$102 Cheap Flights from Hyannis (HYA) to Chicago (ORD)

View $102 flight on Sat, Sep 5, 2026Opens in a new window

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

Cheap Flights from Hyannis to Chicago (HYA-ORD)

Prices were available within the past 7 days and start at $102 for one-way flights and $290 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Tue, Aug 11 - Mon, Aug 17
HYA
Hyannis
ORD
Chicago
$290 Roundtrip, found 1 day ago
$290
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Aug 11 from Hyannis to Chicago, returning Mon, Aug 17, priced at $290 found 1 day ago
American Airlines
Tue, Aug 11 - Mon, Aug 17
HYA
Hyannis
ORD
Chicago
$325 Roundtrip, found 1 day ago
$325
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Aug 11 from Hyannis to Chicago, returning Mon, Aug 17, priced at $325 found 1 day ago
American Airlines
Tue, Aug 11 - Mon, Aug 17
HYA
Hyannis
ORD
Chicago
$359 Roundtrip, found 1 day ago
$359
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Aug 11 from Hyannis to Chicago, returning Mon, Aug 17, priced at $359 found 1 day ago
JetBlue Airways
Sat, Aug 8 - Wed, Aug 12
HYA
Hyannis
ORD
Chicago
$366 Roundtrip, found 5 days ago
$366
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sat, Aug 8 from Hyannis to Chicago, returning Wed, Aug 12, priced at $366 found 5 days ago
JetBlue Airways
Tue, Aug 11 - Mon, Aug 17
HYA
Hyannis
ORD
Chicago
$378 Roundtrip, found 1 day ago
$378
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Aug 11 from Hyannis to Chicago, returning Mon, Aug 17, priced at $378 found 1 day ago
American Airlines
Tue, Aug 11 - Mon, Aug 17
HYA
Hyannis
ORD
Chicago
$381 Roundtrip, found 1 day ago
$381
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Aug 11 from Hyannis to Chicago, returning Mon, Aug 17, priced at $381 found 1 day ago
American Airlines
Tue, Aug 11 - Mon, Aug 17
HYA
Hyannis
ORD
Chicago
$389 Roundtrip, found 1 day ago
$389
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Aug 11 from Hyannis to Chicago, returning Mon, Aug 17, priced at $389 found 1 day ago
JetBlue Airways
Tue, Aug 11 - Mon, Aug 17
HYA
Hyannis
ORD
Chicago
$418 Roundtrip, found 1 day ago
$418
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Aug 11 from Hyannis to Chicago, returning Mon, Aug 17, priced at $418 found 1 day ago
American Airlines
Sat, Jun 20 - Sat, Jun 27
HYA
Hyannis
ORD
Chicago
$423 Roundtrip, found 4 days ago
$423
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Jun 20 from Hyannis to Chicago, returning Sat, Jun 27, priced at $423 found 4 days ago
Cape Air
Tue, Aug 11 - Mon, Aug 17
HYA
Hyannis
ORD
Chicago
$475 Roundtrip, found 1 day ago
$475
Roundtrip
found 1 day ago
Select Cape Air flight, departing Tue, Aug 11 from Hyannis to Chicago, returning Mon, Aug 17, priced at $475 found 1 day ago

Frequently asked questions

How much does a flight from Hyannis, MA (HYA-Barnstable Municipal) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find cheap one-way flights from $102 and cheap return flights from $290 Hyannis, MA (HYA-Barnstable Municipal) to Chicago, IL (ORD-O'Hare Intl.) with Expedia. Return flights often range between $482 and $1247. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Hyannis, MA (HYA-Barnstable Municipal) to Chicago, IL (ORD-O'Hare Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Hyannis, MA (HYA-Barnstable Municipal) to Chicago, IL (ORD-O'Hare Intl.)?
The cheapest month to fly from HYA to ORD is August when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Hyannis, MA (HYA-Barnstable Municipal) to Chicago, IL (ORD-O'Hare Intl.)?
Enter HYA to ORD and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Hyannis, MA (HYA-Barnstable Municipal) to Chicago, IL (ORD-O'Hare Intl.)?
American Airlines is one of the cheapest airlines offering connecting flights from Hyannis, MA (HYA) to Chicago, IL (ORD), starting from around $398. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Hyannis, MA (HYA-Barnstable Municipal) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from Hyannis, MA (HYA-Barnstable Municipal) to Chicago, IL (ORD-O'Hare Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Hyannis, MA (HYA-Barnstable Municipal) to Chicago, IL (ORD-O'Hare Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
What is the earliest flight from Hyannis, MA (HYA-Barnstable Municipal) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Barnstable Municipal (HYA) to O'Hare Intl. (ORD) usually departs at around 6:00 AM, operated by JetBlue Airways. This early departure allows you to maximize your time in Chicago, whether for business or leisure. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Hyannis, MA (HYA-Barnstable Municipal) to Chicago, IL (ORD-O'Hare Intl.)?
You'll usually find the most flights from Barnstable Municipal (HYA) to O'Hare Intl. (ORD) on a Friday, with around 12 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include American Airlines and JetBlue Airways.
What are the most popular departure times for flights from Hyannis, MA (HYA-Barnstable Municipal) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from Hyannis, MA (HYA-Barnstable Municipal) to Chicago, IL (ORD-O'Hare Intl.) are in the early morning, from 6am to 9am. About 50% of passengers prefer this time window. Many major carriers, including United Airlines and Delta Airlines, offer flights during this window. This timing works well because it allows you to start your day early and arrive in Chicago with plenty of time to explore.
How long does it take to fly from Hyannis, MA (HYA-Barnstable Municipal) to Chicago, IL (ORD-O'Hare Intl.)?
Flights from HYA to ORD with one stop typically take around 7 hours, covering approximately 906 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Hyannis, MA (HYA-Barnstable Municipal) to Chicago, IL (ORD-O'Hare Intl.)?
First class seats are offered on the HYA to ORD route with American Airlines.
How do I earn miles on a Hyannis, MA (HYA-Barnstable Municipal) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a Hyannis, MA (HYA-Barnstable Municipal) to Chicago, IL (ORD-O'Hare Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Barnstable Municipal (HYA)?
From Barnstable Municipal (HYA), you can fly into O'Hare Intl. (ORD) to reach Chicago. Some flights may connect through major hubs like Nantucket Memorial (ACK), Logan Intl. (BOS), Martha's Vineyard (MVY) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Hyannis, MA (HYA-Barnstable Municipal) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from Hyannis, MA (HYA-Barnstable Municipal) to Chicago, IL (ORD-O'Hare Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Hyannis, MA (HYA-Barnstable Municipal) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a Hyannis, MA (HYA-Barnstable Municipal) to Chicago, IL (ORD-O'Hare Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Hyannis, MA (HYA-Barnstable Municipal) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your Hyannis, MA (HYA-Barnstable Municipal) to Chicago, IL (ORD-O'Hare Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Barnstable Municipal
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, JetBlue Airways
Roundtrip price
$290
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 $102 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

*Flight schedules are subject to change.

*Available to One Key members.

 

Explore a world of travel with Expedia