Chicago is a city that makes a reasonable eating schedule feel unnecessary. Breakfast can spill into lunch, breweries count as afternoon activities, and deep-dish pizza is less of a meal than a commitment you make to yourself.
I recently spent a weekend eating my way across the city, with no real strategy beyond following recommendations, wandering into places that looked interesting, and accepting that vegetables might not be the main priority. Some stops were Chicago institutions. Others were complete accidents. One restaurant was so good that we went twice, despite encountering a line out the door both times.
Here is everything I ate and drank during one very filling weekend in Chicago.
Gino’s East delivered the Chicago deep-dish experience
You cannot go to Chicago and skip deep-dish pizza. Those are the rules, or at least the rules I followed when we visited Gino’s East.
When we arrived, the line was already out the door. Thankfully, we had made a reservation, so we got to bypass the crowd and head straight inside. Our server immediately warned us that the pizza would take between 45 minutes and an hour to prepare. Somehow, that only made us more excited. If I am going to wait nearly an hour for a pizza, I want to know it is being made fresh rather than sitting beneath a heat lamp.
We ordered two beers to keep us occupied, both of which paired dangerously well with the anticipation. When the deep-dish finally arrived, it looked like it could double as cookware. The thick golden crust held an almost unreasonable amount of gooey cheese and chunky tomato sauce, making every slice feel like its own meal.
Yes, I know Gino’s East is a chain, and we visited a location in one of the most touristy parts of Chicago. I also know Chicagoans have some very strong opinions about deep-dish pizza. Still, speaking as an Ohioan with no interest in entering the city’s pizza wars, I thought it was well worth the hype.
Cafe Tola was the weekend’s best surprise
Some of the best travel meals happen when you are not looking for them. We stumbled across Cafe Tola without a plan and walked away convinced we had discovered a neighborhood secret.
The colorful cafe is known for its hand-rolled empanadas, which chef Victoria Salamanca began serving at the original Southport location in 2012. The fillings draw inspiration from Latin American cooking but are not afraid to get creative, with options ranging from classic beef sirloin to Buffalo chicken and vegan coconut curry.
These were genuinely the best empanadas I have ever had. The pastry was flaky without disintegrating everywhere, and the filling-to-dough ratio was perfect. I immediately understood why Cafe Tola has grown to several Chicago locations and earned a cameo on The Bear.
It was quick, casual, and one of the biggest highlights of the entire weekend.
Pilot Project Brewing made beer tasting more interesting
Our next stop was Pilot Project Brewing, a spacious Logan Square brewery with a concept that goes beyond simply producing its own beer. Pilot Project operates as a beverage incubator, giving emerging brewers access to the equipment and resources needed to develop their brands.
That means the tap list is constantly evolving, and ordering a flight feels like discovering several breweries at once. It also makes the experience more interesting for anyone who has ever stared at a massive beer menu and chosen something based entirely on whether the name sounded fun.
The beer was great, but the space itself made us want to hang around. It had a lively, laid-back atmosphere that worked equally well for an afternoon drink or the beginning of a much longer night.
Gotham Bagels was worth waiting for twice
We visited Gotham Bagels twice, which should tell you everything you need to know.
Both times, the line stretched out the door. Normally, seeing a breakfast line before I have consumed coffee is enough to send me elsewhere. Still, everyone waiting seemed confident that the payoff would be worth it. They were right.
Founded by a New Yorker determined to bring legitimate New York-style bagels to the Midwest, Gotham serves hand-rolled bagels with the dense, chewy texture that separates a real bagel from circular bread. The breakfast sandwiches are generously loaded, so do not expect a dainty meal you can eat without making a mess.
Waiting once could have been curiosity. Going back and joining the line again was devotion.
Wildberry Pancakes justified ordering two breakfasts
Wildberry Pancakes and Cafe presented me with an important dilemma: Do I order the savory breakfast I genuinely want, or pancakes because the word is literally in the restaurant’s name?
The answer was both.
I ordered the breakfast burrito, which comes wrapped in a garlic-herb tortilla with chorizo, scrambled eggs, Chihuahua cheese, avocado, fresh jalapeños, and cilantro. It was the kind of enormous, satisfying breakfast that makes lunch seem like a distant and unnecessary concept.
Of course, I still had to try the pancakes. Going to Wildberry and skipping them would be like visiting Chicago and refusing to look at the lake. And they were worth sacrificing whatever productivity I had planned for the rest of the morning.
The Starbucks Reserve Roastery made Starbucks feel glamorous
I understand that visiting Starbucks in a major food city may sound questionable, but the Starbucks Reserve Roastery Chicago is not a typical neighborhood Starbucks.
The multi-story space on Michigan Avenue is essentially a caffeinated theme park, with specialty coffee experiences, food counters, and a cocktail bar. We headed to the fourth-floor Arriviamo Bar for the Starbucks Reserve Espresso Martini Flight.
The flight includes espresso martinis in three different seasonal flavors. Was it pricey? Yes. Was I paying partly for the novelty and the glamorous setting? Also yes. Still, the cocktails were fun to compare, and the atmosphere made it feel like a worthwhile weekend splurge.
Sometimes travel is about finding a tiny local cafe. Sometimes it is about drinking miniature espresso martinis inside an enormous Starbucks.
Ema ended the weekend on a lighter note
After deep-dish pizza, loaded bagel sandwiches, and a breakfast that could have fed a small family, Ema felt refreshingly balanced.
Located in River North, Ema serves Mediterranean small plates influenced by chef CJ Jacobson’s California-style cooking. The menu centers on spreads, vegetables, raw dishes, and kebabs, with everything designed for sharing.
We filled the table with plates and sampled a little of everything. The sharing format kept the meal social and relaxed, while the bright Mediterranean flavors offered a welcome contrast to the weekend’s heavier dishes.
Chicago has a food scene where even a short visit becomes organized around the next meal. By Sunday, I was full, happy, and already thinking about everything I had not managed to try. Apparently, eating your way through Chicago takes more than one weekend. And I’m willing to conduct further research.
