My Special Birthday Long Weekend in Chicago

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Crazy to believe, but after not visiting Chicago in 10 years, just 3 weeks after my return to the city I was back again. This time to celebrate my birthday. After many years of spending birthdays suffering in the sweltering heat of New York or Nashville, I wanted try something different. At the time of planning my birthday trip, I didn’t know I’d have the opportunity for an impromtu quick visit that I couldn’t say no to where I over-indulged in so many Chicago classics. But no matter, I knew my birthday long weekend trip would be nothing like my other few days in Chicago. Of course, it would be over the top delicious, but in completely different ways.

A late afternoon landing at O’Hare coupled with stormy weather, meant being stuck in traffic for almost 2 hours into the city. It meant having to pass on having a Portillos dog, my first planned eating stop for the weekend. No matter though, the hotel graciously greeted us upon arrival with a glass of sparkling and then with a bottle + chocolates in the room as a treat for my special weekend ahead that made me forget that I was hungry. 

Unlike my unplanned trip to Chicago where I did no research, for my birthday trip, I researched the heck out of where I wanted to eat and drink during my time in the city. I quickly realized that I had enough places on my list to spend weeks in Chicago, but knew I had to narrow down my choices. With a solid list of recommendations from friends, I started scouring my other trustworthy sources to come up with a plan for a well-rounded weekend of eating and drinking. I had to make some hard choices, but in the end was very excited about my itinerary.

Dinner the first night was at Rose Mary, a Croatian/Italian inspired restaurant by Top Chef winner Joe Flamm. The large and boisterous restaurant seemed “the place” to go on a 2nd date or girls night which made for great people watching. But more than the people, what caught my eye was the giant charcoal hearth that anchored the open kitchen. 

I sipped on a Snap Pea gimlet while perusing the menu which was filled with too much goodness to choose from. To start, we ordered tuna tartare with beef fat vinaigrette & veal aioli and grilled clams with smoked ramp pesto, both dishes sat in the tops of all tastes I had on the trip. The main part of the meal was a mezzaluna pasta with ricotta and sugo which was good but paled in comparison to the bright and cheerful spring pea risotto. 

Chicago is an incredible cocktail city and I was interested in experiencing the whole range of it. I’d been to The Aviary for the opening of Grant Achatz’ Spinning Plates movie 10 years ago. The evening included a plethora of creative cocktails that seemed to come straight out of the lab rather than from the hands of a bartender.

One that visit, the drinks were creative, but I felt the presentation was the focus than what was inside the glass, (although that was delicious too). I remembered that in Achatz’s own words, “the drinks and service are crafted with the same care as Alinea; a restaurant for cocktails, created. in the kitchen by chefs rather than behind the bar”. I loved the Aviary on that visit but I was less well-versed in cocktailing back then and coupled with the fact that last time, I was there as part of an event where the atmosphere was lively and the food and drink free-flowing.

Returning to the Aviary I was shocked that it looked exactly the same as from my visit 10 years earlier. Seated in one of their pristine white rounded banquettes, I missed seeing bartenders carefully create cocktails and hearing the shaking of ice but rather that let these things get me down, I focused my attention to the guests around the room who were captivated and charmed from being served wild and wonderful concoctions.  

I ordered a Whassuh Bae, which was a delightful combination of gin, shochu, cucumber and yuzu. Inside the frozen serving vessel was a wasabi ice. I was instructed that the longer I let the cocktail sit in the vessel, the more wasabi-ee it would become. My next drink was I Yam What I Yam, made with yam, tequila and. an orange smoked paprika ice. I watched as all the other tables were being served drinks smoking, being poured from intricate vessels, or going through infusions table side and I felt like I ordered the 2 most boring-looking drinks from the menu. I normally wouldn’t be upset about that, especially since both drinks were delicious, but at the Aviary, where the show is a big part of the experience, I felt like I was missing out.

I couldn’t leave the Aviary without a bit of excitement, and since I didn’t have dessert at Rose Mary, it seemed The Buzzed Aldrin would be the perfect order. Definitely more dessert than drink, with Chartreuse, Banana Cream soda and Neopolitan ice cream this was a boozy banana split was a great way to end the evening.

The weather forecast for the weekend wasn’t pleasant, so we decided to take advantage of any non-rainy moment there was. After a morning workout, a wander towards Millennium Park and the Bean seemed like a good plan. By the time we got. to the park, it started to get really warm so I decided rather than continue to be touristy, it was time to grab a bite to eat.

Kasama is a modern Filipino restaurant that has earned a Michelin star for its creative Chef’s menu dinners. There wasn’t time on the itinerary this trip to go for dinner, but since they’re also praised for their daytime menu, I thought it would be a great place for br/lunch. There was a line-up when we arrived and while I wasn’t keen to stand in the blazing sun, I convinced myself it would be worth the wait.

Ordering at the counter, I was enticed by the fabulous looking baked goods but passed on those for a plate of lumpia, (cigarette sized Filipino spring rolls) to start. I was sad that the breakfast sandos were sold out, and instead settled on the chicken adobo and Filipino breakfast with longaniza sausage. Both dishes were pure comfort with seasoning unfamiliarly familiar. The star was the longaniza sausage which I could have eaten 3 portions worth.

The rain started pouring in the early evening, so rooftop pre-dinner patio plans were thwarted. Plan B included a visit to the highly recommended Sportsman’s Club in Ukrainian Village. My 2nd choice turned out to be the perfect choice for a stormy July evening. The Sportsman’s is kind of divey in the best way, and serves deliciously balanced cocktails. I was curious about trying one of the tamales from the various sellers who came through the bar, but alas, I had dinner plans. Their bathroom was strangely reminiscent of Dino’s in Nashville, so I had to take the obligatory selfie.

Dinner plans were in Logan Square but my table wasn’t ready on arrival so they recommended having a drink across the street at Outside Voices, a natural wine bar. Uhhhh yeah… it was probably one of the few times I was happy to have to wait for my reservation.

Outside Voices is a cute hipster natural wine bar that doesn’t take itself too seriously. I knew nothing about the selection they had on offer, but the staff were amazing at guiding me through their offerings.

When our table was ready, we were called back to Giant, a cute neighbourhood restaurant serving “New American” food. It was hard to choose from their varied menu but everything coming out of the kitchen looked so good that I knew I wasn’t going to go wrong.

We started with roasted broccoli with crunchy bits of fried potato and a Jonah crab salad with waffle fries. The tagliatelle with Dungeness crab and chili butter was a dish that combined all of my favorite flavours and their showstopper best dish. I left dinner wishing my neighbourhood had a restaurant like Giant.

The next morning started a bit cloudy but according to the forecast, it was going to be one of the nicer days of the weekend. Since this forecast was nicer than the forecast for my birthday the next day, we once again took the opportunity to walk the city and rearrange lunch plans..

I’d originally booked brunch on the patio at Aba for my birthday brunch but considering the torrential forecast, I cancelled. While the sun was peeking out, it seemed a nice opportunity to walk to the Fulton Market District for a pre-birthday brunch. On short notice, I wasn’t able. toreserve a table out on the patio, but I enjoyed the people watching I was able to do inside the beautiful dining room.

Aba bills itself as Mediterranean and brunch leans towards the Middle East with its menu full of hummus’, dips and kebabs. All of the share plates looked delicious and I wished I were there with a big group to have been able to sample more of the menu. The green garbanzo hummus, Greek Village salad and Kefta and eggs I did order were all delicious, and I’d definitely return to Aba on my next visit to Chicago.

We couldn’t be in Chicago without going to see the Cubs play at Wrigley, but unfortunately the rain prevented us from actually catching the game. After waiting 3 hours in the bowels of the stadium hoping for the rain to let up, I decided (for this trip) it would be enough to have a Wrigley dog with its neon green relish, and giant pickle and peppers and call it a night.

The morning of my birthday, I awoke to a torrential rain storm. I did not want the bad weather to hamper my day, and decided to wade through the flooded streets to Lagree class.

I was totally drenched when I arrived back to the hotel after class and with my phone buzzing with “extreme weather” alerts advising anyone who didn’t need to be out to shelter in place. Feeling like it would be impossible to get a car to go for my planned brunch destination, we chose to stay close and go to Brass Tack,inside the Waldorf Hotel.

If I hadn’t had an epic dinner planned, I might have taken advantage of Brass Tack’s Everlasting (bottomless) Rose brunch for $30. Instead, I was reasonable and ordered a mimosa and indulged in a crab benny and the pochetta dip. Everything was satisfyingly delicious and made me forget about the dreary weather outside. Incredibly enough, a brief mention of my birthday on entry had a birthday cake presented to me at the end of the meal. I love service that’s this attentive.

The extreme weather warning, kept sending alerts to shelter in place so it seemed the perfect opportunity for to check out a movie by my favourite filmmaker.

My birthday wouldn’t be my birthday without starting. the night with a cocktail. I’d been to James Beard Award winning Violet Hour on an epic bar crawl when I was in Chicago a few weeks previously. From my memory of the evening, I enjoyed the candlelit space with its long marble bar and marked it as one to return to. I knew I had an ambitious meal ahead, and didn’t want to overdo it so i paced myself even though I wanted to indulge through Violet Hour’s creative menu. I chose the Vibe Check, a tequila based, espresso martini-esque cocktail with amaro, licor 43, chile and nutmeg. It was the perfect pick me up which I drank a little too quickly, (so much for pacing myself). For my 2nd I asked for a bartender’s choice and was served a lovely and very complex gin based sour garnished with burnt lemon & rosemary.

The dinner that followed at Alinea was too epic to be included in this post. Instead “My Special Birthday Dinner at Alinea” will be posted very shortly.

The sun came out in full force the morning after my birthday so I wanted to take advantage and walk around the city some more.

An early evening flight home meant one last lunch before heading to O’hare. Of all the recommendations I’d had for this trip, Dove’s Luncheonette kept coming at me as a must.

Dove’s is billed as Southern inspired Mexican rather than Tex-Mex, and kind of old-diner divey (again) in the best way possible. I was in the mood for their lunch offerings over breakfast, so we ordered the broccoli Caesar (huge hit), the taco norteño with smoked brisket, Guajillo salsa, crispy cheese in a flour tortilla and a side of Al pastor fries.

My final tastes of Chicago left me into feeling so fondly about the 2 Chicago experiences I had back to back. Couple that with my desire while watching every episode of The Bear to go back, I will definitely not be waiting another 10 years before I return.

Places I mention in this post:

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