(To be crossposted at carfreechicago; please add comments there)
Got a free weekend? Like trains? Amtrak offers car-free Chicagoans plenty of chances to make a quick one- or two-day weekend escape with “red-eye” (overnight) trains from Chicago to several cities that are a few hundred miles away. I like traveling overnight, since it offers maximum sightseeing time at your destination and cuts back on expensive hotel stays.
Thrifty, non-fidgety sorts can travel in coach for less than the price of airfare, and typically right into downtown. Those who prefer a little more pampering can spring for a sleeper, which offers complete privacy, a flat bed, and free meals. In either case, you’ll travel without road rage or air rage, and usually without worrying much about ground transportation on the other end. One drawback is that slow trains put most of the East Coast out of reach.
Some cities worth a weekend visit:
- Memphis via the City of New Orleans
- Pittsburgh or Cleveland (a long day) via Capitol Limited
- Cincinnati (a long day); Charleston, W.Va.; Beckley, W.Va. (near the Winterplace ski resort); White Sulphur Springs, W.Va. via Cardinal
- Cleveland (a long day) or Buffalo via Lake Shore Limited
- It might be possible to arrange a long weekend, although with an early departure and late arrival, in Denver or Winter Park via the California Zephyr
The many short-haul lines out of Chicago can be used for day trips to locations too close for an overnight. Destinations include:
- Champaign via the Illini & Saluki
- St. Louis via the Lincoln Services
- Milwaukee via the Hiawatha
- Southwest Michigan’s Harbor Country via Pere Marquette
- Ann Arbor and Detroit via Wolverine
- Kansas City via Southwest Chief
Megabus also offers many overnight trips for cities that are a little bit closer by, or for which Amtrak has inconvenient day schedules — and boasts its famously low prices. Granted, it doesn’t offer quite the space that Amtrak affords you, but its (mostly) clean, new buses certainly put a new face onto intercity buses. Their overnight destinations include Cleveland, Columbus, Cincinnati (a long day), Minneapolis, Kansas City (a short day), and St. Louis. Day trip options include Indianapolis, Madison, and Milwaukee.