$354+ Cheap flights from Hyannis (HYA) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
HYA — CHI
Nov 12 — Nov 191
Round-trip
1 adult, Economy
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Find cheap flights from Hyannis to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Hyannis to Chicago
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Best
Last-minute
One-way
Cheapest flights from Hyannis to ChicagoExplore 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 October 13, 2026.
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 October 13, 2026.
This FlightHub deal was found by Cheapflights users on 10/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/210:26 am -
1 stop9h 51m
Fri 11/68:15 pm -
1 stop12h 00m
Deal found 10/12![Multiple Airlines logo]()
$917
Best flights from Hyannis to ChicagoDiscover carefully curated flight deals from Hyannis to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 13, 2026.
Discover carefully curated flight deals from Hyannis to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 13, 2026.
This FlightHub deal was found by Cheapflights users on 10/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/210:26 am -
1 stop9h 51m
Fri 11/68:15 pm -
1 stop12h 00m
Deal found 10/12![Multiple Airlines logo]()
$917
Last-minute flights from Hyannis to ChicagoDiscover last-minute flight deals from Hyannis to Chicago. Data last updated October 13, 2026 and is based on user searches.
Discover last-minute flight deals from Hyannis to Chicago. Data last updated October 13, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 10/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/210:26 am -
1 stop9h 51m
Fri 11/68:15 pm -
1 stop12h 00m
Deal found 10/12![Multiple Airlines logo]()
$917
One-way flights from Hyannis to ChicagoSearch for one-way flight options from Hyannis to Chicago. Find affordable one-way fares based on user searches. Data last updated October 13, 2026.
Search for one-way flight options from Hyannis to Chicago. Find affordable one-way fares based on user searches. Data last updated October 13, 2026.
This Priceline deal was found by Cheapflights users on 10/8. 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.
Sat 1/96:10 am -
2 stops8h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$354
This KAYAK deal was found by Cheapflights users on 10/8. 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 1/66:10 am -
2 stops8h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$374
This Expedia deal was found by Cheapflights users on 10/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:10 am -
2 stops14h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Multiple Airlines logo]()
$394
This United deal was found by Cheapflights users on 10/8. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/96:10 am -
2 stops13h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$399
This Priceline deal was found by Cheapflights users on 10/10. 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.
Sun 1/106:10 am -
2 stops8h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Multiple Airlines logo]()
$406
This KAYAK deal was found by Cheapflights users on 10/8. 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.
Tue 12/86:10 am -
2 stops11h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$414
This United deal was found by Cheapflights users on 10/8. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/912:45 pm -
2 stops23h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$429
This Priceline deal was found by Cheapflights users on 10/11. 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.
Sun 4/118:48 am -
1 stop9h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Multiple Airlines logo]()
$437
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:10 am -
3 stops37h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$440
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 October 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $917 (FlightHub) |
One-way from | $354 (Priceline) |
Popular in | October |
Cheapest in | January |
Average price | $308 |
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 7,457,451 searches. Data last updated October 13, 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
Cheapest round-trip
HyannisChicago
HYA Hyannis Barnstable - ORD Chicago O'Hare Intl
HYAORD
Hyannis Barnstable
Wed 12/9
6:10 am-6:48 pm
2 stops13h 38m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$399
HyannisChicago
HYA Hyannis Barnstable - ORD Chicago O'Hare Intl
HYAORD
Hyannis Barnstable
Tue 1/12
6:10 am-1:49 pm
2 stops8h 39m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$426
HyannisChicago
HYA Hyannis Barnstable - ORD Chicago O'Hare Intl
HYAORD
Hyannis Barnstable
Mon 11/9
12:45 pm-11:15 am
2 stops23h 30m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$429
Quickest round-trip
HyannisChicago
HYA Hyannis Barnstable - ORD Chicago O'Hare Intl
HYAORD
Hyannis Barnstable
Tue 11/10
7:05 am-12:00 pm
1 stop5h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$439
HyannisChicago
HYA Hyannis Barnstable - ORD Chicago O'Hare Intl
HYAORD
Hyannis Barnstable
Thu 11/12
6:10 am-6:45 pm
3 stops37h 35m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$449
HyannisChicago
HYA Hyannis Barnstable - ORD Chicago O'Hare Intl
HYAORD
Hyannis Barnstable
Wed 1/13
8:48 am-1:49 pm
1 stop6h 01m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$451
HyannisChicago
HYA Hyannis Barnstable - ORD Chicago O'Hare Intl
HYAORD
Hyannis Barnstable
Sat 12/12
6:10 am-6:48 pm
2 stops13h 38m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$455
HyannisChicago
HYA Hyannis Barnstable - ORD Chicago O'Hare Intl
HYAORD
Hyannis Barnstable
Sun 4/11
8:48 am-10:10 am
1 stop26h 22m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$457
HyannisChicago
HYA Hyannis Barnstable - ORD Chicago O'Hare Intl
HYAORD
Hyannis Barnstable
Wed 11/11
7:05 am-12:00 pm
1 stop5h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$459
HyannisChicago
HYA Hyannis Barnstable - ORD Chicago O'Hare Intl
HYAORD
Hyannis Barnstable
Mon 11/2
10:26 am-7:17 pm
1 stop9h 51m
Chicago O'Hare Intl
Fri 11/6
8:15 pm-9:15 am
1 stop12h 00m
$917
Sorted by cheapest first
- 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.
HYA-CHI
HYA-ORD
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
HYA-CHI
HYA-ORD
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
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