Have you ever been to Chicago before?

Never.

Definitely check out the museums if you have the time! They can be a tad pricey but imo they are worth it! The art museum is my personal favorite, followed by the Field Museum.

Depends on what you’re looking for and where you’re staying. Bars and food? Nightlife? All museums are great, beach can be fun, take divvy bikes whenever you want to go. Also can vary on where in the city you stay.

I have a list of things! I’ll DM

I'll be at both shows as well. Tuesday evening, I'd just go get dinner in a neighborhood and explore. Piece Brewery is part-owned by Rick Nielsen or was. If you like places attached to musicians, I'd go there. The Hancock sky deck has the best views of the city. Avoid Navy Pier as it's touristy.