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Cheap flights from Chicago to Boston from $149

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 8/3. 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

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American Airlines Logo
7:00 am - 2:13 pm
ORD
-
HYA
6h 13m
1 stop
American Airlines Logo
3:00 pm - 4:52 pm
HYA
-
ORD
2h 52mnonstop
$301American Airlines
Sat, Jul 4 - Sat, Jul 11
American Airlines Logo
7:00 am - 2:13 pm
ORD
-
HYA
6h 13m
1 stop
American Airlines Logo
2:44 pm - 9:43 pm
HYA
-
ORD
7h 59m
1 stop
$310American Airlines
Sat, Jul 4 - Sat, Jul 11
American Airlines Logo
9:56 am - 5:27 pm
ORD
-
HYA
6h 31m
1 stop
American Airlines Logo
3:00 pm - 4:52 pm
HYA
-
ORD
2h 52mnonstop
$370American Airlines
Sat, Jul 4 - Sat, Jul 11
American Airlines Logo
7:00 am - 2:13 pm
ORD
-
HYA
6h 13m
1 stop
American Airlines Logo
1:33 pm - 5:56 pm
HYA
-
ORD
5h 23m
1 stop
$379American Airlines
Sat, Jul 4 - Sat, Jul 11
American Airlines Logo
10:50 am - 2:25 pm
ORD
-
HYA
2h 35mnonstop
American Airlines Logo
3:00 pm - 4:52 pm
HYA
-
ORD
2h 52mnonstop
$419American Airlines
Sat, Jul 4 - Sat, Jul 11
Multiple Airlines Logo
10:00 am - 5:20 pm
ORD
-
HYA
6h 20m
1 stop
Multiple Airlines Logo
12:07 pm - 11:26 pm
HYA
-
ORD
12h 19m
2 stops
$456Multiple Airlines
Tue, Feb 17 - Sat, Feb 21
Multiple Airlines Logo
9:18 am - 11:02 am
ORD
-
HYA
24h 44m
2 stops
Multiple Airlines Logo
7:05 am - 7:47 pm
HYA
-
ORD
13h 42m
2 stops
$476Multiple Airlines
Tue, Feb 17 - Sat, Feb 21
Multiple Airlines Logo
9:18 am - 11:02 am
ORD
-
HYA
24h 44m
2 stops
Multiple Airlines Logo
7:05 am - 11:47 pm
HYA
-
ORD
17h 42m
3 stops
$504Multiple Airlines
Tue, Feb 17 - Sat, Feb 21
Multiple Airlines Logo
10:19 am - 11:02 am
ORD
-
HYA
23h 43m
3 stops
Multiple Airlines Logo
7:05 am - 11:47 pm
HYA
-
ORD
17h 42m
3 stops
$535Multiple Airlines
Tue, Feb 17 - Sat, Feb 21
Multiple Airlines Logo
4:43 pm - 5:20 pm
ORD
-
HYA
23h 37m
3 stops
Multiple Airlines Logo
12:41 pm - 7:11 pm
HYA
-
ORD
31h 30m
3 stops
$818Multiple Airlines
Thu, Feb 19 - Mon, Feb 23

American Airlines flights from Chicago to Hyannis

Our best American Airlines deals on Chicago to Hyannis flight tickets
American Airlines
Jul 4
ORD7:00 amChicago O'Hare Intl
6h 13m
1 stop
HYA2:13 pmHyannis Barnstable
Jul 11
HYA3:00 pmHyannis Barnstable
2h 52m
ORD4:52 pmChicago O'Hare Intl
$301
American Airlines
Jul 4
ORD7:00 amChicago O'Hare Intl
6h 13m
1 stop
HYA2:13 pmHyannis Barnstable
Jul 11
HYA2:44 pmHyannis Barnstable
7h 59m
1 stop
ORD9:43 pmChicago O'Hare Intl
$310
American Airlines
Jul 4
ORD9:56 amChicago O'Hare Intl
6h 31m
1 stop
HYA5:27 pmHyannis Barnstable
Jul 11
HYA3:00 pmHyannis Barnstable
2h 52m
ORD4:52 pmChicago O'Hare Intl
$370

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 February 4, 2026.
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 7/4

7:00 am-2:13 pm

1 stop6h 13m

Hyannis Barnstable

Sat 7/11

3:00 pm-4:52 pm

Nonstop2h 52m

$301

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Sat 7/4

7:00 am-2:13 pm

1 stop6h 13m

Hyannis Barnstable

Sat 7/11

2:44 pm-9:43 pm

1 stop7h 59m

$310

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Sat 7/4

9:56 am-5:27 pm

1 stop6h 31m

Hyannis Barnstable

Sat 7/11

3:00 pm-4:52 pm

Nonstop2h 52m

$370

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Sat 7/4

7:00 am-2:13 pm

1 stop6h 13m

Hyannis Barnstable

Sat 7/11

1:33 pm-5:56 pm

1 stop5h 23m

$379

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Sat 7/4

10:50 am-2:25 pm

Nonstop2h 35m

Hyannis Barnstable

Sat 7/11

3:00 pm-4:52 pm

Nonstop2h 52m

$419

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Tue 2/17

10:00 am-5:20 pm

1 stop6h 20m

Hyannis Barnstable

Sat 2/21

12:07 pm-11:26 pm

2 stops12h 19m

$456

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Tue 2/17

9:18 am-11:02 am

2 stops24h 44m

Hyannis Barnstable

Sat 2/21

7:05 am-7:47 pm

2 stops13h 42m

$476

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Tue 2/17

9:18 am-11:02 am

2 stops24h 44m

Hyannis Barnstable

Sat 2/21

7:05 am-11:47 pm

3 stops17h 42m

$504

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Tue 2/17

10:19 am-11:02 am

3 stops23h 43m

Hyannis Barnstable

Sat 2/21

7:05 am-11:47 pm

3 stops17h 42m

$535

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Thu 2/19

4:43 pm-5:20 pm

3 stops23h 37m

Hyannis Barnstable

Mon 2/23

12:41 pm-7:11 pm

3 stops31h 30m

$818

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 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 is only 1 cabin class 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?

You could potentially save up to 6% 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

Fastest flight time

2h 35m

Direct flights

Sun

Airports in Hyannis

1 airport
The fastest flight from Chicago to Hyannis takes 2h 35m
Direct flights go from Chicago to Hyannis on Sunday. There are no airlines offering direct flights.
There is 1 airport in Hyannis. From Chicago there are direct flights to 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 35m.

  • 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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