The Best Reason to Buy New Jeans: A Weekend Full of Food and Friends in Chicago

If you have to buy bigger pants, make sure it’s because you just spent a long weekend eating amazing food and drinking too much champagne with your favorite people.

This past weekend, one of my best friends and I traveled to Chicago to see my sister for some fun, girls-only weekend action.  I arrived in Chicago just before dinner on Friday night, at which point my sister, Patty, and our friend, Allison, were about three glasses of champagne deep and more than half-way through a cheese board (sometimes you just meet people who really get you).  I quickly caught up (on the champagne, not the cheese – hydration is key) and the three of us headed out to dinner.  One of my favorite spots in Chicago is Big Star, which is a taco joint in the Wicker Park neighborhood of the city, not too far from where my sister lives in Wrigleyville (which leaves no one guessing about exactly where it’s located – my sister’s balcony is a stone’s throw from Wrigley Field).  Wicker Park is a 10-ish minute cab ride from my sister’s spot and is a cool, if not slightly too hipster area for my liking (very tight man jeans everywhere you look, lots of flannel…you get the idea), but this place remains a favorite Friday night spot of mine. The three of us caught up over a pitcher of margaritas, tacos and several (OK, like five) baskets of chips and salsa and got our check.

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The breakfast skillet at Lokal, complete with chorizo, potatoes and two sunny eggs.

We left Big Star, just the right amount of tipsy but way too full, and headed to Big Joe’s bar in Lincoln Park.  Big Joe’s is a dive, complete with a cash-only policy and bottles of PBR, but their claim to fame is their weekly turtle races.  Yes, you read that right: turtle races. If you’re reading this thinking that racing turtles sounds like an oxymoron, you are 100% right.  These guys (and gals – my favorite is a lady turtle named Yolanda) are not known for their speed, but that’s why its so damn fun.  Seriously, if you ever find yourself in Chicago on a Friday night looking for something different to do – head out to Big Joe’s (early, to avoid the line – turtle racing is a popular spectator sport in Lincoln Square) and spend your night cheering on my girl Yolanda, who never, ever, ever wins – seriously, she just sits in the middle of the racing ring and looks around like “I’m just here so I don’t get fined.” People always talk about finding their “spirit animal;” I may have met mine in Yolanda.

The next day, after plenty of Advil and lots of complaints from Yours Truly (working out on vacation – not my thing), the three of us headed to Flywheel spin studio to sweat out some of the tacos and booze from the night before so that we could promptly head to brunch to bring everything back to equilibrium.  Brunch at Lokal was amazing, if not a bit too ambitious: the skillet that I ordered probably weighed 2 or 3 pounds and that is not an exaggeration…this thing was huge.  I ate about half of it, which still likely exceeded FDA recommendations for caloric intake in a single day, but the FDA also says you shouldn’t have full-fat dairy products or drink more than one glass of wine at a time, so I’m skeptical of their judgment, anyhow.

After brunch, we made our way home for a much-needed nap (a/k/a “food coma”) and later that night we headed out for blow-outs and difullsizerender-copy-39nner at Pequod’s, which is a deep-dish spot on Clybourn Ave. that serves up some seriously good pie. I’ve written before about Colorado-style pizza, which is sort of a cross between a ‘normal’ pizza and a deep dish pizza due to it’s thicker crust, but the stuff they dish out at Pequod’s takes “thick crust” to a whole new level.  As you can see from the picture, the crust is at least two inches deep, and if I had to guess, they slather the skillet in butter and Parmesan cheese before they throw it in the oven for baking.  The pie really is some of the best stuff around: it comes out piping hot, beautifully golden brown, the crust is salty and cheesy and the dough-cheese-sauce ratio is perfection.  We actually didn’t end up eating there Saturday night for dinner, because the line was outrageously long and we were hungry, but we made it there Sunday for a light lunch (if mozz sticks and salads with a pepperoni deep dish tail is considered light), and it was just what I needed before we went out for an afternoon of shopping.  I just love trying on jeans after eating my body weight in pizza.

Even if a decent amount of the weekend was spent wishing I were in sweatpants, I still had the absolute best time and it’s not lost on me how lucky I am to be able to go to fun places and spend quality time with my family and best friends.  At the bar at a gorgeous restaurant called The Kitchen on Sunday, the three of us took a moment to reflect on how incredible it is to be able to meet up in a beautiful city and go out and do the things we want to do.  For me, right now, life is very much in flux and sometimes it feels like things are just plain old hard – looking for a job in another country isn’t the easiest thing in the world, switching careers has been emotionally pretty draining and planning a trans-Atlantic move hasn’t been without it hiccups – but, at the end of the day, if I find myself sitting at a bar with my sister and best friend, drinking a glass of red wine while watching the sunset over the Chicago River after a weekend full of eating, drinking and good conversation, it’s pretty damn easy to remind myself just how (insanely) good I have it, even if it means I need to go out and buy bigger pants.

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