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$100+ 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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
HYA — CHI
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap 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 31, 2025.

Round-trip from

$343
(American Airlines)

One-way from

$100
(JetBlue)

Popular in

March

Cheapest in

September

Average price

$227

Good one-way deal

$158 or less
From Hyannis Barnstable to Chicago (CHI)
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One-way flight from Hyannis Barnstable to Chicago (CHI)
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Highest demand for flights based on searches. 9% potential increase in price ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a one-way flight from Hyannis Barnstable to Chicago (CHI).
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Find 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 31, 2025.

This American Airlines deal was found by Cheapflights users on 7/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/131:44 pmHYA - ORD
1 stop5h 08mAmerican Airlines
Sun 8/176:06 amORD - HYA
1 stop6h 45mAmerican Airlines
Deal found 7/28$343
This JetBlue deal was found by Cheapflights users on 7/30. 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.
Wed 8/275:15 pmHYA - ORD
1 stop6h 13mJetBlue
Sun 8/318:40 amORD - HYA
1 stop6h 05mJetBlue
Deal found 7/30$422
This Mytrip deal was found by Cheapflights users on 7/31. 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 8/158:55 amHYA - ORD
2 stops14h 27mMultiple Airlines
Tue 8/198:12 pmORD - HYA
2 stops17h 58mMultiple Airlines
Deal found 7/31$602

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 31, 2025.
Use the filters below to find and compare flights from Hyannis to Chicago that are best for you.

Fly from

Hyannis

Fly to

Chicago

Route

Depart

Return

Price

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 8/13

1:44 pm-5:52 pm

1 stop5h 08m

Chicago O'Hare Intl

Sun 8/17

6:06 am-1:51 pm

1 stop6h 45m

$343

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 8/27

5:15 pm-10:28 pm

1 stop6h 13m

Chicago O'Hare Intl

Sun 8/31

8:40 am-3:45 pm

1 stop6h 05m

$422

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 8/15

8:55 am-10:22 pm

2 stops14h 27m

Chicago O'Hare Intl

Tue 8/19

8:12 pm-3:10 pm

2 stops17h 58m

$602

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 8/27

5:15 pm-10:28 pm

1 stop6h 13m

$100

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 8/18

1:44 pm-9:12 pm

1 stop8h 28m

$216

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 8/18

10:29 am-10:31 am

2 stops25h 02m

$295

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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, August is the cheapest month in which you can book a flight from Hyannis to Chicago (average of $245). Flying from Hyannis to Chicago in March is currently the most expensive (average of $321). 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.

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 31, 2025.

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.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated July 31, 2025.
Read reviews from past customers who have flown JetBlue and American Airlines from Hyannis to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
JetBlue
7.3
Good
2,914 reviews

Crew

8.0

Food

6.7

Boarding

7.4

Comfort

7.6

Entertainment

7.3

Overall

7.3

Reviews

1 / 20
10.0
Excellent

Geri,May 2025

RSW - BOS

Full flight, even thought I had priority A boarding, the flight was more than 1/2 full with Mint & Mosaic members, before I could board and get overhead space.
JetBlue
7.3
Good
2,914 reviews
JetBlue
7.3
Good
2,914 reviews

Crew

8.0

Food

6.7

Boarding

7.4

Comfort

7.6

Entertainment

7.3

Overall

7.3

Reviews

1 / 20
10.0
Excellent

Geri,May 2025

RSW - BOS

Full flight, even thought I had priority A boarding, the flight was more than 1/2 full with Mint & Mosaic members, before I could board and get overhead space.
American Airlines
7.2
Good
10,000 reviews
JetBlue
7.3
Good
2,914 reviews

Crew

8.0

Food

6.7

Boarding

7.4

Comfort

7.6

Entertainment

7.3

Overall

7.3

Reviews

1 / 20
10.0
Excellent

Geri,May 2025

RSW - BOS

Full flight, even thought I had priority A boarding, the flight was more than 1/2 full with Mint & Mosaic members, before I could board and get overhead space.

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.

  • What are the cheapest flights from Hyannis to Chicago?

    The cheapest flight price from Hyannis to Chicago is $158. On average you can expect to pay $304. The most popular route, (Hyannis Barnstable - Chicago O'Hare Intl), can usually be booked for $384.

  • 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, August is the cheapest month in which you can book a flight from Hyannis to Chicago (average of $245). Flying from Hyannis to Chicago in March is currently the most expensive (average of $321). 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?

Book flights to Chicago if you plan to visit one of these locations
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Lansing
Hammond
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Porter
Valparaiso
Chesterton

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