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$137+ 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 7/21. Fares are subject to change and may not be available on all flights or dates of travel.
HYA — CHI
Apr 23 — Apr 301
Thu 4/23
Thu 4/30
1 adult, Economy
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Cheap 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 March 24, 2026.

This KAYAK deal was found by Cheapflights users on 3/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/264:20 pm
HYA
-
ORD
1 stop5h 24m
JetBlue
Mon 6/296:00 am
ORD
-
HYA
1 stop8h 17m
JetBlue
Deal found 3/21$357
This KAYAK deal was found by Cheapflights users on 3/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/254:20 pm
HYA
-
ORD
1 stop5h 24m
JetBlue
Mon 6/299:33 am
ORD
-
HYA
1 stop4h 44m
JetBlue
Deal found 3/21$387
This KAYAK deal was found by Cheapflights users on 3/22. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/264:20 pm
HYA
-
ORD
1 stop5h 24m
JetBlue
Sun 6/289:33 am
ORD
-
HYA
1 stop4h 44m
JetBlue
Deal found 3/22$413
This KAYAK deal was found by Cheapflights users on 3/22. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/254:20 pm
HYA
-
ORD
1 stop5h 24m
JetBlue
Sun 6/289:33 am
ORD
-
HYA
1 stop4h 44m
JetBlue
Deal found 3/22$443
This KAYAK deal was found by Cheapflights users on 3/19. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/294:20 pm
HYA
-
ORD
1 stop5h 24m
JetBlue
Tue 8/49:33 am
ORD
-
HYA
1 stop4h 44m
JetBlue
Deal found 3/19$448
This JetBlue deal was found by Cheapflights users on 3/22. 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 8/74:20 pm
HYA
-
ORD
1 stop5h 24m
JetBlue
Tue 8/116:00 am
ORD
-
HYA
1 stop8h 17m
JetBlue
Deal found 3/22$488
This KAYAK deal was found by Cheapflights users on 3/23. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/134:20 pm
HYA
-
ORD
1 stop5h 24m
JetBlue
Sun 8/169:33 am
ORD
-
HYA
1 stop4h 44m
JetBlue
Deal found 3/23$518
This KAYAK deal was found by Cheapflights users on 3/19. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/304:20 pm
HYA
-
ORD
1 stop5h 24m
JetBlue
Sun 8/26:00 am
ORD
-
HYA
1 stop8h 17m
JetBlue
Deal found 3/19$593
This KAYAK deal was found by Cheapflights users on 3/23. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/154:20 pm
HYA
-
ORD
1 stop5h 24m
JetBlue
Thu 7/169:33 am
ORD
-
HYA
1 stop4h 44m
JetBlue
Deal found 3/23$618
This KAYAK deal was found by Cheapflights users on 3/23. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/2712:07 pm
HYA
-
ORD
1 stop6h 17m
JetBlue
Sun 3/2911:00 am
ORD
-
HYA
1 stop5h 20m
JetBlue
Deal found 3/23$642
This KAYAK deal was found by Cheapflights users on 3/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/224:20 pm
HYA
-
ORD
1 stop5h 24m
JetBlue
Fri 7/246:00 am
ORD
-
HYA
1 stop8h 17m
JetBlue
Deal found 3/21$728
This Mytrip deal was found by Cheapflights users on 3/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/37:05 am
HYA
-
ORD
2 stops10h 51m
Multiple Airlines
Tue 4/77:17 am
ORD
-
HYA
2 stops9h 03m
Multiple Airlines
Deal found 3/19$787

Find 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 March 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$357
(KAYAK)

One-way from

$137
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$267

Good one-way deal

$450 or less
Provider with most accurate pricing for Hyannis Barnstable-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Hyannis Barnstable-Chicago (CHI) flights.
Search Deals
From Hyannis Barnstable to Chicago (CHI)
Search Deals
One-way flight from Hyannis Barnstable to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($12 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a one-way flight from Hyannis Barnstable to Chicago (CHI).
Search Deals

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 March 24, 2026.
Use the filters below to find and compare flights from Hyannis to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 8/21

4:20 pm-8:44 pm

1 stop5h 24m

Chicago O'Hare Intl

Mon 8/24

6:00 am-3:17 pm

1 stop8h 17m

$413
Quickest round-trip

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 6/26

4:20 pm-8:44 pm

1 stop5h 24m

Chicago O'Hare Intl

Sun 6/28

9:33 am-3:17 pm

1 stop4h 44m

$413

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 6/25

4:20 pm-8:44 pm

1 stop5h 24m

Chicago O'Hare Intl

Sun 6/28

9:33 am-3:17 pm

1 stop4h 44m

$443

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 8/7

4:20 pm-8:44 pm

1 stop5h 24m

Chicago O'Hare Intl

Tue 8/11

6:00 am-3:17 pm

1 stop8h 17m

$448

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 7/23

4:20 pm-8:44 pm

1 stop5h 24m

Chicago O'Hare Intl

Tue 7/28

6:00 am-3:17 pm

1 stop8h 17m

$488

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 8/13

4:20 pm-8:44 pm

1 stop5h 24m

Chicago O'Hare Intl

Sun 8/16

9:33 am-3:17 pm

1 stop4h 44m

$518

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sat 8/8

4:20 pm-8:44 pm

1 stop5h 24m

Chicago O'Hare Intl

Sun 8/9

9:33 am-3:17 pm

1 stop4h 44m

$518

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 7/29

4:20 pm-8:44 pm

1 stop5h 24m

Chicago O'Hare Intl

Sun 8/2

9:33 am-3:17 pm

1 stop4h 44m

$518
Cheapest one-way
Quickest one-way

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 7/15

4:20 pm-8:44 pm

1 stop5h 24m

$191

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 4/22

12:07 pm-9:39 pm

1 stop10h 32m

$268

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/23

Showing 1-10 of 17 resultsSorted by cheapest first
1
2
  • Most accurate provider: When it comes to deals on Hyannis-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Hyannis-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Hyannis-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Hyannis-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Hyannis-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, September is the cheapest month in which you can book a flight from Hyannis to Chicago (average of $91). Flying from Hyannis to Chicago in January is currently the most expensive (average of $123). 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 5h 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 $406. On average you can expect to pay $450. The most popular route, (Hyannis Barnstable - Chicago O'Hare Intl), can usually be booked for $413.

  • 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, September is the cheapest month in which you can book a flight from Hyannis to Chicago (average of $91). Flying from Hyannis to Chicago in January is currently the most expensive (average of $123). 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?

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Porter
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