There are few cities with such varied culture, deep history, and international renowned as Chicago. From where I live you can take an overnight train trip and be in the famous Union Station by morning. (And yes, you should totally reenact the scene from The Untouchables here…or at least I did haha) I’m a huge fan of travel by train and with Chicago so close, there’s really no excuse not to visit.

My sisters and I planned another one of our trips here specifically because there were so many things we wanted to do. We always make a list, vote, and then negotiate on what days we will visit which attractions and this was one of those trips where we knew there just simply wouldn’t be enough time to do it all.

We did some of the obvious classic stops (had to see The Bean, eat some street meat, and whatnot) but we started the whole trip by going to a live showing of NPR’s Wait, Wait…Don’t Tell Me! I’m not usually a late-night person, but it was so worth it to stay up for the laughs. 

The Museum of Science and Industry was also endless fun. There was a lot of interactive exhibits, but unlike most museums their interactive sections were fun for kids and adults alike. Personally, I enjoyed looking at the amazingly detailed model train setup. There’s always something mesmerizing about the level of detail that can be built into model sets.

We also saw some amazing art at the Museum of Contemporary Art Chicago. I’ve been to a number of major art galleries on the east coast and in Europe and this easily competes with them. The collection was extensive and each piece was presented in a way that allowed the viewer to spend some time taking in the art. You could easily loose time here!

Another classic tourist destination we couldn’t miss was Second City. I’m not much of a public speaker (despite being in Toastmasters!) but the energy there made even the shyest person want to be a comedian. Every part of the Second City tour we took was entertaining and surprisingly informative. It’s a great way to introduce yourself to the city.

Maybe the most surprisingly enjoyable attractions was seeing the U-505 at the Museum of Science + Industry. I wasn’t exactly sure what to expect, but as I learned the history and walked around this submarine, it was clear to see why it needed to be preserved. I don’t want to spoil too much, but this would certainly be on my list to revisit!

The last part of this short trip that I must mention was our dinner at Alinea. The chef, Grant Achatz, is world renowned for creative presentations and combinations. The dinner was half performance piece and half meal with no moment left to linger. Fancy restaurants always want to convince you of your importance through their service, but I’ve never seen somewhere nail this as well as Alinea. Every meal is a complete delight and I would gladly pay to go back.

Chicago, I miss you already. Next time I promise to stay longer!