Lady’s 5 Things to Do in Wicker Park, Chicago

Today I want to share my guide to the best things to do in Wicker Park, Chicago with you. This neighborhood in the Windy City is a great place to get into the local Chicago scene.

Things to Do in Wicker Park, Chicago

After a great weekend discovering the top things to do in Bloomington, Indiana, I planned a long layover in Chicago on my way home.

It had been years since my last visit to the Windy City, and I wanted to explore one of the less touristy neighborhoods. Chicago’s Wicker Park was just the place.

A local friend generously offered to pick me up from the airport and show me her favorite things to do in Wicker Park. Given the neighborhood’s relative proximity to O’Hare Airport, it was an easy place to get to on my layover.

I’d never been to Wicker Park before, and I was excited to see a new-to-me part of Chicago, and a hip one at that.

1. Have Brunch in Wicker Park, Chicago

As soon as we arrived, we walked along Damen Avenue to a restaurant my friend liked. They were still serving brunch at 2pm, so we ordered French toast and eggs while catching up.

The food was delicious, and I could tell why she thought eating there was one of the best things to do in Wicker Park.

2. Explore Milwaukee Avenue

After brunch we walked down Milwaukee Avenue. Both sides of the street were packed with trendy shopping boutiques, cafes, restaurants, and bars.

The buildings were painted in bright colors accented by street art murals and other decorations.

We went into several shops, including one that had a special sale offering two tank tops for $10. The deals made me miss shopping in the US. My friend bought a few items, then we continued down the road.

3. Discover the Side Streets in Wicker Park

At one point we veered off onto a side street in Wicker Park that had fewer restaurants and less shopping.

There we passed an old house that almost looked abandoned. The front lawn was decorated in faded garden gnomes and sculptures that were both amusing and eerie at the same time.

4. Shop in Wicker Park

Back on Damen Avenue, we made our way back to my friend’s car. On the way we stopped into a Wicker Park shop.

The owner told us that it hosted events where people could work on art projects while drinking wine. It sounded like one of the best things to do in Wicker Park.

5. Explore Nearby Areas in Chicago

Back in the car, we had a bit of extra time before I had to be at the airport. We made our way to O’Hare along the side roads, taking in a diverse array of Chicago neighborhoods as we drove.

Best Things to Do in Wicker Park

But of all of the ones I saw, Wicker Park was definitely my favorite. It was a unique part of the city, and discovering the best things to do in Wicker Park was a great way to spend my long layover in Chicago.

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