$147 Cheap Flights from Hyannis (HYA) to Chicago (ORD)

View $147 flight on Fri, Aug 14, 2026Opens in a new window

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

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Cheap Flights from Hyannis to Chicago (HYA-ORD)

Prices were available within the past 7 days and start at $147 for one-way flights and $298 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, Aug 22 - Fri, Aug 28
HYA
Hyannis
ORD
Chicago
$298 Roundtrip, found 5 days ago
$298
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Aug 22 from Hyannis to Chicago, returning Fri, Aug 28, priced at $298 found 5 days ago
American Airlines
Sat, Aug 22 - Fri, Aug 28
HYA
Hyannis
ORD
Chicago
$308 Roundtrip, found 5 days ago
$308
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Aug 22 from Hyannis to Chicago, returning Fri, Aug 28, priced at $308 found 5 days ago
American Airlines
Sat, Aug 22 - Fri, Aug 28
HYA
Hyannis
ORD
Chicago
$315 Roundtrip, found 5 days ago
$315
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Aug 22 from Hyannis to Chicago, returning Fri, Aug 28, priced at $315 found 5 days ago
American Airlines
Sat, Aug 22 - Fri, Aug 28
HYA
Hyannis
ORD
Chicago
$317 Roundtrip, found 5 days ago
$317
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Aug 22 from Hyannis to Chicago, returning Fri, Aug 28, priced at $317 found 5 days ago
American Airlines
Sat, Aug 22 - Fri, Aug 28
HYA
Hyannis
ORD
Chicago
$325 Roundtrip, found 5 days ago
$325
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Aug 22 from Hyannis to Chicago, returning Fri, Aug 28, priced at $325 found 5 days ago
American Airlines
Sat, Aug 22 - Fri, Aug 28
HYA
Hyannis
ORD
Chicago
$327 Roundtrip, found 5 days ago
$327
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Aug 22 from Hyannis to Chicago, returning Fri, Aug 28, priced at $327 found 5 days ago
American Airlines
Sat, Aug 22 - Fri, Aug 28
HYA
Hyannis
ORD
Chicago
$341 Roundtrip, found 5 days ago
$341
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Aug 22 from Hyannis to Chicago, returning Fri, Aug 28, priced at $341 found 5 days ago
American Airlines
Mon, Aug 3 - Tue, Aug 4
HYA
Hyannis
ORD
Chicago
$350 Roundtrip, found 6 days ago
$350
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Aug 3 from Hyannis to Chicago, returning Tue, Aug 4, priced at $350 found 6 days ago
Cape Air
Thu, Jan 29 - Mon, Feb 16
HYA
Hyannis
ORD
Chicago
$364 Roundtrip, found 5 days ago
$364
Roundtrip
found 5 days ago
Select Cape Air flight, departing Thu, Jan 29 from Hyannis to Chicago, returning Mon, Feb 16, priced at $364 found 5 days ago
JetBlue Airways
Thu, Jan 29 - Mon, Feb 2
HYA
Hyannis
ORD
Chicago
$385 Roundtrip, found 22 hours ago
$385
Roundtrip
found 22 hours ago
Select JetBlue Airways flight, departing Thu, Jan 29 from Hyannis to Chicago, returning Mon, Feb 2, priced at $385 found 22 hours ago

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $385
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $385

Frequently asked questions

How much does a flight from Barnstable Municipal Airport (HYA) to O'Hare Intl. Airport (ORD) cost?
Grab a cheap one-way flight from $147 or cheap return flight from $298 from Barnstable Municipal Airport (HYA) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Barnstable Municipal Airport (HYA) to O'Hare Intl. Airport (ORD)?
August is the cheapest month to fly from HYA to ORD. Timing your trip outside of the busy season is often the key to landing a great deal.
Which airlines fly direct from Barnstable Municipal Airport (HYA) to O'Hare Intl. Airport (ORD)?
There are no direct flights from Hyannis, MA (HYA-Barnstable Municipal) to O'Hare Intl. Airport (ORD). However, you'll find other airports that have nonstop flights. Hop on your plane at Logan Intl. Airport (BOS) and head straight to Chicago without any detours.
What is the cheapest airline that flies from Barnstable Municipal Airport (HYA) to O'Hare Intl. Airport (ORD)?
To find the cheapest airline that'll fly you from HYA to ORD, use Expedia's filter tool. Tailor your search based on your travel needs, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
How many flights per day from Barnstable Municipal Airport (HYA) to O'Hare Intl. Airport (ORD)?
You'll need to take a flight with a layover when traveling from Barnstable Municipal Airport (HYA) to O'Hare Intl. Airport (ORD). There are no daily direct flights on this route. However, simply 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 HYA to ORD?
You'll usually find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary 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 Barnstable Municipal Airport (HYA) to O'Hare Intl. Airport (ORD)?
To avoid potential delays on the Barnstable Municipal Airport (HYA) to O'Hare Intl. Airport (ORD) route, fly before 3 PM. Departures after this time have a 22% higher chance of cancellation.**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.
Is it cheaper to buy a plane ticket from Barnstable Municipal Airport (HYA) to O'Hare Intl. Airport (ORD) last-minute?
Last-minute fares from HYA to ORD are usually more expensive. To lock in the cheapest rates, start searching for flights well ahead of time. That said, if you're flexible with your travel dates, it's possible to land a cheap fare just before your departure.
Is it cheaper to book a HYA to ORD flight and hotel package?
Opting for a HYA to ORD flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip in one place. Choose from our impressive range of accommodations and then add activities, car rentals and flights to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Barnstable Municipal Airport (HYA) to O'Hare Intl. Airport (ORD)?
In most cases, you can cancel or reschedule your HYA to ORD flight. However, there may be additional fees, especially if your booking was made over 24 hours ago. Check your itinerary for the airline's rules and fees on flight changes, or if you'd like more details, visit our Customer Service portal.

Travel information

Origin airport
Barnstable Municipal
Destination airport
O'Hare Intl.
Airlines serving
JetBlue Airways
Roundtrip price
$297
Distance
905 mi

Book with confidence

Hyannis to Chicago Flights

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

 

The best time to book a flight from Hyannis to Chicago

Sunday is one of the best days to book for cheap flights from Hyannis 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 Hyannis 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 Hyannis to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $147 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 Hyannis 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 Hyannis 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.

 

Hyannis to Chicago Flights

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