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Flights from Chicago O'Hare International Airport to Massachusetts

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Flight deals from Chicago O'Hare International Airport to Massachusetts

Looking for cheap tickets from Chicago O'Hare International Airport to Massachusetts, or a last-minute trip? Find the lowest prices on one-way and return tickets right here.
Boston.90 € per passenger.Departing Wed, 14 May, returning Sat, 17 May.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Wed, 14 May, arriving in Boston Logan International.Inbound indirect flight with Spirit Airlines, departs from Boston Logan International on Sat, 17 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From 90 €, select.
Worcester.196 € per passenger.Departing Fri, 4 Apr, returning Mon, 14 Apr.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Fri, 4 Apr, arriving in Worcester.Inbound indirect flight with Delta, departs from Worcester on Mon, 14 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From 196 €, select.
Nantucket.617 € per passenger.Departing Fri, 1 Aug, returning Mon, 4 Aug.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Fri, 1 Aug, arriving in Nantucket.Inbound indirect flight with Delta, departs from Nantucket on Mon, 4 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From 617 €, select.

Flying from Chicago O'Hare International Airport to Massachusetts

Arm yourself with these facts on the fly.
Cheapest flight found90 €, Boston
Cheapest month to flyMay
Average flight time2 hrs, 37 mins
Average flights per week552
Most popular airlineAmerican Airlines

Frequently asked questions

Yes - direct flights currently operate from Chicago O'Hare International Airport to Boston Logan International Airport in Massachusetts.
We looked at all of the upcoming return flights from Chicago O'Hare International Airport to Massachusetts we could find over the next 12 months. It looks like 90 € is the best price. This is good, compared to the average Massachusetts ticket price of 218 €.
The cheapest month to fly from Chicago O'Hare International Airport to Boston Logan International Airport is currently May.
The cheapest month to fly from Chicago O'Hare International Airport to Worcester Airport is currently April.
And the cheapest month to fly from Chicago O'Hare International Airport to Nantucket Airport is usually August.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago O'Hare International Airport to Massachusetts on Wednesday, 14 May 2025.
If you're flying from Chicago O'Hare International, 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 O'Hare International Airport and Massachusetts is 2 hours and 37 minutes.

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