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Cheap flights from Hyannis to Chicago from $99

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 8/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Hyannis to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
4:20 pm - 9:58 pm
HYA
-
ORD
6h 38m
1 stop
JetBlue Logo
6:00 am - 3:13 pm
ORD
-
HYA
8h 13m
1 stop
$199JetBlue
Fri, Aug 28 - Mon, Aug 31
JetBlue Logo
4:20 pm - 9:58 pm
HYA
-
ORD
6h 38m
1 stop
JetBlue Logo
6:00 am - 3:13 pm
ORD
-
HYA
8h 13m
1 stop
$209JetBlue
Fri, Aug 28 - Tue, Sep 1
JetBlue Logo
4:20 pm - 9:58 pm
HYA
-
ORD
6h 38m
1 stop
JetBlue Logo
6:00 am - 3:13 pm
ORD
-
HYA
8h 13m
1 stop
$227JetBlue
Wed, Aug 5 - Mon, Aug 10
JetBlue Logo
4:20 pm - 9:58 pm
HYA
-
ORD
6h 38m
1 stop
JetBlue Logo
6:00 am - 3:13 pm
ORD
-
HYA
8h 13m
1 stop
$255JetBlue
Fri, Aug 14 - Mon, Aug 17
JetBlue Logo
4:53 pm - 9:58 pm
HYA
-
ORD
6h 05m
1 stop
JetBlue Logo
6:00 am - 3:13 pm
ORD
-
HYA
8h 13m
1 stop
$262JetBlue
Tue, Aug 4 - Fri, Aug 7
JetBlue Logo
4:20 pm - 9:58 pm
HYA
-
ORD
6h 38m
1 stop
JetBlue Logo
6:00 am - 3:13 pm
ORD
-
HYA
8h 13m
1 stop
$272JetBlue
Fri, Aug 28 - Sun, Aug 30
JetBlue Logo
4:20 pm - 9:58 pm
HYA
-
ORD
6h 38m
1 stop
JetBlue Logo
9:35 am - 3:13 pm
ORD
-
HYA
4h 38m
1 stop
$306JetBlue
Mon, Aug 10 - Wed, Aug 12
JetBlue Logo
4:20 pm - 9:58 pm
HYA
-
ORD
6h 38m
1 stop
JetBlue Logo
6:00 am - 3:13 pm
ORD
-
HYA
8h 13m
1 stop
$316JetBlue
Thu, Aug 27 - Sun, Aug 30
JetBlue Logo
4:20 pm - 9:58 pm
HYA
-
ORD
6h 38m
1 stop
JetBlue Logo
9:41 am - 3:13 pm
ORD
-
HYA
4h 32m
1 stop
$325JetBlue
Thu, Sep 3 - Sat, Sep 5
JetBlue Logo
4:20 pm - 9:58 pm
HYA
-
ORD
6h 38m
1 stop
JetBlue Logo
9:42 am - 3:13 pm
ORD
-
HYA
4h 31m
1 stop
$335JetBlue
Wed, Aug 5 - Mon, Aug 10

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JetBlue flights from Hyannis to Chicago O'Hare Intl Airport

Our best JetBlue deals on Hyannis to Chicago O'Hare Intl Airport flight tickets
JetBlue
Aug 28
HYA4:20 pmHyannis Barnstable
6h 38m
1 stop
ORD9:58 pmChicago O'Hare Intl
Aug 31
ORD6:00 amChicago O'Hare Intl
8h 13m
1 stop
HYA3:13 pmHyannis Barnstable
$199
JetBlue
Aug 28
HYA4:20 pmHyannis Barnstable
6h 38m
1 stop
ORD9:58 pmChicago O'Hare Intl
Sep 1
ORD6:00 amChicago O'Hare Intl
8h 13m
1 stop
HYA3:13 pmHyannis Barnstable
$209
JetBlue
Aug 5
HYA4:20 pmHyannis Barnstable
6h 38m
1 stop
ORD9:58 pmChicago O'Hare Intl
Aug 10
ORD6:00 amChicago O'Hare Intl
8h 13m
1 stop
HYA3:13 pmHyannis Barnstable
$227

American Airlines flights from Hyannis to Chicago O'Hare Intl Airport

Our best American Airlines deals on Hyannis to Chicago O'Hare Intl Airport flight tickets
American Airlines
Aug 20
HYA12:42 pmHyannis Barnstable
8h 04m
1 stop
ORD7:46 pmChicago O'Hare Intl
Aug 23
ORD6:45 amChicago O'Hare Intl
4h 27m
1 stop
HYA12:12 pmHyannis Barnstable
$359
American Airlines
Aug 13
HYA5:59 pmHyannis Barnstable
5h 12m
1 stop
ORD10:11 pmChicago O'Hare Intl
Aug 20
ORD6:45 amChicago O'Hare Intl
4h 27m
1 stop
HYA12:12 pmHyannis Barnstable
$430
American Airlines
Jul 21
HYA1:26 pmHyannis Barnstable
7h 17m
1 stop
ORD7:43 pmChicago O'Hare Intl
Jul 26
ORD7:02 amChicago O'Hare Intl
5h 34m
1 stop
HYA1:36 pmHyannis Barnstable
$453

momondo Fare Finder

 
Customize your flight search to find flights from Hyannis to Chicago O'Hare Intl Airport 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 July 18, 2026.
Use the filters below to find and compare flights from Hyannis to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 8/28

4:20 pm-9:58 pm

1 stop6h 38m

Chicago O'Hare Intl

Mon 8/31

6:00 am-3:13 pm

1 stop8h 13m

$199

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 8/28

4:20 pm-9:58 pm

1 stop6h 38m

Chicago O'Hare Intl

Tue 9/1

6:00 am-3:13 pm

1 stop8h 13m

$209

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 8/5

4:20 pm-9:58 pm

1 stop6h 38m

Chicago O'Hare Intl

Mon 8/10

6:00 am-3:13 pm

1 stop8h 13m

$227

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 8/14

4:20 pm-9:58 pm

1 stop6h 38m

Chicago O'Hare Intl

Mon 8/17

6:00 am-3:13 pm

1 stop8h 13m

$255

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 8/4

4:53 pm-9:58 pm

1 stop6h 05m

Chicago O'Hare Intl

Fri 8/7

6:00 am-3:13 pm

1 stop8h 13m

$262

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 8/28

4:20 pm-9:58 pm

1 stop6h 38m

Chicago O'Hare Intl

Sun 8/30

6:00 am-3:13 pm

1 stop8h 13m

$272

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 8/10

4:20 pm-9:58 pm

1 stop6h 38m

Chicago O'Hare Intl

Wed 8/12

9:35 am-3:13 pm

1 stop4h 38m

$306

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 8/27

4:20 pm-9:58 pm

1 stop6h 38m

Chicago O'Hare Intl

Sun 8/30

6:00 am-3:13 pm

1 stop8h 13m

$316

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 9/3

4:20 pm-9:58 pm

1 stop6h 38m

Chicago O'Hare Intl

Sat 9/5

9:41 am-3:13 pm

1 stop4h 32m

$325
Quickest round-trip

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 8/5

4:20 pm-9:58 pm

1 stop6h 38m

Chicago O'Hare Intl

Mon 8/10

9:42 am-3:13 pm

1 stop4h 31m

$335

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 O'Hare Intl Airport

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 O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $311. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Hyannis because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $410.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Hyannis in the evening is the least expensive time of day to depart. momondo users have found prices as low as $270 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $387. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Hyannis Barnstable to Chicago O'Hare Intl flight route?

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

What cabin class options are available on Hyannis to Chicago O'Hare Intl Airport flights?

There are 2 cabin classes available to choose from on Hyannis to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between Hyannis to Chicago O'Hare Intl Airport.

When to book flights from Hyannis to Chicago O'Hare Intl Airport

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

Cheap Hyannis to Chicago O'Hare Intl Airport (HYA to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Hyannis to Chicago O'Hare Intl Airport

Fastest flight time

6h 05m

Direct flights

Sun
The fastest flight from Hyannis to Chicago O'Hare Intl Airport takes 6h 05m
Direct flights go from Hyannis to Chicago O'Hare Intl Airport on Sunday. The only airline offering direct flights is American Airlines.
Search flight deals

Frequently asked questions about flying from Hyannis to Chicago O'Hare Intl Airport

  • How far is Hyannis Barnstable to Chicago O'Hare Intl by plane?

    A flight from Hyannis Barnstable to Chicago O'Hare Intl will travel around 905.2 mi. A reasonable flight in good conditions will take 6h 05m.

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

    Prices for flights from Hyannis Barnstable Airport to Chicago O'Hare Intl Airport were last updated today.

  • How old do you have to be to fly from Hyannis Barnstable Airport to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Hyannis Barnstable Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl Airport 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 O'Hare Intl Airport?

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Merrillville
Rockford
Gurnee
Rosemont
Orland Park
Naperville
Oak Brook
Joliet
New Buffalo
Kenosha
Hammond
Aurora
Racine
Janesville
Elgin
Evanston
South Holland

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Hyannis.

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

Yes. momondo enables you to select and highlight flights to Chicago from Hyannis with this policy.

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

Once you have performed a search for Hyannis to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

If you are not ready to book a flight from Hyannis to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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