Getting to 3 Floyds from Chicago

you can give them your cell number and wait in your car. they'll call when your table is ready.

 

This was my experience at 18th as well. We took my non-drinking in-laws to 18th (having not been there), and quite frankly, it was embarrassing. The beer was good, though overpriced. The food and atmosphere left quite a bit to be desired.

As a local tack-on to Three Floyds, I much prefer One Trick Pony.

 

Off peak should be little to no wait time. If it's just the two of you and there's a wait, you may be able to get bar seating sooner. Just let the guy at the door know you're cool with that. Assuming, you know, you're cool with bar seating.

As far as weather... May is typically pretty mild. Not a lot of rain. Temps in the 60's.

If you're wondering about the biggest natural concern in the FFF area? Well, that honor goes to the occasional tornado... probably won't happen while you're there

 

I've seen snow in Chicago in the first week of June, so no, rain is not the only concern.

As for 18th Street, I ran in and bought, then left. I saw a number of people hanging out, though; it was a pretty basic environment. I did not find it unpleasant, or unclean, but Miller is still Gary, so if you are worried about rough neighborhoods, it probably is not for you. I used to catch the South Shore sometimes from the station when I lived in NWI, and drove through Gary regularly to get to work in the Chicago, so I suspect it is all what you are used to.

 

Honestly with the time you have to spend. Use it in Chicago proper. You'll get the same bang for your buck, and more than a few places are easy to get to if you're having problems with a vehicle. The longer journey with the metra and southshore lines don't mind brown bagging it for your two brothers, 18th street, flossmoor, etc. choices.
believe the hype on 18th. your wife will probably like that they offer something other than beer and Sour Note. The neighborhood is fine, and super easy to get to using the nict.