Finding flights from Boston to Chicago is very easy. There are several flights per day offered by many airlines which means competition keeps the prices at bay. Therefore, the prices don’t vary too much from month to month. Still, if you need to fly during the peak tourist season, the prices will be a bit higher than usual.

Airport choices

The first choice when you need to fly into Chicago is O’Hare International Airport. However, the city is served by several other airports. O’Hare is the busiest airport serving the city and is located just 17 miles from downtown Chicago. It is the largest hub for United Airlines and second largest hub for American Airlines. Another airport serving Chicago is Midway International Airport. It is located 10 miles south of downtown Chicago and serves as hub for Southwest Airlines. In some cases it might be cheaper to fly into Midway than into O’Hare.

When you need to fly out of Boston, the first choice is Logan International Airport. It is one of the busiest airports in the States and a focus city airport for American Airlines, Delta Air Lines, US Airways and JetBlue Airways.

Best airline choices

Direct flights from Boston to Chicago are offered by the following carriers:

  • AirTran Airways
  • United Airlines
  • American Airlines
  • US Airways
  • JetBlue Airways


Typical prices

The ticket prices for flights from Boston to Chicago tend to be seasonal but because there are so many flights available daily, the prices don’t change that much from season to season. Still, it’s a good idea to avoid the peak tourist season (summer, winter holidays, and national holidays).

In some cases it might be cheaper to catch an indirect flight rather than a direct flight. If you need to fly from Boston to Chicago during mid-September expect to pay between $158 for a round trip indirect flight and $178 for a round trip direct flight. However, if you choose the indirect flight you’ll be spending over 4 hours traveling (as opposed to 2 hours if you catch the direct flight). If you need to fly a month later, the prices are the same.

Money saving tips

It’s always recommended to start looking at discount websites such as Hotwire, Travelocity, Expedia, and Priceline, before you look at specific airlines. However, with so many airlines using the airports as hubs, there are a lot of chances to find cheap fares and even some deals directly on the airlines’ websites. If you don’t mind spending some time in airports, you can also look for indirect flights. In some cases you can find better deals for an indirect flight rather than for a direct flight.

It’s a good idea to be flexible when you plan to fly. Generally, if you fly during mid-week you’ll be able to get a cheaper ticket. Avoid flying during the high season (summer, winter holidays) to save some money on airfare. Plus, the off season months (April, May, September) are excellent to visit Chicago.

You can book the flight in advance but with so many flights between the two cities you won’t be saving too much. Still, if you book your flight too close to the departure date you might have to pay a bit too much.