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Cheap flights from Hyannis to Chicago from $182

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 1/5. 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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Find the cheapest flights from Hyannis to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
12:07 pm - 5:44 pmHYA-ORD
6h 37m1 stop
JetBlue Logo
10:00 am - 6:39 pmORD-HYA
7h 39m1 stop
$395JetBlue
Find Deal
Tue, Feb 10 - Thu, Feb 12
JetBlue Logo
12:07 pm - 5:31 pmHYA-ORD
6h 24m1 stop
JetBlue Logo
12:10 pm - 6:39 pmORD-HYA
5h 29m1 stop
$435JetBlue
Find Deal
Mon, Mar 16 - Wed, Mar 18
JetBlue Logo
12:07 pm - 5:31 pmHYA-ORD
6h 24m1 stop
JetBlue Logo
12:10 pm - 6:39 pmORD-HYA
5h 29m1 stop
$465JetBlue
Find Deal
Mon, Mar 16 - Wed, Mar 18
JetBlue Logo
12:07 pm - 9:52 pmHYA-ORD
10h 45m2 stops
JetBlue Logo
11:25 am - 6:39 pmORD-HYA
6h 14m1 stop
$513JetBlue
Find Deal
Sat, Dec 6 - Sat, Dec 13
JetBlue Logo
2:30 pm - 7:27 pmHYA-ORD
5h 57m1 stop
JetBlue Logo
11:25 am - 6:39 pmORD-HYA
6h 14m1 stop
$515JetBlue
Find Deal
Mon, Nov 24 - Tue, Dec 2
JetBlue Logo
12:07 pm - 7:39 pmHYA-ORD
8h 32m1 stop
JetBlue Logo
1:00 pm - 6:39 pmORD-HYA
4h 39m1 stop
$635JetBlue
Find Deal
Fri, Nov 21 - Tue, Nov 25
JetBlue Logo
2:30 pm - 7:27 pmHYA-ORD
5h 57m1 stop
JetBlue Logo
11:25 am - 6:39 pmORD-HYA
6h 14m1 stop
$667JetBlue
Find Deal
Mon, Nov 24 - Wed, Dec 3
Multiple Airlines Logo
9:35 am - 5:59 pmHYA-ORD
9h 24m1 stop
Multiple Airlines Logo
3:43 pm - 2:00 pmORD-HYA
21h 17m2 stops
$738Multiple Airlines
Find Deal
Fri, Nov 21 - Tue, Nov 25

JetBlue flights from Hyannis to Chicago

Our best JetBlue deals on Hyannis to Chicago flight tickets
JetBlue
Feb 10
HYA12:07 pmHyannis Barnstable
6h 37m
1 stop
ORD5:44 pmChicago O'Hare Intl
Feb 12
ORD10:00 amChicago O'Hare Intl
7h 39m
1 stop
HYA6:39 pmHyannis Barnstable
$395
Find similar
JetBlue
Mar 16
HYA12:07 pmHyannis Barnstable
6h 24m
1 stop
ORD5:31 pmChicago O'Hare Intl
Mar 18
ORD12:10 pmChicago O'Hare Intl
5h 29m
1 stop
HYA6:39 pmHyannis Barnstable
$435
Find similar
JetBlue
Mar 16
HYA12:07 pmHyannis Barnstable
6h 24m
1 stop
ORD5:31 pmChicago O'Hare Intl
Mar 18
ORD12:10 pmChicago O'Hare Intl
5h 29m
1 stop
HYA6:39 pmHyannis Barnstable
$465
Find similar

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 November 7, 2025.
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

Tue 2/10

12:07 pm-5:44 pm

1 stop6h 37m

Chicago O'Hare Intl

Thu 2/12

10:00 am-6:39 pm

1 stop7h 39m

$395

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 3/16

12:07 pm-5:31 pm

1 stop6h 24m

Chicago O'Hare Intl

Wed 3/18

12:10 pm-6:39 pm

1 stop5h 29m

$435

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 3/16

12:07 pm-5:31 pm

1 stop6h 24m

Chicago O'Hare Intl

Wed 3/18

12:10 pm-6:39 pm

1 stop5h 29m

$465

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sat 12/6

12:07 pm-9:52 pm

2 stops10h 45m

Chicago O'Hare Intl

Sat 12/13

11:25 am-6:39 pm

1 stop6h 14m

$513

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 11/24

2:30 pm-7:27 pm

1 stop5h 57m

Chicago O'Hare Intl

Tue 12/2

11:25 am-6:39 pm

1 stop6h 14m

$515

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 11/21

12:07 pm-7:39 pm

1 stop8h 32m

Chicago O'Hare Intl

Tue 11/25

1:00 pm-6:39 pm

1 stop4h 39m

$635

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 11/24

2:30 pm-7:27 pm

1 stop5h 57m

Chicago O'Hare Intl

Wed 12/3

11:25 am-6:39 pm

1 stop6h 14m

$667

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 11/21

9:35 am-5:59 pm

1 stop9h 24m

Chicago O'Hare Intl

Tue 11/25

3:43 pm-2:00 pm

2 stops21h 17m

$738

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 1/5

12:07 pm-6:46 pm

1 stop7h 39m

$182

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 1/6

12:07 pm-5:44 pm

1 stop6h 37m

$188

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 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 $321. 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 $429.

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 $272. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $351.

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

Direct flights

None
There are no direct flights from Hyannis to Chicago. There are no popular flight routes from Hyannis to Chicago.
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 5h 57m.

  • 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
Crown Point
Munster
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