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$193+ Cheap flights from Hyannis (HYA) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
HYA — CHI
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Hyannis to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Hyannis (HYA) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 16, 2025.

Round-trip from

$410
(JetBlue)

One-way from

$193
(JetBlue)

Popular in

March

Cheapest in

January

Average price

$199

Good one-way deal

$207 or less
From Hyannis Barnstable to Chicago (CHI)
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One-way flight from Hyannis Barnstable to Chicago (CHI)
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Highest demand for flights based on searches. 6% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a one-way flight from Hyannis Barnstable to Chicago (CHI).
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Find flight deals from Hyannis to Chicago

Cheapest flights from Hyannis to Chicago
Explore the most affordable flight options available from Hyannis to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This JetBlue deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1212:07 pmHYA - ORD
1 stop8h 36mJetBlue
Mon 12/1511:25 amORD - HYA
1 stop6h 14mJetBlue
Deal found 9/13$555
This JetBlue deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2112:07 pmHYA - ORD
1 stop8h 56mJetBlue
Sun 11/231:20 pmORD - HYA
1 stop4h 19mJetBlue
Deal found 9/13$645
This JetBlue deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2612:07 pmHYA - ORD
1 stop6h 48mJetBlue
Tue 10/2811:20 amORD - HYA
1 stop6h 19mJetBlue
Deal found 9/14$685
This JetBlue deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2312:07 pmHYA - ORD
1 stop7h 11mJetBlue
Sun 10/2611:20 amORD - HYA
1 stop6h 19mJetBlue
Deal found 9/14$725
This JetBlue deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/712:07 pmHYA - ORD
1 stop6h 48mJetBlue
Sun 11/911:20 amORD - HYA
1 stop6h 19mJetBlue
Deal found 9/14$845

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hyannis to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 16, 2025.
Use the filters below to find and compare flights from Hyannis to Chicago that are best for you.

Fly from

Hyannis

Fly to

Chicago

Route

Depart

Return

Price

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sun 2/22

12:07 pm-5:31 pm

1 stop6h 24m

Chicago O'Hare Intl

Wed 2/25

12:10 pm-6:39 pm

1 stop5h 29m

$410

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 12/12

12:07 pm-7:43 pm

1 stop8h 36m

Chicago O'Hare Intl

Mon 12/15

11:25 am-6:39 pm

1 stop6h 14m

$555

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 11/21

12:07 pm-8:03 pm

1 stop8h 56m

Chicago O'Hare Intl

Sun 11/23

1:20 pm-6:39 pm

1 stop4h 19m

$645

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 3/13

11:00 am-5:31 pm

1 stop7h 31m

Chicago O'Hare Intl

Sun 3/15

12:10 pm-6:46 pm

1 stop5h 36m

$645

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sun 10/26

12:07 pm-5:55 pm

1 stop6h 48m

Chicago O'Hare Intl

Tue 10/28

11:20 am-6:39 pm

1 stop6h 19m

$685

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 11/7

12:07 pm-5:55 pm

1 stop6h 48m

Chicago O'Hare Intl

Sun 11/9

11:20 am-6:39 pm

1 stop6h 19m

$845

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 3/12

12:07 pm-5:31 pm

1 stop6h 24m

$193

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sun 3/15

12:07 pm-5:31 pm

1 stop6h 24m

$198

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sun 12/14

12:07 pm-7:43 pm

1 stop8h 36m

$203

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 3/13

12:07 pm-5:31 pm

1 stop6h 24m

$223

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 14 results
1
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Best time to book a flight from Hyannis to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Hyannis with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Hyannis to Chicago

What is the cheapest month to book a flight from Hyannis to Chicago?

Currently, August is the cheapest month in which you can book a flight from Hyannis to Chicago (average of $245). Flying from Hyannis to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Hyannis to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Hyannis to Chicago?

    If you book a flight to Chicago from Hyannis, you will be flying from Barnstable, which is the city’s only airport. Hyannis Barnstable (HYA) is located 1.0 mi from the center of Hyannis. There are 0 flights from Barnstable to Chicago per day from 0 different airlines.

  • How long is the flight from Hyannis to Chicago?

    Departing from Hyannis to Chicago will take you 6h 24m. The distance from Hyannis to Chicago is about 905 mi.

  • What are the cheapest flights from Hyannis to Chicago?

    The cheapest flight price from Hyannis to Chicago is $207. On average you can expect to pay $340. The most popular route, (Hyannis Barnstable - Chicago O'Hare Intl), can usually be booked for $410.

  • Can I find deals for flights from Hyannis to Chicago that include hotel bookings?

    Yes. In addition to deals on Hyannis to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Hyannis to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hyannis to Chicago.

  • Can I find deals for business class flights from Hyannis to Chicago?

    Yes. Cheapflights offers flight deals from Hyannis to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Hyannis to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Hyannis to Chicago (average of $245). Flying from Hyannis to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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