$181 Cheap Flights from Chicago (ORD) to Vineyard Haven (MVY)

View $181 flight on Mon, Sep 1, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Vineyard Haven, MA (MVY-Martha's Vineyard)

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Cheap Flights from Chicago to Vineyard Haven (ORD-MVY)

Prices were available within the past 7 days and start at $181 for one-way flights and $237 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Tue, Aug 19 - Thu, Sep 4
ORD
Chicago
MVY
Vineyard Haven
$237 Roundtrip, found 3 days ago
$237
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Aug 19 from Chicago to Vineyard Haven, returning Thu, Sep 4, priced at $237 found 3 days ago
JetBlue Airways
Tue, Aug 12 - Wed, Aug 27
ORD
Chicago
MVY
Vineyard Haven
$259 Roundtrip, found 3 days ago
$259
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Aug 12 from Chicago to Vineyard Haven, returning Wed, Aug 27, priced at $259 found 3 days ago
JetBlue Airways
Wed, Sep 17 - Sat, Sep 27
ORD
Chicago
MVY
Vineyard Haven
$264 Roundtrip, found 2 days ago
$264
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, Sep 17 from Chicago to Vineyard Haven, returning Sat, Sep 27, priced at $264 found 2 days ago
JetBlue Airways
Tue, Aug 19 - Sun, Aug 31
ORD
Chicago
MVY
Vineyard Haven
$266 Roundtrip, found 3 days ago
$266
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Aug 19 from Chicago to Vineyard Haven, returning Sun, Aug 31, priced at $266 found 3 days ago
American Airlines
Sat, Aug 23 - Sat, Aug 30
ORD
Chicago
MVY
Vineyard Haven
$290 Roundtrip, found 6 days ago
$290
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Aug 23 from Chicago to Vineyard Haven, returning Sat, Aug 30, priced at $290 found 6 days ago
JetBlue Airways
Sat, Aug 23 - Wed, Aug 27
ORD
Chicago
MVY
Vineyard Haven
$294 Roundtrip, found 2 days ago
$294
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sat, Aug 23 from Chicago to Vineyard Haven, returning Wed, Aug 27, priced at $294 found 2 days ago
JetBlue Airways
Wed, Aug 13 - Wed, Aug 27
ORD
Chicago
MVY
Vineyard Haven
$298 Roundtrip, just found
$298
Roundtrip
just found
Select JetBlue Airways flight, departing Wed, Aug 13 from Chicago to Vineyard Haven, returning Wed, Aug 27, priced at $298 just found
American Airlines
Wed, Aug 20 - Wed, Aug 27
ORD
Chicago
MVY
Vineyard Haven
$300 Roundtrip, found 1 day ago
$300
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Aug 20 from Chicago to Vineyard Haven, returning Wed, Aug 27, priced at $300 found 1 day ago
JetBlue Airways
Tue, Aug 12 - Fri, Aug 29
ORD
Chicago
MVY
Vineyard Haven
$304 Roundtrip, found 3 days ago
$304
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Aug 12 from Chicago to Vineyard Haven, returning Fri, Aug 29, priced at $304 found 3 days ago
Delta
Sat, Aug 23 - Wed, Aug 27
ORD
Chicago
MVY
Vineyard Haven
$379 Roundtrip, found 1 day ago
$379
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Aug 23 from Chicago to Vineyard Haven, returning Wed, Aug 27, priced at $379 found 1 day ago

Find the cheapest month to fly from Chicago (ORD) to Vineyard Haven (MVY)

August is typically the cheapest month to fly

From $200 - $814 per traveler.

Graph displaying average flight prices per month

Alternative airports near Vineyard Haven

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

Select flight to Nantucket Memorial ACK. Flights from $792
ACK
Nantucket Memorial
Flights from $792
Select flight to Barnstable Municipal HYA. Average driving time to city center is 1 hour 45 minutes. Flights from $665
HYA
Barnstable Municipal
Average driving time to city center1 h 45 min
Flights from $665
Flights from Chicago (ORD) to Vineyard Haven (MVY)
Origin airport
O'Hare Intl.
Destination airport
Martha's Vineyard
Airlines serving
American Airlines, Delta, JetBlue Airways
Roundtrip price
$237
Distance
891 mi

Chicago to Vineyard Haven Flights

The cheapest times to fly from Chicago to Vineyard Haven

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

 

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

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

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 Vineyard Haven in 2025. You can also book with separate airlines for your outbound and return journeys, from $181 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 Vineyard Haven 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 Vineyard Haven 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 O'Hare Intl. Airport (ORD) to Martha's Vineyard Airport (MVY) cost?
Find cheap return tickets from O'Hare Intl. Airport (ORD) to Martha's Vineyard Airport (MVY) starting from $1384. Grab a seat and take off on your trip. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a American Airlines flight leaving ORD on August 9 2025 and touching down at MVY. The price was last updated on July 23 2025 and has not changed since.
What is the cheapest month to fly from ORD to MVY?
The cheapest flights from ORD to MVY are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from ORD to MVY?
Currently, the cheapest carrier offering one-way flights from ORD to MVY is American Airlines. You can jet off on this route from $595. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on July 26 2025. Prices were last updated on July 23 2025 and have not changed since.
How many flights per day from O'Hare Intl. Airport (ORD) to Martha's Vineyard Airport (MVY)?
Nonstop flights from O'Hare Intl. Airport (ORD) to Martha's Vineyard Airport (MVY) aren't available daily, so you'll need to take a flight with a layover. Explore your options with our filter tool. Enter your travel details and select either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ORD to MVY?
Typically you'll find the largest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* However, this can change based on the season, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What airline has the least delays from ORD to MVY?
With 90% of flights typically arriving as scheduled, American Airlines has the best on-time performance for nonstop flights from O'Hare Intl. Airport (ORD) to Martha's Vineyard Airport (MVY). To keep track of your flight status and get notified if anything changes, simply head to the Expedia App.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Martha's Vineyard Airport (MVY)?
Select a flight from O'Hare Intl. Airport (ORD) to Martha's Vineyard Airport (MVY) that takes off before 3 PM to reduce the risk of cancellations and delays. Later departures are on average 22% more likely to be 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 Martha's Vineyard from O'Hare Intl. Airport (ORD)?
T.F. Green Airport (PVD) is the only airport in Martha's Vineyard with direct flights from O'Hare Intl. Airport (ORD). Check out the options and find affordable fares on Expedia.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Martha's Vineyard Airport (MVY) last-minute?
Booking your plane ticket from ORD to MVY right before your journey is usually more expensive. But if you're flexible with your schedule, you could land a cheap last-minute fare.
Is it cheaper to book an ORD to MVY flight and hotel package?
Compared with arranging flights and hotels separately, booking an ORD to MVY flight and hotel package with Expedia could lead to significant savings. Better still, managing everything in one place takes the hassle out of planning your trip. Just pick your flights and select from our wide range of stays, then customize your trip with other add-ons like car rentals and activities.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Martha's Vineyard Airport (MVY)?
Typically, you can modify or cancel your ORD to MVY flight. However, additional charges may apply, especially if your booking was made over 24 hours ago. Double-check your itinerary for the airline's fees and rules on flight changes, or if you need more details, go to our Customer Service portal.

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*Available to One Key members.