Cheap Flights from Chicago (MDW) to Hyannis (HYA)

Popular airlines from Chicago Midway Airport (MDW) to Hyannis, MA (HYA-Barnstable Municipal)

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Cheap Flights from Chicago to Hyannis (MDW-HYA)

Prices were available within the past 7 days and start at for one-way flights and $627 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Sep 27 - Thu, Oct 2
MDW
Chicago
HYA
Hyannis
$627 Roundtrip, found 3 days ago
$627
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Sep 27 from Chicago to Hyannis, returning Thu, Oct 2, priced at $627 found 3 days ago
Delta
Tue, Sep 23 - Thu, Oct 2
MDW
Chicago
HYA
Hyannis
$647 Roundtrip, found 3 days ago
$647
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Sep 23 from Chicago to Hyannis, returning Thu, Oct 2, priced at $647 found 3 days ago
Delta
Thu, Sep 25 - Thu, Oct 2
MDW
Chicago
HYA
Hyannis
$667 Roundtrip, found 3 days ago
$667
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Sep 25 from Chicago to Hyannis, returning Thu, Oct 2, priced at $667 found 3 days ago
Delta
Fri, Sep 26 - Tue, Sep 30
MDW
Chicago
HYA
Hyannis
$882 Roundtrip, found 3 days ago
$882
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Sep 26 from Chicago to Hyannis, returning Tue, Sep 30, priced at $882 found 3 days ago
Delta
Fri, Sep 26 - Tue, Sep 30
MDW
Chicago
HYA
Hyannis
$902 Roundtrip, found 3 days ago
$902
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Sep 26 from Chicago to Hyannis, returning Tue, Sep 30, priced at $902 found 3 days ago
Delta
Fri, Sep 26 - Tue, Sep 30
MDW
Chicago
HYA
Hyannis
$922 Roundtrip, found 3 days ago
$922
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Sep 26 from Chicago to Hyannis, returning Tue, Sep 30, priced at $922 found 3 days ago
Delta
Fri, Sep 26 - Tue, Sep 30
MDW
Chicago
HYA
Hyannis
$932 Roundtrip, found 3 days ago
$932
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Sep 26 from Chicago to Hyannis, returning Tue, Sep 30, priced at $932 found 3 days ago
Delta
Fri, Sep 26 - Tue, Sep 30
MDW
Chicago
HYA
Hyannis
$942 Roundtrip, found 3 days ago
$942
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Sep 26 from Chicago to Hyannis, returning Tue, Sep 30, priced at $942 found 3 days ago
Delta
Fri, Sep 26 - Tue, Sep 30
MDW
Chicago
HYA
Hyannis
$952 Roundtrip, found 3 days ago
$952
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Sep 26 from Chicago to Hyannis, returning Tue, Sep 30, priced at $952 found 3 days ago
Delta
Fri, Sep 26 - Tue, Sep 30
MDW
Chicago
HYA
Hyannis
$972 Roundtrip, found 3 days ago
$972
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Sep 26 from Chicago to Hyannis, returning Tue, Sep 30, priced at $972 found 3 days ago
Delta
Fri, Sep 26 - Tue, Sep 30
MDW
Chicago
HYA
Hyannis
$1,062 Roundtrip, found 3 days ago
$1,062
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Sep 26 from Chicago to Hyannis, returning Tue, Sep 30, priced at $1,062 found 3 days ago
Delta
Fri, Sep 26 - Tue, Sep 30
MDW
Chicago
HYA
Hyannis
$1,082 Roundtrip, found 3 days ago
$1,082
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Sep 26 from Chicago to Hyannis, returning Tue, Sep 30, priced at $1,082 found 3 days ago
Delta
Fri, Sep 26 - Tue, Sep 30
MDW
Chicago
HYA
Hyannis
$1,112 Roundtrip, found 3 days ago
$1,112
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Sep 26 from Chicago to Hyannis, returning Tue, Sep 30, priced at $1,112 found 3 days ago
Delta
Fri, Sep 26 - Tue, Sep 30
MDW
Chicago
HYA
Hyannis
$1,132 Roundtrip, found 3 days ago
$1,132
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Sep 26 from Chicago to Hyannis, returning Tue, Sep 30, priced at $1,132 found 3 days ago

Frequently asked questions

How much is a flight from Midway Airport to Boardman/Polando Field?
Based on fares available within the last 7 days on Expedia for flights departing within the next year, round-trip journeys between Midway Intl. Airport (MDW) and HYA start from $627. Make your booking ASAP to get the best price for your big adventure. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from MDW to Barnstable Municipal Airport (HYA)?
The majority of flights can be conveniently canceled online, but whether or not you are charged a fee all comes down to your airline. If you do need to cancel your vacation, follow the easy instructions in the Customer Service Portal.
How do I find cheap flights from MDW to Boardman/Polando Field that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Midway Intl. Airport (MDW) to Boardman/Polando Field flights, you'll see a "no change fees" filter for you to select.
How far is the flight from MDW to Boardman/Polando Field?
You can forget about a movie marathon on this flight — it's only 901 mi from Chicago to Hyannis. Find your way to your seat, order some food and you'll be there before you know it.
Which airlines fly direct from Midway Intl. Airport (MDW) to Barnstable Municipal Airport (HYA)?
There are no direct flights, so you'll have to make at least one stop between Midway Intl. Airport (MDW) and Barnstable Municipal Airport (HYA). Make the most of the layover time to stretch your legs and grab a bite to eat.
Are Chicago Airport to Boardman/Polando Field flight tickets cheaper when they're purchased at the last minute?
Late planners can sometimes score a bargain, with some of the cheapest fares from Midway Intl. Airport (MDW) to HYA popping up a few weeks before the departure date. If you'd rather plan ahead of time, Expedia compares and updates the best flight deals continually — as early as a year in advance in some cases. It does depend on the carrier though, as not every airline advertises prices so far in advance.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Barnstable Municipal
Roundtrip price
$626
Distance
898 mi

Book with confidence

Book with confidence

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 September. 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 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.

 

Chicago to Hyannis Flights
*Available to One Key members.