Flights from Chicago O'Hare International Airport to Massachusetts

Flight deals from Chicago O'Hare International Airport to Massachusetts

Looking for a cheap last-minute deal or the best return flight from Chicago O'Hare International Airport to Massachusetts? If you want to travel next month, return fares start from R 2,254. Find the lowest prices on one-way and return tickets right here.

Boston.R 1,044 per passenger.Departing Sat, 26 Sep.One-way flight with British Airways.Outbound direct flight with British Airways departs from Chicago O'Hare International on Sat, 26 Sep, arriving in Boston Logan International.Price includes taxes and charges.From R 1,044, select.

Worcester.R 1,708 per passenger.Departing Wed, 5 Aug.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Wed, 5 Aug, arriving in Worcester.Price includes taxes and charges.From R 1,708, select.

Nantucket.R 2,870 per passenger.Departing Fri, 12 Jun.One-way flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Fri, 12 Jun, arriving in Nantucket.Price includes taxes and charges.From R 2,870, select.

Hyannis.R 4,422 per passenger.Departing Fri, 29 May.One-way flight with jetBlue.Outbound indirect flight with jetBlue, departs from Chicago O'Hare International on Fri, 29 May, arriving in Hyannis.Price includes taxes and charges.From R 4,422, select.

Norwood.R 12,032 per passenger.Departing Wed, 27 May.One-way flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Wed, 27 May, arriving in Norwood.Price includes taxes and charges.From R 12,032, select.

Bedford / Hanscom.R 13,316 per passenger.Departing Sun, 21 Jun.One-way flight with jetBlue.Outbound indirect flight with jetBlue, departs from Chicago O'Hare International on Sun, 21 Jun, arriving in Bedford / Hanscom.Price includes taxes and charges.From R 13,316, select.

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Flying from Chicago O'Hare International Airport to Massachusetts

Arm yourself with these facts on the fly.

Cheapest flight found	R 1,044
Cheapest month to fly	September
Average flight time	2 hrs, 44 mins
Average flights per week	704
Most popular airline	American Airlines

How to find cheap flights from Chicago O'Hare International Airport to Massachusetts

We've compared the best online travel agents and flight providers on the internet to find the cheapest plane tickets from Chicago O'Hare International Airport to Massachusetts. Other savvy travellers recently found return flights from R 2,237 and one-way tickets from R 1,044. Ready to join them? Here are a few tips to help you do it the smart way.

Fly in September

The cheapest time to fly from Chicago O'Hare International Airport to Massachusetts is currently September.

Flex your dates for the best rates

If you’re flexible on your departure dates, you can use Skyscanner's whole month tool to find the cheapest day of the year to fly from Chicago O'Hare International Airport to anywhere you choose in Massachusetts.

Watch as fares rise and fall

With Price Alerts, we'll let you know when flight prices from Chicago O'Hare International Airport to your chosen airport in Massachusetts go up or down so you can book when the time is just right.

Relax – these are fee-free flight tickets

With us, there are no added fees – the Massachusetts Airport to Massachusetts flight price you see when you search with us is what you pay to the provider.

Frequently asked questions

Are there any direct flights from Chicago O'Hare International Airport to Massachusetts?

Yes - direct flights currently operate from Chicago O'Hare International Airport to Boston Logan International Airport and Nantucket Airport in Massachusetts.

Which other Chicago airports offer direct flights to Massachusetts?

Chicago Midway Airport offers direct flights to Massachusetts.

What is the average price of a flight from Chicago O'Hare International Airport to 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 R 2,237 is the best price. This is good, compared to the average Massachusetts ticket price of R 10,755.

What is the cheapest month to fly from Chicago O'Hare International Airport to Massachusetts?

The cheapest month to fly from Chicago O'Hare International Airport to Fall River Airport is currently June.
The cheapest month to fly from Chicago O'Hare International Airport to Boston Logan International Airport is currently September.
The cheapest month to fly from Chicago O'Hare International Airport to Norwood Airport is currently May.
And the cheapest month to fly from Chicago O'Hare International Airport to Worcester Airport is usually May.

Which upcoming date is cheapest to fly from Chicago O'Hare International Airport to Massachusetts on?

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, 9 September 2026.

If I'm flying from Chicago O'Hare International Airport, where in Massachusetts is cheapest to fly into?

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.