Cheap Flights from Chicago O'Hare International Airport to Massachusetts from $169 Return

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.$84 per passenger.Departing Wed, 18 Feb.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Wed, 18 Feb, arriving in Boston Logan International.Price includes taxes and charges.From $84, select.

Worcester.$151 per passenger.Departing Tue, 6 Jan.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Tue, 6 Jan, arriving in Worcester.Price includes taxes and charges.From $151, select.

See more deals

Flying from Chicago O'Hare International Airport to Massachusetts

Arm yourself with these facts on the fly.

Cheapest flight found	$84
Cheapest month to fly	February
Average flight time	2 hrs, 36 mins
Average flights per week	1,262
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 $169 and one-way tickets from $84. Ready to join them? Here are a few tips to help you do it the smart way.

Fly in January

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

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 in 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 $169 is the best price. This is good, compared to the average Massachusetts ticket price of $433.

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 Boston Logan International Airport is currently January.
The cheapest month to fly from Chicago O'Hare International Airport to Worcester Airport is currently December.
And the cheapest month to fly from Chicago O'Hare International Airport to Nantucket Airport is usually August.

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 Saturday, 10 January 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.