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

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Find available prices by choosing your travel dates.
Flights from Chicago (ORD) to Plymouth (PYM)
Origin airport
O'Hare Intl.
Destination airport
Plymouth Municipal
Distance
881 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

Is it cheaper to buy a plane ticket from ORD to PYM last minute?
Being the spontaneous type is an awesome way to travel, but it isn’t necessarily the best way to grab a cheap fare. It’s better to book your O’Hare Intl. Airport (ORD) to PYM trip in advance instead of waiting till the last minute. Based on flight pricing and demand studies in 2022, we have found that the best time to book domestic flights is between 28 – 35 days ahead of the departure date, and international flights three to four months in advance. Leave your spontaneous side for when you’re exploring PYM!
What airports do you fly into for Plymouth from Chicago?
With Plymouth, MA (PYM-Plymouth Municipal), New Bedford Regional Airport (EWB) and Barnstable Municipal Airport (HYA) to select from, traveling from Chicago to Plymouth is a snap. The city’s busiest terminal, Plymouth, MA (PYM-Plymouth Municipal), is around 5 mi southwest of the downtown area. Apart from ticket costs, consider factors like public transportation options from the airport and the distance to your hotel before making your decision. Get your Plymouth adventure off to a superb start by visiting Plymouth Rock and National Monument to the Forefathers.
Can I change the date of my flight from O'Hare Intl. Airport (ORD) to PYM?
It’s so easy to make amendments to your O’Hare Airport to PYM journey yourself. Just log in to the Expedia Trips portal and tap “change flight.” Look for new flights and secure the one that works best. You’ll see an estimate of any flight change costs. You can also head to our Customer Service portal to chat to our Virtual Agent and quickly get answers to all your questions.

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