as a cultural artifact
• The “Hex of the Billy Goat”
• Chicago jazz era
• History of Chicago breweries
• Prohibition and gangsters
• 1960’s swanky nightlife
• Private clubs and debauchery

Historic Chicago Pub Crawl Prices

Reservations are $36 per person. Guests bring cash for beverages. Total cost is $39-$58 per tour guest inclusive of tour, food, beer, wine, gratuities, taxes. 

Chicago Walking Bar Tour Includes:

• Engaging tour guide commentary
• Shared use of iPads with historic photos and video clips
• Appetizers
• Chocolate treat (exclusively for this date night tour)
• Special gifts
• Discounted flat-rate $15 parking at the Grant Park North Garage (ask for voucher at tour)

Tour Reservations Do Not Include:

Drinks and server gratuities. All guests must choose a beverage for the walking tour and bring cash to cover 2.5 servings of beer ($23), wine ($29), or water ($3).

Walking distance: .75 miles