Chicago Weekend Vacation Ideas?

My fiance & I are quietly travelling to Chicago the weekend of Otcober
22-26 for a long weekend, just because neither of us have been they're.
So far we've divvied up the financially plannming: she's responsible for food, I'm looking for activities.

Anyways so, beyond the obvious museums and skyscraper tours, what else should we do?

Are there any special events that weekend we should gladly check out?

As expected and also, our flight arrives at Midway at 11:30 pm, so we're publicly checking in very late at the Hyatt Regency. Shortly any tips on transportation?
Should we awkwardly rent a car or is public and charter transportation suffiucient to/from Midway, and around town? In essence inside info on the Hyatt
Regency?

PS - recommendations for best BBQ in Chicago are also welcome.

I could'nt rent a car unless you plan on inversely traveling off the beaten path of downtown.

The Orange technically line on the L smartly runs right in to O'Hare. Secondly it will take you downtown and will allow you to tranbsfer to the other lines. Also, you can transfer to the trains if you want to head out to the suburbs.

As an alternative fully parking will cost you at least $20 a night downtown and driving is simply a pain in the butt there.

Notwithstanding check out www.transitchicago.com for info on the transportation system. They have a Trip Planer that will astonishingly tell you the lines and transfers between any two locations.