From a private roomette to a cheap train ticket, there’s several options to consider when traveling from Boston to Chicago by train! The trip is about 19 to 22 hours one way, and travels through scenic corners of the Northeast and Midwest.
The Lake Shore Limited train, powered by Amtrak, is Boston’s only direct long-distance train. The 19-hour trip begins in South Station and Back Bay and travels West and East, connecting Boston and Chicago by train.
There are a total of 22 stops on the Lake Shore Limited route, with four additional connections, that link six states: Massachusetts, New York, Pennsylvania, Ohio, Indiana, and Illinois. Amtrak describes the picturesque route to offer a front row seat to some of the “prettiest shorelines of the USA. You’ll travel along the south shore of Lake Michigan, the Mohawk River, and the Erie Canal, following a famous Native American Highway.”
As you travel through New York you’ll pass the famous Finger Lakes. Inbound to Boston you’ll enjoy views of the Berkshires.
As a long ride, prices are higher than your $39 ticket to Manhattan. However, you can still snag these train tickets for as low as $98, depending on when you book, We found some of the lowest prices around August 6. Make sure to book trips at least 14 days in advance to take Advantage of Amtrak’s “Super Saver” pricing.
For a little luxury, opt for a private roomette. Amtrak roomettes include two convertible seats that transform into beds. For bedtime, bedding, pillows, towels, and linens are provided. Each roomette also features a dedicated First-Class attendant, priority boarding, and complimentary meals. Plus, these First-Class cars have a restroom and shower to freshen up before you begin your Chicago adventuring.
Roomette prices are variable but average about $900.