How to Travel from Boston to Chicago by Train, Bus, Car, and Plane

There are multiple ways to travel from Boston to Chicago, a distance of 996 miles. The quickest way to get to the Windy City is to fly, which will take you about 4 hours, 42 minutes. With flights starting at around $78, this can be the least expensive mode of transportation as well.

There are no buses that run directly to Chicago from Boston; if you choose to take a bus, you will have to transfer in New York, the total journey lasting roughly 20 hours. Alternatively, there is a direct train, which departs once a day. Driving the nearly 1,000 miles between the two cities will take about 16 hours, 32 minutes.

What Is the Fastest Way to Get From Boston to Chicago?

The quickest way to get from Boston to Chicago is to take a plane, as the average flight duration is three hours. Even when you factor in the time it takes to get to Boston Logan International Airport, check in, and go through security, flying is still the most efficient option.

Depending on the route, flying can be the most cost-friendly option as well. Multiple airlines fly from Boston to Chicago (Chicago O’Hare International Airport or Chicago Midway Airport) every hour. Southwest Airlines, Delta, American Airlines, United Airlines, JetBlue Airways, Porter Airlines, Air Canada, and Spirit Airlines all service the two cities. This gives passengers many options when it comes to price and departure times.

How Long Is the Train Ride?

The entire journey from Boston's busiest hub, South Station, to Chicago Union Station takes 22 hours. Amtrak services this direct route. Train tickets may be purchased online or in-person at the train station. On board, you can enjoy generous baggage allowances, Wi-Fi, and coffee amenities.

Traveling by train will allow you to see quite a bit of the Midwest without having to worry about traffic or driving in inclement weather. Plus, if you’re traveling with a companion or kids, you can socialize instead of focusing on the rules of the road. Trains are also comfortable, clean, and smooth.

Is There a Bus That Goes From Boston to Chicago?

There is a Greyhound that goes from Boston to Chicago, though you will have to transfer in New York City. To get to NYC, first head to Boston’s South Station bus terminal (a 2 minute walk from the train terminal). Buses on this route leave hourly.

When you arrive in NYC, transfer to a Greyhound bound towards the Chicago Amtrak, II station. The bus leaves once a day and the journey will take approximately 20 hours.

The advantage of taking the bus is that it’s less expensive than the train and takes a little less time. This might be the best option for those who don't want to drive or fly.

How Long Does It Take to Drive?

Driving 996 miles is quite the road trip. As you travel on I-90 west, you’ll touch five states before reaching Illinois: Massachusetts, New York, Pennsylvania, Ohio, and Indiana. The journey will take approximately 16 hours and 32 minutes, though it will likely take longer when you factor in pit stops.

If you drive, either by yourself or with a group, you will see a lot of the country from the comfort of your own vehicle. You will also be able to go at your own pace and stop at sights and attractions along the way. Plus, you’ll have a car to use when you reach your destination. However, when deciding whether or not this is the optimal route for you, you should consider the costs of gas, tolls, and a hotel.

What Time Is It in Chicago?

Chicago is in Central Daylight Time, which runs 1 hour behind Boston. For example, 12 p.m. in Boston would be 11 a.m. in Chicago.

Can I Use Public Transportation to Travel From the Airport?

You can get from Chicago O'Hare to downtown via the Chicago Transit Authority (CTA) Blue Line. It runs 24 hours a day, and stops at Jefferson Park, Logan Square, Clark/Lane, UIC-Halsted, Cicero, and Forest Park. The total route from O'Hare to Forest Park terminal in downtown Chicago takes 40 minutes.

If you are flying into Chicago Midway, the CTA Orange Line will take you downtown in about 20 to 25 minutes. This train line runs daily from around 4 a.m. or 4:30 a.m. to 1 a.m.

What Is There to Do in Chicago?

The Windy City has much to see, do, and eat. From award-winning museums to kid-friendly favorites, this metropolis has something for everyone.

Explore art museums like the Art Institute of Chicago and the Museum of Contemporary Art Chicago, or take the whole family to the Lincoln Park Zoo, Shedd Aquarium, and Field Museum.

Try deep dish pizza and Chicago-style hot dogs. Visit interesting art showcases like wndr Museum or Nevermore Park. Check out live theatre and comedy like Broadway in Chicago, Royal George Theatre, Drury Lane Theatre, Marriott Theatre, and The Second City. If the weather is nice—or even if it isn’t—stroll, jog, or bike along the Chicago Riverwalk, the Chicago Lakefront Trail, or The 606. The Chicago Architecture Foundation River Cruise is fantastic as well and offers insight into the city’s incredible architecture.

Of course, there is a plethora of hotels in Chicago that will suit your pocket book and interests. While Hotel Zachary offers views of famed Wrigley Field, Swissotel Chicago overlooks the Chicago River. Fairmont Chicago Millennium Park is one of the best properties for families, though The Ritz-Carlton Chicago is located right in the heart of the city, with easy access to shopping and dining. 

Be sure to review our complete guide to Chicago while planning your itinerary, and check out our Chicago weather guide so you know what to pack.