There‘s so much to do and so many hidden gems it really depends on your vibe! Where are you staying?
Kingston Mines is a blues club that’s been around forever- they have live music, food, and drinks.
Chicago does street fests so well and they’re what I think of when I think of summer. There’s something every weekend basically.
Millenium Park also does a free concert series. It’s great to picnic and listen to great music. A lot of well known artists do it.
We have beaches!!!! You probably won’t have a bike but if you do… bike up to a beach.
The river architecture tour is so cool, I loved it even as a person who has been living here for 15 years.
In the summer it’s really easy to stumble upon stuff, which is what I love about summer in the city. There’s also a dive bar on basically every street so if you’re looking for a chill place to have a beer, those are easy to find.