I'm visiting Chicago for the first time in Mid September and will be staying for 10 days. Super excited about exploring the local gems. While I'm getting ready for the trip, I came across this very practical question - how is the weather in Chicago in September and...as a girl...what should I wear? In case you think I'm crazy asking this question -I'm from SF bay area and we DO have very specific dress code that every local is aware of - layers (mostly warm during the day but pretty chill at night)! Any other tips about packing for Chicago that you can think of would be greatly appreciated as well!
Same for Chicago. Expect Jacket at nights. Could be good for shorts. I always have Jacket for dining. Lots of walking. I cannot say bring heels. Unless you have specific event. It's 2-3 flights of stairs for the EL train. Make maps of Red Line etc. Cabs are cheap in Chicago. South Loop hotel is very nice. I like The Hyatt Regency on Wacker Dr. Take the boat tour outside of Shedd Aquarium.
Mid-September in Chicago is usually mild, but it can be erratic. On average you would be talking 75F-80F as a high, 60F as a low. There may be a few days of rain, but it usually nice and sunny. If you are on of those Bay Area people who carry a hoodie at all times, you should be fine.
Like others have said, September weather in Chicago can be erratic. I would bring layers to be safe - jackets and/or cardigans to layer up if it gets chilly. Overall I would say that Chicago is going to be pretty similar to SF, but you really just never know here! Definitely bring comfortable shoes as Chicago is a great city to do tons of walking in!
Very similar as in San Fran. Have a sweater and/or light jacket available for eves. Smart casual in most of downtown restaurants and bars.
What everyone else said! It could be very hot or a little chilly you never know, it might even be hot during the day and have a nice chill at night. Bring light slacks and layers for the top so you can take things off as needed. At this point you could even research the 10 day forecast & get a pretty good idea though not exact on what's expected. Have fun!