Self-Guided Tour: Tom’s Ultimate Pub Crawl

Self-Guided Tour: Tom’s Ultimate Pub Crawl

5 Neighborhoods, 11 bars, 3.7 miles on foot

Tom on a Chicago Pub Crawl

This Chicago pub crawl requires pacing and a bit of stamina, no doubt about it.  But it is a beautiful walk. On this walk, you’ll see North Michigan Avenue, the Rush Street entertainment district, Old Town, DePaul, Lincoln Park, and Lakeview.

Happy pubbing (or crawling, as the case may be).

If you’d like a guide to take you through a similarly historic pub crawl, then consider booking our Chicago pub tour this spring and summer! For other adventures, take a look at our other Chicago Tours.


Tour Origins

When I was in my early twenties, I worked in an office on North Michigan Avenue near the Wrigley Building.  My home at the time was in East Lakeview — 3.7 miles north of the office.

Tom's Ultimate Chicago Pub CrawlEvery day after work I had a difficult transportation decision to make in order to get home — take the L (usually too crowded), take the bus (generally too slow), or take a cab (always too expensive).  There were no ride-sharing businesses in those days and even if there had been, we didn’t have smartphones with which to initiate an order. Many evenings I chose to walk home, a journey that would take about one hour and 15 minutes if no stops were made along the way.

When I wasn’t in a hurry to get home, I’d take my sweet time and make all kinds of stops on the way home. The best walks were those where I explored the many bars, taverns, and saloons that populated my meandering path home.  After much trial and error, I developed a sacred list of favorite establishments — a list that I would later describe as “The Ultimate Pub Crawl.”  It was a wide array of drinking establishments — old standards, singles bars, places with happy hour and appetizer specials, bars with 4 a.m. licenses, and many more.  Literally, a cornucopia of drinking joints.

Although many of my favorites vanished long ago, the vast majority of “Ultimate Pub Crawl” joints are, incredibly, still in business 40 years later — a testament to their stamina and staying power. Here, in proper order, is the “Ultimate Pub Crawl” — drinking establishments that were popular in or around 1980 and are still going strong today.

Take a look at the map below for an itinerary of pubs, bars, and lounges for you and your group to explore. Like our other Chicago walking tours, this map of some of Chicago’s most iconic bars takes you to historic and unique establishments that only come from knowing a lifelong Chicago native.


Tom’s Ultimate Pub Crawl – Self Guided Map


Duration: 2-4 Hours

Price: Free

  • Best Days: Weds, Thurs, Fri
  • Best time to start: late afternoon
  • Before you begin: We recommend checking bar hours ahead of time as they do change
  • Getting Around: Walk or Ride the Red, Purple or Brown Line trains
Self-Guided Tour: Tom’s Ultimate Pub Crawl Logo

Recommended Stops

  • Billy Goat Tavern
  • Pippin's Tavern
  • Hangge Uppe
  • Butch McGuire's
  • The Lodge
  • Old Town Ale House
  • Marge's Still
  • Kincaide's Bar and Grill
  • Glascott's Groggery
  • Budwoord Tap & Durkins