Cheap Flights from Vineyard Haven (MVY) to Chicago (MDW)

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Find available prices by choosing your travel dates.
Flights from Vineyard Haven (MVY) to Chicago (MDW)
Origin airport
Martha's Vineyard
Destination airport
Midway Intl.
Distance
884 mi

Vineyard Haven to Chicago Flights

The cheapest times to fly from Vineyard Haven to Chicago

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 Vineyard Haven to Chicago are during the month of . You can find some of the cheapest flights from Vineyard Haven to Chicago with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Vineyard Haven to Chicago

Sunday is one of the best days to book for cheap flights from Vineyard Haven to Chicago: 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 Vineyard Haven to Chicago

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 Vineyard Haven to Chicago 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 Vineyard Haven to Chicago 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 Vineyard Haven to Chicago 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 Martha's Vineyard Airport to MDW last minute?
Booking your trip from Martha’s Vineyard Airport to MDW last minute could save you a tidy sum if you strike it lucky and find an epic deal. However, airfares don’t usually get cheaper as the departure date nears. If you choose to wait, flights could also be booked up or the best seats taken (don’t get stuck in the middle!). If you don’t want to risk it, book well in advance of your departure date. Don’t forget that some of the biggest bargains can be found up to 12 months in advance. If your preferred airline hasn’t released tickets yet, check back regularly as deals are constantly updated on Expedia.
What airports do you fly into for Chicago from Martha's Vineyard?
With Midway Intl. Airport (MDW), O’Hare Intl. Airport (ORD) and Lewis University Airport (LOT) to choose from, making your way from Martha’s Vineyard to Chicago is a breeze. The city’s main gateway, Midway Intl. Airport (MDW), is roughly 9 mi southwest of the downtown area. Besides the price of tickets, consider factors like train or bus options from the airport and the distance to your hotel when choosing where to fly into. Get your Chicago vacation off to a flying start by visiting Wrigley Field and Millennium Park.
Can I change the date of my flight from Martha's Vineyard Airport (MVY) to Chicago Airport?
It’s a piece of cake to make changes to your Martha’s Vineyard Airport (MVY) to Midway Intl. Airport (MDW) journey yourself. Just log in to the Expedia Trips portal and tap “change flight.” Browse around for new flights and lock in the one that works with your new plans. You’ll see an estimate of the extra charges, if applicable. Alternatively, use our Customer Service portal to connect with our Virtual Agent and get answers to all your questions.

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