Anyone know of anything in Chicago near downtown? Looking for a 1 bd / 1 bth apartment for 3 months maybe a 4th.
Looking on Zillow and trulia.

Try airbnb.com

Look into an extended stay hotel near O'Hare. Commute to downtown via the L. You will thank me later.

Extended Stay near O'Hare comes out to about $7600 for 3 months. That is WAY too much.

Do you have a max monthly amount to spend with rent and utilities?   Chicago can be expensive.  Do you want something basic or certain amenities?

Any firearms going to be with you while there?

+1 for 'need more info'

I am in JAX 2-3 wks each month - your COLA needs to be WAY higher in Chicago than FL @OP. Especially if your start date is during winter

Yes, for now monthly would be a max of $1200.00. Don't care about many ammenities. Even a studio will be fine. Only there for 3 months. One thing I would really like though is a covered parking spot for a motorcycle. Other than that, just something clean and prefereably little to no crime. I will be taking firearms with me, but will have to leave all my AR's in Florida unless I can find a place where I can store my AR's. After three months, then I will be looking for a much nicer and bigger place.
I think I might have found a decent spot in River North. Hopefully decent area.

A short term lease in a low crime area of Chicago is likely to cost a lot more than $1,200/mo.

Accurate.

Actually, covered parking for a vehicle can be this much - unsure about a bike.

River North can be awesome. It's totally walkable - leave the bike in FL