Three days in Chicago

“I’m going to Chicago. I’ve never been there before…”

I sometimes overhear this phrase, and it flips a switch in me that unleashes a flood of nostalgia and engages my instinct to offer my unsolicited opinions to the prospective visitor in florid detail. Incidentally this is the very same instinct that has rendered me a writer and filmmaker and general producer of unsolicited content of all stripes, which is another story altogether.

But as a native of the region, Chicago’s downtown, that crosshatch of stone, steel and glass canyons on the shore of the magnificent inland sea known as Lake Michigan always sets my heart atwitter and my stomach to rumbling. Washington Irving once wrote that we are defined by the geography of our youth. For him it was the mighty Hudson River. But for me, it was that vast, featureless plain of prairie country and the human geography, the home of the skyscraper, that captured my imagination. I eventually moved west, seeking real mountains, and as stunning as I find the volcanoes of Oregon’s Cascade Range today, there’s still a piece of me that can’t help but marvel at the manmade mountains built so audaciously on the swamps at the edge of that greatest of the world’s sweetwater seas.

I’ve typed up a novelistic advisory email on how a prospective visitor should spend a few days in Chicago so many times that it seems more efficient to finally memorialize that information in a blog post. So here you have it, your thumbnail guide to a weekend in the Windy City. So enjoy your time in one of the greatest, food, sports and cultural cities on the planet, and my sweet home, Chicago.


Gino’s original deep dish.

Any visitor to Chicago is required to sample the signature dish. You may think of New York or Napoli when it comes to pizza, and that’s fine, but what Chicago produces is several styles of actual pizza, which is a different thing altogether. It’s closer to a religious experience than it is a meal. Below are the establishments where you can sample examples from each of the major classifications of Chicago pizza.

1) Deep Dish at Gino’s – Cheese on bottom, sauce on top. An entire layer of Italian sausage in the middle. Gino’s is the original of the “deep dish” style. Some people prefer Lou Malnati’s. Giordano’s is fine, but only if you’re in a pinch. If you only try one style of pizza on your visit, this is it.

Joe Aurelio is a holy figure for many in the south ‘burbs.

2) Aurelio’s – This style of pizza is driven by the soft crust and the sauce. It’s also smothered by a continuous layer of cheese…sheets of it, not shredded, baked until it’s golden brown and pitted with pools of pure cheese oil. This is my preferred variety. It’s known for its suburban locations, where it originated in the outer ring in the 1950s and is typical of the style now served all over in the suburbs. I believe it’s also the nation’s very first pizza chain. The Homewood location in the South ‘burbs is worth a pilgrimage by train for the true pizza aficionado, but there are locations downtown as well. 

3) Home Run Inn – This style features a flakey crust and lots of Italian sausage. This is a classic North Side style where the sauce plays a lesser role to the textures of the other ingredients. Its legacy is tied closely to the Cubs and the legendary ballpark of the formerly hapless team, though now recent champions.

4) Vito and Nick’s – This variety has an intense sauce and a very thin cracker crust cut into squares. It’s the polar opposite of the deep dish and very typical of the South Side style. Calvin Trillin, food writer of the New Yorker rated it best in the country, and indeed it hearkens back to the early days of American pizza. Old timers will find themselves reminiscing about pies shared with high school sweethearts, and it’s not just because of the Old Style on tap and the shag carpet on the walls. It’s like stepping back into the 1960s.

Other Food

Portillos –

Try the Italian beef combo (or just a regular Italian beef). This sandwich is a pure celebration of meat. Served with thin slices of marinated roast beef and giardiniera peppers and smothered in the spicy au jus, it’s what a humble “French dip” sandwich dreams of becoming when it grows up. Add some mozzarella and insert an entire butterflied, grilled Italian sausage for the “combo” experience and you’ll experience life as a true Pleistocene carnivore. The Maxwell Street Polish sausage harkens back to the flea market days of the near West side and features grilled onions. The Chicago style hot dog takes a humble Vienna sausage to its pinnacle by the addition of a poppyseed bun, sport peppers, hot mustard and a garden’s worth of vegetables.

Laschett’s –

Laschett’s is a hole-in-the-wall German restaurant. There used to be a million just like it, but they’re mostly gone. Lincoln Park was primarily German speaking until the 1970s. They had their own Chicago newspaper printed entirely in German (the publisher ran for Mayor in the 1800s but lost) and even the public schools taught the German language first. Now, most of the Germans have assimilated. There’s also a decent German deli a few blocks away called Gene’s plus a few German shops. Anyway, the food is solid and cheap and the whole place is typical of a bygone immigrant era that most tourists won’t ever see.

Things to See

Chicago’s architecture is one of the greatest, most audacious feats of human endeavor. Marvel at the Taj Mahal or Notre Dame Cathedral if you’d like, but nothing compares to the landscape that Lewis Sullivan, Daniel Burnham and Mies Van Der Rohe crafted out of stone and steel on a swamp at the edge of the great lake. “Make no little plans; they have no magic to stir men’s (and women’s) blood,” Burnham famously said, and if your breath isn’t stolen by a glimpse of the magnificent mile and the museum complex, this edifice of magnificent buildings at the edge of the great, blue expanse, then you lack the proper capacity for awe.

True, awful glass structures dominate today’s skyline (including the Trump monstrosity, complete with the asshole’s name gaudily slapped on the outside) but if you look between the seams you can find the real glory of Chicago’s grand history of classic sckyscrapers.

To take a tour of Chicago’s architectural heritage, just download the app featuring Geoffrey Baer of the local PBS station. Or pony up for an architectural river cruise to go in style.

And here are some other sights you shouldn’t miss –

  • Museum of Science and Industry (only building still remaining from the White City world’s fair) – on the South Side in Hyde Park.
  • The silver bean/Grant Park – Walking the lakefront and looping back through the museum campus park is pretty amazing.
  • Navy Pier – Kind of touristy, but the Ferris wheel is definitely worth it for the views.
  • Hancock Building – this is the coolest example of modern skyscrapers. None of this blah glassy garbage they build now…it’s graceful and elegant and special when you look up from below. Go to the 95th floor Signature Lounge for an overpriced drink or two, and you get the views without the hassle of the Sears Tower observation deck and it’ll wind up being cheaper. I like the views at night, seeing the grid of the city stretch out, and best of all the Sears Tower is in the view. And the best view is from the women’s restroom…or so I’m told.
  • Garfield Park Conservatory – Cool 18th century building. Indoor botanical garden. Nice place to spend indoor time if the weather sucks. Neighborhood is rough and tumble, but the Conservatory is an amazing building.
  • Museum of Contemporary Art – Right near Gino’s! Great museum and not too pricy.
  • The Chicago Water Taxi is a cheap way to cruise the river. At 10 bucks for an all-day pass you can plan some boat trips into your walking tour and get a river view of the buildings.

Of course there’s so much more to see. You could spend weeks exploring and not even begin to scratch the surface. But this will make for a great start to exploring the Windy City.

Oak Park

The suburb of Oak Park is right off the Green El line. It has an amazing cluster of Frank Lloyd Wright houses and buildings. You can do a walking tour of the neighborhood and see most of them. His home and studio is well worth the full tour. If you’re into literature, Hemingway’s home and birthplace is here, too.

Blues and Jazz

Kingston Mines in Lincoln Park is a classic. Kind of touristy, but they get all the best acts. Usually multiple bands every night.

Buddy Guy is a Chicago legend and his place has been a home for great blues for generations.

The Green Mill is a classic, seedy jazz club on the North Side.


Here are a few books you can read on the plane to get a little flavor of the city before you land.

Chicago  by Brian Doyle – A Portlander got it right in this nostalgic and magic recreation of his life on Chicago’s North Side in the 1970s.

Devil in the White City by Eric Larsen – Follows Daniel Burnham’s audacious quest to create a World’s Fair in Chicago that could outshine the legendary Paris exhibition, launching the new era of modernity, told in parallel with the story of that other modern creation, the serial murder. Fascinating, inspiring and horrifying all at once.

So Big by Edna Ferber – The author of such classics as Giant and Showboat offers glimpse into Chicago’s rural past. This book captures the city and its architecture right at the moment where it grew from a prairie town into a world-class city.

Native SonRichard Wright’s classic novel of race, poverty and crime is set in a divided Chicago of the 1930s, remaining as heartbreakingly real today as it was seventy-five years ago.

Published by David

Writer (Vintage), filmmaker (Three Days of Glory and Saving Atlantis), bookreader.

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