The Chicago Blues Festival is a good excuse to see the Windy City, but it’s the incredible food, deep history and vibrant culture that wins visitors over.

Story by Bill Robert, Photos by Adam Alexander Photography

In March of 1914, Carl Sandburg penned the following free verse about his adopted city of Chicago: “Hog Butcher for the World/ Tool Maker, Stacker of Wheat/ Player with Railroads and the Nation’s Freight Handler/ Stormy, husky, brawling/ City of the Big Shoulders…”

It was a plain-speaking chant of defiance, celebrating the wicked, crooked, brutal toiling urban adventure that was becoming America’s third largest city. Indeed, the name “Chicago” comes from a French translation of the aboriginal word shikaakwa—the word for an indigenous local plant that is a wild combination of today’s garlic and onion.

Further into Sandburg’s poem he anchors those lines with “Come and show me another city with lifted head singing so proud to be alive and coarse and strong and cunning.”

As it was in 1914, it is today in 2014—music is the body spiritual of this city, and jazz and the blues are its heart and soul. So, in June 2014, with friends including Ross Porter and Jaymz Bee from JazzFM.91 (Toronto), I attended the Chicago Blues Festival, the largest free blues festival in the world, and the largest “Windy City” musical event of the year.

This was an expedition for the natural progeny of Delta Blues as it travelled north along the Mississippi River to its urban habitat of Chicago. Over three days and five lakefront stages in Grant Park, close to 600,000 musical adventurers reconfirmed this city’s proud tagline as “Blues Capital of the World,” the heritage home of greats like Ray Charles, B.B. King, Buddy Guy, Bonnie Raitt and the departed Muddy Waters.

More than 30 years since 1984, this annual festival has witnessed moments of pure blues greatness—T-Bone Walker singing at 80 years of age, Chuck Berry and Keith Richards doing their infamous pirate duet, and John Lee Hooker whiplashing his thing with the tune “Boogie Chillen.” The year I went saw the talented likes of Billy Boy Arnold, Bettye LaVette, Dr. John, Aaron Neville (my favourite), Nikki Hill (who always sings her ass off) and an up-and-coming talent in Eden Brent.

Former Toronto resident Harmonica Hinds.But the “Great Migration” of impoverished black workers during the first half of the 20th century from the American South to Sandburg’s Chicago brought not only the blues, but also what became known as Chicago-style Dixieland jazz. Indeed, one of the compelling features of the Chicago blues genre is its jazz feel. Dixieland, or “hot” jazz, came from the mecca of New Orleans through King Oliver and Jelly Roll Morton. And thanks to Louis Armstrong, it gave birth to the sophisticated Chicago jazz style with its great embrace of full solo choruses in lieu of tiny homage solo breaks.

Chicago Lives the Blues

This unique festival is here for a reason. The incredible Chicago blues and jazz club scene is defiantly the best on the planet, and with great food to trumpet.

Carl Sandburg’s poetry touched upon not just the musicality of this occasionally wanton city, but also its sense of building and rising up: “Flinging magnetic curses amid the toil of piling job on job, here is a tall bold slugger set vivid against the little soft cities/ Fierce as a dog with tongue lapping for action, cunning as a savage pitted against the wilderness/ Bareheaded/ Shoveling/ Wrecking/ Planning/ Building, breaking, rebuilding…”

Because amid the rise of a new music, the place burned down. The Great Chicago Fire of 1871 was a three-day conflagration that levelled the city’s business core and burnt through huge swaths of its residential area. The carnage left more than 100,000 homeless (a third of the population) and killed at least 300 people—with many more victims unknown due to drownings and incinerations. But as my godmother once said to me, “There’s nothing so bad that there’s not a little good in it.”

Today, the Chicago Architecture Foundation offers close to 90 architecture tours of this city that changed urban construction forever. And, in my view, the only way to fully appreciate the genius and diversity of Chicago’s stunning skyline is by boat on the Chicago River, as it twists and turns through the city core. Bonus: many of the boat tours are guided by professors or doctoral candidates from nearby faculties of architecture. The better ones last about three hours.

Grooving in Chicago’s famed Grant Park.However, a more active approach to Chicago’s architectural canyons is by kayak. There are several options for this “duck’s-eye” vantage point of exploring Chicago’s physical and living history. Some also include evening guided paddles with summer fireworks, sunset outings and a focus on particular architects or communities (e.g. Chinatown).

Howling Music Makes for Growling Stomachs

Being “hog butcher for the world” also comes with some gastronomic responsibility.  The jazz and blues clubs, mentioned below, do a fine job. But, especially over lunch hour, you may want to search out some of Chicago’s culinary staples elsewhere too. Deep-dish pizza, Chicago-style hot dogs (poppy seed bun, all-beef wiener, baseball mustard, chopped white onion, green pickle relish, a dill spear, tomato wedges, peppers and a dash of celery salt) and Italian beef sandwiches are just a few of the local specialties.

Gino’s East of Chicago (162 E. Superior Street) will get you launched on the deep-dish ‘za. And Portillo’s Hot Dogs (100 W. Ontario Street) is a classic. The beer-fetching, food-ordering and dessert-serving lines at Portillo’s are a bit confusing, but that’s part of the adventurous ambiance, and is balanced by the staff wailing over microphones to “stay out of our way.”

An after-hours gem frequented by hotel staff, bouncers and late-night shift workers coming off the job is Ristorante Quartino (626 N. State Street). Friendly, bustling and featuring Italian regional specialties, with serving portions meant to be shared. And the wine bar doesn’t close until 3:00 a.m.

Lastly, and to stay with the Italian theme, trek around to Eataly (43 East Ohio Street). This is a true eat, shop, learn expedition housing a dozen individual restaurants in one midrise building, complete with cooking school. My advice is to wander around the floors, then plan your high-quality and fairly-priced assault on the tastebuds at Vino Libere, the well-situated wine bar that offers free salumi and verdure to get your juices flowing.

And so, back to the Chicago Blues Festival. Aaron Neville, at 73, still had the stuff that garnered four platinum albums, four top-20 singles hits and a fistful of Billboard number one toppers for their categories. Songs like “Everybody Plays The Fool,” “Don’t Take My Heaven Away,” and his breakout single from 1967, “Tell It Like It Is,” were just hand-wavingly great. In fact, every time I hear Neville sing it conjures memories of his magical duet with Linda Ronstadt on “Don’t Know Much.”

A relatively new act from Jackson, Mississippi, where they have their own annual blues fest, the Southern Komfort Brass Band put on a string of solid, soulful harmonies, and had 88-year-old “Tony The Dancer” up and doing his dance moves to applause. Dr. John (The Night Tripper) headlined an evening of his New Orleans blues tunes with clear zydeco influences—not to mention that slightly voodoo thing he always has going. And for much of the Chicago crowd it was evident that he still has a major cult following, and a deserving one for this Rock and Roll Hall of Fame honouree. For me, Dr. John’s simply unforgettable for his performance with The Band of “Such a Night” in Martin Scorsese’s documentary The Last Waltz.

So mark your journey calendars now—Chicago Blues Festival returns to the city each year in early June. Go explore Barack Obama’s hood. But gently keep your calm and wits about you. This is still a city that spurred an incredible spree of gunfire over its 2013 Fourth of July weekend: 17 dead and 53 people shot. (That said, shooting deaths for Chicago were down for 2014.)

Yet, it remains today everything Carl Sandburg said it was in 1914: “Laughing even as an ignorant fighter laughs who has never lost a battle/ Bragging and laughing that under his wrist is the pulse, and under his ribs the heart of the people/ Laughing!”

Today’s Chicago, magnificently alive and throbbing with vigour and life, is arguably the most worthy and fun urban safari of music, architecture, food and the complexity of modern North America, ever. And I can’t wait to go back.

Where to eat, chill and hear some great Chicago blues year-round

• Green Mill (4802 N. Broadway Avenue), which may be Chicago’s most famous club for its after-hours jam session. Named as a salute to Paris’ Moulin Rouge, it has a gritty history connected to the mob—and still features Al Capone’s personal booth. Eight feature films have been shot in or about this music venue, including the iconic The Joker Is Wild in 1957.

• Andy’s Jazz Club & Restaurant (11 East Hubbard Street). The food here is so-so, but the music they book is frequently outstanding. Moreover, this is a favourite hangout of Ramsey Lewis, the incredible jazz pianist and composer. Lewis has three Grammy Awards and seven gold records, with eternal tunes such as “The In Crowd” and “Wade in the Water.” And, apparently, much of his genius inspiration for tickling those ivories happened here at Andy’s, so put it on your list.

• Katerina’s (1920 West Irving Park Road). Depending on where you’re staying in Chicago, this place should be less than a 20-minute cab ride from city-centre. But it’s a world away from the tourist scene; very hip and cozy.

• Jazz Showcase (806 S. Plymouth Court). This is the oldest historic jazz club in Chicago, founded in 1947 by Joe Segal. At times the jazz can be a tad experimental—a.k.a., inaccessible. But the very greats have played here and continue to do so. In fact, Dizzy Gillespie made a point of playing this club on his birthday, year after year. It’s a nice mix of top local and international talents. And the Segal family (either Joe or son Wayne) are still likely to greet you in person at the door. The Jeremy Pelt Quintet, if they’re performing, is a fair balance between more demanding jazz and Jeremy’s gift for solo trumpet.

• Tortoise Club (350 North State Street). Not far from the House of Blues, on the north side of the Chicago River, is this charmer. It’s a classy joint with a clubhouse vibe and celebrated kitchen. I wouldn’t call the live music here cutting edge, but as a dinner venue splurging in a comfy jazz milieu, it could be the best in the city. For foodies the chef (Gray McNally) has quite the reputation for creative takes on classic American fare. I started with a Barry Bonds’ sized steak tartare that was incredible, followed by perfect halibut over a nifty potato-based puree—spectacular. (Hey, you gotta eat!) If you have a choice, try to book this dinner when The Mark Burnell Trio is playing. Mark is a gifted piano player, and has taught jazz at universities such as Yale and Northwestern. An excellent soundtrack to a memorable evening.

• Kingston Mines (2548 N. Halsted). At the radical end of the spectrum from the Tortoise Club is this happy mayhem. This is Chicago’s oldest and largest late-night blues joint. Sixteen-dollar five-bottle buckets of beer jostle in every direction, and the crowd is both jammed and jamming. Two stages alternate between sets so the blues are nonstop, interspersed from time to time with soul and/or reggae, depending on the evening.

This is the musical nightlife centre for north Chicago. And dancing like a maniac with the locals is a hoot. Don’t bother to show up before 11:00 p.m. (shutters around 4:00/5:00 a.m.) and, if you’re aged 60 and up and trying to keep up with the grooving millennials, be prepared to feel like death the next morning. But—this is Chicago blues nailed and delivered. Again, if you’re flexible, look for an evening that features award-winning Vance “Guitar” Kelly. Kelly isn’t that well-known outside of the Windy City, but he’s the sublime incarnation of classic Chicago bar blues without being pinched in by the past. Or, look for Eddie Shaw, the 77-year-old sax player and singer who began as a tot with the likes of Muddy Waters, Ike Turner and Howlin’ Wolf.

Postscript: Before you head out, scroll around JazzFM91. These cats curate trips to many other iconic blues and jazz venues such as Monterey (CA), Newport (CT), New Orleans and Havana, Cuba. And as Canada’s only jazz and arts station, you gotta love that funk.

• This story originally appeared in Outpost magazine.