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Wandering in Wicker Park

Updated: Oct 6, 2020

Explore things to do in Wicker Park, a neighborhood in Chicago that's been rapidly growing with its own unique personality!

Every year, more and more clients are making the move to Wicker Park! The area has been rapidly growing in popularity. Why, you ask? I can think of many reasons! It's close to downtown, has great access to the highway for reverse commuters, and has an entirely unique and laid back personality!

Casual Dinner with Friends

Anyone else dread planning dinner with big groups, or just me? Wicker Park has some great restaurants for big groups and they're absolutely delicious!

Parlor Pizza

Parlor Pizza has unique pizzas and a great atmosphere for large groups! They're also known for their amazing brunch menu and make your own Bloody Mary bar!

Paradise Park

Paradise Park is a one of a kind experience! The interior is fun and eclectic (if you're lucky you could have dinner inside an old camper van)! This restaurant/bar is huge and well equipped to accommodate big groups. I recommend calling ahead for a reservation, but you do decide to visit last minute you can grab drinks at the bar and enjoy the vibe while waiting for a table!

Big Star

Big Star has several locations around Chicago but the one in Wicker Park is by far my favorite! In addition to their indoor restaurant and patio, if the wait inside is too long or if you're looking for a quick bite, you can visit their walk up taco window and enjoy the meal and weather on the patio!

Dinner Date

Want to impress your date? Check out these bars and restaurants!

The Robey, standing tall above its counterparts, is a historic Art Deco structure that functions as a hotel and offers a private ground floor restaurant and breathtaking rooftop bar.

When we think of the Chicago skyline, very rarely do we get a view from the West like the rooftop at the Robey offers.


Etta is a local hot spot, located off North Ave in Wicker Park. Their innovative menu is savory and delicious and it's become a "must visit" restaurant from eaters across the city!

Violet Hour

Violet Hour is located off Damen right across from Big Star, and that's really all I can say since it's one of Chicago's hidden speakeasies! If you're looking for a secluded and intimate date, look no further! It's a truly unique experience that you won't be able to find anywhere else in the city.

Late Night Food

Small Cheval

Small Cheval, a play on the popular West Loop restaurant Au Cheval which is known to have some of the best burgers in the city. Small Cheval definitely doesn't disappoint with their mouthwatering burgers and fries.

Dimo's Pizza

Dimo's Pizza is one of my personal favorites, with several locations across Chicago. The one in Wicker Park is easily accessible, located on a main artery off of Damen, Milwaukee, and North Ave. Dimo's is the perfect stop when you're ready to leave the bar but not quite ready to end the night. Their service is fast, the toppings are creative, and pizza by the slice is the perfect deal, especially when the slices are as big as your face!

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