When my wife was unexpectedly able to join me on my trip to Chicago, it turned a baseball trip into a restaurant exploration trip pretty quickly. My original plans called for a lot of ballpark food and craft beer, but I was thrilled to spin those plans on a dime and make each evening about heading out on the town in search of deliciousness.

With the last minute nature of our new plans, we used points to get my wife into Chicago flying a different route and airline than was I. When we parted ways at the Saskatoon airport, she didn’t yet have a seat assignment, so we weren’t sure if we’d actually meet up in Chicago. In light of that, we kept our dinner plans simple – at Fisk & Co, a hotel bar in the loop, for some seafood and (surprise, surprise) craft beer for me. It ended up being a great choice. She did make it into Chicago, and our first order of business was crushing some oysters. Delicious!

My wife made the pick for our second night. Looking for something interesting, different, and gluten-free, she found Aba, a Mediterranean restaurant a few subway stops west of the downtown. This meal was nothing short of spectacular. While the overall vibe of the place was a touch on the hipster side for my liking, there was no disputing the food. Succulent hummus, amazing chicken kefta, olives bursting with flavour were all washed down with my spicy aloe-based mezcal cocktail. We capped it off with a frozen greek yogurt, olive oil and sea salt treat before making our way back to the hotel.

No trip to Chicago is complete without at least one visit to a Rick Bayless restaurant. We had dinner at Frontera on our third night – second time for her, third time eating here for me. This is my Chicago favourite and as you can tell by her smile, it’s pretty high up on her list too.

Everything on this night was perfect. The tequila based cocktails, salsas and guacamole were all on point. The taquitos were so good I considered canceling the rest of my order and just asking to keep them coming until I passed out at the table from a food coma. I ordered swordfish in a mole because I can’t get enough delicious seafood living in Saskatoon and because I wish everything came with a rich mole sauce. The dish was fresh, earthy and one of the best things I’ve eaten at a Bayless restaurant in Chicago (and that’s saying something).

While my wife was away exploring the Lincoln Park Zoo, I took the opportunity to visit Fat Rice near Logan Square for lunch. I wanted everything on the menu, but ended up leaving it to the server to pick for me and her selection didn’t disappoint. I can’t actually remember what I had, but I remember savouring every last bite of it and wishing this restaurant wasn’t so far away from where we were staying.

I said earlier that no trip to Chicago is complete without a trip to a Rick Bayless restaurant. The truth is, no trip is complete without multiple trips to Rick Bayless restaurants. His realtively new joint, Leña Brava, gave us another great meal. It was also a great lesson in listening to your server. I picked a cocktail. She said it was 10/10 spicy. I thought, I like spicy. Before I took a sip, this is the last picture of me on the evening that doesn’t involve tears streaming down my face. I finished that drink, but wow.

The food was off the charts good. Garlic and lime-cured shrimp, and black cod al pastor were the runaway hits from this meal.

I’m more of a coffee and a pastry breakfast guy when traveling. While I was heading to my conference the first few days, my wife found Wildberry Pancakes and Cafe, a place with exceptional gluten-free breakfast options. Before we headed out to an afternoon Cubs game, she brought me here for an incredible breakfast feed. The bacon was otherworldly, and that gluten-free waffle tasted like it was chocked full of gluten. I ate so much, that I skipped a ballpark lunch at Wrigley. Yes, it was that good!

For our last meal in Chicago, we went to an underground bar in the River North area owned by (wait for it….) the daughter of Rick Bayless. Bar Sótano is a small plates and tequila/mezcal-based cocktail joint, so pretty much my idea of perfection. Everyhting here was delicious including the broiled oysters and a take on charcuterie involving Mexican ingredients.

The change of plans for Chicago was perfect. This ended up being a very different, and much more delicious and enjoyable trip than the one I had originally planned.