$136 Cheap Flights from Chicago (ORD) to Hyannis (HYA)

View $136 flight on Wed, Aug 13, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Hyannis, MA (HYA-Barnstable Municipal)

Find available prices by choosing your travel dates.

Cheap Flights from Chicago to Hyannis (ORD-HYA)

Prices were available within the past 7 days and start at $136 for one-way flights and $199 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Mon, Jun 30 - Tue, Jul 15
ORD
Chicago
HYA
Hyannis
$199 Roundtrip, found 1 hour ago
$199
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Mon, Jun 30 from Chicago to Hyannis, returning Tue, Jul 15, priced at $199 found 1 hour ago
JetBlue Airways
Sat, Jun 28 - Sat, Jul 12
ORD
Chicago
HYA
Hyannis
$235 Roundtrip, found 1 hour ago
$235
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Sat, Jun 28 from Chicago to Hyannis, returning Sat, Jul 12, priced at $235 found 1 hour ago
JetBlue Airways
Mon, Jun 30 - Wed, Jul 9
ORD
Chicago
HYA
Hyannis
$240 Roundtrip, found 2 hours ago
$240
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Mon, Jun 30 from Chicago to Hyannis, returning Wed, Jul 9, priced at $240 found 2 hours ago
American Airlines
Wed, Jul 16 - Wed, Jul 23
ORD
Chicago
HYA
Hyannis
$258 Roundtrip, found 3 hours ago
$258
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Wed, Jul 16 from Chicago to Hyannis, returning Wed, Jul 23, priced at $258 found 3 hours ago
American Airlines
Wed, Jul 16 - Wed, Jul 23
ORD
Chicago
HYA
Hyannis
$268 Roundtrip, found 3 hours ago
$268
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Wed, Jul 16 from Chicago to Hyannis, returning Wed, Jul 23, priced at $268 found 3 hours ago
American Airlines
Sat, Jul 19 - Fri, Jul 25
ORD
Chicago
HYA
Hyannis
$269 Roundtrip, found 2 hours ago
$269
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Sat, Jul 19 from Chicago to Hyannis, returning Fri, Jul 25, priced at $269 found 2 hours ago
American Airlines
Sat, Jul 19 - Fri, Jul 25
ORD
Chicago
HYA
Hyannis
$287 Roundtrip, found 2 hours ago
$287
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Sat, Jul 19 from Chicago to Hyannis, returning Fri, Jul 25, priced at $287 found 2 hours ago
American Airlines
Fri, Jul 11 - Sun, Jul 13
ORD
Chicago
HYA
Hyannis
$289 Roundtrip, found 2 hours ago
$289
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Fri, Jul 11 from Chicago to Hyannis, returning Sun, Jul 13, priced at $289 found 2 hours ago
American Airlines
Wed, Jul 16 - Wed, Jul 23
ORD
Chicago
HYA
Hyannis
$298 Roundtrip, found 3 hours ago
$298
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Wed, Jul 16 from Chicago to Hyannis, returning Wed, Jul 23, priced at $298 found 3 hours ago
American Airlines
Tue, Aug 12 - Sat, Aug 23
ORD
Chicago
HYA
Hyannis
$302 Roundtrip, found 6 hours ago
$302
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Tue, Aug 12 from Chicago to Hyannis, returning Sat, Aug 23, priced at $302 found 6 hours ago
Flights from Chicago (ORD) to Hyannis (HYA)
Origin airport
O'Hare Intl.
Destination airport
Barnstable Municipal
Airlines serving
American Airlines, JetBlue Airways
Roundtrip price
$199
Distance
905 mi

Chicago to Hyannis Flights

The cheapest times to fly from Chicago to Hyannis

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

The best time to book a flight from Chicago to Hyannis

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

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 Hyannis in 2025. You can also book with separate airlines for your outbound and return journeys, from $136 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 Hyannis 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 Hyannis 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 Barnstable Municipal Airport (HYA) cost?
Discover the latest flight deals from ORD to HYA by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from ORD to HYA?
The cheapest flights from ORD to HYA 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 HYA?
Jet off from ORD to HYA with American Airlines. This carrier currently offers the cheapest one-way fare on this route, starting from $311. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on June 21 2025. Prices were last updated on April 23 2025 and have not changed since.
How many flights per day from O'Hare Intl. Airport (ORD) to Barnstable Municipal Airport (HYA)?
You’ll have to book a flight with a layover when traveling from O’Hare Intl. Airport (ORD) to Barnstable Municipal Airport (HYA). There are no daily direct flights on this route. However, just filter your search to include one or more stops to find the best option for your trip.
What day of the week has the most flights from ORD to HYA?
You’ll generally find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Barnstable Municipal Airport (HYA)?
To avoid possible delays on the O’Hare Intl. Airport (ORD) to Barnstable Municipal Airport (HYA) route, travel before 3 PM. Departures after this time are 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 Cape Cod from O'Hare Intl. Airport (ORD)?
Logan Intl. Airport (BOS) is the only airport in Cape Cod with direct flights from O’Hare Intl. Airport (ORD). Explore the options and find affordable fares on Expedia.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Barnstable Municipal Airport (HYA) last-minute?
Waiting until just before your trip to book a flight from ORD to HYA generally means paying more. While you may come across some last-minute offers, there’s no guarantee. Keep your travel plans flexible for a better chance of scoring a bargain.
Is it cheaper to book an ORD to HYA flight and hotel package?
Compared with arranging flights and hotels separately, booking an ORD to HYA flight and hotel package with Expedia could lead to significant savings. Better still, having it all in one place will take the stress out of planning your trip. Just secure your flights and select from our wide range of hotels, then personalize your trip with extras like activities and car rentals.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Barnstable Municipal Airport (HYA)?
Typically, it’s possible to cancel or reschedule your ORD to HYA flight. However, if it’s been more than 24 hours since booking, additional fees may apply. Refer to your airline’s policies in your itinerary to see what changes are allowed and if any costs are involved. You’ll also find more information on our Customer Service portal.

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*Available to One Key members.