What's the average Chicago to Massachusetts flight price?

We looked at all of the upcoming round-trip flights from Chicago to Massachusetts we could find over the next 12 months. It looks like $40 is the best price. This is good, compared to the average Massachusetts ticket price of $261.

What is the cheapest month to fly from Chicago to Massachusetts?

The cheapest month to fly from Chicago to Nantucket Airport is currently June . The cheapest month to fly from Chicago to Boston Logan International Airport is usually June . And the cheapest month to fly from Chicago to Worcester Airport is usually June .

On which upcoming date is it cheapest to fly from Chicago to Massachusetts?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Massachusetts on Wednesday, June 5, 2024 .

Are there any direct flights from Chicago to Massachusetts?

Chicago O'Hare International Airport offers direct flights to Massachusetts.

If I'm flying from Chicago, where in Massachusetts is cheapest to fly to?

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.

How long is the flight from Chicago to Massachusetts?

The average flight time between Chicago and Massachusetts is 2 hours and 24 minutes.

Cheap Flights from Chicago to Massachusetts from $40 Roundtrip

Flight deals from Chicago to Massachusetts

Looking for cheap flights from Chicago to Massachusetts, or a last-minute trip? Find the lowest prices on one-way and round-trip flights right here.

Boston.$40 per passenger.Departing Wed, Jun 5, returning Tue, Jun 11.Round-trip flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departing from Chicago O'Hare International on Wed, Jun 5, arriving in Boston Logan International.Inbound direct flight with Spirit Airlines departing from Boston Logan International on Tue, Jun 11, arriving in Chicago O'Hare International.Price includes taxes and charges.From $40, select.

Worcester.$232 per passenger.Departing Tue, Jun 11, returning Tue, Jun 18.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Chicago O'Hare International on Tue, Jun 11, arriving in Worcester.Inbound indirect flight with Delta, departing from Worcester on Tue, Jun 18, arriving in Chicago O'Hare International.Price includes taxes and charges.From $232, select.

Nantucket.$263 per passenger.Departing Tue, Jun 25, returning Mon, Jul 1.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Chicago O'Hare International on Tue, Jun 25, arriving in Nantucket.Inbound indirect flight with Delta, departing from Nantucket on Mon, Jul 1, arriving in Chicago O'Hare International.Price includes taxes and charges.From $263, select.

Flying from Chicago to Massachusetts

Arm yourself with these facts on the fly.

Cheapest flight found	$40, Boston
Cheapest month to fly	June
Average flight time	2 hrs, 25 mins
Cheapest airport to fly from	Chicago O'Hare International
Most popular airline	American Airlines

How to find cheap flights from Chicago to Massachusetts

We've compared the best online travel agents and flight providers on the Internet to find the cheapest plane tickets from Chicago to Massachusetts. Other savvy travelers recently found round-trip flights from $40 and one-way tickets from $18. Ready to join them? Here are a few tips to help you do it the smart way.

Fly from Chicago O'Hare International into Boston

At the moment, the lowest-priced flight tickets to Massachusetts are from Chicago O'Hare International Airport to Boston Logan International Airport.

Fly in August

We crunched the flight calendar and found the cheapest time to fly from Chicago to Massachusetts is currently August.

Fly on a Tuesday

From our data, we can see that Tuesday seems to be the cheapest time to fly from Chicago to Massachusetts.

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 to anywhere you choose in Massachusetts.

Watch as flight prices go up and down

With Price Alerts, we'll let you know when flight prices from Chicago to Massachusetts go up or down so you can book when the time is just right.

Relax – these are fee-free plane tickets

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

Frequently asked questions

: We looked at all of the upcoming round-trip flights from Chicago to Massachusetts we could find over the next 12 months. It looks like $40 is the best price. This is good, compared to the average Massachusetts ticket price of $261.
: The cheapest month to fly from Chicago to Nantucket Airport is currently June. The cheapest month to fly from Chicago to Boston Logan International Airport is usually June. And the cheapest month to fly from Chicago to Worcester Airport is usually June.
: After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Massachusetts on Wednesday, June 5, 2024.
: 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 24 minutes.

Flights from Chicago to Massachusetts