A Walk Through Historic Chicago


Arts and Culture   Explore Chicago  


Chicago is a city rich with history and chock full of interesting stories. When visiting Chicago, you’ll want to hit some of the classic spots in order to best get a feel for the history and culture of the Windy City. Read on for some suggestions including favorites of Frank Sinatra, Prohibition-era speakeasies, a century-year-old theatre, and some of the oldest and most historic restaurants and pubs in the city.


Prohibition Tours

Prohibition Tours Picture Credits: Prohibition Tours


Enjoy a sip of history with Prohibition Tours. The talented and passionate guides will take you on an adventure through Chicago’s prohibition era. You’ll embark on a bus tour and visit four historical Chicago locales that operated as speakeasies during prohibition and continue to operate today. Over the course of about 3.5 hours you will get a crash course in Prohibition nationally, and then an emphasis on what was happening in Chicago, all the while sipping on some of the most delicious beverages the city has to offer. If you love drinks and discussions, this is the tour for you.


Longman & Eagle

Longman & Eagle Picture Credits: Clayton Hauck


Drinking in Chicago has multiple origins, the most influential and oldest of which is the inn – an establishment that offered to drink, eating and sleeping options. The Longman & Eagle is a look back, reimagining this age-old concept through a contemporary lens, providing urban ‘travelers’ a refuge that appeals to a variety of senses – be they aesthetic, consumptive, culinary or restorative – done in a way that is accessible, considered and innovative. The sort of place where a man can get a shot with breakfast, where local politicians might trade votes for whiskey, and one that reflects Chicago’s unique neighborhood-based diversity, the Longman & Eagle is a must-see stop on your Chicago itinerary.



Billy Goat Tavern

Billy Goat Tavern Picture Credits: Billy Goat Tavern


The Billy Goat Tavern is the stuff of local legend. The original Billy Goat Tavern location was “born” in 1934 when Greek immigrant, William “Billy Goat” Sianis, purchased the Lincoln Tavern. Sianis became known as “Billy Goat,” when a goat fell off a passing truck and wandered inside. Sianis adopted the goat, grew a goatee, acquired the nickname “Billy Goat,” and changed the name of the bar to the Billy Goat Tavern, a classic ever since.

Now with several locations around Chicago, as well as one in Concourse A of the airport, you’ve got plenty of opportunities to check out a little bit of Chicago history. If you visit, be sure to grab one of their famous Cheezborgers – a Chicago classic cooked up with delicious, thin 100% beef patties, cheese, and their famous Kosher Dill Pickle Cheeps (made exclusively for the Billy Goat). You won’t find any lettuce or tomatoes on this cheesy extravaganza – the goat probably ate them all.



Twin Anchors

Twin Anchors Picture Credits: Twin Anchors


Located in a historic Old Town building that dates back to 1881, Twin Anchors Restaurant & Tavern is one of the oldest restaurants in the city of Chicago. Since its founding in 1932, Twin Anchors has always been known for great, tender, barbequed baby-back ribs that can be enjoyed in a quaint neighborhood tavern.

The historical building has been the location of some kind of tavern since as early as 1910 including a Prohibition-era speakeasy known as “Tante Lee Soft Drinks” that provided refreshments for the “thirsty” in this location. The Twin Anchors is a staple of Chicago history. Twin Anchors was a favorite of Frank Sinatra and more recently culinary great Emeril Lagasse and late night TV host Conan O’Brien. If you want to get to know true historic Chicago, you’ve got to swing through the historic Twin Anchors.


Goodman Theatre

Goodman Theater Picture Credits: Goodman Theatre


A historical-cultural icon and a leading regional company, Goodman Theatre is the oldest and largest not-for-profit theatre in Chicago. The proud recipient of the Special Tony for Outstanding Regional Theatre, it has been captivating audiences since it was originally established in 1922.

Delivering upon their mission of arts as education under the direction of Artistic Director Robert Falls and Executive Director Roche Schulfer, they host a revolving selection of shows at the high level of quality they have been internationally recognized for. They even offer youth and adult programs for those looking to learn about the craft and actually take part in the stunning work they do there! Don’t miss out on a chance to see a phenomenon that’s been part of the Windy City for almost 100 years!

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About the Author: Keith Perrotta

Keith is a freelance writer, English teacher, baker, and travel junkie currently based in Madrid, Spain. When not creating content or teaching ESL he enjoys going to the beach, researching bread recipes, looking through bookstores, and relaxing with a glass of wine. Having lived in the USA, France, Ghana, Kenya, and now Spain, his main goal in life is to visit every continent once (including Antarctica). You can usually catch him eating ice cream in the park or stopping someone in the street to ask to pet their dog.

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