Chicago, IL

Chicago is a bit of a haul from Williamstown, but you still have a handful of transportation options to choose from.

  • How: United Airlines and American Airlines both fly multiple nonstops between Albany and Chicago-O'Hare every day. (Not sure how to get to Albany? Check the Albany page for some ideas). O'Hare lies to the northwest of downtown Chicago; driving into the city center from O'Hare can be a nightmare during rush hour, and can take anywhere from 20 minutes to 1:30. Taking the Blue Line "L" train into the city center takes about 50 minutes. A variety of connecting flights are also available and may be cheaper, especially if you book last minute—however, these flights take significantly longer and are much less eco-friendly.

    Travel Time: ~2:10

    Cost: ~$350-600 round trip, depending heavily on the flight you choose and when you book

    Environmental Impact: Flying is never great, but nonstop flights are not horrible compared to some other transportation methods. They are generally worse, but on the same order of magnitude.

  • How: Southwest offers two nonstop flights a day between Albany and Chicago-Midway. (Not sure how to get to Albany? Check the Albany page for some ideas). Midway lies to the southwest of downtown Chicago, and can be anywhere between a 15 minute and a 1 hour drive from the city center, depending on traffic. Taking the Orange Line "L" train to the city takes about 25 minutes. A variety of connecting flights are also available and may be cheaper, especially if you book last minute—however, these flights take significantly longer and are much less eco-friendly.

    Travel Time: ~2:10

    Cost: ~$350-600 round trip, depending heavily on the flight you choose and when you book

    Environmental Impact: Flying is never great, but nonstop flights are not horrible compared to some other transportation methods. They are generally worse, but on the same order of magnitude.

  • How: If you're looking to save money or booking last minute, flying from Boston or NYC can be the fastest cheaper option—even better than taking a connecting flight out of Albany. Flights abound from Boston and New York to both O'Hare and Midway. Nonstop flights from Albany will almost certainly mean a shorter trip overall, but this can be a good, cheap option nonetheless.

    Travel Time: ~2:20-2:50 between Boston/NYC and Chicago

    Cost: ~$100-300 round trip, depending heavily on the flight you choose and when you book

    Environmental Impact: Flying is never great, but nonstop flights are not horrible compared to some other transportation methods. They are generally worse, but on the same order of magnitude. Here, getting to Boston or New York also could produce noticeable emissions depending on how you do it.

  • How: Feeling adventurous? Or perhaps a bit like Cary Grant? Amtrak runs an overnight train between Boston and Chicago—and you can hop on in Pittsfield or Albany! You can book a seat in coach, or purchase a ticket for a sleeping car if you'd like to ride in style. Click here for a schedule and tickets.

    Travel Time: 15:45 between Albany and Chicago, +1 hour to Pittsfield

    Cost: ~$60-150 one-way for a coach seat. A small room costs about~$400-700 one-way for two people, depending on the train.

    Environmental Impact: Super clean. For reference, the entire train trip results in fewer emissions per passenger than driving an average car to Albany.

  • It may seem far, but it's doable in a single day, especially if you have a few drivers.

    Travel Time: ~13 hours

    Environmental Impact: Because of the distance, the specifics matter a lot here. A small hybrid with four people? Almost as good as the Amtrak. A Hummer with just the driver? Worse than flying.


Need to know how to get around the city once you’re there? Using the “L” trains is the most popular way, but check out a full guide here.