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Date Night Historic Walking Bar Tour – Feb 15

Eat, drink and learn about architecture and party times of Chicago history!

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!


In business since 2010, we are proud to be a top-rated Chicago tour company with five-stars on Yelp and TripAdvisor. Many of our Chicago architecture walking tours integrate historic bars, food, and music history. We hope you’ll join us to explore stories and places locals don’t even know, both downtown and in Chicago neighborhoods!

Got a time conflict? You can always book a spot on the regularly-scheduled Historic Chicago Walking Bar Tour. It runs at 5:45pm on Fridays and 3pm on Saturdays.

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!


2.5 Hours


.75 Miles


$42, plus optional drink package

  • Days & Times

  • Saturday, Feb 15


  • See the secret side of Michigan Ave, aka "Magnificent Mile"
  • Step into the opulent interior of a Jazz Age hotel
  • Enjoy drinks in a Gilded Age mansion
  • Descend into Chicago's underground layers
  • Snack on a “cheezborger” in the famous Billy Goat Tavern
  • View a former historic jazz club and speakeasy

Stories & Ideas

  • Architecture as a cultural artifact
  • The “Curse of the Billy Goat”
  • Jazz Age Chicago
  • History of Chicago breweries
  • Prohibition and gangsters
  • 1960s swanky nightlife

Tour Includes

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

Tour Reservations Do Not Include:

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

Vegetarians are easily accommodated for appetizers. Gluten-free and/or vegan have lighter apps.

Tour Location

Walking tour begins inside Fannie May Candies, 343 N. Michigan Ave.
We end inside the Intercontinental Hotel, 505 N. Michigan Ave.

Book Now


Call: 312.350.1131
E-Mail: [email protected]