Flights from Chicago to Massachusetts

Flight deals from Chicago to Massachusetts

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

Boston.71 € per passenger.Departing Tue, 21 Oct, returning Wed, 29 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 21 Oct, arriving in Boston Logan International.Inbound direct flight with Southwest Airlines departs from Boston Logan International on Wed, 29 Oct, arriving in Chicago Midway.Price includes taxes and charges.From 71 €, select.

Worcester.215 € per passenger.Departing Fri, 19 Sep, returning Sun, 21 Sep.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Fri, 19 Sep, arriving in Worcester.Inbound indirect flight with Delta, departs from Worcester on Sun, 21 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From 215 €, select.

Fall River.308 € per passenger.Departing Fri, 10 Oct, returning Mon, 13 Oct.Return flight with Spirit Airlines and Cape Air.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Fri, 10 Oct, arriving in Fall River.Inbound indirect flight with Cape Air, departs from Fall River on Mon, 13 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From 308 €, select.

Provincetown.404 € per passenger.Departing Sat, 27 Sep, returning Sat, 4 Oct.Return flight with Spirit Airlines and Cape Air.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Sat, 27 Sep, arriving in Provincetown.Inbound indirect flight with Cape Air, departs from Provincetown on Sat, 4 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From 404 €, select.

Hyannis.518 € per passenger.Departing Mon, 22 Sep, returning Fri, 26 Sep.Return flight with Frontier Airlines and Cape Air.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Mon, 22 Sep, arriving in Hyannis.Inbound indirect flight with Cape Air, departs from Hyannis on Fri, 26 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From 518 €, select.

Nantucket.597 € per passenger.Departing Fri, 26 Sep, returning Tue, 30 Sep.Return flight with Spirit Airlines and Cape Air.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Fri, 26 Sep, arriving in Nantucket.Inbound indirect flight with Cape Air, departs from Nantucket on Tue, 30 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From 597 €, select.

Flying from Chicago to Massachusetts

Arm yourself with these facts on the fly.

Cheapest flight found	71 €, Boston
Cheapest month to fly	October
Average flight time	2 hrs, 26 mins
Cheapest airport to fly from	Chicago Midway
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 travellers recently found return flights from 71 € and one-way tickets from 36 € one-way. Ready to join them? Here are a few tips to help you do it the smart way.

Fly from Chicago Midway into Boston

At the moment, the lowest priced flight tickets to Massachusetts are from Chicago Midway Airport to Boston Logan International Airport.

Fly in October

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

Fly on a Wednesday

From our data, we can see that Wednesday 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 fares rise and fall

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 flight 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

What's the average Chicago to Massachusetts flight price?

We looked at all of the upcoming return flights from Chicago to Massachusetts we could find over the next 12 months. It looks like 71 € is the best price. This is good, compared to the average Massachusetts ticket price of 352 €.

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

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

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

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Massachusetts on Tuesday, 21 October 2025.

Are there any direct flights from Chicago to Massachusetts?

Chicago Midway Airport offers direct flights to Massachusetts.

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

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.