Boston and Chicago have a few things in common: they both have freezing cold winters and hot, humid summers; both have large, proud Irish populations; and both offer lots of history and culture than can be soaked up in a short trip. With plentiful transportation options between the two cities, it’s easy to visit one from the other.
Boston to Chicago
Flights
Most major airlines, including America, United, Southwest, Continental, US Airways and Delta airlines offer frequent service from Boston to Chicago. Flying is the easiest way to get between the two cities, and flights from Boston to Chicago are relatively inexpensive most times of the year. Price go up around holidays and special events, but booking your flights farther in advance can help you score cheap tickets to Chicago.
Journey time: About 2 hours.
Typical price: $150 to $300 round-trip per person
Trains
Amtrak trains do travel between Chicago and Boston, but the journey is a long and pretty boring one, taking nearly a full day. When you consider than flying often costs the same (or not much more) it makes more sense to fly. If you do want to take the bus, you’ll find that the train are comfortable and generally on time, and ticket prices range from $90-150 each way.
Journey time: About 22 hours.
Buses
Bus is not an ideal way to travel between Chicago and Boston. Greyhound does offer several trips per day, but the journey takes a whole day is a fairly boring drive. The average cost is about $120 each way, so for the price, you may as well take the train or try to score cheap plane tickets.
Journey time: About 23 hours.
Driving
The drive between Chicago and Boston can be done in about half a day. It passes through Michigan, Ohio, Pennsylvania and New York before Massachusetts. Unless you specifically want to have access to a car in either city, taking a train or plane may end up being more economical though as parking in both cities is expensive and hard to come by.
Journey time: 13 hours.
