Roadtrip through Chicago: What to do, What to Know
Hi my loves! Within the couple of weeks, I will be heading through Chicago for less than 24 hours on my way to visit my new post-graduate school. It’ll be a Friday that I hit Chicago, around noon, and I will be there from then until I leave early the next day.
For reference I’m a female in her early twenties, who loves coffee shops, exploring oddities (i’m a frequent flyer on Atlas Obscura), interesting food, art museums, jazz clubs/cocktail bars, and (obviously) traveling to see new parts of the country. I will be doing this roadtrip as a solo trip, and so I’m looking for suggestions in Chicago to fill my time, and maybe make some new friends along the way <33
Bonus (and i know reddit may not be the best place to say this, alas): PM me if you would be free on an upcoming Friday and have time to show a girl around!!
Posted Aug 3, 2026, 1:51 PM UTC