Cheap flights from Boston (BOS) to Chicago (CHI) from $39

Travelers have found that booking a Friday departure is the best way to save up to 32% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.

Due to multiple factors, expect to potentially pay more when booking in June. For low rates, January can be a great choice for travel to Chicago. Flights to Chicago from Boston in January are about $251 on average during January, but can be found for as low as $118.

Unlike at noon, when flights are generally more expensive, you can save up to 16% on flights from Boston to Chicago by exploring options for tickets in the evening.

Located just 2.6 mi from the city center, Boston Logan Intl is the airport most travelers will use when flying to Chicago from Boston. Booking flights from Logan Intl (BOS) to Chicago should be relatively easy as there are 51 daily outbound flights to Chicago from 7 different airlines.

Yes, there are multiple flights from Boston to Chicago for under $100. The cheapest flight booked recently is on Frontier for just $78, but on average you can expect to pay $99.

Cheapflights has at least 20 direct flights from Boston to Chicago under $100. A good price for a nonstop flight from Boston to Chicago is less than $126.

There are currently 20+ open flights from Boston to Chicago within the next 7 days for less than $200.

You can find nonstop flights on the following days: Sunday, Monday, Tuesday, Thursday, Friday, Saturday.

82 flight departures from Boston to Chicago per day on average.
Early Morning (Midnight to 6am) - 7% of flight departures
Morning (6am - Noon) - 33% of flight departures
Afternoon (Noon - 6pm) - 51% of flight departures
Evening (6pm - Midnight) - 9% of flight departures

For as low as $78, Frontier can have you in Chicago from Boston in 2h 48m. Airlines will cover a distance of 869 mi. This flight may include one or multiple stops.

Our cheapest airline available from Boston to Chicago is Frontier. Our recent data shows that you can find tickets from as low as $78 on this airline. Additional options worth looking into are JetBlue and American Airlines, starting at $88 and $90 round-trip. You may be able to fly from Boston to Chicago for 68% less than the average price by searching for these airlines.

To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $39. JetBlue flights start at $44 while deals on Spirit Airlines start at $51 one-way.

Most travelers choose Boston Logan Intl - Chicago O'Hare Intl, Boston Logan Intl - Chicago Midway or Boston Logan Intl - Chicago Greater Rockford when deciding on the best route from Boston to Chicago.

The most popular airlines flying from Boston to Chicago are Undisclosed Carrier, American Airlines and Alaska Airlines. Something to consider prior to booking your flight.

Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Boston to Chicago on time: Japan Airlines (90%), ANA (88%), SkyWest Airlines (82%).

The cheapest flight price from Boston to Chicago is $79. On average you can expect to pay $600. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $88.

BOS and ORD are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. BOS to ORD refers to a flight route from Boston Logan Intl Airport to Chicago O'Hare Intl Airport. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight route and their unique identifiers/IATA codes.

Cheapflights makes it easy to find Boston to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Millions of users choose and trust Cheapflights to book the best flight deals from Boston to Chicago for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

Yes, we can. To see specific flights from Boston to Chicago with no change fees, users can toggle flexible booking options after using the search form above to find flights.

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