Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Chicago O'Hare Intl Airport to Boston from $239

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago O'Hare Intl Airport to Boston departing on 9/12. 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 Chicago O'Hare Intl Airport to Boston

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
11:15 am - 2:57 pmORD  Chicago O'Hare Intl-HYA Hyannis Barnstable
2h 42mnonstop
American Airlines Logo
5:59 pm - 11:37 pmHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
6h 38m1 stop Washington, D.C. Reagan-National
$300American Airlines
Sat, Sep 5 - Sun, Sep 6
American Airlines Logo
6:45 am - 12:12 pmORD  Chicago O'Hare Intl-HYA Hyannis Barnstable
4h 27m1 stop Philadelphia
American Airlines Logo
12:42 pm - 7:46 pmHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
8h 04m1 stop Philadelphia
$309American Airlines
Sat, Sep 5 - Sun, Sep 6
JetBlue Logo
9:35 am - 3:13 pmORD  Chicago O'Hare Intl-HYA Hyannis Barnstable
4h 38m1 stop New York John F Kennedy Intl
JetBlue Logo
4:53 pm - 9:58 pmHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
6h 05m1 stop New York John F Kennedy Intl
$323JetBlue
Wed, Sep 2 - Sat, Sep 5
American Airlines Logo
11:15 am - 2:57 pmORD  Chicago O'Hare Intl-HYA Hyannis Barnstable
2h 42mnonstop
American Airlines Logo
5:59 pm - 11:37 pmHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
6h 38m1 stop Washington, D.C. Reagan-National
$406American Airlines
Sat, Aug 29 - Wed, Sep 2
American Airlines Logo
9:57 am - 4:32 pmORD  Chicago O'Hare Intl-HYA Hyannis Barnstable
5h 35m1 stop Washington, D.C. Reagan-National
American Airlines Logo
5:59 pm - 11:37 pmHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
6h 38m1 stop Washington, D.C. Reagan-National
$415American Airlines
Sat, Aug 29 - Wed, Sep 2
JetBlue Logo
9:40 am - 3:13 pmORD  Chicago O'Hare Intl-HYA Hyannis Barnstable
4h 33m1 stop New York John F Kennedy Intl
JetBlue Logo
4:20 pm - 9:58 pmHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
6h 38m1 stop New York John F Kennedy Intl
$535JetBlue
Sat, Aug 29 - Wed, Sep 2
Multiple Airlines Logo
7:00 am - 10:55 pmORD  Chicago O'Hare Intl-HYA Hyannis Barnstable
14h 55m2 stops New York John F Kennedy Intl West Tisbury Martha's Vineyard
Multiple Airlines Logo
11:02 am - 7:01 pmHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
8h 59m1 stop Boston Logan Intl
$546Multiple Airlines
Mon, Sep 14 - Fri, Sep 18
Multiple Airlines Logo
6:10 am - 12:50 pmORD  Chicago O'Hare Intl-HYA Hyannis Barnstable
5h 40m1 stop Boston Logan Intl
Multiple Airlines Logo
11:02 am - 10:30 pmHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
12h 28m1 stop Boston Logan Intl
$556Multiple Airlines
Mon, Sep 14 - Fri, Sep 18
Multiple Airlines Logo
7:00 am - 10:55 pmORD  Chicago O'Hare Intl-HYA Hyannis Barnstable
14h 55m2 stops New York John F Kennedy Intl West Tisbury Martha's Vineyard
Multiple Airlines Logo
11:02 am - 7:01 pmHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
8h 59m1 stop Boston Logan Intl
$575Multiple Airlines
Mon, Sep 14 - Mon, Sep 21
Multiple Airlines Logo
7:05 am - 10:55 pmORD  Chicago O'Hare Intl-HYA Hyannis Barnstable
14h 50m2 stops New York John F Kennedy Intl West Tisbury Martha's Vineyard
Multiple Airlines Logo
7:00 am - 8:48 amHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
26h 48m1 stop Boston Logan Intl
$608Multiple Airlines
Tue, Sep 22 - Sun, Sep 27

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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

Our best American Airlines deals on Chicago O'Hare Intl Airport to Hyannis flight tickets
American Airlines
Sep 5
ORD11:15 amChicago O'Hare Intl
2h 42m
HYA2:57 pmHyannis Barnstable
Sep 6
HYA5:59 pmHyannis Barnstable
6h 38m
1 stop
ORD11:37 pmChicago O'Hare Intl
$300
American Airlines
Sep 5
ORD6:45 amChicago O'Hare Intl
4h 27m
1 stop
HYA12:12 pmHyannis Barnstable
Sep 6
HYA12:42 pmHyannis Barnstable
8h 04m
1 stop
ORD7:46 pmChicago O'Hare Intl
$309
American Airlines
Aug 29
ORD11:15 amChicago O'Hare Intl
2h 42m
HYA2:57 pmHyannis Barnstable
Sep 2
HYA5:59 pmHyannis Barnstable
6h 38m
1 stop
ORD11:37 pmChicago O'Hare Intl
$406

JetBlue flights from Chicago O'Hare Intl Airport to Hyannis

Our best JetBlue deals on Chicago O'Hare Intl Airport to Hyannis flight tickets
JetBlue
Sep 2
ORD9:35 amChicago O'Hare Intl
4h 38m
1 stop
HYA3:13 pmHyannis Barnstable
Sep 5
HYA4:53 pmHyannis Barnstable
6h 05m
1 stop
ORD9:58 pmChicago O'Hare Intl
$323
JetBlue
Aug 29
ORD9:40 amChicago O'Hare Intl
4h 33m
1 stop
HYA3:13 pmHyannis Barnstable
Sep 2
HYA4:20 pmHyannis Barnstable
6h 38m
1 stop
ORD9:58 pmChicago O'Hare Intl
$535
JetBlue
Aug 28
ORD9:42 amChicago O'Hare Intl
4h 31m
1 stop
HYA3:13 pmHyannis Barnstable
Sep 1
HYA4:20 pmHyannis Barnstable
6h 38m
1 stop
ORD9:58 pmChicago O'Hare Intl
$641

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Sat 9/5

11:15 am-2:57 pm

Nonstop2h 42m

Hyannis Barnstable

Sun 9/6

5:59 pm-11:37 pm

1 stop6h 38m

$300

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Sat 9/5

6:45 am-12:12 pm

1 stop4h 27m

Hyannis Barnstable

Sun 9/6

12:42 pm-7:46 pm

1 stop8h 04m

$309

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Wed 9/2

9:35 am-3:13 pm

1 stop4h 38m

Hyannis Barnstable

Sat 9/5

4:53 pm-9:58 pm

1 stop6h 05m

$323

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Sat 8/29

11:15 am-2:57 pm

Nonstop2h 42m

Hyannis Barnstable

Wed 9/2

5:59 pm-11:37 pm

1 stop6h 38m

$406

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Sat 8/29

9:57 am-4:32 pm

1 stop5h 35m

Hyannis Barnstable

Wed 9/2

5:59 pm-11:37 pm

1 stop6h 38m

$415

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Sat 8/29

9:40 am-3:13 pm

1 stop4h 33m

Hyannis Barnstable

Wed 9/2

4:20 pm-9:58 pm

1 stop6h 38m

$535

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Mon 9/14

7:00 am-10:55 pm

2 stops14h 55m

Hyannis Barnstable

Fri 9/18

11:02 am-7:01 pm

1 stop8h 59m

$546

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Mon 9/14

6:10 am-12:50 pm

1 stop5h 40m

Hyannis Barnstable

Fri 9/18

11:02 am-10:30 pm

1 stop12h 28m

$556

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Mon 9/14

7:00 am-10:55 pm

2 stops14h 55m

Hyannis Barnstable

Mon 9/21

11:02 am-7:01 pm

1 stop8h 59m

$575

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Tue 9/22

7:05 am-10:55 pm

2 stops14h 50m

Hyannis Barnstable

Sun 9/27

7:00 am-8:48 am

1 stop26h 48m

$608

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Boston from

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to Hyannis

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 Chicago O'Hare Intl to Hyannis Barnstable flight route?

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

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

There is only 1 cabin class available to choose from on Chicago O'Hare Intl Airport to Hyannis 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 Chicago O'Hare Intl Airport to Hyannis flights?

You could potentially save up to 73% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Hyannis flight.

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

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

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

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

Best Price Found

$239

Fastest flight time

4h 31m

Direct flights

Sun

Airports in Hyannis

1 airport
The best one-way flight to Hyannis from Chicago O'Hare Intl Airport in the past 72 hours is $239. The best round-trip flight deal from Chicago O'Hare Intl Airport to Hyannis found on momondo in the last 72 hours is $300.
The fastest flight from Chicago O'Hare Intl Airport to Hyannis takes 4h 31m
Direct flights go from Chicago O'Hare Intl Airport to Hyannis on Sunday. There are no airlines offering direct flights.
There is 1 airport in Hyannis. From Chicago O'Hare Intl Airport there are direct flights to Hyannis Barnstable (HYA).
Search flight deals

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

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

    A flight from Chicago O'Hare Intl to Hyannis Barnstable will travel around 905.2 mi. Flights usually cover this in 4h 31m, depending on flying conditions and air traffic around both airports.

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

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

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

    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 Chicago O'Hare Intl Airport to Hyannis Barnstable Airport.

  • What documentation or ID do you need to fly to Hyannis Barnstable Airport?

    The travel and health documents you'll need for your trip to Hyannis Barnstable Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Hyannis Barnstable Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago O'Hare Intl Airport to Hyannis?

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Hyannis for you.

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

Flights from Chicago to Hyannis 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 Chicago to Hyannis?

momondo provides multiple filters to help you find the best flight to Hyannis from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Yes. momondo can track prices for Chicago to Hyannis flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Hyannis trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 9/17
Thu 9/24
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States