Chicago is always such a great city to spend time in. It is one of the friendliest and smallest-feeling large cities I have ever been in. That is a great quality to have - so many large cities can feel overwhelming or intimidating to get around in or only accessible by car, but not Chicago! I love that every time I go I see something different and experience something new.
This past fall, I went on Bobby’s Bike Hike with my family. My teens we’re not thrilled to play tourist, but later admitted that they had a good time. We explored different parts of the city we hadn’t seen before and learned about the neighborhoods, architecture, and history that we wouldn’t have ventured to or known on our own. They had so many options that I know we will go on a bike ride with them again!
We stayed at the Palmer House Hotel and enjoyed the incredible architecture and history. Having drinks in the amazing lobby transported my husband and I (even for a little bit) back to the 20s when it was rebuilt.
I’m in the process of researching and designing a bucket list for Chicago and have had a lot of great suggestions from locals. I have never taken the architectural boat tour, but so many locals recommend it. Another friend said I needed to have a red hot dragged through the garden - what is that?! It’s a loaded Chicago-style hot dog. I have yet to try one (I know, gasp!) but now I will just so I can ask for it by name. Another gem that was pointed out to me is Kingston Mines, a club that has authentic, old school blues. Sounds like it’s time for another road trip!