How to Spend 48 Hours Eating Everything in Chicago

What do Ferris Bueller’s titular day off, the 1893 World’s Columbian Exposition, and the Valentine’s Day Massacre all have in common?

They are each set upon the elusively magnificent backdrop of Chicago. 

There’s much to be said about the third largest city in America. Despite its magnitude, Chicago still retains its midwestern reputation — a metropolis populated with small-town folk.

It has been culturally relevant in just about every facet: sports (the still-legendary 1985 Bears as well as the MJ-led Bulls), comedy (dozens of the most influential figures in comedy built their bones here, from Tina Fey to Stephen Colbert), and music (Kanye West, The Smashing Pumpkins, and, and this may surprise you, the band Chicago).

But the food is what drew me to the Second City. There are not many places that claim so many iconic dishes as their trademarks. One could reasonably say that Chicago is best known for their hot dogs, Italian beef sandwiches, or, of course, deep dish.

Each of these foods shines a new light on what makes Chicago such a unique melting pot of cultures and tastes. 

I flew out early on Friday morning to gain my own perspective.

Day 1

After landing at Midway, I hopped on the L (note my speaking like a local) to meet my friend at his place in Lincoln Park. As the train entered the city, I began observing the architecture for the first time in my life. History was dripping off of each building, completely varied in style.

By the time I got to my buddy’s house, I became abundantly aware that practices for the Chicago Air & Water Show were in full swing, so every thirty seconds we were treated to the deafening sounds of a blitzkrieg. 

Cacophony be damned, we had tickets to the Cubs game so we made moves.

After grabbing a few beers at a Wrigleyville spot called Deuces, we made our way into the century-plus old stadium and I was immediately in awe at the famous diamond. I’m admittedly lukewarm about baseball but, at that moment, my enthusiasm for the sport was somewhere between a character from The Sandlot and Field of Dreams.

Now that the romance of baseball had been re-kindled, it was time for the real action: food and beer. 

There are few foods better at a baseball game than hot dogs. A grilled polish, or kielbasa, might just be one of them.

I got mine with the customary grilled onions and topped it with spicy mustard (I’ll forever be Team Spicy over Team Yellow), ketchup (grow up, anti-ketchup-on-hot-dog camp), and relish on the trademark poppy seed bun. It had a perfect kick along with the sweetness of the onions. Paired with the Bud Light, I was in bliss.

After a long and sweaty afternoon, I washed off and was ready to tackle the big boy: deep dish pizza, one of the most controversial foods in gastronomy. Pizza purists consider it borderline sacrilege and Chicago residents hail it as a second coming of sorts. I’ve always been a fan so I knew it had to be on my itinerary.

While the animosity between White Sox and Cubs fans is legendary, one that runs even deeper is between Giordano’s and Lou Malnati’s fans. As a student of the scientific method, I would not have felt comfortable eating at only one, and since I had such a short trip, we instead settled on a neutral Lincoln Park spot called Bacino’s.

Despite being quite spacious with a massive party room in the basement, Bacino’s was pretty empty. This would normally be a benefit except deep dish always takes 45 minutes so we had time to kill over a pitcher of ale. We ordered the Bacino’s Special Stuffed Pizza (sausage, green peppers, onions, and mushrooms) with no mushrooms, which our waitress was quick to tell us meant it was no longer the Special, so I guess we built our own stuffed pizza with green peppers, onions, and sausage.

The pizza was fat, cheesy, and delicious. The real star was the sauce, or “gravy,” as The Sopranos has taught me to call it. It was garlicky without being overwhelming, and had a perfect texture so it didn’t make the crust soggy. I ate two slices and could’ve easily had another but we had plans that night that did not involve me laying down and immediately falling asleep, so we took our leftovers back.

We ended our night going to an apartment and then hitting up a few local watering holes, so I had a feeling I’d be nursing a bit of a headache the next day.

Day 2

My hunch was correct. I woke up with a throbbing headache and knew that I’d need something greasy and meaty to exorcise the hangover demons from my body.

Luckily for me, Al’s Italian Beef has been serving greasy and meaty food since 1938.

The first thing I noticed was the Wall of Fame, featuring an eclectic mix of food icons (Anthony Bourdain, Guy Fieri, Bobby Flay), sports legends (1985 Bears coach Mike Ditka and Muhammad Ali), and miscelleanous (Apollo 13 astronaut Jim Lovell AKA the one played in the movie by Tom Hanks).

Our morning was flexible, but we had plans to take a water taxi to Chinatown early in the afternoon so we didn’t want to go too hard and compromise our appetites for authentic Chinese food. Thus we decided to split an Italian beef sandwich. 

The three style options are Dry (a touch of gravy), Wet (extra gravy), or Dipped (submerged in gravy). Given that it was not even noon, I wasn’t mentally prepared to drench myself in jus quite yet so we compromised and went with Wet, topped with hot giardiniera.

These sandwiches are comfort food to the max. I was initially expecting a flavor similar to a cheesesteak, but it had almost a bolognese-esque flavor. Not too heavy, not too light.

With just the right amount of meat and bread sticking to our ribs, we were ready to face the mean streets of Chicago.

We boarded our river taxi (which, as the name implies, is quite literally a boat that serves as a taxi) and enjoyed the breathtaking riverside views of the city and the older industrial area that held tomes of history, undoubtedly in despicable working and sanitary conditions. 

After a few stops (including one for the purposes of maintenance that I’m quite convinced was more of an emergency than we were led to believe because we didn’t move for 45 minutes while our captain was below the poop deck (I don’t know if I’m using the nautical term correctly but it’s very fun to say)), we made it to Chinatown.

This district of Chicago was like Atlanta’s Buford Highway if it was centralized in a plaza instead of scattered among a dreary road.

We sat down at MCCB (Modern Chinese Cookbook) and were immediately overwhelmed by the menu. It wasn’t nearly as large as the novellas of the Cheesecake Factory menu, or even other Chinese menus, but the issue was that everything looked and sounded delectable. After a bit of guidance from our server and plenty of neurotic decision-making, we ordered four dishes.

What followed was the best Chinese meal I’ve ever had in my life.

First, out came the Dan Dan noodles with ground pork. There was a delightful spicy sauce at the bottom and the pork itself was rich and deeply flavorful. Mixed together, this was a knockout all across the senses.

This orange chicken was our control group of sorts, complementing the authentic dishes. While this dish is probably best known at Panda Express, we were intrigued by counteracting all of the spicy items with something a bit sweeter (and yet tarter!) This orange chicken was the first time I’ve ever actually tasted the fruit, undoubtedly aided by the orange garnish.

There’s not much to say about these Cheng du spicy pork dumplings besides my usual praise for dumplings as a whole. I love the texture, the salty sauce, the flavor of the meat, and the textural contrast of the garnishes. Dumplings rule, and these were no exception.

The real star of the show was the Signature dry chili chicken. This was practically a 50:50 ratio of fried chicken chunks and a pepper medley (dry chilis, serranos, pepper flakes, and peppercorns), yet it had a balanced level of heat. Like a perfectly-sauced hot wing, you were aware of the heat without being bullied by it.

I declared to the table that I was done eating around seven times and seven times I went back and ate more of the dry chili chicken. It was an absolute knockout, from texture to flavor, the likes of which I’ve never encountered before and likely will not again for quite some time. Perhaps I was still hungry…perhaps I was dreading the idea of this meal ending.

After the type of nap earned only after baking in the summer sun and then stuffing your face with spicy Chinese food, we made our way over to the Annoyance Theater, an improv theatre with a deep alumni pool. We went to see a group called Fire and Beer, who were as average as an improv group can be. 

While the show itself left some to be desired, the highlight of the evening came at the very start. The long-haired troupe member greeted our intimate crowd of 20 or so with a rousing “Hello, Chicago!” This was a riveting moment for an Atlantan, to respond back as the aforementioned “Chicago” without a sense of fraud. In that moment, I was Chicago.

After the show, we stopped by the bar for a Chicago Handshake.

A Chicago Handshake is the name for an eclectic drink pair: an Old Style Beer and a shot of Jeppson’s Malört, neither of which I had tried before. They didn’t carry Old Style, so we settled for a Miller Lite to chase the Malört.  

For anybody who has understandably never had a Malört shot, I’d describe it as the bastard child of gin and hand sanitizer. It made every hair on my body stand up and sent a wince shooting through my body like a charley horse. I’ve never appreciated the taste of Miller Lite like I did in that moment.

But none of that mattered to an authentic Chicagoan like myself. I had been initiated via Chicago Handshake.

Day 3

The final day of a weekend trip always has an asterisk next to it. No matter what you do, you’re ending your day back at home and your day will involve significant amounts of transit and waiting. Add that to the usual Sunday malaise and you’ve got a bittersweet day ahead of you.

Thus, our itinerary was sparse before my 4pm flight.

First, we started with a bagel sandwich at Chicago Bagel Authority, a place that felt like a college town restaurant in every way except for proximity to a college. It was littered with 4/20 references and quirky drawings on the wall.

After a deep scan of the dozens of options, I settled on The Sausage Fest.

The Sausage Fest was a kosher person’s worst nightmare: egg, bacon, sausage, and American cheese. The bagel itself was passable, but the steamed sandwich was great. 

With our bellies full, we made our way to the North Avenue Beach to enjoy the sun for a few hours. This was unlike any beach I’ve been to because you’ve got a broad view of Lake Michigan at 12-o’clock and then turn 90-degrees any other direction and you’re looking at the Chicago skyline.

The rest of the afternoon consisted of packing up my bags and hopping back on the L to get to Midway.

As I was sitting at the gate and waiting to board, I remembered one last treat I had in store.

In my backpack, wrapped in foil, was one last half slice of deep dish from Bacino’s. Normally, I’m a quick eater, but I wanted this final relic of my trip to last as long as possible. With my mask hugging my chin, I ate it slowly, savoring the garlicky sauce and the light and flaky crust with the mozzarella still stringy and chewy.

To paraphrase Ferris Bueller, life moves pretty fast. If you don’t stop and enjoy the deep dish, you could miss it.

Until we meet again, Chicago.