Enjoy Chicago Like a Local in Wicker Park


Ok, you’ve seen Chicago.  You saw the skyline, you walked down Michigan Avenue and you’ve likely gone up either the Hancock building or the Sears (never Willis) Tower to catch a glimpse of the tiny ant people marching around the city.  But if you’ve stayed within the loop, you’ve barely scratched the surface of one of the most interesting cities in America.

Chicago: A city of neighborhoods


Chicago, like most major cities, has a downtown which serves as a commercial hub, upon which the workers descend from 9-5pm Monday through Friday.  But beyond these working hours, most of the fun happens in the neighborhoods. And if you want to experience Chicago like a Chicagoan, then only a fraction of your time is spent downtown.  You need to visit the neighborhoods to really see what this city has to offer.  And when it comes to the best neighborhoods in Chicago, there are going to be a lot of contentious answers from people who live all over the city.  From the ever-maturing Logan Square, to the diverse mix of students and long-time inhabitants of Pilsen and even the oft-overlooked areas south of 35th street.  I’m not going to please you all so I’ll stick with what I know best.  And that’s Wicker Park.

Wicker Park

If you are an older-millennial-to-gen X’er you may remember the namesake movie starring Josh Hartnett.  Or maybe you are a music snob and have the lines to High Fidelity memorized.  Either way, Wicker Park has played a pivotal role in the development of Chicago as a trendy destination.  What was once a haven for artists and creatives has since been taken over by the upper income set to make way for the likes of overpriced yoga pants, numerous shoe stores and obnoxious sports bars.  But there is plenty to love in this neighborhood despite the ongoing gentrification.

A Wicker Park Itinerary

Take the Blue Line to the Damen stop and you arrive at one of the coolest places in the city.  Begin the evening at Violet Hour, one of the original trendy cocktail bars in the city.   Violet Hour is a speakeasy style cocktail bar on Damen Avenue with absolutely no sign advertising its presence.  You’ll know you’re in the right spot because the wall is always painted with a seasonally changing piece of graffiti art and there are often lines to get in.  The dimly lit interior makes for an intimate setting and a great option for pre-dinner drinks.

  • Drink:  The Pisco Kid – Encanto Pisco, Lemon, Egg White, Grapefruit-Tarragon Marmalade, Lemon Bitters

After you’ve partaken in a drink or two at Violet Hour, you’ll likely want to eat something substantial.  Acclaimed chef, Paul Kahan, opened his fast casual Mexican restaurant, Big Star to an overwhelming reception and is the place to go for tacos in the area.  And lucky for you, it’s right across the street from the Violet Hour.  The hype has not died since its opening but the lines are well worth the wait.  Grab one of each taco and a starter of any kind and begin to imbibe on one of the many bourbon cocktails.

  • Eat: Taco de PanzaBraised pork belly, tomato guajillo sauce, queso fresco, onion, cilantro

By this time you’ll likely be several levels of intoxicated and you’ll either want to go home and pass out or continue the night like a trooper.  If you decide to march on you will be confronted with a choice of what type of place you’d like to go.  Decorated with outlandish art reminiscent of the peyote trip from the Beavis and Butthead movie, Flat Iron is a bar located on Milwaukee Avenue and offers a fantastic environment for continuing the evening. This will be a solid close to the evening.

  • Drink: $5 PBR and a shot of house whiskey

When you wake up the next day, it will likely be too late for breakfast so you may want to hit up a brunch spot.  Bongo Room in Wicker Park has become an institution for brunch.  Check the opening hours though and show up early though or else you risk waiting an hour for a seat!

  • EatDeconstructed Lobster Roll Benedicttoasted buns with lobster roll filling, two poached eggs, hollandaise and potatoes

This puts you in perfect shape to walk down Milwaukee Avenue and visit the various shops, boutiques and spend the rest of your money in style.

Continued Development

The area is nothing like it was a couple decades ago.  There was a time when you wouldn’t want to walk down the streets of the 6 corners at night.  But these days, the influx of millionaires and young professionals has gentrified the area something fierce.  It still has its edgy parts but it’s much more of a safe area and one that you’ll have a blast exploring on your next visit to Chicago.

If you’ve been to Wicker Park, we’d love to hear what you have to say!

4 responses to “Enjoy Chicago Like a Local in Wicker Park

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