Cheap flights from Massachusetts to Chicago (CHI)
What is the cheapest month to fly from Massachusetts to Chicago?
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 Massachusetts in January are about $218 on average during January, but can be found for as low as $97.
When is the cheapest time to fly from Massachusetts to Chicago (MA - CHI)?
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Massachusetts to Chicago as you normally would.
Cheap flights from Massachusetts to Chicago in August, September 2022
The best prices found for Massachusetts to CHI flights for August, September
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 52mChicago O'Hare Intl
Boston Logan Intl
Nonstop
2h 17mAmerican Airlines
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 56mChicago O'Hare Intl
Boston Logan Intl
Nonstop
2h 17mJetBlue
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
3h 03mChicago O'Hare Intl
Boston Logan Intl
Nonstop
2h 26mJetBlue
Massachusetts to Chicago 2022 flight deals
Cheap flights to Chicago from Massachusetts found for this year
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
3h 03mChicago O'Hare Intl
Boston Logan Intl
Nonstop
2h 26mJetBlue
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 52mChicago O'Hare Intl
Boston Logan Intl
Nonstop
2h 17mAmerican Airlines
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 56mChicago O'Hare Intl
Boston Logan Intl
Nonstop
2h 17mJetBlue
Cheap United Airlines flights from Massachusetts to Chicago
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 51mChicago O'Hare Intl
Boston Logan Intl
Nonstop
2h 21mUnited Airlines
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 50mChicago O'Hare Intl
Boston Logan Intl
Nonstop
2h 21mUnited Airlines
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 50mChicago O'Hare Intl
Boston Logan Intl
1 stop
5h 02mUnited Airlines
Cheap Delta flights from Massachusetts to Chicago
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 58mChicago O'Hare Intl
Boston Logan Intl
Nonstop
2h 25mDelta
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 58mChicago O'Hare Intl
Boston Logan Intl
Nonstop
2h 25mDelta
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 39mChicago O'Hare Intl
Boston Logan Intl
Nonstop
2h 34mDelta
Non-stop flights to Chicago from Massachusetts
Save time with Massachusetts to Chicago direct flight deals
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
3h 03mChicago O'Hare Intl
Boston Logan Intl
Nonstop
2h 26mJetBlue
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 41mChicago O'Hare Intl
Boston Logan Intl
Nonstop
2h 34mDelta
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
3h 02mChicago O'Hare Intl
Boston Logan Intl
Nonstop
2h 24mJetBlue
Last minute flights from Massachusetts to Chicago
Late deals on return flights to Chicago from Massachusetts, departing today and this week
Boston Logan Intl
Chicago O'Hare Intl
1 stop
5h 05mChicago O'Hare Intl
Boston Logan Intl
Nonstop
2h 17mAmerican Airlines
Boston Logan Intl
Chicago O'Hare Intl
1 stop
8h 15mChicago O'Hare Intl
Boston Logan Intl
Nonstop
2h 18mAmerican Airlines
Boston Logan Intl
Chicago O'Hare Intl
1 stop
5h 22mChicago O'Hare Intl
Boston Logan Intl
1 stop
5h 51mAmerican Airlines
One-way flights to Chicago from Massachusetts
The cheapest one-way flights from Massachusetts to Chicago
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
3h 02mJetBlue
Boston Logan Intl
Chicago O'Hare Intl
Nonstop
2h 50mUnited Airlines
Boston Logan Intl
Chicago O'Hare Intl
1 stop
9h 00mSpirit Airlines
Related info for your journey
Useful info, stats and facts about Massachusetts to Chicago flights.
Which airlines flying from Massachusetts to Chicago have flexible cancellations due to COVID-19?
Some of the carriers operating flights from Massachusetts to Chicago that may be offering flexible cancellation policies are United Airlines, American Airlines, and JetBlue. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.
Can I find flights from Massachusetts to Chicago for under $200 on Cheapflights?
Yes, there are multiple flights from Massachusetts to Chicago for under $200. The cheapest flight booked recently is on JetBlue for just $122, but on average you can expect to pay $142.
Are there nonstop flights from Massachusetts to Chicago for under $200 on Cheapflights?
Cheapflights has at least 20 direct flights from Massachusetts to Chicago under $200. A good price for a nonstop flight from Massachusetts to Chicago is less than $149.
Are there last-minute flights available from Massachusetts to Chicago for under $200?
There are currently 20+ open flights from Massachusetts to Chicago within the next 7 days for less than $200.
What days are nonstop flights available from Massachusetts to Chicago?
Nonstop flights are available for this route on the following days: Sunday, Wednesday, Friday, Saturday.
How many flights depart from Massachusetts to Chicago on average per day?
On average, you can expect to see 9 flights from Massachusetts to Chicago a day.
Morning (6am - Noon) - 56% of flight departures
Evening (6pm - Midnight) - 44% of flight departures
How long is the flight from Massachusetts to Chicago?
A quick flight from Massachusetts to Chicago can take about 2h 51m. JetBlue provides one of the quickest options available for as low as $122. The distance from Massachusetts to Chicago is about 869 mi. All flights are typically nonstop.
What are the cheapest airlines to fly from Massachusetts to Chicago one-way?
To fly one-way, consider booking your trip with JetBlue, which is currently one of the cheapest options available, starting at $64. United Airlines flights start at $69 while deals on Spirit Airlines start at $71 one-way.
What are the most popular routes from Massachusetts to Chicago?
While some choose either Boston Logan Intl - Chicago Midway or Worcester - Chicago O'Hare Intl, Boston Logan Intl - Chicago O'Hare Intl is the most popular route from Massachusetts to Chicago.
What are the most popular airlines that fly from Massachusetts to Chicago?
Consider Undisclosed Carrier, American Airlines or Alaska Airlines when booking your flight. These represent the most popular airlines when flying from Massachusetts to Chicago.
What are the most reliable airlines from Massachusetts to Chicago?
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 Massachusetts to Chicago on time: ANA (92%), Japan Airlines (83%), United Airlines (83%).
What are the cheapest flights from Massachusetts to Chicago?
Looking for the cheapest flight from Massachusetts to Chicago? While on average our users pay $462, our data indicates the cheapest price to be $73. The most popular route (Boston Logan Intl - Chicago O'Hare Intl), is priced around $122.
Flights to Chicago from Massachusetts
Departure points for flights from Massachusetts to Chicago
Select to see more specific information for flights to Chicago from all departure points in Massachusetts
Top 7 airlines flying from Massachusetts to Chicago
The chart below displays the airlines Cheapflights users traveling from Massachusetts to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Hourly flight availability from Massachusetts to Chicago
See what time of day planes typically take off from Massachusetts to Chicago
| 17%of flight departures | Early morningMidnight to 6 am |
|---|---|
| 32%of flight departures | Morning6 am to noon |
| 42%of flight departures | AfternoonNoon to 6 pm |
| 9%of flight departures | Evening6 pm to midnight |