BOS - CHI Price | $56 - $206 |
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CHI Temperature | 23 - 73.4 °F |
CHI Rainfall | 1.7 - 4.9 inches |
Popular in | December | High demand for flights, 29% potential price rise |
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Cheapest in | August | Best time to find cheap flights, 62% potential price drop |
Average price | $127 | Average for round-trip flights in May 2022 |
Round-trip from | $56 | From Boston Logan Intl to Chicago (CHI) |
Travelers have found that booking a Monday departure is the best way to save up to 29% 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 December. For low rates, August can be a great choice for travel to Chicago. Flights to Chicago from Boston in August are about $146 on average during August, but can be found for as low as $34.
Unlike in the afternoon, when flights are generally more expensive, you can save up to 19% on flights from Boston to Chicago by exploring options for tickets in the evening.
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 55mChicago O'Hare Intl
Boston Logan Intl
Nonstop
2h 22mJetBlue
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 50mChicago O'Hare Intl
Boston Logan Intl
1 stop
7h 41mMultiple Airlines
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 50mChicago O'Hare Intl
Boston Logan Intl
1 stop
7h 41mMultiple Airlines
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 54mChicago O'Hare Intl
Boston Logan Intl
Nonstop
2h 21mJetBlue
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 50mChicago O'Hare Intl
Boston Logan Intl
1 stop
7h 41mMultiple Airlines
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 50mChicago O'Hare Intl
Boston Logan Intl
1 stop
7h 41mMultiple Airlines
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 57mChicago O'Hare Intl
Boston Logan Intl
1 stop
5h 33mAmerican Airlines
Boston Logan Intl
Chicago O'Hare Intl
1 stop
4h 45mChicago O'Hare Intl
Boston Logan Intl
1 stop
5h 02mAmerican Airlines
Boston Logan Intl
Chicago O'Hare Intl
1 stop
5h 05mChicago O'Hare Intl
Boston Logan Intl
1 stop
4h 43mAmerican Airlines
Boston Logan Intl
Chicago O'Hare Intl
1 stop
8h 41mChicago O'Hare Intl
Boston Logan Intl
1 stop
7h 41mSpirit Airlines
Boston Logan Intl
Chicago O'Hare Intl
1 stop
26h 10mChicago O'Hare Intl
Boston Logan Intl
2 stops
20h 14mSpirit Airlines
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 54mChicago O'Hare Intl
Boston Logan Intl
Nonstop
2h 24mJetBlue
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 57mChicago O'Hare Intl
Boston Logan Intl
Nonstop
2h 15mJetBlue
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 50mChicago O'Hare Intl
Boston Logan Intl
Nonstop
2h 17mMultiple Airlines
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 59mChicago O'Hare Intl
Boston Logan Intl
1 stop
7h 41mMultiple Airlines
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 57mChicago O'Hare Intl
Boston Logan Intl
1 stop
5h 00mDelta
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 55mChicago O'Hare Intl
Boston Logan Intl
Nonstop
2h 23mJetBlue
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 56mJetBlue
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 50mUnited Airlines
Boston Logan Intl
Chicago O'Hare Intl
1 stop
6h 27mSpirit Airlines
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 64 daily outbound flights to Chicago from 10 different airlines.
United Airlines, JetBlue, and American Airlines are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.
Yes, there are multiple flights from Boston to Chicago for under $200. The cheapest flight booked recently is on JetBlue for just $150, but on average you can expect to pay $167.
Cheapflights has at least 20 direct flights from Boston to Chicago under $200. A good price for a nonstop flight from Boston to Chicago is less than $186.
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.
16 flight departures from Boston to Chicago per day on average.
Early Morning (Midnight to 6am) - 25% of flight departures
Morning (6am - Noon) - 25% of flight departures
Afternoon (Noon - 6pm) - 25% of flight departures
Evening (6pm - Midnight) - 25% of flight departures
For as low as $150, JetBlue can have you in Chicago from Boston in 2h 54m. 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 JetBlue. Our recent data shows that you can find tickets from as low as $150 on this airline. Additional options worth looking into are American Airlines and Delta, starting at $159 and $168 round-trip.
To fly one-way, consider booking your trip with JetBlue, which is currently one of the cheapest options available, starting at $75. United Airlines flights start at $76 while deals on Spirit Airlines start at $79 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 Major Airline, 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: ANA (96%), SkyWest Airlines (94%), Japan Airlines (92%).
The cheapest flight price from Boston to Chicago is $75. On average you can expect to pay $359. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $150.
8%of flight departures | Early morningMidnight to 6 am |
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43%of flight departures | Morning6 am to noon |
42%of flight departures | AfternoonNoon to 6 pm |
7%of flight departures | Evening6 pm to midnight |
Sunday | 65daily flights |
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Monday | 74daily flights |
Tuesday | 64daily flights |
Wednesday | 75daily flights |
Thursday | 68daily flights |
Friday | 68daily flights |
Saturday | 37daily flights |