Chicago is one of the (few) cities in the US that can support hostels, so due to their lower costs, excellent locations, and tourism support I decided to go that route. As is often the case, wandering the streets alone was replaced by more social activities, which certainly changes the dynamic of the experience.

Since I’ve driven across the US once and flown a few times, I decided it was time to complete the Planes, Trains, and Automobiles trifecta. Amtrak’s USA Rail Pass gives you 10 segments (rides, basically) over the course of 30 days for $499. Which might save you a little money, but what it certainly does is helps structure a trip.