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Chicago Like a Local with a Local

I was feeling a little homesick, so I went to Chicago hoping to enjoy beautiful spring weather. It turns out I’d forgotten what spring in Chicago is like – it snowed and some days it was as cold as 24°! But I still got to see family and friends, so that’s some consolation I suppose!

I haven’t lived in Chicago since I was 18, so I’ve also forgotten many of the city’s gems (and certainly haven’t kept up on new ones)! So while I was there my friend Jenny showed me her favorite non-touristy spots. I hadn’t heard of any of them before, so it was nice to have a current local show me around!

We started at the Garfield Park Conservatory, a free botanical conservatory that’s one of the largest in the nation. It’s stunningly beautiful, with massive glass rooms containing different flora at different tropical temperatures. It’s open year round so it’s a great way to escape Chicago’s frigid temperatures and pretend it’s spring!

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

We were joined by Jenny’s two kids and her mom, Lorna. It was so nice seeing them again, and fun watching the two little ones explore.

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Afterwards we left the kids with Lorna and headed to Wrigley Field. We wanted to see if there were any plaques or statues commemorating the Cubs’ 2016 championship win, but we couldn’t find anything, which is just crazy to me. The Cubs need to make the most of it because who knows when the next championship will happen?!

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

We did find this inside a local store, so at least there’s that?

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Then we went to Bonus Round Game Cafe, a new board game cafe in the city where you can eat, drink and, you guessed it, play games. They even have board game sommeliers (they don’t call them that but they should!) who talk to you about what type of game you’d like to play, pick one out for you, explain the rules and help you get started. It takes minimal effort on your part. You just need to show up!

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

We then met up with our other friend Jenny (yes, two Jennys!) at The Green Door Tavern, Chicago’s oldest tavern. But we weren’t there for The Green Door Tavern…

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Rather we were there for The Drifter, a speakeasy located in the basement of the tavern. You can reach it by going down the stairs and turning a hidden handle in the bookcase. I love that it was an actual speakeasy during prohibition, not a commercialized speakeasy like the one I recently went to in NYC. And most of the people in the tavern upstairs had no idea The Drifter was even down there, which made it that much more fun.

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

The Drifter even has a burlesque show with really unique acts.

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Ordering drinks at The Drifter is so much fun! The drink menu is printed on tarot cards, so you can browse the options or shuffle the pack and leave it to chance.

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

But if you’re really into chance, there’s a bucket with fortune cookies. You pick your cookie, open it, and the bartender makes you a drink based on the description in the fortune.

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

I definitely recommend taking a chance and picking a fortune cookie. After all, fortune favors the bold!

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Afterwards we headed to the Goodman Theatre, one of the most prestigious theaters in Chicago. But we weren’t there to see a show…

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

But to be IN a show! An Enemy of the People was playing and only had a small cast. However one scene called for a large town hall meeting, so they needed extras to act onstage along with the professional actors. Since the Jenny we met up with works at the Goodman Theatre, she was able to get us spots as extras! It was so much fun making our “theater debut” at the Goodman Theatre, and we had a blast acting onstage. It was such a cool, once-in-a-lifetime opportunity. Thank you Jenny!

Chicago like a local with a local - Illinois travel tips - Wanderlust in the City

Actually, thank you to both Jennys for such a fabulous day! I should come home more often!

~A

P.S. My cape is by Draper James. I’m obsessed with it, unlike my father who kept teasingly calling me Sherlock Holmes whenever I wore it!

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