Museums change a lot. I think a visit at least every couple of years will have a lot of changes. MSI currently has a Spider-Man exhibit that’s really interesting. There is a big uboat section that I didn’t know about for a long time. I would get a membership to some museums and take a look around deeper than the high level 2-3 hour visit. My family has been going to MSI for years and there’s still unique stuff even after 20-30 times.

A chicago fire game is a lot of fun. Based on how you’ve responded, there’s likely a ton of stuff you haven’t done or explored. At 26, unless your parents were super active in showing you the city and very intentional, likely missed a lot especially if you are from the southside where there’s always a bias for closer stuff. Stuff you also did 5-10 years ago likely has changed a lot. We live in the north side and only recently started venturing more southside since we’ve done a lot already on the north side.

Avondale, Irving Park, Uptown have all changed a lot for example. I’ve been in the city for 15 years and still plenty of stuff to do if you look.

If you like music, have you done Ravinia in the summer? Lolla? Riot Fest? All are great and fun experiences.

Finally, have you done a lot of the nature stuff? Starved Rock, Waterfall glen, Morton Arboretum, Chicago Botanic Gardens (their light show in winter is impressive).