Best Neighborhoods for Historic Chicago Pub Crawls

We love good Chicago historic pub crawls. Just ask the guests from our Historic Chicago Walking Bar Tour. Or the 1893 World’s Fair Tour with Bars. Or the Big Shoulders Historic Bar and Food Bus Tour, which takes guests through the working-class neighborhood of Bridgeport for stops in historic bars. Seems safe to say that we think local history goes great with a drink. Needless to say we think a guided tour is the best way to experience Chicago’s historic bars, but we also encourage you to explore on your own. Thus, we created a list of the best neighborhoods for a historic Chicago pub crawl. So save this link, assemble the squad, and enjoy these Chicago historic pub crawls.

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Irving Park

deer smoking cigarette chicago holiday bar crawl
The mounted deer head with a cigarette in its lips. Hard to get more Irving Park than that. Photo by Amanda Scotese.

I am willing to stand the scorn of many and admit that I’ve always lived near the lakefront. So any trip west of the river of the freeways always feels like an exotic adventure to me. Irving Park, a Northwest Side neighborhood, has the added bonus of feeling like I’ve sort of stepped back in time. The glassy high-rises synonymous with gentrification haven’t gotten this far up the Blue Line yet. So the old neighborhood vibe, and old neighborhood bars, make this a great area for a historic Chicago pub crawl.

Start things off in The Cabin at Old Irving, the latest iteration of an Irving Park pub that dates to the ’30s. Their antique wooden cooler was the signature part of the establishment, so all the decorating makes it look like a little cabin in the big woods. It lends the place a relaxed vibe that carries through even after the drinks are really flowing.

Next up, swing over to Lizard’s Liquid Lounge. It checks all the boxes for classic Chicago neighborhood bar. Corner of a side street and thoroughfare. Cutaway entrance at the corner. Tiny little windows like its a prison. Absolutely ancient structure when you look at it without beer glasses. Stuffed animals and other random kitschy accoutrements. A dog-friendliness which verges on code violations. Check, check, check, check, check, and check. Check it out.

Finally, conclude your night at La Villa, an old-fashioned pizza and beer joint. The staff are still slinging pies and pouring brews in an environment which looks like an unused set from Goodfellas. They’re open until the witching hour (or later) on weekend nights, though you could always start the evening there as well. Either way, they’re a must for historic pub crawls in Chicago’s Irving Park.

Lincoln Park

Historic Chicago pub crawls Lincoln Park Red Lion Pub
The atmospheric interior of the Red Lion is ripe for drinking and haunting. Photo by Alex Bean.

These days Lincoln Park is the land of Trixies and Chads and historic workers cottages being demolished for new McMansions. This neighborhood is the very epitome of bougie, gentrified Chicago (to the point that I’m sometimes embarrassed to admit that I live there). That was not always the case, though. The site of the Valentine’s Day Massacre belies the fact that this used to be a working-class, bar-heavy neighborhood like Irving Park. Myriad venues here were actually speakeasies during Prohibition. So it only makes sense to include Lincoln Park in our list of good neighborhoods for historic Chicago pub crawls.

Start in Old Town, but not at the Old Town Ale House. Nothing against that iconic spot, but we want to go further off the beaten path at Twin Anchors. This neighborhood joint has been serving famous ribs with delicious drinks since 1932. The site was a tavern-turned-speakeasy for at least a generation prior to that. The venue still holds that vintage charm, with a neon sign, striped awning, wood-paneled walls, and a vibe that can only be described as classic. No wonder it was a favorite of Sinatra’s.

Keep that old-school classy vibe going by heading up to the Red Lion Pub. This British-style pub is a popular spot for the neighborhood yuppies (hello!) who don’t like the area’s many sports bars. The pub features a roaring fireplace, delicious curry, imported sour ales from old England, and endless shelves of books about the World Wars. The bar also (supposedly) boasts a wide array of ghosts, including former residents of the 1882 building, the shady former proprietor, and a terrifying female specter who traps women in the bathroom. Fun!

Historic Chicago pub crawls Lincoln Park Burwood Tap
The candy-striped awnings give away the Burwood Taps’s speakeasy past. Photo by Alex Bean.

Now wash away that classiness with a visit to Burwood Tap, a rowdy former speakeasy. Located at the corner of Burling and Wrightwood (hence the name, folks), this is the kind of place DePaul students have been getting sloshed in for eons. And for good reason! It’s a former speakeasy that went legit in 1933, holding onto random bits of memorabilia and good times in every decade since. It is also, much to my amusement, where my cousin met her husband. Probably a pretty common story in that neighborhood.


The oldest neighborhood in Chicago was, until recently, also home to the oldest bar in Chicago. Sadly, Schaller’s Pump closed in 2017, so you can no longer swig a stein with Irish politicos and meatpackers in that venue. Bridgeport has no shortage of other wonderful historic bars, though. Only appropriate, since this section of the South Side has been home to working class grunts (and their powerful political machinery) for over 150 years.

historic Chicago pub crawls Shinnicks Bridgeport
Shinnick’s is now the oldest bar in Bridgeport. Suds have been served here since the 1880s.

Start off your evening at Shinnick’s Pub. The tavern’s history (and that of the gorgeous Brunswick back bar pictured above) dates to the 1880s. The joint had different owners back then, of course. Still, some of the Irish laborers who helped construct the Columbian Exposition would have had post-work drinks in here. The Shinnick family has run the bar for three generations, first taking over in 1938. Drinking at Shinnick’s is an outstanding way to absorb the history of Bridgeport.

Come to think of it, I will refrain from suggesting further drink stops in Bridgeport. I don’t want to spoil the fun for anyone interested in signing on for our Big Shoulders Historic Bar and Food Bus Tour in Bridgeport on Sunday, September 15th. We normally only run this tour for private bookings, but wanted to share its rollicking good times with everyone for one day only in 2019. The tour includes three drink stops in Bridgeport, including a “secret” bar not open to the public, and a full meal of foods that tell the story of this changing neighborhood. I’ll see you then! You can also see more of Bridgeport on our Chicago Neighborhoods and Cultural Diversity South Side Bus Tour–give us a ring!

Northwest Side Holiday Bars

Finally, for themed neighborhood historic Chicago pub crawls, you might try hitting our favorite Northwest side spots that really go big for the holidays. Check out this video by Amanda describing classics, including the Cabin, Frank and Mary’s, and Marie’s Pizza:


Private Tour Coordinator and Tour Guide

There is no shortage of things to discover in Chicago—I love being an urban explorer and uncovering its hidden places. I have an MA in Public History from Loyola University Chicago, and I have worked as a museum educator and kindergarten teacher. My desire to learn new things fuels my passion for educating others, which I get to experience every day as a Chicago tour guide. I live in the northern neighborhood of Rogers Park.

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Whether you are a first-time visitor or a lifelong resident, the vibrant history and modern majesty of Chicago never ceases to amaze. I’m a graduate of Columbia College with an M.A. in Interdisciplinary Art. I’ve worked for many years as an educator at City Colleges of Chicago. As tour guide at Chicago Detours, I integrate my enthusiasm for culture and architecture with my passion as an educator. West Town/Noble Square area is home for me.

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With our Chicago neighborhoods, vibrant cultural institutions and nearly two centuries of larger-than-life stories, there’s never a dull moment here! I’m a fifth generation Chicagoan and a graduate of Washington University in St. Louis. In addition to guiding tours, I’m a creative writer and amateur genealogist. I also enjoy the city’s dynamic theater scene. You can also read overlooked stories from 19th-century newspapers on my “Second Glance History” blog. I live in River North.


Tour Guide

Chicago is unique as it always evolves into the future while holding on to the past. I’m fascinated by how people latch on to old architecture but happily pave over others. My background is in theater and performance and I’ve been a tour guide here for more than 10 years. Currently I’m finishing my Master’s in Public History at Loyola University because I love to teach the history of this scrappy city. I’m in the Edgewater neighborhood.


Operations Coordinator and Tour Guide

Chicago’s history is so fascinating, you could spend a lifetime uncovering its secrets…I’m willing to give it a try! I have an M.A. in US History from the University of Nevada-Las Vegas and then pursued doctoral studies in Urban History at the University of Illinois at Chicago. I love to learn new aspects of Chicago’s rich history and then share my knowledge as a tour guide with Chicago Detours. I live in Ravenswood.

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Operations Coordinator and Tour Guide

As a fourth generation Chicagoan, I have been living and loving Chicago by bike, on foot, public transit or automobile. I am a graduate of UIC where through the College of Urban Planning and Public Affairs, began my eagerness to understand the nature, history and impacts of urban planning and development. It is incredibly rewarding to give back to this wonderful city by helping out in the office of Chicago Detours. I live in the incredibly diverse neighborhood of Albany Park.
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Content Manager and Tour Guide

Chicago has so many neighborhoods, buildings, and by-ways that it’s hard to go long without seeing something new, or something familiar from a new angle. I studied Cinema History for my M.A. from the University of Chicago. I’ve worked as a culture writer for various publications and as an educator of the humanities at the City Colleges of Chicago. I’m thrilled to share my love of this city’s busy past and unique architectural spaces with Chicago Detours. I live in the Chicago neighborhood of Lincoln Park.

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Amanda Scotese

Executive Director and Tour Guide

I’m an interpreter of personal stories from the past and the city’s landscape. I love to imagine what originally happened inside old unmarked buildings, and what forces have shaped their design. I studied Chicago history, architectural history, and anything Chicago-related through my M.A. in the Humanities at the University of Chicago. My love for stories was enriched by my B.A. in Literature from the University of Michigan. I’ve written travel articles for publications like Rick Steves’ Italy best-selling travel guides, the San Francisco Bay Guardian, and The Chicago Food Encyclopedia. I live in the Chicago neighborhood of West Avondale.
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