Getting from Boston to Chicago

Best ways to travel from Boston to Chicago

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 that can be soaked up in a short trip. With plentiful transportation options between the two cities, visiting one from the other is easy.

Boston to Chicago

  • Driving distance – 983 miles/1580 kilometers


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 inexpensive most of the year. Prices increase 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


Amtrak trains travel between Chicago and Boston, but the journey is long and pretty boring, taking nearly a full day. When you consider that flying often costs the same (or not much more), flying makes more sense. If you want to take the bus, you’ll find that the trains are comfortable and generally on time, and ticket prices range from $90-150  each way.

Journey time: About 22 hours.


The 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.


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 access to a car in either city, taking a train or plane may be more economical, though, as parking in both cities is expensive and hard to come by.

Journey time:  13 hours.

Flying from Boston to Chicago

Flying from Boston to Chicago is the fastest and most convenient way to travel between cities. Many airlines offer direct flights between Boston Logan International Airport, Chicago O’Hare, and Midway International Airports, providing plenty of options.

The flight time usually takes 2-3 hours, depending on the airline and specific flight. Many airlines also offer multiple flights daily, making finding a flight that fits your schedule easy.

When booking your flight, compare prices and check for additional fees, such as baggage or seat selection fees. Booking your flight in advance is also a good idea to secure the best possible price.

Once you arrive at either O’Hare or Midway, several transportation options get you to your final destination, including taxis, rideshare apps, public transportation, and rental cars. If you are staying in downtown Chicago, the Chicago Transit Authority’s (CTA) “L” train system is a cost-effective and efficient way to get around the city.

Driving from Boston to Chicago

Driving from Boston to Chicago is a great option for those who enjoy road trips and want to explore the beauty of the United States. The distance between Boston and Chicago is approximately 1,000 miles, and depending on the route you take, it can take around 16 hours to complete the journey.

To make the most of your road trip, plan your route in advance so that you can take breaks at interesting locations along the way. You can take the scenic route through the Appalachian Mountains or the faster and more direct route through the Midwest. Both options have their own unique charms and attractions.

If you decide to drive, ensure your vehicle is in good condition for a long journey. Check your tires, brakes, oil levels, and other essential components to ensure a safe and comfortable ride. You should also plan your gas stops and accommodations in advance to avoid any surprises along the way.

Taking the train from Boston to Chicago

The train from Boston to Chicago can be a great option for scenic and comfortable journeys. Amtrak’s Lake Shore Limited train service offers a direct route between the two cities, with stops in Albany, Syracuse, Rochester, Buffalo, Erie, Cleveland, and Toledo.

This train service provides a classic travel experience with comfortable seating, large windows, and dining options. The journey takes approximately 20 hours, providing ample time for relaxation and sightseeing.

Passengers can choose from seating options, including a coach, business class, and sleeper cars with private rooms. The sleeper car option offers a private bedroom and bathroom, ideal for those seeking a more luxurious travel experience.

One of the highlights of this train journey is the stunning scenery you will witness along the way. Passengers will be able to see the picturesque views of the Hudson River Valley, the Berkshires’ landscapes, and Lake Erie’s shores.

Bus travel from Boston to Chicago

Bus travel from Boston to Chicago is a great option for those who want to experience a comfortable and affordable journey. The distance from Boston to Chicago is roughly 1,000 miles, and the average bus journey time is around 22 hours. Several bus companies offer this route, including Greyhound and Megabus.

These companies offer several amenities, such as free Wi-Fi, reclining seats, air conditioning, and power outlets, to ensure passengers have a comfortable journey. Most buses also have restrooms on board, so you don’t have to worry about frequent stops.

Bus travel is also one of the cheapest ways to travel from Boston to Chicago. Depending on the time of year, you can find bus tickets for as low as $40 one way. Additionally, bus stations are conveniently located in Boston and Chicago, making it easy to reach your final destination.

One of the biggest advantages of taking a bus is its flexibility. You can choose from several departure and arrival times to suit your schedule. Furthermore, buses operate seven days a week, so you can travel whenever convenient.

Comparing prices and travel time

When traveling from Boston to Chicago, comparing prices and travel time is essential to make the best decision for your trip. Depending on your preferences, you may want to prioritize either cost or time in your decision-making process.

There are several ways to travel between these two cities, including by plane, train, bus, or car. Each mode of transportation has its own advantages and disadvantages in terms of cost and travel time.

For example, flying can be the fastest option, with flights taking around 2-3 hours, but it can also be costly, especially if you don’t book your ticket in advance. On the other hand, taking a train or bus can be less expensive, but it may take longer, with travel times of around 20-24 hours.

Another factor to consider is convenience and comfort. Taking a train or flying may offer more legroom and amenities, while driving or taking a bus may be less comfortable but offer more flexibility regarding stops and schedules.

You can use online travel booking websites like Expedia, Kayak, or Google Flights to compare prices and travel times. These sites allow you to compare prices across different airlines, trains, and buses and see the travel time for each option.

Which method of transportation is best for you?

Each mode of transportation has its own benefits and drawbacks, so it’s important to consider which is best suited for your travel needs.

Driving is a popular option, as it gives you more control over your travel schedule and allows you to see more of the country during your trip. However, remember that this long journey will take at least 14 hours. You will also need to factor in the cost of gas, tolls, and potential overnight stays.

Flying is the fastest and most convenient way to travel from Boston to Chicago, with many daily flights between the cities. Airlines such as Delta, American, United, and JetBlue all offer direct flights, and the flight time is around 2.5 hours. However, be prepared to pay a premium for airfare during peak travel times.

Taking a train is another option, and it can offer a more scenic and relaxed journey than flying or driving. Amtrak’s Lake Shore Limited service operates daily between Boston and Chicago, taking around 20 hours to complete. While this is longer than flying, it can be more enjoyable and comfortable.

Finally, consider taking a bus if you’re looking for an eco-friendly and budget-friendly option. Greyhound and Megabus both offer regular services between Boston and Chicago, with prices starting at around $50 for a one-way trip. Remember that bus travel can be slower and less comfortable than other modes of transportation, but it can be a great option for those on a tight budget.

Things to do in Boston and Chicago

Boston and Chicago are two of the most popular cities in the United States. They offer distinct cultures and attractions, making them great destinations for tourists and travelers. If you are planning to travel from Boston to Chicago, you should take some time to explore both cities.

In Boston, some top attractions include walking the Freedom Trail to see the city’s historical sites, visiting the USS Constitution Museum, and taking a stroll through the Boston Public Garden. Catching a Red Sox game at Fenway Park is a must-do activity for sports fans.

In Chicago, you can’t miss walking along the Chicago Riverwalk, seeing the city from the top of the Willis Tower, and visiting the Art Institute of Chicago. For foodies, a visit to Chicago wouldn’t be complete without a deep-dish pizza at Lou Malnati’s or Giordano’s.

Both cities are known for their nightlife, so check out some local bars and clubs to get a taste of the local scene. With so much to see and do in both Boston and Chicago, you won’t be disappointed in taking some extra time to explore these two amazing cities.


We hope you enjoyed our article on the best ways to travel from Boston to Chicago. Whether you’re traveling for work or pleasure, various options are available, and we’ve covered the most popular ones. We hope this article has helped you decide which mode of transportation is best for you and your needs. Safe travels, and don’t forget to enjoy the journey!

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