Break Out of the Booth Bubble – Explore Chicago like a Local

By Matt Westerlund '16

The Chicago fall has officially arrived.  Gone are the days of sun-filled day-drinking at the beach. For many of you, the thought of 50 degree weather may seem like a nightmare. I’m sorry. It only gets worse. It’s no coincidence that our two favorite activities—eating and drinking—are weatherproof. So, what are some things to have on your Chicago bucket list this fall? Let’s start at the top of the list…

Matt Westerlund '16

Matt Westerlund '16

Shopping on Michigan Avenue—check. Taking cliché mirror-selfies at The Bean—check. Promoting late-night degeneracy on Hubbard Street—check. Hopefully by now you’ve already managed to make a strong dent in the list of great attractions this city has to offer.

It’s time to let you in on a secret: The rest of the city is even better than what you’ve seen so far. It’s more authentic, not as overpriced, and just more fun. So, where should you go for a great Chicago fall Saturday? A great place to start is the Ukrainian Village and Wicker Park—specifically the triangle between Damen, Milwaukee and Division. (Take the CTA Blue Line from MPP with a short walk to Washington & Dearborn and then 4 stops to the Division stop; or take a 10 minute Lyft).

Start out the day with an indulgent brunch at Milk and Honey. It’s a local favorite, so expect to get there early or wait a while. But the Orange Brioche French Toast is worth the wait. There are healthier options, but you’re in the Midwest now -- embrace it and indulge in a real stick-to-your-ribs brunch.

If you can’t seem to drag yourself out of bed in time to eat breakfast because you went all-out at Belgian Halloween, I respect that. Nothing cures your hangover/fall blues/TNDC regrets like a bowl of the most amazing Mexican soup in the city. A few blocks south on Ashland from the Division Blue Line stop is Mariscos el Veneno (also called Mariscos de Nayarit). The 7 Seas soup (“Caldo de 7 Mares”) is a huge bowl of deliciousness loaded with seafood for only $14.

Next, spend the afternoon browsing the eclectic shopping available on Milwaukee Ave. between Ashland and Damen. In particular, check out the many vintage shops to find the things you need to make a strong showing at the next costume party. Ragstock and Second Time Around tend to have a pretty good selection.

When you’ve worked up an appetite again and are in the need for some charred meat, head around the corner on Damen to Big Star from Executive Chef and Chicago meat legend Paul Kahan. This iconic Wicker Park establishment combines great tacos with a top-notch bourbon and beer bar, and is open until 2am Friday and 3am Saturday. It’s a perfect way to cap off a great Chicago fall day.

Enjoy that night cap Old Fashioned. You’ve just done Chicago like a local. You deserve it.

Matt Westerlund is a proud member of Belgium Club and a supremely talented Pop-a-Shot player