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Cheap flights from Chicago to Boston from $85

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 8/25. 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 to Boston

Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
6:00 am - 3:13 pm
ORD
-
HYA
8h 13m
1 stop
JetBlue Logo
4:53 pm - 9:58 pm
HYA
-
ORD
6h 05m
1 stop
$167JetBlue
Tue, Aug 25 - Sat, Aug 29
JetBlue Logo
9:35 am - 3:13 pm
ORD
-
HYA
4h 38m
1 stop
JetBlue Logo
4:53 pm - 9:58 pm
HYA
-
ORD
6h 05m
1 stop
$183JetBlue
Wed, Aug 12 - Sat, Aug 15
JetBlue Logo
6:00 am - 3:13 pm
ORD
-
HYA
8h 13m
1 stop
JetBlue Logo
4:53 pm - 9:58 pm
HYA
-
ORD
6h 05m
1 stop
$199JetBlue
Tue, Aug 25 - Sat, Aug 29
JetBlue Logo
6:00 am - 3:13 pm
ORD
-
HYA
8h 13m
1 stop
JetBlue Logo
4:20 pm - 9:58 pm
HYA
-
ORD
6h 38m
1 stop
$211JetBlue
Wed, Jul 29 - Wed, Aug 5
JetBlue Logo
6:00 am - 3:13 pm
ORD
-
HYA
8h 13m
1 stop
JetBlue Logo
4:53 pm - 9:58 pm
HYA
-
ORD
6h 05m
1 stop
$227JetBlue
Sat, Aug 15 - Sat, Aug 22
JetBlue Logo
6:00 am - 3:13 pm
ORD
-
HYA
8h 13m
1 stop
JetBlue Logo
4:53 pm - 9:58 pm
HYA
-
ORD
6h 05m
1 stop
$246JetBlue
Wed, Jul 22 - Sat, Jul 25
JetBlue Logo
6:00 am - 3:13 pm
ORD
-
HYA
8h 13m
1 stop
JetBlue Logo
4:20 pm - 9:58 pm
HYA
-
ORD
6h 38m
1 stop
$262JetBlue
Sat, Aug 22 - Mon, Aug 24
JetBlue Logo
9:40 am - 3:13 pm
ORD
-
HYA
4h 33m
1 stop
JetBlue Logo
4:53 pm - 9:58 pm
HYA
-
ORD
6h 05m
1 stop
$277JetBlue
Tue, Aug 25 - Sat, Aug 29
JetBlue Logo
6:00 am - 3:13 pm
ORD
-
HYA
8h 13m
1 stop
JetBlue Logo
4:20 pm - 9:58 pm
HYA
-
ORD
6h 38m
1 stop
$290JetBlue
Tue, Aug 4 - Thu, Aug 6
JetBlue Logo
6:00 am - 3:13 pm
ORD
-
HYA
8h 13m
1 stop
JetBlue Logo
4:20 pm - 9:58 pm
HYA
-
ORD
6h 38m
1 stop
$298JetBlue
Mon, Aug 24 - Mon, Aug 31

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American Airlines flights from Chicago to Hyannis

Our best American Airlines deals on Chicago to Hyannis flight tickets
American Airlines
Aug 15
ORD9:57 amChicago O'Hare Intl
5h 35m
1 stop
HYA4:32 pmHyannis Barnstable
Aug 22
HYA12:42 pmHyannis Barnstable
8h 04m
1 stop
ORD7:46 pmChicago O'Hare Intl
$299
American Airlines
Aug 12
ORD6:45 amChicago O'Hare Intl
4h 27m
1 stop
HYA12:12 pmHyannis Barnstable
Aug 24
HYA12:42 pmHyannis Barnstable
8h 04m
1 stop
ORD7:46 pmChicago O'Hare Intl
$329
American Airlines
Jul 18
ORD11:45 amChicago O'Hare Intl
2h 50m
HYA3:35 pmHyannis Barnstable
Jul 25
HYA6:08 pmHyannis Barnstable
6h 22m
1 stop
ORD11:30 pmChicago O'Hare Intl
$396

JetBlue flights from Chicago to Hyannis

Our best JetBlue deals on Chicago to Hyannis flight tickets
JetBlue
Aug 25
ORD6:00 amChicago O'Hare Intl
8h 13m
1 stop
HYA3:13 pmHyannis Barnstable
Aug 29
HYA4:53 pmHyannis Barnstable
6h 05m
1 stop
ORD9:58 pmChicago O'Hare Intl
$167
JetBlue
Aug 12
ORD9:35 amChicago O'Hare Intl
4h 38m
1 stop
HYA3:13 pmHyannis Barnstable
Aug 15
HYA4:53 pmHyannis Barnstable
6h 05m
1 stop
ORD9:58 pmChicago O'Hare Intl
$183
JetBlue
Aug 25
ORD6:00 amChicago O'Hare Intl
8h 13m
1 stop
HYA3:13 pmHyannis Barnstable
Aug 29
HYA4:53 pmHyannis Barnstable
6h 05m
1 stop
ORD9:58 pmChicago O'Hare Intl
$199

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 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

Cheapest round-trip

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Tue 8/25

6:00 am-3:13 pm

1 stop8h 13m

Hyannis Barnstable

Sat 8/29

4:53 pm-9:58 pm

1 stop6h 05m

$167

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Wed 8/12

9:35 am-3:13 pm

1 stop4h 38m

Hyannis Barnstable

Sat 8/15

4:53 pm-9:58 pm

1 stop6h 05m

$183

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Tue 8/25

6:00 am-3:13 pm

1 stop8h 13m

Hyannis Barnstable

Sat 8/29

4:53 pm-9:58 pm

1 stop6h 05m

$199

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Wed 7/29

6:00 am-3:13 pm

1 stop8h 13m

Hyannis Barnstable

Wed 8/5

4:20 pm-9:58 pm

1 stop6h 38m

$211

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Sat 8/15

6:00 am-3:13 pm

1 stop8h 13m

Hyannis Barnstable

Sat 8/22

4:53 pm-9:58 pm

1 stop6h 05m

$227

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Wed 7/22

6:00 am-3:13 pm

1 stop8h 13m

Hyannis Barnstable

Sat 7/25

4:53 pm-9:58 pm

1 stop6h 05m

$246

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Sat 8/22

6:00 am-3:13 pm

1 stop8h 13m

Hyannis Barnstable

Mon 8/24

4:20 pm-9:58 pm

1 stop6h 38m

$262
Quickest round-trip

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Tue 8/25

9:40 am-3:13 pm

1 stop4h 33m

Hyannis Barnstable

Sat 8/29

4:53 pm-9:58 pm

1 stop6h 05m

$277

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Tue 8/4

6:00 am-3:13 pm

1 stop8h 13m

Hyannis Barnstable

Thu 8/6

4:20 pm-9:58 pm

1 stop6h 38m

$290

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Mon 8/24

6:00 am-3:13 pm

1 stop8h 13m

Hyannis Barnstable

Mon 8/31

4:20 pm-9:58 pm

1 stop6h 38m

$298

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
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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 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 33% 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

4h 33m

Direct flights

Sun

Airports in Hyannis

1 airport
The fastest flight from Chicago to Hyannis takes 4h 33m
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

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 4h 33m.

  • 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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