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Cheap flights from Hyannis to Chicago from $137

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 7/21. 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

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Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
4:20 pm - 8:44 pm
HYA
-
ORD
5h 24m
1 stop
JetBlue Logo
6:00 am - 3:17 pm
ORD
-
HYA
8h 17m
1 stop
$357JetBlue
Fri, Jun 26 - Mon, Jun 29
JetBlue Logo
4:20 pm - 8:44 pm
HYA
-
ORD
5h 24m
1 stop
JetBlue Logo
9:33 am - 3:17 pm
ORD
-
HYA
4h 44m
1 stop
$366JetBlue
Mon, Jul 27 - Wed, Jul 29
JetBlue Logo
4:20 pm - 8:44 pm
HYA
-
ORD
5h 24m
1 stop
JetBlue Logo
9:33 am - 3:17 pm
ORD
-
HYA
4h 44m
1 stop
$387JetBlue
Thu, Jun 25 - Mon, Jun 29
JetBlue Logo
4:20 pm - 8:44 pm
HYA
-
ORD
5h 24m
1 stop
JetBlue Logo
9:33 am - 3:17 pm
ORD
-
HYA
4h 44m
1 stop
$413JetBlue
Fri, Jun 26 - Sun, Jun 28
JetBlue Logo
4:20 pm - 8:44 pm
HYA
-
ORD
5h 24m
1 stop
JetBlue Logo
9:33 am - 3:17 pm
ORD
-
HYA
4h 44m
1 stop
$443JetBlue
Thu, Jun 25 - Sun, Jun 28
JetBlue Logo
4:20 pm - 8:44 pm
HYA
-
ORD
5h 24m
1 stop
JetBlue Logo
9:33 am - 3:17 pm
ORD
-
HYA
4h 44m
1 stop
$488JetBlue
Fri, Jul 17 - Mon, Jul 20
JetBlue Logo
4:20 pm - 8:44 pm
HYA
-
ORD
5h 24m
1 stop
JetBlue Logo
6:00 am - 3:17 pm
ORD
-
HYA
8h 17m
1 stop
$513JetBlue
Thu, Jul 23 - Tue, Jul 28
JetBlue Logo
4:20 pm - 8:44 pm
HYA
-
ORD
5h 24m
1 stop
JetBlue Logo
9:33 am - 3:17 pm
ORD
-
HYA
4h 44m
1 stop
$518JetBlue
Thu, Aug 13 - Sun, Aug 16
JetBlue Logo
4:20 pm - 8:44 pm
HYA
-
ORD
5h 24m
1 stop
JetBlue Logo
9:33 am - 3:17 pm
ORD
-
HYA
4h 44m
1 stop
$573JetBlue
Thu, Aug 13 - Sun, Aug 16
JetBlue Logo
4:20 pm - 8:44 pm
HYA
-
ORD
5h 24m
1 stop
JetBlue Logo
9:33 am - 3:17 pm
ORD
-
HYA
4h 44m
1 stop
$588JetBlue
Thu, Jul 16 - Sun, Jul 19

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
Jul 27
HYA4:20 pmHyannis Barnstable
5h 24m
1 stop
ORD8:44 pmChicago O'Hare Intl
Jul 29
ORD9:33 amChicago O'Hare Intl
4h 44m
1 stop
HYA3:17 pmHyannis Barnstable
$366
JetBlue
Aug 21
HYA4:20 pmHyannis Barnstable
5h 24m
1 stop
ORD8:44 pmChicago O'Hare Intl
Aug 24
ORD9:33 amChicago O'Hare Intl
4h 44m
1 stop
HYA3:17 pmHyannis Barnstable
$413
JetBlue
Jun 25
HYA4:20 pmHyannis Barnstable
5h 24m
1 stop
ORD8:44 pmChicago O'Hare Intl
Jun 28
ORD9:33 amChicago O'Hare Intl
4h 44m
1 stop
HYA3:17 pmHyannis Barnstable
$443

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 March 27, 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 6/26

4:20 pm-8:44 pm

1 stop5h 24m

Chicago O'Hare Intl

Mon 6/29

6:00 am-3:17 pm

1 stop8h 17m

$357
Quickest round-trip

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 7/27

4:20 pm-8:44 pm

1 stop5h 24m

Chicago O'Hare Intl

Wed 7/29

9:33 am-3:17 pm

1 stop4h 44m

$366

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 6/25

4:20 pm-8:44 pm

1 stop5h 24m

Chicago O'Hare Intl

Mon 6/29

9:33 am-3:17 pm

1 stop4h 44m

$387

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 6/26

4:20 pm-8:44 pm

1 stop5h 24m

Chicago O'Hare Intl

Sun 6/28

9:33 am-3:17 pm

1 stop4h 44m

$413

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 6/25

4:20 pm-8:44 pm

1 stop5h 24m

Chicago O'Hare Intl

Sun 6/28

9:33 am-3:17 pm

1 stop4h 44m

$443

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 7/17

4:20 pm-8:44 pm

1 stop5h 24m

Chicago O'Hare Intl

Mon 7/20

9:33 am-3:17 pm

1 stop4h 44m

$488

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 7/23

4:20 pm-8:44 pm

1 stop5h 24m

Chicago O'Hare Intl

Tue 7/28

6:00 am-3:17 pm

1 stop8h 17m

$513

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 8/13

4:20 pm-8:44 pm

1 stop5h 24m

Chicago O'Hare Intl

Sun 8/16

9:33 am-3:17 pm

1 stop4h 44m

$518

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 8/13

4:20 pm-8:44 pm

1 stop5h 24m

Chicago O'Hare Intl

Sun 8/16

9:33 am-3:17 pm

1 stop4h 44m

$573

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 7/16

4:20 pm-8:44 pm

1 stop5h 24m

Chicago O'Hare Intl

Sun 7/19

9:33 am-3:17 pm

1 stop4h 44m

$588

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 Wednesday 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 $400.

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 $388. 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 Barnstable to Chicago O'Hare Intl flights?

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

5h 24m

Direct flights

Sun
The fastest flight from Hyannis to Chicago O'Hare Intl Airport takes 5h 24m
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

  • 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 5h 24m.

  • 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
Rockford
Merrillville
Gurnee
Rosemont
Naperville
New Buffalo
Orland Park
Kenosha
Oak Brook
Joliet
Janesville
Racine
Hammond
Aurora
Elgin
Tinley Park
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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