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Cheap flights from Hyannis to Chicago from $147

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Hyannis to Chicago departing on 7/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
1:33 pm - 5:56 pm
HYA
-
ORD
5h 23m
1 stop
American Airlines Logo
6:00 am - 12:59 pm
ORD
-
HYA
5h 59m
1 stop
$478American Airlines
Thu, Jul 9 - Mon, Jul 13
American Airlines Logo
1:02 pm - 7:26 pm
HYA
-
ORD
7h 24m
1 stop
American Airlines Logo
5:24 pm - 12:32 pm
ORD
-
HYA
18h 08m
2 stops
$630American Airlines
Thu, Jul 9 - Mon, Jul 13
American Airlines Logo
1:33 pm - 10:07 pm
HYA
-
ORD
9h 34m
1 stop
American Airlines Logo
6:00 am - 12:59 pm
ORD
-
HYA
5h 59m
1 stop
$655American Airlines
Fri, Jul 10 - Mon, Jul 13

American Airlines flights from Hyannis to Chicago

Our best American Airlines deals on Hyannis to Chicago flight tickets
American Airlines
Jul 9
HYA1:33 pmHyannis Barnstable
5h 23m
1 stop
ORD5:56 pmChicago O'Hare Intl
Jul 13
ORD6:00 amChicago O'Hare Intl
5h 59m
1 stop
HYA12:59 pmHyannis Barnstable
$478
American Airlines
Jul 9
HYA1:02 pmHyannis Barnstable
7h 24m
1 stop
ORD7:26 pmChicago O'Hare Intl
Jul 13
ORD5:24 pmChicago O'Hare Intl
18h 08m
2 stops
HYA12:32 pmHyannis Barnstable
$630
American Airlines
Jul 10
HYA1:33 pmHyannis Barnstable
9h 34m
1 stop
ORD10:07 pmChicago O'Hare Intl
Jul 13
ORD6:00 amChicago O'Hare Intl
5h 59m
1 stop
HYA12:59 pmHyannis Barnstable
$655

momondo 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, momondo users made 832,500 searches. Data last updated January 29, 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

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 7/9

1:33 pm-5:56 pm

1 stop5h 23m

Chicago O'Hare Intl

Mon 7/13

6:00 am-12:59 pm

1 stop5h 59m

$478

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 7/9

1:02 pm-7:26 pm

1 stop7h 24m

Chicago O'Hare Intl

Mon 7/13

5:24 pm-12:32 pm

2 stops18h 08m

$630

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 7/10

1:33 pm-10:07 pm

1 stop9h 34m

Chicago O'Hare Intl

Mon 7/13

6:00 am-12:59 pm

1 stop5h 59m

$655

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 7/16

1:33 pm-5:56 pm

1 stop5h 23m

$147

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 7/28

1:33 pm-8:50 pm

1 stop8h 17m

$162

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 2/26

12:07 pm-10:51 am

2 stops47h 44m

$180

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 7/23

1:33 pm-8:50 pm

1 stop8h 17m

$182

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 2/6

12:07 pm-5:43 pm

1 stop6h 36m

$192

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 7/21

5:57 pm-10:56 pm

1 stop5h 59m

$196

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 2/24

12:07 pm-9:39 am

2 stops22h 32m

$197

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Hyannis to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $308. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Hyannis to Chicago for around $408.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Hyannis to Chicago during this time can be as low as $270. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $363.

What is the cheapest Hyannis Barnstable to Chicago flight route?

Fly from Hyannis Barnstable to Chicago O'Hare Intl for the best Hyannis Barnstable - Chicago flight prices

What cabin class options are available on Hyannis Barnstable to Chicago flights?

There are 2 cabin classes available to choose from on Hyannis Barnstable to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Hyannis to Chicago flights?

No. A direct flight is the cheapest option for a flight between Hyannis to Chicago.

When to book flights from Hyannis to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Hyannis to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Hyannis to Chicago (HYA to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Hyannis to Chicago

Fastest flight time

6h 36m

Direct flights

Sun

Airports in Chicago

3 airports
The fastest flight from Hyannis to Chicago takes 6h 36m
Direct flights go from Hyannis to Chicago on Sunday. The only airline offering direct flights is American Airlines.
There are 3 airports in Chicago. From Hyannis there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

  • How far is Hyannis Barnstable to Chicago by plane?

    Chicago is 891.6 mi away from Hyannis Barnstable. A reasonable flight in good conditions will take 6h 36m.

  • When did momondo last update prices for flights from Hyannis Barnstable Airport to Chicago?

    Prices for flights from Hyannis Barnstable Airport to Chicago are updated daily.

  • How old do you have to be to fly from Hyannis Barnstable Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Hyannis Barnstable Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Hyannis to Chicago?

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Hyannis to Chicago?

It is quick and easy to find Hyannis to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Hyannis to Chicago with flexible booking policies on momondo?

Flights from Hyannis to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Hyannis to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Hyannis to Chicago.

I’m not ready to book a flight from Hyannis to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Hyannis are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport