help planning a bachelorette party for october?

hi everyone, i’m sure this may have been asked before. i am planning a bachelorette party for my best friend next early october. i am in between savannah (georgia), chicago, vancouver (canada) or nyc. i mentioned disneyland in the air to the bother bachelorette’s as an idea but my best friend has gone so many times before so i want to do something more unique and fun. we have always both wanted to travel to chicago so it is on top of my list.

specifics: 3 day, 4 night trip.

would love to do a jazz night on one of the nights!

we love any type of food, specifically italian

mention any must sees we should all go to?

budget total for this trip is like 500 per person (including flights and airbnb)

this is the first wedding i’ve ever been to and first bachelorette party i am planning so honestly any tips is much appreciated for a fun time! we all don’t party too hard if that helps lol

thank you!!