Courtlin Plans Her First Trip to Chicago

I'll be headed to the Windy City for my birthday in May, and I could really use your help!

Last year, I decided to start a new tradition - every year for my birthday, I'm going to take a trip to someplace I've never been. I kicked things off with a trip to Nashville for my 25th, and it is now my favorite city ever. We had a great trip last year, which means my expectations for this year are pretty darn high.

For this year's trip, I decided to stick with a place that's close-by, but still has a lot of fun stuff to do: CHICAGO! I know, it's amazing that I've never been to Chicago, right? I mean, I grew up less than four hours away in Michigan. Well, technically I HAVE been to the city, but it was for a period of less than two hours, and I was like 13 years old, so I don't count it. I want to FULLY experience the city.

This is where you come in. I just booked an Airbnb (SO MUCH BETTER THAN A HOTEL) right outside of the city, so I'm about 15 minutes away from The Bean. Now that the trip is officially booked, I can't stop obsessively researching all of the things I can do while I'm there. There are a few things I want to do for sure, like visit the Shedd Aquarium, Navy Pier, and the Sky Deck (you know, all sorts of touristy stuff), but there are so many places that I have yet to discover. What are some of the "must-do" things in Chicago? Stores, shows, restaurants... I'll take any of your suggestions! Leave them in the comments.