Flights from Chicago Midway Airport to Massachusetts

Flight deals from Chicago Midway Airport to Massachusetts

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Massachusetts? If you want to travel next month, return fares start from 151 €. Find the lowest prices on one-way and return tickets right here.

Boston.147 € per passenger.Departing Tue, 21 Jul, returning Mon, 27 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 21 Jul, arriving in Boston Logan International.Inbound direct flight with Southwest Airlines departs from Boston Logan International on Mon, 27 Jul, arriving in Chicago Midway.Price includes taxes and charges.From 147 €, select.

Worcester.402 € per passenger.Departing Mon, 8 Jun, returning Sun, 14 Jun.Return flight with Allegiant Air and jetBlue.Outbound indirect flight with Allegiant Air, departs from Chicago Midway on Mon, 8 Jun, arriving in Worcester.Inbound indirect flight with jetBlue, departs from Worcester on Sun, 14 Jun, arriving in Chicago Midway.Price includes taxes and charges.From 402 €, select.

Nantucket.477 € per passenger.Departing Fri, 29 May, returning Tue, 2 Jun.Return flight with Allegiant Air and jetBlue.Outbound indirect flight with Allegiant Air, departs from Chicago Midway on Fri, 29 May, arriving in Nantucket.Inbound indirect flight with jetBlue, departs from Nantucket on Tue, 2 Jun, arriving in Chicago Midway.Price includes taxes and charges.From 477 €, select.

Hyannis.554 € per passenger.Departing Fri, 7 Aug, returning Mon, 10 Aug.Return flight with Frontier Airlines and jetBlue.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Fri, 7 Aug, arriving in Hyannis.Inbound indirect flight with jetBlue, departs from Hyannis on Mon, 10 Aug, arriving in Chicago Midway.Price includes taxes and charges.From 554 €, select.

Provincetown.680 € per passenger.Departing Wed, 10 Jun, returning Tue, 16 Jun.Return flight with Frontier Airlines and Cape Air.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 10 Jun, arriving in Provincetown.Inbound indirect flight with Cape Air, departs from Provincetown on Tue, 16 Jun, arriving in Chicago Midway.Price includes taxes and charges.From 680 €, select.

Fall River.1.240 € per passenger.Departing Thu, 11 Jun, returning Wed, 17 Jun.Return flight with Frontier Airlines and Cape Air.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Thu, 11 Jun, arriving in Fall River.Inbound indirect flight with Cape Air, departs from Fall River on Wed, 17 Jun, arriving in Chicago Midway.Price includes taxes and charges.From 1.240 €, select.

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Flying from Chicago Midway Airport to Massachusetts

Arm yourself with these facts on the fly.

Cheapest flight found	147 €
Cheapest month to fly	July
Average flight time	2 hrs, 19 mins
Average flights per week	27
Most popular airline	Southwest Airlines

How to find cheap flights from Chicago Midway 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 Midway Airport to Massachusetts. Other savvy travellers recently found return flights from 147 € and one-way tickets from 70 €. Ready to join them? Here are a few tips to help you do it the smart way.

Fly in July

The cheapest time to fly from Chicago Midway Airport to Massachusetts is currently July.

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 Midway 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 Midway 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 Midway Airport to Massachusetts?

Yes - direct flights currently operate from Chicago Midway Airport to Boston Logan International Airport in Massachusetts.

Which other Chicago airports offer direct flights to Massachusetts?

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

What is the average price of a flight from Chicago Midway Airport to Massachusetts?

We looked at all of the upcoming return flights from Chicago Midway Airport to Massachusetts we could find over the next 12 months. It looks like 147 € is the best price. This is good, compared to the average Massachusetts ticket price of 583 €.

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

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

Which upcoming date is cheapest to fly from Chicago Midway Airport to Massachusetts on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago Midway Airport to Massachusetts on Tuesday, 21 July 2026.

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

If you're flying from Chicago Midway, the cheapest city in Massachusetts to fly into is Boston. The cheapest airport serving Boston at the moment is Boston Logan International.