Re: If we make it to Chicago:
Actually, the areas right near Midway are relatively safe nowadays. You have to go a little bit East a few miles if you want to run into the actual dangerous areas.
Anyway, OP - look in River North. It's the best bet and if you're concerned about being cheap, there are deals on sites like HotWire that make it just as cheap as staying near one of the airports, or not much more expensive.
There's plenty to do. You could try getting mugged. Or if you're really bored, maybe even get stabbed.
Actually, the areas right near Midway are relatively safe nowadays. You have to go a little bit East a few miles if you want to run into the actual dangerous areas.
Anyway, OP - look in River North. It's the best bet and if you're concerned about being cheap, there are deals on sites like HotWire that make it just as cheap as staying near one of the airports, or not much more expensive.