The cheapest times to fly from BOS to ORD are
- April 23rd to May 13th
- August 20th to November 18th (except the week of October 8th)
- December 3rd to March 4th (except the weeks of December 17th and February 12th)
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 BOS to ORD is early to mid September. Prices can be as high as $364 for Sunday flights during mid April, or as low as $143 for Tuesday flights around early to mid September.
When to Fly to Chicago
Flying from Boston, MA (BOS) to Chicago, IL (ORD) will usually cost between $148 to $270 per person if booking more than four weeks in advance. On average the very cheapest time to fly is early to mid September with an average ticket price of $143. Due to high demand the most expensive time to fly is mid April, with an average price of $250. Planning your trip to low-cost times can easily save you $107 on economy flights and even more on first-class flights. Generally, any price below $166 can be considered a good price for a round-trip BOS to ORD flight.
See below for a graph of average weekly prices for the BOS to ORD route. All prices are for round-trip tickets in USD.
Compared to other flights, the BOS to ORD flight is much cheaper than the average and costs much less than the average flight leaving from Boston. 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 ORD to BOS flight, and often highlight the quality of our data in showing the same trend.
Departing Prices by Day
Return Trip Prices by Day
Nonstop Flights and Layovers
Travelers looking to fly from BOS to ORD 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 BOS to ORD? 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 Chicago O’Hare International Airport to Logan International Airport?
The distance between the two airports is roughly 864 miles or 1390 kilometers.
How long does it take to fly from BOS to ORD?
The real-world flight time for a nonstop BOS to ORD flight is about 2 hour 32 minutes.
How many flights go between Boston, MA and Chicago, IL?
It depends on the day of the week and the date, but a typical day might have around 68 available flights from BOS to ORD.
Airport Location Info
|Origination airport name||Logan International Airport|
|Country||the United States|
|Destination airport name||Chicago O’Hare International Airport|
|Country||the United States|
Late and Early Flight Data
Flights from BOS to ORD tend to depart as late as the average flight. According to our recently updated data, 30% of flights departed 5 or more minutes late, and 30% of flights left 5 or more minutes early. On average you can expect to leave ORD heading for BOS about 21 minutes late. This does significantly impact arrival time, as the average landing time in Chicago, IL is about 14 minutes late. The numbers below show a recent average of take-off times versus the scheduled departure flight:
- American: 19 minutes late
- United: 20 minutes late
- JetBlue: 27 minutes late
- Spirit: 16 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.