Three Cheers for These Historic Bars Near the Mag Mile

Guests on our Historic Chicago Walking Bar Tour often ask for the guides’ recommendations for other historic bars near the Mag Mile. So we polled the guides and decided to share the Detours crew’s favorite spots. Of course some of the coolest historic bars in the Mag Mile area are featured on our bar tour, and you won’t see them included on this list. You can register for a public tour or book a private group tour to hear all the hidden stories we dug up about those historic drinking spots while you sip your beer or wine. After you’ve taken our tour, here are a few more historic bars near the Mag Mile you can check out.

#1. Harry Caray’s

Harry Carray's historic bars near the mag mile
Harry Caray’s is one of our favorite historic bars near the Mag Mile. Photo courtesy of Harry Caray’s.

This quirky-looking structure contains over 100 years of Chicago history, with ties to Gilded Age industry, Prohibition Era gangsters, and the Chicago Cubs. Nowadays it’s Harry Caray’s, popular sports bar and steakhouse. Named after the late (and deeply beloved) baseball commentator, this historic bar near the Mag Mile has served satisfied Cubbies fans since 1987. Curse of the Billy Goat aficionados know this as the spot where the infamous Bartman baseball was blown up.

The structure dates to 1895, when it was the headquarters for the Chicago Varnish Company. Its unique architecture is the work of Henry Ives Cobb, Chicago’s Gilded Age master of Romanesque and Gothic revival. He broke out of his typical style here with Dutch Revival architecture, with its steeply-pitched gables and tiled mansard roofs. This ornate style is a rarity in Chicago, making this one of those most visually striking buildings near the Mag Mile.

Harry Caray’s also has some surprising ties to the always-exciting gangster history of Chicago. Al Capone’s fearsome mob enforcer Frank Nitti lived in the building during the 1920s. Secret tunnels in the basement allowed Nitti and his associates to sneak in and out of the building undetected. In 1998, an electrician uncovered a hidden room in the building, containing items from Nitti’s criminal dealings like his personal safe. You can get a taste of that illicit past by ordering a drink in Nitti’s Speakeasy on the building’s second floor. That element really cinches it as one of the best historic bars near the Mag Mile.

#2. Rossi’s

Rossi's River North historic bars near the Mag Mile Chicago
Rossi’s is an old-fashioned dive located in an ancient River North building. One of the most unique historic bars near the Mag Mile, for sure. Photo by Alex Bean

You can find lots of historic bars near the Mag Mile, but no others quite like Rossi’s. A dive bar in a building that is positively ancient by Chicago standards, Rossi’s Italianate building must date to the 1870s or ’80s. It feels like a real time warp to the 1970s though. In fact, Rossi’s looks, feels, and acts like the past forty years never happened. In fact, no one seems to even know when Rossi’s first opened. According to the Chicago Bar Project, their all-star bartender Desiree has been serving cheap beer and handling rowdy patrons since the ’80s. Yet she acknowledges that the bar was around well before she was hired.

Regardless of its mysterious provenance, Rossi’s feels like a blast from the past. This little stretch of State Street is one of those rundown blocks that still exist in downtown (like Little Cheyenne) that seem frozen in time. Rossi’s is the sort of place working men would have popped into for liquid strength on their lunch break back when River North still had, ya know, blue collar industrial jobs. Unlike today. Seriously, how is this place still around?!

You can pop in for a cheap draft beer or opt to buy a six pack from the fridge and carry it home. Don’t expect to order any grub, though – this is one of the only historic bars near the Mag Mile with no kitchen.

#3. Watershed

One of the more atmospheric historic bars near the Mag Mile is in a basement. Specifically, the basement of Pops for Champagne in the old Tree Studios on State Street. There you’ll find Watershed, a basement bar that only serves drinks from the Great Lakes region. (Hence the watershed name – you get it.) Watershed has only been around since 2010, but the venue has more than enough history to deserve inclusion here.

The Tree Studio buildings date all the way back to 1894 when local judge Lambert Tree established an artists’ colony. The historic cast iron storefront facade on State and lofted studio spaces above were built in the backyard of Tree’s mansion. By the Roaring Twenties, the Tree Studios were the beating heart of a vibrant Bohemian district named Tower Town. Think something like a Midwestern Montmartre and you’re on the right track.

Today, the Tree Studio buildings are home to architects, artists, offices, boutique shops, and, of course, historic bars. Pops for Champagne has been manning that Ohio and State corner spot for decades. Watershed replaced the jazz club which had previously been in their basement space. It’s a great spot to grab some after-work drinks and admire Prairie School architecture before heading to dinner.

The Pleasure of Historic Bars Near the Mag Mile

historic bar tour laughing guest
You have more fun when you’re learning… and drinking. That’s our motto. Photo by Pawel Skrabacz

Like I said up top, we created this list because our guides are so often asked where to go next at the end of the Historic Chicago Walking Bar Tour. For both visitors and locals, the Mag Mile area doesn’t seem like a likely venue for such historic spots. Its image is so glamorous and contemporary that it’s easy to overlook the neighborhood’s past. The shopping district only really came into existence after World War II, though. Which means there’s plenty of history around if you know where to look for it.

– Alex Bean, Content Manager and Tour Guide


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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.

“Our guide Ellen was exceptional and gifted with a great personal touch.”


Tour Guide

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.

“Jen was a perfect storyteller and kept us spellbound for hours.”


Tour Guide

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.

“Marie was a bubbling fountain of information and contagious enthusiasm.”


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.
“Sonny was extremely knowledgeable about all things Chi-town.”
Wade K


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.

“Alex was fascinating to listen to. He clearly knows his history and it shows.”
Katie K

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.
“You can TELL Amanda is hyper-passionate about doing the research and getting the story that nobody’s heard before.”
Shelby F

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