$282+ 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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
HYA — CHI
Sep 30 — Oct 71
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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
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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 August 31, 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 August 31, 2026.
This American Airlines deal was found by Cheapflights users on 8/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:47 pm -
1 stop6h 42m
Sat 9/511:15 am -
Nonstop2h 42m
Deal found 8/30![American Airlines logo]()
$426
This United deal was found by Cheapflights users on 8/29. 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.
Sat 9/192:10 pm -
1 stop19h 53m
Sat 9/269:24 pm -
1 stop21h 16m
Deal found 8/29![Multiple Airlines logo]()
$622
This United deal was found by Cheapflights users on 8/30. 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 9/212:50 pm -
2 stops11h 50m
Sat 9/59:45 pm -
1 stop16h 10m
Deal found 8/30![Multiple Airlines logo]()
$709
This FlightHub deal was found by Cheapflights users on 8/27. 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.
Thu 9/311:02 am -
1 stop9h 53m
Thu 9/108:24 pm -
1 stop24h 31m
Deal found 8/27![Multiple Airlines logo]()
$756
This Priceline deal was found by Cheapflights users on 8/27. 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.
Fri 9/112:10 pm -
1 stop5h 51m
Tue 9/159:38 am -
1 stop6h 34m
Deal found 8/27![Multiple Airlines logo]()
$802
This United deal was found by Cheapflights users on 8/28. 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.
Thu 10/151:20 pm -
1 stop20h 40m
Sat 10/176:10 am -
1 stop7h 50m
Deal found 8/28![Multiple Airlines logo]()
$822
This United deal was found by Cheapflights users on 8/29. 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.
Thu 9/2411:02 am -
1 stop12h 27m
Sun 9/278:50 am -
2 stops9h 50m
Deal found 8/29![Multiple Airlines logo]()
$843
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 August 31, 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 August 31, 2026.
This United deal was found by Cheapflights users on 8/29. 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.
Thu 9/2412:50 pm -
1 stop20h 09m
Sun 9/276:10 am -
1 stop12h 30m
Deal found 8/29![Multiple Airlines logo]()
$622
This United deal was found by Cheapflights users on 8/29. 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.
Sat 9/192:10 pm -
2 stops11h 18m
Sat 9/269:24 pm -
1 stop21h 16m
Deal found 8/29![Multiple Airlines logo]()
$627
This Priceline deal was found by Cheapflights users on 8/27. 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.
Fri 9/112:10 pm -
1 stop5h 51m
Tue 9/159:38 am -
1 stop6h 34m
Deal found 8/27![Multiple Airlines logo]()
$802
This United deal was found by Cheapflights users on 8/28. 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.
Thu 10/151:20 pm -
1 stop20h 40m
Sat 10/176:00 am -
2 stops8h 00m
Deal found 8/28![Multiple Airlines logo]()
$827
This Priceline deal was found by Cheapflights users on 8/29. 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.
Mon 9/142:15 pm -
1 stop5h 46m
Fri 9/189:38 am -
1 stop6h 34m
Deal found 8/29![Multiple Airlines logo]()
$953
This United deal was found by Cheapflights users on 8/28. 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.
Thu 10/151:20 pm -
1 stop20h 40m
Sun 10/186:10 am -
2 stops7h 29m
Deal found 8/28![Multiple Airlines logo]()
$997
Last-minute flights from Hyannis to ChicagoDiscover last-minute flight deals from Hyannis to Chicago. Data last updated August 31, 2026 and is based on user searches.
Discover last-minute flight deals from Hyannis to Chicago. Data last updated August 31, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 8/26. 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.
Fri 9/41:05 pm -
1 stop7h 21m
Tue 9/86:00 am -
1 stop8h 13m
Deal found 8/26![Multiple Airlines logo]()
$814
This JetBlue deal was found by Cheapflights users on 8/30. 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 9/44:20 pm -
1 stop6h 38m
Mon 9/79:41 am -
1 stop4h 32m
Deal found 8/30![JetBlue logo]()
$1,546
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 August 31, 2026.
Search for one-way flight options from Hyannis to Chicago. Find affordable one-way fares based on user searches. Data last updated August 31, 2026.
This United deal was found by Cheapflights users on 8/26. 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.
Sat 9/262:10 pm -
1 stop7h 30m
Deal found 8/26![Multiple Airlines logo]()
$282
This United deal was found by Cheapflights users on 8/26. 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.
Fri 9/252:10 pm -
1 stop18h 49m
Deal found 8/26![Multiple Airlines logo]()
$288
This American Airlines deal was found by Cheapflights users on 8/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/53:27 pm -
Nonstop3h 20m
Deal found 8/29![American Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 8/29. 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.
Sat 9/52:10 pm -
2 stops30h 54m
Deal found 8/29![Multiple Airlines logo]()
$323
This United deal was found by Cheapflights users on 8/30. 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.
Tue 9/2912:50 pm -
1 stop7h 10m
Deal found 8/30![Multiple Airlines logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 8/28. 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.
Wed 9/3011:02 am -
2 stops36h 57m
Deal found 8/28![Multiple Airlines logo]()
$364
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 10/22:10 pm -
2 stops29h 13m
Deal found 8/30![Multiple Airlines logo]()
$367
This Kiwi.com deal was found by Cheapflights users on 8/26. 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.
Wed 9/2311:02 am -
2 stops36h 57m
Deal found 8/26![Multiple Airlines logo]()
$373
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 August 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $622 (United) |
One-way from | $282 (United) |
Popular in | June |
Cheapest in | January |
Average price | $256 |
Good one-way deal | $450 or less |
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 August 31, 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
Thu 9/24
12:50 pm-7:59 am
1 stop20h 09m
Chicago O'Hare Intl
Sun 9/27
6:10 am-7:40 pm
1 stop12h 30m
$622
HyannisChicago
HYA Hyannis Barnstable - ORD Chicago O'Hare Intl
HYAORD
Hyannis Barnstable
Sat 9/19
2:10 pm-12:28 am
2 stops11h 18m
Chicago O'Hare Intl
Sat 9/26
9:24 pm-7:40 pm
1 stop21h 16m
$627
HyannisChicago
HYA Hyannis Barnstable - ORD Chicago O'Hare Intl
HYAORD
Hyannis Barnstable
Fri 9/11
2:10 pm-7:01 pm
1 stop5h 51m
Chicago O'Hare Intl
Tue 9/15
9:38 am-5:12 pm
1 stop6h 34m
$802
HyannisChicago
HYA Hyannis Barnstable - ORD Chicago O'Hare Intl
HYAORD
Hyannis Barnstable
Thu 10/15
1:20 pm-9:00 am
1 stop20h 40m
Chicago O'Hare Intl
Sat 10/17
6:00 am-3:00 pm
2 stops8h 00m
$827
Quickest round-trip
HyannisChicago
HYA Hyannis Barnstable - ORD Chicago O'Hare Intl
HYAORD
Hyannis Barnstable
Mon 9/14
2:15 pm-7:01 pm
1 stop5h 46m
Chicago O'Hare Intl
Fri 9/18
9:38 am-5:12 pm
1 stop6h 34m
$953
HyannisChicago
HYA Hyannis Barnstable - ORD Chicago O'Hare Intl
HYAORD
Hyannis Barnstable
Thu 10/15
1:20 pm-9:00 am
1 stop20h 40m
Chicago O'Hare Intl
Sun 10/18
6:10 am-2:39 pm
2 stops7h 29m
$997
Cheapest one-way
HyannisChicago
HYA Hyannis Barnstable - ORD Chicago O'Hare Intl
HYAORD
Hyannis Barnstable
Sat 9/26
2:10 pm-8:40 pm
1 stop7h 30m
$282
HyannisChicago
HYA Hyannis Barnstable - ORD Chicago O'Hare Intl
HYAORD
Hyannis Barnstable
Fri 9/25
2:10 pm-7:59 am
1 stop18h 49m
$288
HyannisChicago
HYA Hyannis Barnstable - ORD Chicago O'Hare Intl
HYAORD
Hyannis Barnstable
Tue 9/29
12:50 pm-2:42 pm
3 stops26h 52m
$348
HyannisChicago
HYA Hyannis Barnstable - ORD Chicago O'Hare Intl
HYAORD
Hyannis Barnstable
Mon 9/28
11:02 am-11:21 pm
2 stops13h 19m
$382
Showing 1-10 of 16 resultsSorted 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
What is the cheapest time of day to fly from HYA to CHI?
Find hourly flight availability from Hyannis to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 31, 2026.
When flying from Hyannis to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
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
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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