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Cheap flights from Hyannis (HYA) to Chicago (CHI) from $138

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 7/5. 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
Jun 4 — Jun 111
From?
To?
Tue 6/4
Tue 6/11
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 38% 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 $271 on average during January, but can be found for as low as $106.

What is the cheapest time of day to fly from HYA to 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 2,784,634 searches. Data last updated May 30, 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.
Fri 8/1612:53 pmHYA - ORD
1 stop5h 46mAmerican Airlines
Tue 8/206:11 amORD - HYA
1 stop6h 16mAmerican Airlines
Deal found 5/29$272
Tue 6/1112:54 pmHYA - ORD
1 stop5h 49mAmerican Airlines
Tue 6/187:00 amORD - HYA
1 stop4h 19mAmerican Airlines
Deal found 5/28$277
Wed 6/1212:54 pmHYA - ORD
1 stop5h 49mAmerican Airlines
Thu 6/136:01 amORD - HYA
1 stop5h 18mAmerican Airlines
Deal found 5/29$312
Mon 7/112:54 pmHYA - ORD
1 stop5h 49mAmerican Airlines
Sun 7/76:30 amORD - HYA
1 stop6h 13mAmerican Airlines
Deal found 5/28$327
Mon 6/2412:54 pmHYA - ORD
1 stop19h 40mAmerican Airlines
Thu 6/278:28 pmORD - HYA
2 stops14h 51mAmerican Airlines
Deal found 5/29$346
Thu 6/1312:54 pmHYA - ORD
1 stop5h 49mAmerican Airlines
Sat 6/157:00 amORD - HYA
1 stop4h 39mAmerican Airlines
Deal found 5/29$347
Thu 6/1312:54 pmHYA - ORD
1 stop5h 49mAmerican Airlines
Thu 6/206:01 amORD - HYA
1 stop5h 18mAmerican Airlines
Deal found 5/30$362
Mon 6/2412:54 pmHYA - ORD
1 stop19h 40mAmerican Airlines
Thu 6/278:28 pmORD - HYA
2 stops14h 51mAmerican Airlines
Deal found 5/30$367
Wed 8/142:15 pmHYA - ORD
1 stop6h 07mAmerican Airlines
Sat 8/178:20 amORD - HYA
1 stop4h 07mAmerican Airlines
Deal found 5/29$412

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 2,784,634 searches. Data last updated May 30, 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.
Thu 6/133:50 pmHYA - ORD
1 stop4h 57mJetBlue
Thu 6/208:30 amORD - HYA
1 stop6h 20mJetBlue
Deal found 5/30$655
Fri 9/61:15 pmHYA - ORD
1 stop6h 49mJetBlue
Mon 9/910:59 amORD - HYA
1 stop4h 01mJetBlue
Deal found 5/29$690

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 2,784,634 searches. Prices were last updated on May 30, 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 6/1112:54 pmHYA - ORD
1 stop5h 49mAmerican Airlines
Tue 6/187:00 amORD - HYA
1 stop4h 19mAmerican Airlines
Deal found 5/28$277
Tue 6/1112:54 pmHYA - ORD
1 stop5h 49mAmerican Airlines
Wed 6/127:00 amORD - HYA
1 stop4h 19mAmerican Airlines
Deal found 5/30$307
Wed 6/1212:54 pmHYA - ORD
1 stop5h 49mAmerican Airlines
Thu 6/136:01 amORD - HYA
1 stop5h 18mAmerican Airlines
Deal found 5/29$312
Mon 6/2412:54 pmHYA - ORD
1 stop19h 40mAmerican Airlines
Thu 6/278:28 pmORD - HYA
2 stops14h 51mAmerican Airlines
Deal found 5/29$346
Thu 6/1312:54 pmHYA - ORD
1 stop5h 49mAmerican Airlines
Sat 6/157:00 amORD - HYA
1 stop4h 39mAmerican Airlines
Deal found 5/29$347
Thu 6/1312:54 pmHYA - ORD
1 stop5h 49mAmerican Airlines
Thu 6/206:01 amORD - HYA
1 stop5h 18mAmerican Airlines
Deal found 5/30$362
Mon 6/2412:54 pmHYA - ORD
1 stop19h 40mAmerican Airlines
Thu 6/278:28 pmORD - HYA
2 stops14h 51mAmerican Airlines
Deal found 5/30$367
Mon 6/2412:54 pmHYA - ORD
2 stops12h 04mAmerican Airlines
Thu 6/278:28 pmORD - HYA
2 stops14h 51mAmerican Airlines
Deal found 5/29$416
Fri 6/2112:54 pmHYA - ORD
1 stop5h 49mAmerican Airlines
Tue 6/257:00 amORD - HYA
1 stop4h 19mAmerican Airlines
Deal found 5/28$417

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 2,784,634 searches. Data last updated May 30, 2024.
These are some of the most attractive deals on flights from Hyannis to Chicago in 2024. Check back regularly for other flight deals.
Fri 8/1612:53 pmHYA - ORD
1 stop5h 46mAmerican Airlines
Tue 8/206:11 amORD - HYA
1 stop6h 16mAmerican Airlines
Deal found 5/29$272
Tue 6/1112:54 pmHYA - ORD
1 stop5h 49mAmerican Airlines
Tue 6/187:00 amORD - HYA
1 stop4h 19mAmerican Airlines
Deal found 5/28$277
Tue 6/1112:54 pmHYA - ORD
1 stop5h 49mAmerican Airlines
Wed 6/127:00 amORD - HYA
1 stop4h 19mAmerican Airlines
Deal found 5/30$307
Wed 6/1212:54 pmHYA - ORD
1 stop5h 49mAmerican Airlines
Thu 6/136:01 amORD - HYA
1 stop5h 18mAmerican Airlines
Deal found 5/29$312
Mon 7/112:54 pmHYA - ORD
1 stop5h 49mAmerican Airlines
Sun 7/76:30 amORD - HYA
1 stop6h 13mAmerican Airlines
Deal found 5/28$327
Mon 6/2412:54 pmHYA - ORD
1 stop19h 40mAmerican Airlines
Thu 6/278:28 pmORD - HYA
2 stops14h 51mAmerican Airlines
Deal found 5/29$346
Thu 6/1312:54 pmHYA - ORD
1 stop5h 49mAmerican Airlines
Sat 6/157:00 amORD - HYA
1 stop4h 39mAmerican Airlines
Deal found 5/29$347
Thu 6/1312:54 pmHYA - ORD
1 stop5h 49mAmerican Airlines
Thu 6/206:01 amORD - HYA
1 stop5h 18mAmerican Airlines
Deal found 5/30$362
Mon 6/2412:54 pmHYA - ORD
1 stop19h 40mAmerican Airlines
Thu 6/278:28 pmORD - HYA
2 stops14h 51mAmerican Airlines
Deal found 5/30$367

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 2,784,634 searches. Data last updated May 30, 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.
Fri 6/712:54 pmHYA - ORD
1 stop5h 49mAmerican Airlines
Tue 6/117:00 amORD - HYA
1 stop4h 19mAmerican Airlines
Deal found 5/30$431
Fri 6/712:54 pmHYA - ORD
1 stop5h 49mAmerican Airlines
Sun 6/96:01 amORD - HYA
1 stop5h 18mAmerican Airlines
Deal found 5/29$555

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 2,784,634 searches. Data last updated May 30, 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.
Fri 7/512:53 pmHYA - ORD
1 stop5h 50mAmerican Airlines
Deal found 5/28$138
Sat 6/81:09 pmHYA - ORD
1 stop7h 34mAmerican Airlines
Deal found 5/29$153
Sat 7/201:15 pmHYA - ORD
1 stop7h 29mAmerican Airlines
Deal found 5/29$172
Sat 6/151:00 pmHYA - ORD
1 stop7h 47mJetBlue
Deal found 5/29$249
Sat 6/151:09 pmHYA - ORD
1 stop7h 34mAmerican Airlines
Deal found 5/28$287
Sun 6/161:15 pmHYA - ORD
1 stop7h 32mJetBlue
Deal found 5/29$393
Sat 7/201:15 pmHYA - ORD
2 stops7h 14mAmerican Airlines
Deal found 5/29$493
Sat 6/151:09 pmHYA - ORD
2 stops7h 21mAmerican Airlines
Deal found 5/29$513
Sat 6/81:09 pmHYA - ORD
2 stops7h 38mAmerican Airlines
Deal found 5/29$560

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 2,784,634 searches. Data last updated May 30, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$272 - $655

Route

Depart

Return

Price

Hyannis BarnstableChicago O'Hare Intl

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 8/16

1 stop5h 46m

Chicago O'Hare Intl

Tue 8/20

1 stop6h 16m

$272

Hyannis BarnstableChicago O'Hare Intl

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 6/11

1 stop5h 49m

Chicago O'Hare Intl

Tue 6/18

1 stop4h 19m

$277

Hyannis BarnstableChicago O'Hare Intl

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 6/12

1 stop5h 49m

Chicago O'Hare Intl

Thu 6/13

1 stop5h 18m

$312

Hyannis BarnstableChicago O'Hare Intl

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 7/1

1 stop5h 49m

Chicago O'Hare Intl

Sun 7/7

1 stop6h 13m

$327

Hyannis BarnstableChicago O'Hare Intl

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 6/24

1 stop19h 40m

Chicago O'Hare Intl

Thu 6/27

2 stops14h 51m

$346

Hyannis BarnstableChicago O'Hare Intl

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 6/13

1 stop5h 49m

Chicago O'Hare Intl

Sat 6/15

1 stop4h 39m

$347

Hyannis BarnstableChicago O'Hare Intl

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 6/13

1 stop5h 49m

Chicago O'Hare Intl

Thu 6/20

1 stop5h 18m

$362

Hyannis BarnstableChicago O'Hare Intl

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 6/24

1 stop19h 40m

Chicago O'Hare Intl

Thu 6/27

2 stops14h 51m

$367

Hyannis BarnstableChicago O'Hare Intl

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 6/13

1 stop4h 57m

Chicago O'Hare Intl

Thu 6/20

1 stop6h 20m

$655

Flights are sorted by cheapest first

Deals found on 5/29

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

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.

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 30, 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
4,365 reviews
Check prices

Food

7.1

Boarding

7.8

Entertainment

7.5

Overall

7.6

Comfort

7.8

Crew

8.3

Reviews

1 / 10

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

JetBlue
7.6
Good
4,365 reviews
JetBlue
7.6
Good
4,365 reviews
Check prices

Food

7.1

Boarding

7.8

Entertainment

7.5

Overall

7.6

Comfort

7.8

Crew

8.3

Reviews

1 / 10

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

American Airlines
7.3
Good
14,284 reviews
JetBlue
7.6
Good
4,365 reviews
Check prices

Food

7.1

Boarding

7.8

Entertainment

7.5

Overall

7.6

Comfort

7.8

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 $272, but on average you can expect to pay $436.

  • Are there last-minute flights available from Hyannis to Chicago for under $500?

    There are currently 2+ open flights from Hyannis to Chicago within the next 7 days for less than $500.

  • 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 5/30.

  • What is the cheapest month to book a flight from Hyannis to Chicago?

    Currently, February is the cheapest month in which you can book a flight from Hyannis to Chicago (average of $244). Flying from Hyannis to Chicago in June is currently the most expensive (average of $326). 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

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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

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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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