Cheap Flights from ORD to BOS: When to Fly from Chicago to Boston

 

The cheapest times to fly from ORD to BOS are

• August 13th to November 18th
• December 3rd to March 4th (except the weeks of December 10th and February 19th)

based on data collected exclusively by Champion Traveler across tens of millions of flights. Among all the dates above, the very cheapest time to fly from ORD to BOS is mid to late September. Prices can be as high as $401 for Sunday flights during early August, or as low as $143 for Tuesday flights around mid to late September.

 

When to Fly to Boston

Flying from Chicago, IL (ORD) to Boston, MA (BOS) will usually cost between $148 to $267 per person if booking more than four weeks in advance. On average the very cheapest time to fly is mid to late September with an average ticket price of $144. Due to high demand the most expensive time to fly is early August, with an average price of $257. Planning your trip to low-cost times can easily save you $113 on economy flights and even more on first-class flights. Generally, any price below $165 can be considered a good price for a round-trip ORD to BOS flight.

See below for a graph of average weekly prices for the ORD to BOS route. All prices are for round-trip tickets in USD.

Compared to other flights, the ORD to BOS flight is much cheaper than the average and costs much less than the average flight leaving from Chicago. The average price per mile (for a direct flight) is $0.12, which is far below average.

 

Flight Prices by Day of the Week

Tuesday is usually the cheapest day to depart and return on this flight. Sundays are the most expensive days to fly out or take a return trip. Selecting flights on the least expensive days could save you up to $48 (23%) on this flight.

Departing prices are for round-trip flights returning on the day of departure. For example, a flight departing on Tuesday and returning a week later will cost an average of $158. Return trip prices are from the BOS to ORD flight, and often highlight the quality of our data in showing the same trend.

 

Nonstop Flights and Layovers

Travelers looking to fly from ORD to BOS can generally find a 0-layover flight. Because there is a direct flight option the real-world direct flight time of 2 hour 32 minutes may be realistic.

 

Flight Questions Answered

Still have questions about flying from ORD to BOS? We’ve got answers.

Which airlines fly this route?

You can find 14 major airlines flying this route most often: Air Europa, Alaska, American, China Eastern, Delta, Emirates, Frontier, JetBlue, Qantas, Qatar Airways, SAS, Spirit, Sun Country Airlines, United, and potentially more during busy seasons.

How far away is it from Logan International Airport to Chicago O’Hare International Airport?

The distance between the two airports is roughly 864 miles or 1390 kilometers.

How long does it take to fly from ORD to BOS?

The real-world flight time for a nonstop ORD to BOS flight is about 2 hour 32 minutes.

How many flights go between Chicago, IL and Boston, MA?

It depends on the day of the week and the date, but a typical day might have around 76 available flights from ORD to BOS.

 

Airport Location Info

 

 

Late and Early Flight Data

Flights from ORD to BOS tend to depart later than the average flight. According to our recently updated data, 35% of flights departed 5 or more minutes late, and 19% of flights left 5 or more minutes early. On average you can expect to leave BOS heading for ORD about 22 minutes late. This does significantly impact arrival time, as the average landing time in Boston, MA is about 20 minutes late. The numbers below show a recent average of take-off times versus the scheduled departure flight:

• American: 16 minutes late
• United: 22 minutes late
• JetBlue: 27 minutes late
• Spirit: 38 minutes late
• Some airlines not reporting

 

Please note that while we’ve worked hard to analyzed tens of millions of flights to get you this data, we do not calculate current live prices or guarantee pricing. Please see our partners using the links above for current offers.