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$132+ 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
Jun 5 — Jun 121
Fri 6/5
Fri 6/12
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 May 6, 2026.

This JetBlue deal was found by Cheapflights users on 5/5. 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.
Tue 7/144:23 pm
HYA
-
ORD
1 stop6h 32m
JetBlue
Wed 7/156:00 am
ORD
-
HYA
1 stop8h 11m
JetBlue
Deal found 5/5$413
This JetBlue deal was found by Cheapflights users on 5/2. 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.
Sat 7/114:53 pm
HYA
-
ORD
1 stop6h 02m
JetBlue
Mon 7/136:00 am
ORD
-
HYA
1 stop8h 11m
JetBlue
Deal found 5/2$459
This JetBlue deal was found by Cheapflights users on 5/4. 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 7/174:23 pm
HYA
-
ORD
1 stop6h 32m
JetBlue
Mon 7/206:00 am
ORD
-
HYA
1 stop8h 11m
JetBlue
Deal found 5/4$496
This JetBlue deal was found by Cheapflights users on 5/4. 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.
Wed 8/124:23 pm
HYA
-
ORD
1 stop6h 32m
JetBlue
Sun 8/166:00 am
ORD
-
HYA
1 stop8h 11m
JetBlue
Deal found 5/4$511
This JetBlue deal was found by Cheapflights users on 5/4. 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 7/174:23 pm
HYA
-
ORD
1 stop6h 32m
JetBlue
Sun 7/196:00 am
ORD
-
HYA
1 stop8h 11m
JetBlue
Deal found 5/4$535
This KAYAK deal was found by Cheapflights users on 5/6. 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.
Mon 8/31:20 pm
HYA
-
ORD
1 stop7h 05m
JetBlue
Wed 8/56:00 am
ORD
-
HYA
1 stop8h 11m
JetBlue
Deal found 5/6$575
This JetBlue deal was found by Cheapflights users on 5/4. 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 7/164:23 pm
HYA
-
ORD
1 stop6h 32m
JetBlue
Sun 7/196:00 am
ORD
-
HYA
1 stop8h 11m
JetBlue
Deal found 5/4$581
This JetBlue deal was found by Cheapflights users on 5/5. 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 8/141:20 pm
HYA
-
ORD
1 stop7h 05m
JetBlue
Mon 8/176:00 am
ORD
-
HYA
1 stop8h 11m
JetBlue
Deal found 5/5$606
This JetBlue deal was found by Cheapflights users on 5/5. 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 8/201:20 pm
HYA
-
ORD
1 stop7h 05m
JetBlue
Sun 8/236:00 am
ORD
-
HYA
1 stop8h 11m
JetBlue
Deal found 5/5$615
This JetBlue deal was found by Cheapflights users on 5/5. 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 8/131:20 pm
HYA
-
ORD
1 stop7h 05m
JetBlue
Sun 8/166:00 am
ORD
-
HYA
1 stop8h 11m
JetBlue
Deal found 5/5$621
This Priceline deal was found by Cheapflights users on 5/5. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2012:07 pm
HYA
-
ORD
1 stop9h 46m
Multiple Airlines
Sun 5/248:50 am
ORD
-
HYA
1 stop7h 30m
Multiple Airlines
Deal found 5/5$650
This JetBlue deal was found by Cheapflights users on 5/4. 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 7/304:23 pm
HYA
-
ORD
1 stop6h 32m
JetBlue
Sun 8/26:00 am
ORD
-
HYA
1 stop8h 11m
JetBlue
Deal found 5/4$651

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 May 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$345
(American Airlines)

One-way from

$132
(American Airlines)

Popular in

April

Cheapest in

September

Average price

$243

Good one-way deal

$450 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-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. 9% potential increase in price ($24 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 May 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 May 6, 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

Sat 8/15

10:39 am-5:14 pm

1 stop7h 35m

Chicago O'Hare Intl

Sat 8/22

6:34 am-12:12 pm

1 stop4h 38m

$345

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 7/14

4:23 pm-9:55 pm

1 stop6h 32m

Chicago O'Hare Intl

Wed 7/15

6:00 am-3:11 pm

1 stop8h 11m

$413
Quickest round-trip

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 8/19

5:59 pm-10:30 pm

1 stop5h 31m

Chicago O'Hare Intl

Fri 8/21

6:34 am-12:12 pm

1 stop4h 38m

$449

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 8/20

5:59 pm-10:30 pm

1 stop5h 31m

Chicago O'Hare Intl

Sun 8/23

6:34 am-12:12 pm

1 stop4h 38m

$453

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sat 7/11

4:53 pm-9:55 pm

1 stop6h 02m

Chicago O'Hare Intl

Mon 7/13

6:00 am-3:11 pm

1 stop8h 11m

$459

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 8/17

5:59 pm-11:00 am

2 stops18h 01m

Chicago O'Hare Intl

Sat 8/22

6:34 am-12:12 pm

1 stop4h 38m

$488

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 7/17

4:23 pm-9:55 pm

1 stop6h 32m

Chicago O'Hare Intl

Sun 7/19

6:00 am-3:11 pm

1 stop8h 11m

$496

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 7/17

4:23 pm-9:55 pm

1 stop6h 32m

Chicago O'Hare Intl

Mon 7/20

6:00 am-3:11 pm

1 stop8h 11m

$496

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sat 8/15

4:53 pm-9:55 pm

1 stop6h 02m

Chicago O'Hare Intl

Tue 8/18

6:00 am-3:11 pm

1 stop8h 11m

$496
Cheapest one-way
Quickest one-way

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 6/29

6:07 pm-11:30 pm

1 stop6h 23m

$172

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/3

Showing 1-10 of 18 resultsSorted by cheapest first
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
No data available for this route at this time. Please check back soon.

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 32m. The distance from Hyannis to Chicago is about 905 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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.

See more FAQs

Traveling to a place near Chicago?

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

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