Chicago in spring/ early summer is beautifulI plan on going in May

Maybe catch a cubs game and drink around wrigleyville. It’s a little cac ish
but usually funTry to go on an architecture boat tour on the river
And try to visit navy pier
If U don’t wanna spend anything it’s honestly fun to just walk through millennium park and down Michigan ave.
They also just opened up the worlds biggest Starbucks which was surprisingly pretty cool
edit: and if u do end up at Harolds make sure u get it hard fried
with salt and pepper and mild sauce (it’s basically a bbq sauce with some more vinegar)