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$99+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
HYA — CHI
Aug 5 — Aug 121
Wed 8/5
Wed 8/12
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 July 6, 2026.

This JetBlue deal was found by Cheapflights users on 7/3. 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 8/44:53 pm
HYA
-
ORD
1 stop6h 05m
JetBlue
Wed 8/59:37 am
ORD
-
HYA
1 stop4h 36m
JetBlue
Deal found 7/3$199
This Priceline deal was found by Cheapflights users on 7/5. 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.
Tue 7/284:53 pm
HYA
-
ORD
1 stop6h 05m
JetBlue
Tue 8/46:00 am
ORD
-
HYA
1 stop8h 13m
JetBlue
Deal found 7/5$227
This JetBlue deal was found by Cheapflights users on 7/2. 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.
Fri 8/144:20 pm
HYA
-
ORD
1 stop6h 38m
JetBlue
Tue 8/189:35 am
ORD
-
HYA
1 stop4h 38m
JetBlue
Deal found 7/2$262
This JetBlue deal was found by Cheapflights users on 7/2. 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.
Wed 9/24:20 pm
HYA
-
ORD
1 stop6h 38m
JetBlue
Fri 9/46:00 am
ORD
-
HYA
1 stop8h 13m
JetBlue
Deal found 7/2$306
This JetBlue deal was found by Cheapflights users on 7/1. 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 7/174:53 pm
HYA
-
ORD
1 stop6h 05m
JetBlue
Tue 7/216:00 am
ORD
-
HYA
1 stop8h 13m
JetBlue
Deal found 7/1$325
This JetBlue deal was found by Cheapflights users on 7/1. 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 7/174:53 pm
HYA
-
ORD
1 stop6h 05m
JetBlue
Thu 7/239:40 am
ORD
-
HYA
1 stop4h 53m
JetBlue
Deal found 7/1$369
This JetBlue deal was found by Cheapflights users on 7/3. 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 7/154:53 pm
HYA
-
ORD
1 stop6h 05m
JetBlue
Sat 7/189:41 am
ORD
-
HYA
1 stop4h 52m
JetBlue
Deal found 7/3$391
This American Airlines deal was found by Cheapflights users on 7/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/184:05 pm
HYA
-
ORD
Nonstop3h 34m
American Airlines
Sat 7/259:42 am
ORD
-
HYA
1 stop6h 37m
American Airlines
Deal found 7/5$420
This JetBlue deal was found by Cheapflights users on 7/4. 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.
Mon 8/104:20 pm
HYA
-
ORD
1 stop6h 38m
JetBlue
Thu 8/136:00 am
ORD
-
HYA
1 stop8h 13m
JetBlue
Deal found 7/4$425
This JetBlue deal was found by Cheapflights users on 7/1. 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 7/94:53 pm
HYA
-
ORD
1 stop6h 05m
JetBlue
Tue 7/149:40 am
ORD
-
HYA
1 stop4h 33m
JetBlue
Deal found 7/1$457

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 July 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$199
(JetBlue)

One-way from

$99
(JetBlue)

Popular in

June

Cheapest in

January

Average price

$240

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. 7% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 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

Tue 8/4

4:53 pm-9:58 pm

1 stop6h 05m

Chicago O'Hare Intl

Wed 8/5

9:37 am-3:13 pm

1 stop4h 36m

$199

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 8/26

4:20 pm-9:58 pm

1 stop6h 38m

Chicago O'Hare Intl

Tue 9/1

9:35 am-3:13 pm

1 stop4h 38m

$199
Quickest round-trip

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 8/4

4:53 pm-9:58 pm

1 stop6h 05m

Chicago O'Hare Intl

Tue 8/25

9:40 am-3:13 pm

1 stop4h 33m

$199

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 9/4

4:20 pm-9:58 pm

1 stop6h 38m

Chicago O'Hare Intl

Sun 9/6

6:00 am-3:11 pm

1 stop8h 11m

$227

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 8/17

4:20 pm-9:58 pm

1 stop6h 38m

Chicago O'Hare Intl

Mon 8/24

6:00 am-3:13 pm

1 stop8h 13m

$227

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 8/10

4:20 pm-9:58 pm

1 stop6h 38m

Chicago O'Hare Intl

Wed 8/12

9:35 am-3:13 pm

1 stop4h 38m

$262

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 8/14

4:20 pm-9:58 pm

1 stop6h 38m

Chicago O'Hare Intl

Tue 8/18

9:35 am-3:13 pm

1 stop4h 38m

$262

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 9/2

4:20 pm-9:58 pm

1 stop6h 38m

Chicago O'Hare Intl

Sat 9/5

9:41 am-3:13 pm

1 stop4h 32m

$262

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 9/2

4:20 pm-9:58 pm

1 stop6h 38m

Chicago O'Hare Intl

Fri 9/4

6:00 am-3:13 pm

1 stop8h 13m

$306

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 7/21

4:53 pm-9:58 pm

1 stop6h 05m

Chicago O'Hare Intl

Sat 7/25

9:41 am-3:33 pm

1 stop4h 52m

$325

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/5

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 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 July 6, 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.

  • 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 05m. The distance from Hyannis to Chicago is about 905 mi.

  • What are the most reliable airlines from Hyannis to Chicago?

    The top 3 most reliable airlines when flying from Hyannis to Chicago are American Airlines (50%), Qatar Airways (50%) and Republic Airways (50%).

  • 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 $199.

  • 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
Hammond
Lansing
Merrillville
Valparaiso
Porter

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