Exploring Chicago, Illinois in One Day with Anthony Bourdain

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Anthony Bourdain speaking on stage

In his Travel Channel series, “The Layover,” the late Anthony Bourdain observed, “Most layovers in the great city of Chicago are involuntary.” Over the years, more than one ranking has named Chicago’s two international airports, O’Hare and Midway, as the nation’s worst for flight delays. On the bright side, if you do get stuck in this metropolis of the Midwest, there’s arguably no better place to be than such a dynamic city. You might even want to purposely arrange a long layover there after seeing the delicious food Bourdain ate when he spent 43 hours in Chicago on “The Layover.”



The two-season series was itself a sort of layover between Bourdain’s longer-running, more well-known travel shows, “No Reservations” and “Parts Unknown.” In each episode, he only had 24 to 48 hours to spend in a given place. Yet the camera got around this by cutting away from the main action, with Bourdain throwing out ideas in voice-over for other locations across town that the viewer might visit.

When he checked into the Four Seasons Hotel, for instance, he also recommended the more affordable Chicago inn, Longman and Eagle, which has a pub on the premises that’s featured in the Michelin Guide. We’ll follow a similar technique here as we retrace Bourdain’s steps through the Windy City. You may not have time to visit every one of the places he recommended, but they’ll at least get you started on what to do during a short Chicago stay.

Three square meals in Chicago

Jimmy's Red Hots dogs toppings

The Original Jimmy’s Red Hots / Facebook



For those who associate deep-dish pizza with Chicago, Anthony Bourdain was quick to dismiss it (and diss it) as an “appalling” culinary invention. The flip side of that was his love for the Red Hot, a Chicago-style hot dog loaded with toppings — anything but ketchup. Around the 30:51 mark in this episode of “The Layover,” he calls the Red Hot “the finest example of hot dog on the planet.” Jimmy’s Red Hots, more recently visited by Drew Barrymore, is the place where Bourdain scarfs down one of those all-beef frankfurters, discussing the importance of steamed buns.

An alternate lunch option, if you only have one day in Chicago, would be Italian beef at Johnnie’s Beef. This kind of dipped sandwich with peppers and roast beef is another local specialty that Bourdain saves for his last meal in town on “The Layover.” He later named Johnnie’s and Girl & the Goat as two of his favorite Chicago restaurants. The latter dishes out globally-inspired cuisine and is run by Stephanie Izard, the first woman to win Bravo’s “Top Chef.” It opens at 4:30 p.m. every day, so it might be a good dinner choice.

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Bourdain opts for a light breakfast at The Doughnut Vault, but for those with a heartier appetite, he recommends the Sweet Maple Cafe. Its menu, which offers things like home fries and country scrambles, could be a perfect way to prep for a music lover’s road trip from Chicago down through the South.



Other places Bourdain visited in Chicago

Billy Goat's Tavern exterior Chicago

Billy Goat Tavern / Facebook

Some of the other Chicago eateries Anthony Bourdain spotlights in “The Layover” are Urbanbelly, The Publican, and Publican Quality Meats. He also devotes ample screen time to neighborhood bars and taverns, including The Hideout. One bar, Old Town Ale House, showed up again in “Parts Unknown,” as owner Bruce Elliot added a portrait of Vladimir Putin in a tutu to his wall of indecent political art. Legendary film critic Roger Ebert used to drink there; his old TV co-host, Richard Roeper, is one of the journalists on Billy Goat Tavern’s wall of fame. Founded in 1934 just after Prohibition ended, this is where Bourdain eats a “cheezborger.” L & L Tavern, where he sips local Malört liqueur, is right down the street from Wrigley Field, home of the Chicago Cubs.

At 25:39 in the episode, Bourdain begins discussing museums to visit, leading to a glimpse of Edward Hopper’s famous diner painting, “Nighthawks,” at the Art Institute of Chicago. Bourdain spends most of his time at the International Museum of Surgical Science, which bills itself as “North America’s only museum devoted to surgery.” It’s an offbeat destination that feeds his interest in trepanning, the almost medieval surgical practice of drilling a hole into a person’s skull to alleviate pressure on the brain. While mass transit might be only marginally less gruesome, you can also follow in Bourdain’s footsteps by taking a cheap “L” train tour of Chicago or one of many architectural boat tours.

Dave Pennells

By Dave Pennells

Dave Pennells, MS, has contributed his expertise as a career consultant and training specialist across various fields for over 15 years. At City University of Seattle, he offers personal career counseling and conducts workshops focused on practical job search techniques, resume creation, and interview skills. With a Master of Science in Counseling, Pennells specializes in career consulting, conducting career assessments, guiding career transitions, and providing outplacement services. Her professional experience spans multiple sectors, including banking, retail, airlines, non-profit organizations, and the aerospace industry. Additionally, since 2001, he has been actively involved with the Career Development Association of Australia.