"There was only one road back to L.A., US interstate 15. Just a flat out high speed burn through Baker, Barstow and Berdoo. Then on to the Hollywood Freeway straight into frantic oblivion, safety, obscurity. Just another freak...in the freak kingdom."
--Fear and Loathing in Las Vegas

Now for Chicago there are a couple of options. Driving I'd head north to I-80 and take that through Utah, Wyoming, Nebraska, Iowa and Illinois. If I can't find someone I know in Utah I know I can find people in Wyoming and Nebraska. That's my country. Two fifty should get me gas to Utah or Wyoming even at 20mpg. Assuming it's my car, we don't need to pick up food or water or other supplies. If it's a rental, I'd get a couple of $0.50 gallon jugs of drinking water, say eight gallons if I can get my hands on it. For food, I'd get a jar of peanut butter, jelly and a loaf of bread. Food that's familiar for the kid, cheap and full of energy (though not enought to send the kid bouncing off the walls). Finally, I'd get a cheap fleece blanket. $4 water, $8 food, $5 blanket. Say up around $20 with tax. $250 won't get me the whole way, but it should get me to my own territory and help. From there, I can get the rest of the way.

The other way is to fly out of Nellis Air Fore base. That's the first option, if I can get out on an air force flight, that'd be the easiest option. It might be a slightly round about trip, but its the easiest and safest option.