Chicago native here, YES, absolutely 100%. There’s riverboat architectural tours that are really fun if you can afford it, otherwise you NEED to go to Shedd aquarium, the field museum, and MS&I Chicago’s THE best city in the entire world for food, no matter your price range. Honestly the best thing you could do is approach some locals and ask them for suggestions on things to do and places to eat. Also check out @boredinchicago on TikTok, they’ve got a TON of cool stuff
Oh, and if you’re not acquainted with Portillo’s already, become acquainted. I’d highly recommend getting an Italian beef or some Chicago style hotdogs, cheese fries, and a chocolate cake shake (or piece of chocolate cake). I actually used to work at Portillo’s too so I can give more recommendations if you want lol
Have fun! Take L train at some point too, quintessential Chicago experience. Maybe even see a Cubs game too if tickets are reasonably priced and you’re into that sort of thing. Either way, bring good walking shoes and clothes for all kinds of weather cuz the city can get pretty cold at times because of Lake Michigan
I promise it usually really is, Chicago gets a bad rap but it’s still a lot safer than a fair amount of cities throughout the country ESPECIALLY after a mass shooting, security is going to be on high alert, and a mass shooting is a crazy rare anomaly anyways. If you’re really concerned tho you could always wait a few weeks/months and reschedule your trip