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Flights from Chicago to Massachusetts

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Flight deals from Chicago to Massachusetts

Looking for cheap tickets from Chicago to Massachusetts, or a last-minute trip? Find the lowest prices on one-way and return tickets right here.
Boston.80 € per passenger.Departing Wed, 20 Aug, returning Wed, 27 Aug.Return flight with jetBlue.Outbound indirect flight with jetBlue, departs from Chicago O'Hare International on Wed, 20 Aug, arriving in Boston Logan International.Inbound indirect flight with jetBlue, departs from Boston Logan International on Wed, 27 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From 80 €, select.
Worcester.194 € per passenger.Departing Thu, 10 Apr, returning Tue, 22 Apr.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Thu, 10 Apr, arriving in Worcester.Inbound indirect flight with Delta, departs from Worcester on Tue, 22 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From 194 €, select.
Nantucket.444 € per passenger.Departing Sat, 12 Jul, returning Sat, 26 Jul.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Sat, 12 Jul, arriving in Nantucket.Inbound indirect flight with United, departs from Nantucket on Sat, 26 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From 444 €, select.

Flying from Chicago to Massachusetts

Arm yourself with these facts on the fly.
Cheapest flight found80 €, Boston
Cheapest month to flyAugust
Average flight time2 hrs, 28 mins
Cheapest airport to fly fromChicago O'Hare International
Most popular airlineAmerican Airlines

Frequently asked questions

We looked at all of the upcoming return flights from Chicago to Massachusetts we could find over the next 12 months. It looks like 80 € is the best price. This is good, compared to the average Massachusetts ticket price of 130 €.
The cheapest month to fly from Chicago to Nantucket Airport is currently July. The cheapest month to fly from Chicago to Worcester Airport is usually April. And the cheapest month to fly from Chicago to Boston Logan International Airport is usually August.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Massachusetts on Wednesday, 20 August 2025.
Chicago O'Hare International Airport offers direct flights to Massachusetts.
If you're flying from Chicago, the cheapest city in Massachusetts to fly into is Boston. The cheapest airport serving Boston at the moment is Boston Logan International.
The average flight time between Chicago and Massachusetts is 2 hours and 27 minutes.

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