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$140+ 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 6/28. Fares are subject to change and may not be available on all flights or dates of travel.
HYA — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
2 stars

Round-trip from

$516
(JetBlue)

One-way from

$140
(JetBlue)

Popular in

April

Cheapest in

September

Average price

$275
Provider with most accurate pricing for Hyannis Barnstable-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Hyannis Barnstable-Chicago (CHI) flights.
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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. 12% potential increase in price ($33 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 May 2025
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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 May 1, 2025.

This JetBlue deal was found by Cheapflights users on 4/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1411:25 amHYA - ORD
1 stop8h 11mJetBlue
Sun 5/188:45 amORD - HYA
1 stop4h 55mJetBlue
Deal found 4/29$516
This JetBlue Airways deal was found by Cheapflights users on 4/30. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1511:25 amHYA - ORD
1 stop8h 11mMultiple Airlines
Mon 5/197:31 pmORD - HYA
1 stop18h 09mMultiple Airlines
Deal found 4/30$606

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 May 1, 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 5/14

11:25 am-6:36 pm

1 stop8h 11m

Chicago O'Hare Intl

Sun 5/18

8:45 am-2:40 pm

1 stop4h 55m

$516

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 5/15

11:25 am-6:36 pm

1 stop8h 11m

Chicago O'Hare Intl

Mon 5/19

7:31 pm-2:40 pm

1 stop18h 09m

$606

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sat 6/28

4:59 pm-11:25 pm

1 stop7h 26m

$140

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sun 6/22

5:17 pm-11:24 pm

1 stop7h 07m

$211

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 5/30

3:50 pm-7:58 am

1 stop17h 08m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

  • 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.
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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 1, 2025.
JetBlue
7.3
Good
2,922 reviews

Overall

7.3

Entertainment

7.3

Comfort

7.6

Boarding

7.5

Crew

8.0

Food

6.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2025

JFK - CHS

Boarding took a very long time, in fact we were delayed by at least 30mins. There wasn’t many options for snacks and there was only water. The pilot did an excellent job
JetBlue
7.3
Good
2,922 reviews
JetBlue
7.3
Good
2,922 reviews

Overall

7.3

Entertainment

7.3

Comfort

7.6

Boarding

7.5

Crew

8.0

Food

6.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2025

JFK - CHS

Boarding took a very long time, in fact we were delayed by at least 30mins. There wasn’t many options for snacks and there was only water. The pilot did an excellent job
American Airlines
7.2
Good
10,000 reviews
JetBlue
7.3
Good
2,922 reviews

Overall

7.3

Entertainment

7.3

Comfort

7.6

Boarding

7.5

Crew

8.0

Food

6.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2025

JFK - CHS

Boarding took a very long time, in fact we were delayed by at least 30mins. There wasn’t many options for snacks and there was only water. The pilot did an excellent job

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 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 Hyannis?

Book flights to Hyannis if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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