I haven’t been to Chicago in 10 years. It’s a place I’ve been thinking about returning to, and was even in the process of booking another trip to Chicago when an opportunity presented itself for a short whirlwind of a trip to Chi-town. I knew this visit would be very different from any trip I planned myself (as a follower not a leader) so I jumped at the opportunity.
Taking a (too short) 4 hour red-eye from Vancouver, and landing super early in the morning, I was thankful I had a hotel room available to crash for a few hours to try to energize for my day ahead.
I had a friend in town overlapping my visit, so we met up for breakfast, a meal I never eat but was happy to indulge in. We wandered around and ended up at Kanela Breakfast Club, a brunch spot that bills itself as “Greek-inflected”, although I saw none of that on their menu, I did see many people order (and send back their chilaquiles). I was overly ambitious and ordered biscuits and gravy of which was tasty but I could only eat a small portion of. I really should have ordered the açaí bowl…
Crushed from the meal, all I could do was try to rest and catch up on sleep. I wandered the Magnificent Mile in and out of stores hoping to get my blood flowing again. I met up with my friend early in the evening and have a great time imbibing wonderful cocktails.
If you follow along on my food-loving adventures, you probably know that I am the planner. I organize 98% of my trips, to the point of no surprise in my itineraries. On this trip, I had no idea of where I’d be eating/drinking/spending time and while that would normally cause me stress, I had full confidence that I would not be disappointed if I just allowed myself enjoy.
When I found out my friend had arranged a late dinner at Kumiko, I knew I was right to let myself be led blindly on this adventure. Ranked #25 on North America’s Best 50 Bars list in 2023, Kumiko might be more renowned for their cocktails than food, but both were delicious.
I started the meal with a umeboshi chu-hi which was refreshing and perfectly tart. Our meal consisted of beautifully presented oysters, a yuzu-y chicken karaage which rivalled my mom’s in flavour, asari clams in a miso broth and finished with a katsu sando. The meal was deligtful and pure comfort to end a night of delicious consumption.
Feeling over-served from the night before, I started my day off with a run. A good push to my heart and mind was much-needed after a day of over-indulgence, but I love going for a morning run when I’m away as it’s also a great way to see the city before the streets become busy with tourists. The run path along Lake Michigan is one of the nicest running routes I’ve taken in a long time and it gave me the opportunity to once again be amazed with the enormity of the lake and the crazy weather patterns that come off of it..
The theme of the trip was to check off all the Chicago musts, so lunch was deep-dish pizza. Pequods is located north of downtown and is a locals establishment, although I did learn that locals rarely eat deep dish. It was recommended to order a small pizza between 2 people and after watching a reel on their IG feed of their pepperoni and meatball that was the choice. I’d forgotten how filling deep dish can be and barely got through one slice. The pizza was unique and very tasty but I totally understand why it’s not something you can have on the regular.
For dinner I was taken for a Chicago steakhouse experience at RPM Steak. I loved the modern take on an old-school fine dining restaurant with its giant round leather booths and mahogany walls, It felt so “Chicago”.
I love a good steak but rarely eat it, so I was very excited for the meal ahead. What I didn’t count on was being crushed with an enormous amount of food and delicious wine from beginning to end.
Appetizers consisted of oysters with a jalapeño mignonette and a coal roasted king crab. That was followed by a melt in your mouth Takamori drunken wagyu tataki.
Then the star of the show hit the table, a humongous Westholm Wagyu Tomahawk steak which was cooked a delectable medium-rare and carved table-side. Not that we needed any more food, a generous amount of “sides” were also presented including a ramp risotto, Japanese sweet potatoes and asparagus with Bearnaise. Oh, there was also the half a lobster in spicy miso butter sauce that I was told to dredge the steak pieces through after we polished off the succulent pieces of lobster.
I was completely stuffed from the meal, but had seen Baked Alaskas being gracefully torched around the room and seeing as ice cream cake is my favourite dessert, I definitely wanted to have a bite or 2.
After the meal we headed across the street for a nightcap at Three Dots and a Dash, Chicago’s incredible tiki bar. Keeping with the theme of over-indulgence, we ordered a monstrous Sippopotamous punch bowl, meant for 2-3 but probably could have served 8, which was preceded by a towering Shotstapus,
The struggle of excessiveness was real the next day, so skipping breakfast was a given, especially since there was one more Chicago indulgence to try out.
During my short stay in Chicago I’d heard numerous people talk about the burgers at Au Cheval. It’s a popular spot, so there was a line up upon arrival, but it just gave me more time to anticipate the meal. There was a lot on the menu that looked delectable, but I was there for the burger, and fries of course. We ordered the crispy fries which were topped with mornay sauce, and a runny fried egg. I was full from the fries but needed to push on to taste my burger.
A good medium rare burger is something they don’t serve in Vancouver, so I do seek it when I’m away. The burger itself at Au Cheval was perfectly seasoned and I loved their special sauce. The single at Au Cheval is actually a double so I could only get through half, but I admit the other half was the perfect lunch cold the next day on my flight home.
Stuffed from another meal, it seemed the perfect opportunity to take a long leisurely walk back to the hotel and check out Chicago’s interesting skyline.
Completely crushed from all the meats I’d eaten in days previous, I took advantage of a solo dinner to reset myself with lighter flavours. When dining solo while I’m away, I often chose hotel restaurants because it’s the most approachable way to eat at the bar without advance research. I went wandering around the hotels in the Gold Coast neighbourhood where I was staying and Nico Osteria in the Thompson Hotel was bustling and seemed a fun place to pull up the bar for a meal.
I perused the top third of the menu at Nico Osteria, but decided I only had room for one crudo, plus some oysters (of course). My initial choice was the kanpachi crudo but was steered in direction of the snapper and was sold because the dish had Castelvatrano olives. The little meal was exactly the what my body needed to reset from the meat-y indulgence of the previous days.
While I was at dinner, I was contacted by friends for a nightcap, so we decided to meet somewhere lovely and close. I’d been to Bernards at the Waldorf on my first night but in a totally different situation so I was happy to return to sit at the bar for a drink.
I arrived in Chicago with no set plans and was treated to the most indulgent time. I allowed myself to be comfortable going with the flow and I conquered so much deliciousness. I left feeling the need to be vegetable focused and salad happy in the upcoming weeks, leading up to my quick return to Chicago.
Places I visited in this post:
Call Me a Food Lover... 