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Cheap flights from Hyannis (HYA) to Chicago (CHI) from $207

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 6/25. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
HYA — CHI
May 20 — May 271
From?
To?
Mon 5/20
Mon 5/27
1 adult, Economy
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How far in advance should I book a flight from Hyannis to Chicago?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 52 days in advance, which can save you up to 36% on flights from Hyannis to Chicago compared to booking the week you need them. Waiting 52 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $279. For sooner than that we have options available in the next 3 days from $328.

What is the cheapest month to fly from Hyannis to Chicago?

Due to multiple factors, expect to potentially pay more when booking in June. For low rates, January can be a great choice for travel to Chicago. Flights to Chicago from Hyannis in January are about $273 on average during January, but can be found for as low as $106.

When is the cheapest time to fly from Hyannis to Chicago (HYA - CHI)?

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.

Cheap American Airlines flights from Hyannis to Chicago

Explore cheap flight options specifically provided by American Airlines for the route between Hyannis and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated May 15, 2024.
Take a look at some of the lowest-priced American Airlines flights heading from Hyannis to Chicago. Come back soon if you're not finding the exact deal you're looking for.
Tue 6/252:16 pmHYA - ORD
1 stop6h 11mAmerican Airlines
Wed 6/266:01 amORD - HYA
1 stop5h 18mAmerican Airlines
Deal found 5/14$207
Tue 6/2512:54 pmHYA - ORD
2 stops10h 40mAmerican Airlines
Wed 6/267:00 amORD - HYA
1 stop4h 19mAmerican Airlines
Deal found 5/14$315
Tue 6/2512:54 pmHYA - ORD
2 stops10h 40mAmerican Airlines
Wed 6/268:21 pmORD - HYA
2 stops14h 58mAmerican Airlines
Deal found 5/14$446
Fri 6/1412:54 pmHYA - ORD
1 stop5h 49mAmerican Airlines
Sun 6/166:01 amORD - HYA
1 stop5h 18mAmerican Airlines
Deal found 5/14$555

Cheap JetBlue flights from Hyannis to Chicago

Explore cheap flight options specifically provided by JetBlue for the route between Hyannis and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated May 15, 2024.
Some of the lowest-priced JetBlue flights we've found at this time heading from Hyannis to Chicago. If these deals don't fit your criteria, make sure to check back soon as new deals are always added.
Sat 8/31:55 pmHYA - ORD
1 stop5h 34mJetBlue
Tue 8/138:29 amORD - HYA
1 stop6h 21mJetBlue
Deal found 5/14$651
Thu 9/122:15 pmHYA - ORD
1 stop5h 49mJetBlue
Tue 9/2410:59 amORD - HYA
1 stop3h 51mJetBlue
Deal found 5/13$707
Wed 9/186:30 amHYA - ORD
1 stop4h 44mJetBlue
Sun 9/2210:59 amORD - HYA
1 stop5h 46mJetBlue
Deal found 5/14$807
Fri 11/810:35 amHYA - ORD
1 stop6h 44mJetBlue
Sun 11/108:38 amORD - HYA
1 stop5h 01mJetBlue
Deal found 5/14$857
Mon 5/2011:00 amHYA - ORD
1 stop8h 30mJetBlue
Tue 5/218:40 amORD - HYA
1 stop4h 59mJetBlue
Deal found 5/14$1,002

Cheap Hyannis to Chicago flights in May & June 2024

Find cheap flight options from Hyannis to Chicago specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,632,958 searches. Prices were last updated on May 15, 2024.
These are some of the most attractive deals on flights from Hyannis to Chicago in 2024. Check back regularly for other flight deals.
Tue 6/252:16 pmHYA - ORD
1 stop6h 11mAmerican Airlines
Wed 6/266:01 amORD - HYA
1 stop5h 18mAmerican Airlines
Deal found 5/14$207
Tue 6/2512:54 pmHYA - ORD
2 stops10h 40mAmerican Airlines
Wed 6/267:00 amORD - HYA
1 stop4h 19mAmerican Airlines
Deal found 5/14$315
Tue 6/2512:54 pmHYA - ORD
2 stops10h 40mAmerican Airlines
Wed 6/268:21 pmORD - HYA
2 stops14h 58mAmerican Airlines
Deal found 5/14$446
Fri 6/1412:54 pmHYA - ORD
1 stop5h 49mAmerican Airlines
Sun 6/166:01 amORD - HYA
1 stop5h 18mAmerican Airlines
Deal found 5/14$555
Mon 5/2011:00 amHYA - ORD
1 stop8h 30mJetBlue
Tue 5/218:40 amORD - HYA
1 stop4h 59mJetBlue
Deal found 5/14$1,002

Hyannis to Chicago 2024 flight deals

Discover exclusive flight deals for travel between Hyannis and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated May 15, 2024.
These are some of the most attractive deals on flights from Hyannis to Chicago in 2024. Check back regularly for other flight deals.
Tue 6/252:16 pmHYA - ORD
1 stop6h 11mAmerican Airlines
Wed 6/266:01 amORD - HYA
1 stop5h 18mAmerican Airlines
Deal found 5/14$207
Tue 6/2512:54 pmHYA - ORD
2 stops10h 40mAmerican Airlines
Wed 6/267:00 amORD - HYA
1 stop4h 19mAmerican Airlines
Deal found 5/14$315
Tue 6/2512:54 pmHYA - ORD
2 stops10h 40mAmerican Airlines
Wed 6/268:21 pmORD - HYA
2 stops14h 58mAmerican Airlines
Deal found 5/14$446
Fri 6/1412:54 pmHYA - ORD
1 stop5h 49mAmerican Airlines
Sun 6/166:01 amORD - HYA
1 stop5h 18mAmerican Airlines
Deal found 5/14$555
Sat 8/31:55 pmHYA - ORD
1 stop5h 34mJetBlue
Tue 8/138:29 amORD - HYA
1 stop6h 21mJetBlue
Deal found 5/14$651
Thu 9/122:15 pmHYA - ORD
1 stop5h 49mJetBlue
Tue 9/2410:59 amORD - HYA
1 stop3h 51mJetBlue
Deal found 5/13$707
Wed 9/186:30 amHYA - ORD
1 stop4h 44mJetBlue
Sun 9/2210:59 amORD - HYA
1 stop5h 46mJetBlue
Deal found 5/14$807
Fri 11/810:35 amHYA - ORD
1 stop6h 44mJetBlue
Sun 11/108:38 amORD - HYA
1 stop5h 01mJetBlue
Deal found 5/14$857
Mon 5/2011:00 amHYA - ORD
1 stop8h 30mJetBlue
Tue 5/218:40 amORD - HYA
1 stop4h 59mJetBlue
Deal found 5/14$1,002

Hyannis to Chicago flights leaving soon

Find last-minute flight options from Hyannis to Chicago for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated May 15, 2024.
Book one of these great deals on flights from Hyannis to Chicago. To prevent any unwanted surprises, users should verify their flight info before booking.
Mon 5/2011:00 amHYA - ORD
1 stop8h 30mJetBlue
Tue 5/218:40 amORD - HYA
1 stop4h 59mJetBlue
Deal found 5/14$1,002

One-way flights to Chicago from Hyannis

Search for one-way flight options from Hyannis to Chicago. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated May 15, 2024.
Users in need of a one-way flight from Hyannis to Chicago can choose from these deals. For those needing a return trip from Hyannis, there is a search form available above.
Tue 6/1112:54 pmHYA - ORD
1 stop5h 49mAmerican Airlines
Deal found 5/13$277
Wed 5/2911:00 amHYA - ORD
1 stop8h 20mJetBlue
Deal found 5/14$285
Thu 5/3011:00 amHYA - ORD
1 stop8h 20mJetBlue
Deal found 5/14$345
Sun 6/22:38 pmHYA - ORD
1 stop4h 42mJetBlue
Deal found 5/13$429
Fri 5/311:55 pmHYA - ORD
1 stop5h 25mJetBlue
Deal found 5/14$459
Tue 6/1812:54 pmHYA - ORD
2 stops12h 04mAmerican Airlines
Deal found 5/14$501
Wed 6/1212:54 pmHYA - ORD
2 stops6h 30mAmerican Airlines
Deal found 5/13$505
Tue 6/1112:54 pmHYA - ORD
2 stops10h 40mAmerican Airlines
Deal found 5/13$506
Thu 7/42:16 pmHYA - ORD
2 stops7h 40mAmerican Airlines
Deal found 5/13$588

Find flights from Hyannis to Chicago within your budget

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 2,632,958 searches. Data last updated May 15, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$207 - $857

Route

Depart

Return

Price

Hyannis BarnstableChicago O'Hare Intl

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 6/25

1 stop6h 11m

Chicago O'Hare Intl

Wed 6/26

1 stop5h 18m

$207

Hyannis BarnstableChicago O'Hare Intl

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 6/25

2 stops10h 40m

Chicago O'Hare Intl

Wed 6/26

1 stop4h 19m

$315

Hyannis BarnstableChicago O'Hare Intl

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 6/25

2 stops10h 40m

Chicago O'Hare Intl

Wed 6/26

2 stops14h 58m

$446

Hyannis BarnstableChicago O'Hare Intl

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 6/14

1 stop5h 49m

Chicago O'Hare Intl

Sun 6/16

1 stop5h 18m

$555

Hyannis BarnstableChicago O'Hare Intl

HYA - ORD

HYAORD

Hyannis Barnstable

Sat 8/3

1 stop5h 34m

Chicago O'Hare Intl

Tue 8/13

1 stop6h 21m

$651

Hyannis BarnstableChicago O'Hare Intl

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 9/12

1 stop5h 49m

Chicago O'Hare Intl

Tue 9/24

1 stop3h 51m

$707

Hyannis BarnstableChicago O'Hare Intl

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 9/18

1 stop4h 44m

Chicago O'Hare Intl

Sun 9/22

1 stop5h 46m

$807

Hyannis BarnstableChicago O'Hare Intl

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 11/8

1 stop6h 44m

Chicago O'Hare Intl

Sun 11/10

1 stop5h 01m

$857

Flights are sorted by cheapest first

Deals found on 5/14

No data available for this route at this time. Please check back soon.

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 May 15, 2024.
To help decide which airline to fly from Hyannis to Chicago, see what other customers have to say about American Airlines and JetBlue. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
JetBlue
7.6
Good
4,483 reviews
Check prices

Overall

7.6

Boarding

7.8

Comfort

7.9

Entertainment

7.5

Food

7.2

Crew

8.3

Reviews

1 / 10

Haven’t been on a JetBlue flight in years that was on time.

JetBlue
7.6
Good
4,483 reviews
JetBlue
7.6
Good
4,483 reviews
Check prices

Overall

7.6

Boarding

7.8

Comfort

7.9

Entertainment

7.5

Food

7.2

Crew

8.3

Reviews

1 / 10

Haven’t been on a JetBlue flight in years that was on time.

American Airlines
7.3
Good
14,561 reviews
JetBlue
7.6
Good
4,483 reviews
Check prices

Overall

7.6

Boarding

7.8

Comfort

7.9

Entertainment

7.5

Food

7.2

Crew

8.3

Reviews

1 / 10

Haven’t been on a JetBlue flight in years that was on time.

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.

  • Can I find flights from Hyannis to Chicago for under $300 on Cheapflights?

    Yes, there are multiple flights from Hyannis to Chicago for under $300. The cheapest flight booked recently is on American Airlines for just $207, but on average you can expect to pay $568.

  • Are there last-minute flights available from Hyannis to Chicago for under $1,100?

    There are currently 1+ open flights from Hyannis to Chicago within the next 7 days for less than $1,100.

  • What does HYA to ORD mean?

    Hyannis Barnstable Airport is HYA and Chicago O'Hare Intl Airport is ORD. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight route and their unique identifiers/IATA codes.

  • Can I find deals for flights from Hyannis to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Hyannis to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Hyannis to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Hyannis to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Hyannis to Chicago that allow pets onboard?

    Many airlines flying from Hyannis to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Hyannis to Chicago?

    Yes, you can often find last-minute deals on Hyannis to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Hyannis to Chicago flight deals updated?

    The Hyannis to Chicago flight deals you see on this page were last updated on 5/14.

See more FAQs

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Search flights from Hyannis to Chicago by cabin class

Find flights from Hyannis to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Hyannis to Chicago?

Cheapflights helps you search for flights from Hyannis to Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from Hyannis to Chicago?

Millions of users choose and trust Cheapflights to book the best flight deals from Hyannis to Chicago for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

Can Cheapflights find flights from Hyannis to Chicago with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Hyannis to Chicago flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Hyannis to Chicago become cheaper?

Yes, Cheapflights offers price alerts on Hyannis to Chicago flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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