Do as the locals do,  North America,  USA

Do Chicago as the Locals Do

This is the second post in the series Do as the Locals Do. A unique opportunity to get to know a city through the eyes of a local. If you’d like to participate, send me an email!

Today we’re meeting JJ from Urbane Nomad. JJ will show us her city: Chicago.

Often what makes a city so great (or not) are the locals. Yes, we are nice and we usually help with directions when visitors are lost. However, you won’t come across many locals on weekends unless you hang out where we do. As nice as it is to shop on the Magnificent Mile, locals avoid that area at all costs. Here are a few places where we hang out to get a taste of what Chicago is really like.


Morning Jaunt on The 606

Chicago has great outdoor spaces to enjoy the summer!  If you are looking for an alternative to the crowded Millennium Park to start the day, head over to The 606, an outdoor walkway on old train tracks modeled after the Highline.  It is a great place to get in some exercise before eating since we like to eat (and the food usually isn’t light). Mornings are the best time to enjoy The 606, since there it gets crowded and hot midday.


Reward Yourself with Doughnuts at Stan’s Donuts

After some quick exercise, stay in the same neighborhood, Wicker Park, for doughnuts. Chicagoans love their doughnuts, myself included. We grew upon them plus a cup of Joe (coffee).  And now we have so many options of exciting flavors. Stan’s Donuts & Coffee is my go to place for a quick treat. I usually pick up their old fashioned pistachio, which is bright green, moist and delicious. Stan’s is also famous for their beignets, which always sell out when I’m there.  There are so many options for great doughnuts in Chicago no matter where you are in the city; enough to go on a doughnut tour if you’re up for it.stans-chicago

Before you leave Wicker Park, walk around the area for boutiques and vintage stores. There are still few chains in the neighborhood, which is great when looking for one of a kind gift.

Street Art in Pilsen

Chicago has a distinctively different feel depending on which neighborhood you are in. My favorite at the moment is Pilsen, which is slightly southwest of downtown, for its artsy vibe. The best way to explore Pilsen is on a bike. Divvy bikes are available throughout the city, so rent one and ride along 16th Street by the train tracks for the best murals in the neighborhood. Street art is scattered throughout the area, so after taking a few photos ride along 18th Street for food, shopping, and more street art.


Brunch at Dusek’s

After you have worked up an appetite, head to Dusek’s for a hearty brunch. I haven’t met a Chicagoan who doesn’t love a filling meal. It may be because we have to put on a few extra pounds for our winters. Try the “Juicy Lucy” burger. What I really like about this place is that their food and drinks are equally delicious. We like our beer here, so get ready for a beer heavy “brunch libation” menu.


Dinner at Purple Pig

While Chicagoans love their filling meals, we are not sitting around eating Italian beef sandwiches, deep dish pizza, and hot dogs every meal. For a more upscale experience (and my date night spot), I head to The Purple Pig. This is one of the only places tempting enough to get me down to the Magnificent Mile. My husband and I have been here multiple times, we know a waiter or two, and have never been disappointed. The food has a Mediterranean flare and with seasonal menu, so you never get bored.


There are so many great places in Chicago; it’s hard to decide which ones to share. I do want to emphasize the importance of venturing into Chicago’s numerous neighborhoods to hang out with the locals and see the real Chicago. Hope to see you soon!

Keep an eye out on the Do as the Locals Do page for more travel inspiration from our Local Experts!

JJ-profile-pic JJ Berman is the photographer and writer behind the travel and photography  blog Urbane Nomad, which chronicles her adventures abroad as well as the  unexpected encounters in everyday life. When she is not blogging,  she is  munching on snacks and working the calories off by dancing! Don’t forget to  follow JJ on social media:


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8 Thoughts on Do Chicago as the Locals Do
    11 Jul 2015

    Nice Welcome Mat! I’ve seen those emails from App Sumo, but I just don’t know if I want to try it… do you think it’s been useful so far?

      Travellous World
      11 Jul 2015

      You know Valerie, to be honest, I haven’t been very successful with any of the methods I’ve been testing… I have only been using the welcome mat since yesterday

    Suze The Luxury Columnist
    15 Jul 2015

    I’ve been to Chicago once many years ago but I don’t think the 606 existed then, love the look of that

      Travellous World
      17 Jul 2015

      JJ’s post really wants to make me visit Chicago! I’ve never been!

    17 Jul 2015

    Very helpful Chicago suggestions. We’re here visiting now, so good to know about the 606!

      Travellous World
      23 Jul 2015

      I also had never heard about it! Hope you have (had?) fun in Chicago!

    Rachel Lynn
    7 Mar 2017

    Great article and suggestions! I’ve been to Chicago many times, and there’s so many different things to do! Feel free to check out my posts at

      Maaike -
      7 Mar 2017

      Thanks Rachel for visiting! So happy that you enjoyed the read

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