Cheap Flights from Chicago (MDW) to Plymouth (PYM)

Popular airlines from Chicago Midway Airport (MDW) to Plymouth, MA (PYM-Plymouth Municipal)

Alternative airports near Plymouth

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to New Bedford Regional EWB. Cheapest option available. Average driving time to city center is 50 minutes. Flights from $529
EWB
New Bedford Regional
Cheapest
Average driving time to city center50 min
Flights from $529
Flights from Chicago (MDW) to Plymouth (PYM)
Origin airport
Midway Intl.
Destination airport
Plymouth Municipal
Distance
874 mi

Chicago to Plymouth Flights

The cheapest times to fly from Chicago to Plymouth

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Plymouth are during the month of . You can find some of the cheapest flights from Chicago to Plymouth with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Plymouth

Sunday is one of the best days to book for cheap flights from Chicago to Plymouth: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Plymouth

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Plymouth in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Plymouth flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Plymouth airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Plymouth, MA (PYM-Plymouth Municipal) cost?
Snag a cheap one-way flight or cheap return flight from Midway Intl. Airport (MDW) to Plymouth, MA (PYM-Plymouth Municipal) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Plymouth, MA (PYM-Plymouth Municipal)?
is the most affordable month to fly from MDW to PYM. Timing your trip outside of the busy season is often the key to better flight prices.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Plymouth, MA (PYM-Plymouth Municipal)?
Expedia's filter tool lets you easily compare travel time, airlines and fares all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest MDW to PYM flight.
How many flights per day from Midway Intl. Airport (MDW) to Plymouth, MA (PYM-Plymouth Municipal)?
You'll have to catch a flight with a layover when traveling from Midway Intl. Airport (MDW) to Plymouth, MA (PYM-Plymouth Municipal). Direct flights don't operate daily on this route. However, simply filter your search to include one or two stops to find an option that works for you.
What day of the week has the most flights from MDW to PYM?
You'll generally find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can vary from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Plymouth, MA (PYM-Plymouth Municipal)?
To avoid potential delays on the Midway Intl. Airport (MDW) to Plymouth, MA (PYM-Plymouth Municipal) route, aim to fly before 3 PM. Departures after this time have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Plymouth from Midway Intl. Airport (MDW)?
If you're taking a direct flight from Midway Intl. Airport (MDW) to Plymouth, you'll land at either Logan Intl. Airport (BOS) or T.F. Green Airport (PVD).
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Plymouth, MA (PYM-Plymouth Municipal) last-minute?
Waiting until just before your departure to book a ticket from MDW to PYM generally means paying more. While you may come across some last-minute discounts, there's no guarantee. Keep your travel schedule open to maximize your chances of scoring a bargain.
Is it cheaper to book a MDW to PYM flight and hotel package?
Opting for a MDW to PYM flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip all in one place. Pick from our wide range of hotels and then add activities, car rentals and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Plymouth, MA (PYM-Plymouth Municipal)?
You can usually reschedule or cancel your MDW to PYM flight. However, if it's been more than 24 hours since booking, additional charges may apply. Check your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find further details on our Customer Service portal.

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*Available to One Key members.