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Cheap flights from Chicago to Boston from $209

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 to Boston departing on 8/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

American Airlines Logo
11:12 am - 2:51 pmORD-HYA
2h 39mnonstop
American Airlines Logo
3:25 pm - 5:31 pmHYA-ORD
3h 06mnonstop
$310American Airlines
Find Deal
Sat, Aug 16 - Sat, Aug 23
American Airlines Logo
8:09 am - 4:45 pmORD-HYA
7h 36m1 stop
American Airlines Logo
3:25 pm - 5:31 pmHYA-ORD
3h 06mnonstop
$344American Airlines
Find Deal
Sat, Aug 16 - Sat, Aug 23
American Airlines Logo
8:09 am - 4:45 pmORD-HYA
7h 36m1 stop
American Airlines Logo
1:40 pm - 7:15 pmHYA-ORD
6h 35m1 stop
$426American Airlines
Find Deal
Sat, Aug 16 - Sat, Aug 23
American Airlines Logo
8:45 pm - 11:40 amORD-HYA
13h 55m2 stops
American Airlines Logo
2:34 pm - 11:25 pmHYA-ORD
9h 51m1 stop
$462American Airlines
Find Deal
Mon, Aug 25 - Mon, Sep 1
American Airlines Logo
11:12 am - 2:51 pmORD-HYA
2h 39mnonstop
American Airlines Logo
12:10 pm - 5:20 pmHYA-ORD
6h 10m1 stop
$467American Airlines
Find Deal
Sat, Aug 16 - Mon, Aug 18
American Airlines Logo
8:09 am - 4:45 pmORD-HYA
7h 36m1 stop
American Airlines Logo
12:10 pm - 5:20 pmHYA-ORD
6h 10m1 stop
$476American Airlines
Find Deal
Sat, Aug 16 - Mon, Aug 18
Logo
10:12 am - 8:27 pmORD-HYA
9h 15m2 stops
Logo
9:57 am - 10:22 pmHYA-ORD
13h 25m2 stops
$604
Find Deal
Thu, Aug 14 - Mon, Aug 18
JetBlue Logo
8:40 am - 5:38 pmORD-HYA
7h 58m1 stop
JetBlue Logo
5:15 pm - 10:28 pmHYA-ORD
6h 13m1 stop
$809JetBlue
Find Deal
Sun, Aug 10 - Mon, Aug 11
JetBlue Logo
10:10 am - 8:58 pmORD-HYA
9h 48m2 stops
JetBlue Logo
11:00 am - 5:19 pmHYA-ORD
7h 19m1 stop
$929JetBlue
Find Deal
Mon, Dec 22 - Mon, Dec 29
JetBlue Logo
9:42 am - 5:38 pmORD-HYA
6h 56m1 stop
JetBlue Logo
9:18 am - 6:55 pmHYA-ORD
10h 37m2 stops
$1,003JetBlue
Find Deal
Fri, Sep 5 - Sun, Sep 7

American Airlines flights from Chicago to Hyannis

Our best American Airlines deals on Chicago to Hyannis flight tickets
American Airlines
Aug 16
ORD11:12 amChicago O'Hare Intl
2h 39m
HYA2:51 pmHyannis Barnstable
Aug 23
HYA3:25 pmHyannis Barnstable
3h 06m
ORD5:31 pmChicago O'Hare Intl
$310
Find similar
American Airlines
Aug 16
ORD8:09 amChicago O'Hare Intl
7h 36m
1 stop
HYA4:45 pmHyannis Barnstable
Aug 23
HYA3:25 pmHyannis Barnstable
3h 06m
ORD5:31 pmChicago O'Hare Intl
$344
Find similar
American Airlines
Aug 2
ORD5:25 amChicago O'Hare Intl
6h 37m
1 stop
HYA1:02 pmHyannis Barnstable
Aug 5
HYA12:20 pmHyannis Barnstable
6h 35m
1 stop
ORD5:55 pmChicago O'Hare Intl
$402
Find similar

JetBlue flights from Chicago to Hyannis

Our best JetBlue deals on Chicago to Hyannis flight tickets
JetBlue
Aug 6
ORD8:40 amChicago O'Hare Intl
7h 58m
1 stop
HYA5:38 pmHyannis Barnstable
Aug 12
HYA5:15 pmHyannis Barnstable
6h 13m
1 stop
ORD10:28 pmChicago O'Hare Intl
$782
Find similar
JetBlue
Aug 10
ORD8:40 amChicago O'Hare Intl
7h 58m
1 stop
HYA5:38 pmHyannis Barnstable
Aug 11
HYA5:15 pmHyannis Barnstable
6h 13m
1 stop
ORD10:28 pmChicago O'Hare Intl
$809
Find similar
JetBlue
Aug 6
ORD8:40 amChicago O'Hare Intl
7h 58m
1 stop
HYA5:38 pmHyannis Barnstable
Aug 7
HYA5:15 pmHyannis Barnstable
6h 13m
1 stop
ORD10:28 pmChicago O'Hare Intl
$912
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago 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 July 31, 2025.
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

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Sat 8/16

11:12 am-2:51 pm

Nonstop2h 39m

Hyannis Barnstable

Sat 8/23

3:25 pm-5:31 pm

Nonstop3h 06m

$310

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Sat 8/16

8:09 am-4:45 pm

1 stop7h 36m

Hyannis Barnstable

Sat 8/23

3:25 pm-5:31 pm

Nonstop3h 06m

$344

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Sat 8/16

8:09 am-4:45 pm

1 stop7h 36m

Hyannis Barnstable

Sat 8/23

1:40 pm-7:15 pm

1 stop6h 35m

$426

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Mon 8/25

8:45 pm-11:40 am

2 stops13h 55m

Hyannis Barnstable

Mon 9/1

2:34 pm-11:25 pm

1 stop9h 51m

$462

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Sat 8/16

11:12 am-2:51 pm

Nonstop2h 39m

Hyannis Barnstable

Mon 8/18

12:10 pm-5:20 pm

1 stop6h 10m

$467

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Sat 8/16

8:09 am-4:45 pm

1 stop7h 36m

Hyannis Barnstable

Mon 8/18

12:10 pm-5:20 pm

1 stop6h 10m

$476

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Thu 8/14

10:12 am-8:27 pm

2 stops9h 15m

Hyannis Barnstable

Mon 8/18

9:57 am-10:22 pm

2 stops13h 25m

$604

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Sun 8/10

8:40 am-5:38 pm

1 stop7h 58m

Hyannis Barnstable

Mon 8/11

5:15 pm-10:28 pm

1 stop6h 13m

$809

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Mon 12/22

10:10 am-8:58 pm

2 stops9h 48m

Hyannis Barnstable

Mon 12/29

11:00 am-5:19 pm

1 stop7h 19m

$929

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Fri 9/5

9:42 am-5:38 pm

1 stop6h 56m

Hyannis Barnstable

Sun 9/7

9:18 am-6:55 pm

2 stops10h 37m

$1,003

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 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 day to depart on your flight to Hyannis?

The cheapest day to depart from Chicago to Hyannis is on a Wednesday when prices can be found for as low as $289. On the other hand, Thursday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $417.

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 Barnstable flights?

There are 1 cabin classes available to choose from on Chicago to Hyannis Barnstable 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?

No. A direct flight is the cheapest option for a flight between Chicago to Hyannis.

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

$209

Fastest flight time

2h 39m

Direct flights

Sun

Airports in Hyannis

1 airport
The best one-way flight to Hyannis from Chicago in the past 72 hours is $209. The best round-trip flight deal from Chicago to Hyannis found on momondo in the last 72 hours is $310.
The fastest flight from Chicago to Hyannis takes 2h 39m
Direct flights go from Chicago to Hyannis on Sunday. The only airline offering direct flights is American Airlines.
There is 1 airport near Hyannis: Hyannis Barnstable (HYA)
Search flight deals

  • 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 2h 39m.

  • 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.

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