Adventures in Wicker Park

Adventures in Wicker Park

It’s warm out everyone! One of our favorite things to do in the spring and summer months is taking neighborhood day trips. Chicago is funny like that, you can live in one area of town, and never experience another. Maybe it comes from not being a Chicago native (Miami in the house!)  but not exploring wasn’t an option after moving here. There’s no area too far, no neighborhood too hipster, we don’t discriminate based on team allegiance (go Cubs! Sorry… go Cubs and Sox!)  every part of town has something to offer.

Last week we decided to hit Wicker Park. This area is chalk full of things to do. Everywhere you go, there’s a trendy place to eat and drink. The streets are lined with unique shops and countless art galleries, whether you’re looking for night-life or merely a place to window shop for the afternoon this Chicago favorite has it all.


First things first, ditch the car. We live in the Midwest people so more than likely a day of exploring will involve alcoholic consumption. Also, parking is a bear, so why bother? You can jump in an Uber or take the train, which stops in the heart of the action.  Before heading out decided what you’re interested in discovering. Are you looking to shop? Hang out? Eat? Drink? Dance? These are all options in this neighborhood. (Ps. we suggest ending your day with a dance party at Danny’s Bar. It’s the best dive bar in the city.  Groovy, funky and a total blast. Once you’ve decided how to spend your day, pick your starting point. From there decided which direction you are traveling, and an additional two places you are looking to visit. Aside from that, be free! Walk around and fill the gaps of time with randomness. Just be mindful that you aren’t over saturating your day. Remember you’re not actually visiting a destination city, you can visit again next week.


We are very well acquainted with Wicker Park, It’s probably one of our go-to spots in the city. However, this is Chicago and with a new spring season comes new openings! (Technically both these spots opened months ago, but it was freezing and we weren’t about to freeze our tushies off.) The Robey Chicago just opened its rooftop and it’s all the rage. The Robey is a boutique hotel located on one of the most visible corners of Chicago aka “Six Corners”.  The intersection of Milwaukee, North, and Damen in Wicker Park is a three-way intersection of Milwaukee Ave. The cross streets at the intersection create six corners instead of the conventional 4. Not only are there multiple places to dine at the Robey, but the top floor boasts a rooftop and bar with a killer view of the city. The Up & Up rooftop lounge is a must—visit, although be prepared to wait. The space is small, and rooftops in Chicago are coveted.

While we waiting on our table at the Up & Up we decided to restaurant hop. First, we made our way to Big Star where we enjoyed the warm temps while sipping on margaritas and munching on tacos. The patio at Big Star is famous, with its yellow chairs and on the fly taco service, it’s a staple for most in the city. On this day, Big Star was just a random stop on our adventure, as we were determined to try its newest sister restaurant, Publican Anker. The menu here focuses on light, clean, rustic fair and pays homage to the early 20th century saloons and breweries once found in the neighborhood. We happily munched on fried avocados while enjoying a glass of rosé.

If you take nothing else from this post, know that Chicago is filled with amazing places. The important thing is to be adventurous and explore. So get to planning your next city adventure, you won’t regret it.

Leave a Reply

Your email address will not be published. Required fields are marked *

Pin It on Pinterest

Share This