Hotel
Hotel
Hotel
Hotel
Flight
O'Hare has a ton of direct flights from almost any major airport in the US. About 45 minutes from downtown (depending on traffic).
Flight
Sam's favorite airport, about 25-30 minutes from downtown. Lots of Southwest flights here (we're talking to you - CT peeps)!
Train
If you're feeling adventurous and want to take the L, it'll get you downtown pretty easily! Take the Blue Line from O'Hare Take the Orange Line from Midway