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 $51 is the best price. This is good, compared to the average Massachusetts ticket price of $283.

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

The cheapest month to fly from Chicago to Boston Logan International Airport is usually September . The cheapest month to fly from Chicago to Fall River Airport is usually July . The cheapest month to fly from Chicago to Provincetown Airport is usually June . And the cheapest month to fly from Chicago to Nantucket Airport is usually July .

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 Tuesday, September 10, 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 25 minutes.

Flights from Chicago to Massachusetts

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.$51 per passenger.Departing Tue, Sep 10, returning Sun, Sep 15.Round-trip flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departing from Chicago O'Hare International on Tue, Sep 10, arriving in Boston Logan International.Inbound direct flight with Spirit Airlines departing from Boston Logan International on Sun, Sep 15, arriving in Chicago O'Hare International.Price includes taxes and charges.From $51, select.

Hyannis.$195 per passenger.Departing Tue, Aug 27, returning Sat, Aug 31.Round-trip flight with American Airlines.Outbound indirect flight with American Airlines, departing from Chicago O'Hare International on Tue, Aug 27, arriving in Hyannis.Inbound indirect flight with American Airlines, departing from Hyannis on Sat, Aug 31, arriving in Chicago O'Hare International.Price includes taxes and charges.From $195, select.

Worcester.$200 per passenger.Departing Wed, Jun 26, returning Tue, Jul 2.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Chicago O'Hare International on Wed, Jun 26, arriving in Worcester.Inbound indirect flight with Delta, departing from Worcester on Tue, Jul 2, arriving in Chicago O'Hare International.Price includes taxes and charges.From $200, select.

Nantucket.$293 per passenger.Departing Mon, Jul 1, returning Thu, Jul 4.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Chicago O'Hare International on Mon, Jul 1, arriving in Nantucket.Inbound indirect flight with Delta, departing from Nantucket on Thu, Jul 4, arriving in Chicago O'Hare International.Price includes taxes and charges.From $293, select.

Provincetown.$539 per passenger.Departing Fri, Jun 28, returning Fri, Jul 5.Round-trip flight with Spirit Airlines and Cape Air.Outbound indirect flight with Spirit Airlines, departing from Chicago O'Hare International on Fri, Jun 28, arriving in Provincetown.Inbound indirect flight with Cape Air, departing from Provincetown on Fri, Jul 5, arriving in Chicago O'Hare International.Price includes taxes and charges.From $539, select.

Fall River.$624 per passenger.Departing Fri, Jul 5, returning Thu, Jul 11.Round-trip flight with jetBlue and Cape Air.Outbound indirect flight with jetBlue, departing from Chicago O'Hare International on Fri, Jul 5, arriving in Fall River.Inbound indirect flight with Cape Air, departing from Fall River on Thu, Jul 11, arriving in Chicago O'Hare International.Price includes taxes and charges.From $624, select.

Flying from Chicago to Massachusetts

Arm yourself with these facts on the fly.

Cheapest flight found	$51, Boston
Cheapest month to fly	September
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 $51 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 September

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

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 $51 is the best price. This is good, compared to the average Massachusetts ticket price of $283.
: The cheapest month to fly from Chicago to Boston Logan International Airport is usually September. The cheapest month to fly from Chicago to Fall River Airport is usually July. The cheapest month to fly from Chicago to Provincetown Airport is usually June. And the cheapest month to fly from Chicago to Nantucket Airport is usually July.
: After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Massachusetts on Tuesday, September 10, 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 25 minutes.