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Cheap flights from Hyannis to Chicago from $132

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
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
5:03 pm - 9:41 pm
HYA
-
ORD
5h 38m
1 stop
American Airlines Logo
7:00 am - 12:52 pm
ORD
-
HYA
4h 52m
1 stop
$265American Airlines
Sat, Aug 22 - Sat, Aug 29
American Airlines Logo
1:47 pm - 7:22 pm
HYA
-
ORD
6h 35m
1 stop
American Airlines Logo
5:00 am - 12:12 pm
ORD
-
HYA
6h 12m
1 stop
$345American Airlines
Wed, Aug 19 - Mon, Aug 31
American Airlines Logo
5:03 pm - 9:41 pm
HYA
-
ORD
5h 38m
1 stop
American Airlines Logo
11:15 am - 2:59 pm
ORD
-
HYA
2h 44mnonstop
$350American Airlines
Sat, Aug 22 - Sat, Aug 29
American Airlines Logo
5:59 pm - 11:37 pm
HYA
-
ORD
6h 38m
1 stop
American Airlines Logo
5:00 am - 12:12 pm
ORD
-
HYA
6h 12m
1 stop
$386American Airlines
Mon, Aug 31 - Fri, Sep 4
JetBlue Logo
3:45 pm - 9:29 pm
HYA
-
ORD
6h 44m
1 stop
JetBlue Logo
6:00 am - 2:42 pm
ORD
-
HYA
7h 42m
1 stop
$413JetBlue
Tue, Jun 30 - Sat, Jul 4
American Airlines Logo
5:59 pm - 11:37 pm
HYA
-
ORD
6h 38m
1 stop
American Airlines Logo
11:15 am - 2:59 pm
ORD
-
HYA
2h 44mnonstop
$430American Airlines
Wed, Aug 19 - Sat, Aug 29
American Airlines Logo
12:42 pm - 7:46 pm
HYA
-
ORD
8h 04m
1 stop
American Airlines Logo
8:05 am - 1:13 pm
ORD
-
HYA
4h 08m
1 stop
$439American Airlines
Fri, Aug 21 - Wed, Aug 26
JetBlue Logo
4:23 pm - 9:03 pm
HYA
-
ORD
5h 40m
1 stop
JetBlue Logo
9:40 am - 3:33 pm
ORD
-
HYA
4h 53m
1 stop
$459JetBlue
Tue, Jul 7 - Thu, Jul 9
American Airlines Logo
12:42 pm - 7:46 pm
HYA
-
ORD
8h 04m
1 stop
American Airlines Logo
7:00 am - 1:13 pm
ORD
-
HYA
5h 13m
1 stop
$462American Airlines
Sun, Aug 23 - Tue, Sep 1
JetBlue Logo
4:53 pm - 9:59 am
HYA
-
ORD
18h 06m
2 stops
JetBlue Logo
1:55 pm - 3:11 pm
ORD
-
HYA
24h 16m
2 stops
$494JetBlue
Sat, Aug 22 - Sat, Aug 29

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
Jun 30
HYA3:45 pmHyannis Barnstable
6h 44m
1 stop
ORD9:29 pmChicago O'Hare Intl
Jul 4
ORD6:00 amChicago O'Hare Intl
7h 42m
1 stop
HYA2:42 pmHyannis Barnstable
$413
JetBlue
Jul 7
HYA4:23 pmHyannis Barnstable
5h 40m
1 stop
ORD9:03 pmChicago O'Hare Intl
Jul 9
ORD9:40 amChicago O'Hare Intl
4h 53m
1 stop
HYA3:33 pmHyannis Barnstable
$459
JetBlue
Aug 22
HYA4:53 pmHyannis Barnstable
18h 06m
2 stops
ORD9:59 amChicago O'Hare Intl
Aug 29
ORD1:55 pmChicago O'Hare Intl
24h 16m
2 stops
HYA3:11 pmHyannis Barnstable
$494

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 22
HYA5:03 pmHyannis Barnstable
5h 38m
1 stop
ORD9:41 pmChicago O'Hare Intl
Aug 29
ORD7:00 amChicago O'Hare Intl
4h 52m
1 stop
HYA12:52 pmHyannis Barnstable
$265
American Airlines
Aug 19
HYA1:47 pmHyannis Barnstable
6h 35m
1 stop
ORD7:22 pmChicago O'Hare Intl
Aug 31
ORD5:00 amChicago O'Hare Intl
6h 12m
1 stop
HYA12:12 pmHyannis Barnstable
$345
American Airlines
Aug 22
HYA5:03 pmHyannis Barnstable
5h 38m
1 stop
ORD9:41 pmChicago O'Hare Intl
Aug 29
ORD11:15 amChicago O'Hare Intl
2h 44m
HYA2:59 pmHyannis Barnstable
$350

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 May 22, 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

Sat 8/22

5:03 pm-9:41 pm

1 stop5h 38m

Chicago O'Hare Intl

Sat 8/29

7:00 am-12:52 pm

1 stop4h 52m

$265

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 8/19

1:47 pm-7:22 pm

1 stop6h 35m

Chicago O'Hare Intl

Mon 8/31

5:00 am-12:12 pm

1 stop6h 12m

$345
Quickest round-trip

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sat 8/22

5:03 pm-9:41 pm

1 stop5h 38m

Chicago O'Hare Intl

Sat 8/29

11:15 am-2:59 pm

Nonstop2h 44m

$350

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 8/31

5:59 pm-11:37 pm

1 stop6h 38m

Chicago O'Hare Intl

Fri 9/4

5:00 am-12:12 pm

1 stop6h 12m

$386

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 6/30

3:45 pm-9:29 pm

1 stop6h 44m

Chicago O'Hare Intl

Sat 7/4

6:00 am-2:42 pm

1 stop7h 42m

$413

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 8/19

5:59 pm-11:37 pm

1 stop6h 38m

Chicago O'Hare Intl

Sat 8/29

11:15 am-2:59 pm

Nonstop2h 44m

$430

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 8/21

12:42 pm-7:46 pm

1 stop8h 04m

Chicago O'Hare Intl

Wed 8/26

8:05 am-1:13 pm

1 stop4h 08m

$439

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 7/7

4:23 pm-9:03 pm

1 stop5h 40m

Chicago O'Hare Intl

Thu 7/9

9:40 am-3:33 pm

1 stop4h 53m

$459

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sun 8/23

12:42 pm-7:46 pm

1 stop8h 04m

Chicago O'Hare Intl

Tue 9/1

7:00 am-1:13 pm

1 stop5h 13m

$462

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sat 8/22

4:53 pm-9:59 am

2 stops18h 06m

Chicago O'Hare Intl

Sat 8/29

1:55 pm-3:11 pm

2 stops24h 16m

$494

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 $315. 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 $407.

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 $271 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $384. 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

3h 18m

Direct flights

Sun
The fastest flight from Hyannis to Chicago O'Hare Intl Airport takes 3h 18m
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 3h 18m.

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

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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