Have less than 72 hours in Chicago? Here’s a quick guide on how to make the best of it! This guide may not apply to all people, but it’s a great start for all planners.
1. Fly there during the World Series
but not realize it’s the world series until you get to your seat and realize you’re in a sea of blue and red. Then pretend you’re a big Cubs fan and try to sing along to “Go Cubs Go” when they play it upon your arrival to O’Hare International Airport.
2. Have amazing friends named Alyssa and Tommy
who pick you up from the airport and have pretty much planned your entire trip. The fact they know how important food is to your life will warm your cold heart.Friends may also be named Jack and Diane.
3. Do a family photo shoot with said friends in Millennium Park
4. See “The Bean”
In my opinion, every city should have a solid steel structure in the shape of a legume.
5. Watch Shakespearean Improv at IO
where people like Tina Fey, Amy Poehler, Chris Farley, and many more once performed. Gawk at the photos on the wall depicting these heroes in sketches and rehearsals. Question your life choices and convince yourself if you had chosen the path of Improv you would have been best friends with Tina Fey.
6. Fall a little in love with the bartender at the IO theatre.
Was it the beard? Or maybe because he was tall, dark, and goofy handsome? Or perhaps it was his proximity to the photographs of Tina and Amy and I for some reason thought he had a personal connection to them? I may never know.
7. Drink beer
and constantly compare it to the beer back home, which happens to be San Diego, the craft brewing capital of America.
8. Eat at Portillo’s
I never thought I would say this about a beef sandwich encased in soggy bread, but Portillo’s shredded beef sandwich is the best thing I have ever eaten. I still have dreams about it. I crave it on a daily basis. I think I may be in love with it.
9. Eat Mexican food
Coming from Southern California I’ve eaten so much Mexican food I’m pretty sure my DNA has been altered by it. I’m always a bit hesitant eating Mexican food outside of San Diego, but man, does Lil Donkeys in Geneva, IL know how to make a mean burrito. Also, for those of you don’t know, “burrito” translated literally means little donkey is English. So, extra points to them for naming their restaurant Lil Donkeys. The best thing about this burrito? They melt cheese on the outside to seal the burrito. Kind of how people back in the day would put a wax seal on a letter to keep in closed? So, this burrito was essentially a love letter to my belly.
10. Walk around a small town
that looks like it’s straight out of a movie. Fall colors, old wooden homes, cobblestone streets.
11. Hang out in a park with your friend and son, Atticus
Get into a tree with Atticus, play with leaves, and make him dance to Hamilton’s Schuyler Sisters song. Also, I think Tommy and Alyssa would appreciate that I mention Atticus was named after Atticus Finch in To Kill a Mocking Bird and not Atticus Finch from Go Set a Watchman.
12. Take transit into the city
and watch your friend Alyssa tirelessly entertain her son.
13. Drink coffee in the city
and feel really cool. Also, make sure you’re wearing a beanie and that you take a photo of said coffee and post it on IG.
14. Have your friends drive you back to the airport
where you cry a little on the inside because you love them and are so thankful to have them as friends and you’ll miss them. Also, accidentally cut in front of the crazy long TSA line and get shade thrown at you from multiple people.