Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Chicago to Boston from $268

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago to Boston

Cheap round-trip flights

Enter your travel dates to find the best prices.
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
$638Multiple Airlines
Tue, Sep 22 - Sun, Sep 27
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
2:10 pm - 10:00 amHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
20h 50m1 stop Boston Logan Intl
$644Multiple Airlines
Mon, Oct 5 - Tue, Oct 6
Multiple Airlines Logo
7:30 am - 12:50 pmORD  Chicago O'Hare Intl-HYA Hyannis Barnstable
4h 20m1 stop Boston Logan Intl
Multiple Airlines Logo
2:10 pm - 2:42 pmHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
25h 32m3 stops Boston Logan Intl Newark Cleveland Hopkins Intl
$685Multiple Airlines
Mon, Oct 5 - Tue, Oct 6
Multiple Airlines Logo
9:38 am - 5:12 pmORD  Chicago O'Hare Intl-HYA Hyannis Barnstable
6h 34m1 stop Boston Logan Intl
Multiple Airlines Logo
12:50 pm - 7:01 pmHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
7h 11m1 stop Boston Logan Intl
$702Multiple Airlines
Sat, Sep 12 - Wed, Sep 16
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
12:50 pm - 11:32 pmHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
11h 42m2 stops Boston Logan Intl Washington, D.C. Dulles Intl
$705Multiple Airlines
Mon, Oct 5 - Tue, Oct 6
Multiple Airlines Logo
9:24 pm - 5:12 pmORD  Chicago O'Hare Intl-HYA Hyannis Barnstable
18h 48m1 stop Boston Logan Intl
Multiple Airlines Logo
2:10 pm - 9:51 amHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
20h 41m1 stop Boston Logan Intl
$733Multiple Airlines
Fri, Sep 25 - Fri, Oct 2
Multiple Airlines Logo
9:38 am - 2:45 pmORD  Chicago O'Hare Intl-HYA Hyannis Barnstable
4h 07m1 stop Boston Logan Intl
Multiple Airlines Logo
11:02 am - 7:01 pmHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
8h 59m1 stop Boston Logan Intl
$765Multiple Airlines
Mon, Sep 14 - Mon, Sep 21
Multiple Airlines Logo
9:24 pm - 5:12 pmORD  Chicago O'Hare Intl-HYA Hyannis Barnstable
18h 48m1 stop Boston Logan Intl
Multiple Airlines Logo
2:10 pm - 10:29 pmHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
9h 19m1 stop Boston Logan Intl
$782Multiple Airlines
Fri, Sep 25 - Fri, Oct 2
Multiple Airlines Logo
9:49 pm - 3:00 pmORD  Chicago O'Hare Intl-HYA Hyannis Barnstable
16h 11m1 stop Boston Logan Intl
Multiple Airlines Logo
1:20 pm - 9:08 amHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
20h 48m1 stop Boston Logan Intl
$793Multiple Airlines
Sat, Dec 19 - Wed, Jan 6
Multiple Airlines Logo
9:49 pm - 3:00 pmORD  Chicago O'Hare Intl-HYA Hyannis Barnstable
16h 11m1 stop Boston Logan Intl
Multiple Airlines Logo
1:20 pm - 9:39 amHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
21h 19m2 stops Boston Logan Intl Washington, D.C. Dulles Intl
$800Multiple Airlines
Sat, Dec 19 - Wed, Jan 6

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 to Hyannis

Our best American Airlines deals on Chicago to Hyannis flight tickets
American Airlines
Sep 5
ORD11:15 amChicago O'Hare Intl
2h 42m
HYA2:57 pmHyannis Barnstable
Sep 8
HYA5:59 pmHyannis Barnstable
6h 38m
1 stop
ORD11:37 pmChicago O'Hare Intl
$373
American Airlines
Sep 5
ORD5:00 amChicago O'Hare Intl
6h 12m
1 stop
HYA12:12 pmHyannis Barnstable
Sep 8
HYA5:59 pmHyannis Barnstable
6h 38m
1 stop
ORD11:37 pmChicago O'Hare Intl
$382
American Airlines
Sep 5
ORD11:15 amChicago O'Hare Intl
2h 42m
HYA2:57 pmHyannis Barnstable
Sep 7
HYA12:42 pmHyannis Barnstable
12h 02m
1 stop
ORD11:44 pmChicago O'Hare Intl
$993

JetBlue flights from Chicago to Hyannis

Our best JetBlue deals on Chicago 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
$853
JetBlue
Aug 29
ORD9:40 amChicago O'Hare Intl
4h 33m
1 stop
HYA3:13 pmHyannis Barnstable
Sep 1
HYA4:20 pmHyannis Barnstable
6h 38m
1 stop
ORD9:58 pmChicago O'Hare Intl
$920
JetBlue
Sep 2
ORD6:00 amChicago O'Hare Intl
8h 13m
1 stop
HYA3:13 pmHyannis Barnstable
Sep 5
HYA4:53 pmHyannis Barnstable
6h 05m
1 stop
ORD9:58 pmChicago O'Hare Intl
$976

momondo Fare Finder

 
Use the filters below to find and compare flights from Chicago to Hyannis that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

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

$638

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Mon 10/5

6:10 am-12:50 pm

1 stop5h 40m

Hyannis Barnstable

Tue 10/6

2:10 pm-10:00 am

1 stop20h 50m

$644

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Mon 10/5

7:30 am-12:50 pm

1 stop4h 20m

Hyannis Barnstable

Tue 10/6

2:10 pm-2:42 pm

3 stops25h 32m

$685

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Sat 9/12

9:38 am-5:12 pm

1 stop6h 34m

Hyannis Barnstable

Wed 9/16

12:50 pm-7:01 pm

1 stop7h 11m

$702

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Mon 10/5

6:10 am-12:50 pm

1 stop5h 40m

Hyannis Barnstable

Tue 10/6

12:50 pm-11:32 pm

2 stops11h 42m

$705

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Fri 9/25

9:24 pm-5:12 pm

1 stop18h 48m

Hyannis Barnstable

Fri 10/2

2:10 pm-9:51 am

1 stop20h 41m

$733
Quickest round-trip

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Mon 9/14

9:38 am-2:45 pm

1 stop4h 07m

Hyannis Barnstable

Mon 9/21

11:02 am-7:01 pm

1 stop8h 59m

$765

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Fri 9/25

9:24 pm-5:12 pm

1 stop18h 48m

Hyannis Barnstable

Fri 10/2

2:10 pm-10:29 pm

1 stop9h 19m

$782

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Sat 12/19

9:49 pm-3:00 pm

1 stop16h 11m

Hyannis Barnstable

Wed 1/6

1:20 pm-9:08 am

1 stop20h 48m

$793

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Sat 12/19

9:49 pm-3:00 pm

1 stop16h 11m

Hyannis Barnstable

Wed 1/6

1:20 pm-9:39 am

2 stops21h 19m

$800

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 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 to Hyannis Barnstable flight route?

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

What cabin class options are available on Chicago to Hyannis flights?

There is only 1 cabin class available to choose from on Chicago 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 to Hyannis flights?

You could potentially save up to 73% on your flight if you consider stops on a Chicago to Hyannis flight.

When to book flights from Chicago to Hyannis

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

Cheap Chicago to Hyannis (CHI to HYA) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Hyannis

Best Price Found

$268

Fastest flight time

5h 11m

Direct flights

None
The best one-way flight to Hyannis from Chicago in the past 72 hours is $268. The best round-trip flight deal from Chicago to Hyannis found on momondo in the last 72 hours is $638.
The fastest flight from Chicago to Hyannis takes 5h 11m
There are no direct flights from Chicago to Hyannis. There are no popular flight routes from Chicago to Hyannis.
Search flight deals

Frequently asked questions about flying from Chicago to Hyannis

  • How far is Chicago to Hyannis Barnstable by plane?

    The straight-line distance from Chicago to Hyannis Barnstable is 891.6 mi. In terms of flight time, this usually takes a little over 5h 11m.

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

    Prices for flights from Chicago to Hyannis Barnstable Airport are updated daily.

  • How old do you have to be to fly from Chicago to Hyannis Barnstable Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago 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 to Hyannis?

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Hyannis. Millions of users trust and use momondo every year so you are in good hands.

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

All flight searches from Chicago to Hyannis on momondo can be filtered to show those which offer flexible booking policies.

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

Once you have performed a search for Chicago to Hyannis 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 Chicago to Hyannis right now. Can momondo alert me if prices change?

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

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
Mon 9/28
Mon 10/5
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States