Getting from Boston to Chicago

Boston and Chicago have a fair amount in common. Both have brutal winters and sticky summers, both have big, proud Irish communities, and both pack a lot of history and culture into a short trip. What they don't have is proximity. It's roughly 1,000 miles by road, so for most people this is a flight. The train is the slow, scenic alternative, and the bus and the drive are for people with a specific reason.

For the Chicago end of the trip, our getting to Chicago page covers the stations, and the airports page covers O'Hare, Midway and the trains into the Loop.

Flying

This is the sensible way to go. Nonstops from Logan run all day, and O'Hare was Logan's busiest domestic route between June 2025 and May 2026 (Wikipedia). American, Delta, JetBlue and United all fly to O'Hare. Southwest flies to Midway, which is closer to the Loop and a lot easier to get out of. Continental and US Airways, named in the first version of this page, are long gone, folded into United in 2012 and American in 2015.

Plan on about three hours in the air heading west, a little less coming back. Search "Chicago (CHI)" to see both airports at once, and see our flights page for when fares tend to be lowest. Once you land, the Blue Line from O'Hare or the Orange Line from Midway gets you downtown without a cab.

The train

Amtrak's Lake Shore Limited runs daily between Boston and Chicago. The Boston section leaves South Station around midday, stops at Back Bay, Worcester, Springfield and Pittsfield, and joins the New York section at Albany-Rensselaer. From there it's one train west along the Mohawk Valley and the Erie Canal, through Buffalo in the middle of the night, then along Lake Erie through Cleveland and Toledo, and into Chicago Union Station mid-morning. The whole trip takes about 22 hours each way.

Coach is a long day and a night in a reclining seat. A roomette gets you a bed and meals, and costs far more than a flight. Take the train because you want the ride, not to save money. The stretch between Albany and Worcester is single track shared with freight, and the Boston section has a history of running late there, so don't book a tight connection at either end. The Boston section also doesn't carry checked baggage, since Amtrak pulled its baggage car in 2019.

If the Boston departure doesn't suit you, another option is to ride a Northeast Regional or Acela to New York and catch the New York section from Moynihan Train Hall in the afternoon. See getting from New York City to Chicago for that half.

By bus

You can do it, but you'll feel it. FlixBus and Greyhound, which sell tickets on the same site, list about a dozen daily trips between the two cities, and the fastest takes more than 23 hours. Boston departures use the bus terminal at South Station, 700 Atlantic Ave. In Chicago you arrive at the Greyhound station at 630 W. Harrison St. or at the curbside stop by Union Station. A cheap bus fare often isn't much below a sale fare on a flight, so price both before you commit to a day on a bus.

Driving

It's about 990 miles, and you'll want two days. The usual route is the Mass Pike (I-90) west to the New York State Thruway, past Buffalo and along the lake through a corner of Pennsylvania, then the Ohio Turnpike and the Indiana Toll Road, which drops you onto the Chicago Skyway. Long stretches are tolled, so an E-ZPass saves you a lot of stopping and paperwork, and it also works on the Illinois tollways. Figure 15 to 16 hours of driving without stops. You gain an hour heading west, since Chicago is on Central Time.

A car is more trouble than it's worth in either city. Parking is expensive and hard to find, and both have trains that go where visitors go. Drive this route only if you need the car at the other end or want to see Buffalo and Cleveland on the way. If you're only renting for part of the trip, see our car rental page.

Photo by Darwin70