So every year my favorite fraternal organization has a professional conference in Chicago. Specifically every FEBRUARY. You see it. Chicago. In February. And I am STILL infatuated with this city. So that’s telling you something right there. This year, my fellow alumni partner-in-crime and I decided to skip the “professional” shenanigans and get as much out of the city as we could. Hint: copious amounts of sinfully delicious food is involved. First off, the train in America is a seriously underrated mode of transportation. You don’t have to drive yourself, or deal with TSA nonsense, and you feel like some sort of special adventurer because hello TRAIN. So if you can, take the Amtrak to Chi-town.
Also, stay at the Hosteling International site in the heart of downtown, next to the beautiful public library (worth exploring). This really isn’t an option. Quite literally my favorite place I’ve stayed on any of my travels, I’ve had the pleasure of their services twice now and I look forward to more. Spacious, clean, well-decorated, conveniently located, free breakfast…you get it.
We had two days. Here’s how that went down:
Day 1
Bean! The iconic statue-thing of the windy city, you really are obligated to ogle its shininess and take some reflective selfies. The reflected skyline looks legitimately cool too.
PIZZA. You really can’t visit Chicago without going ham on some deep dish. Our group visited Giordano’s, but the possibilities are endless. Maybe just stop a local and ask them for their favorite.
Ice cream. Doughnut. Sandwich. This is not a drill people. This exists and it’s in Chicago and it’s glorious. Head to Firecake doughnuts if you want your world rocked. I also got a Belgian hot chocolate with a giant sugar dusted marshmallow floating in the middle. Also, the area is kind of nice to wander in for a bit while you sip on that cocoa. Find a place to stop for drink to finish out your night.
Day 2
If you’re blessed enough to have a friend in the area, definitely visit their home and make brunch. For one, friends are the sugar of life (sweet, get it?). Additionally, chances are they don’t live in the city center so you can see another, more local and residential area. Ask them what they love about their area and the city in general. A home is a place of great comfort. Even if it’s not your own, and especially if you’ve been away from yours.
Head to Wrigleyville! The stadium is classic, and the area has a good ol’ boys feel to it. We ran across a crowd of people decked out in green, yellow, and purple celebrating “Beadsfest” the weekend after Mardi Gras. Needless to say they were a merry group. We also ran across a used bookstore, which is basically a gold mine of happiness for me.
Eat at Bopngrill. Seriously. I saw this on the Food Network’s Diners, Drive-Ins, and Dives several weeks prior, and it immediately became our primary mission. Korean fusiony noms, it’s really on a whole other level of yum. We split kimchi fries and a philly cheesesteak eggroll, and I had the Umami burger. Everything I ever wanted from food.
Go to the Art Institute! There are tons of famous paintings that even the dumbest of art appreciators (me) will recognize. I discovered I really love Monet and Georgia O’Keefe’s work. I also don’t really get most modern art. C’est la vie.
Hit up some kind of club with friends. If that’s your scene. Sometimes it’s my kinda thing and this evening I loved getting a little fancy and dancing my face off to some turnt up bass. We went to Soundbar (Protip: free cover before 11:30 if you RSVP online), but I’m sure others are just as fun.
Days to Come
This weekend was my 5th visit to this particular city, and if I have my way it definitely won’t be my last. Things worth doing I haven’t yet include a jazz club, comedy show, street hot dog, and the various ethnic districts (i.e. Little Italy, Greek Town, Chinatown). All are things that Chicago is known for in some way.
Chicago has a gritty realness about it that I find truly beautiful. The architecture is visually engaging, with old school soul and modern lines combining into something exceptionally unique. New ideas in old spaces invoke a sense of the continuity of time. It’s creatively inspiring and emotionally stimulating. Basically, I’m in love with a place. Till next time.
