Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Chicago to Boston from $193

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 12/11. 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

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

Find the cheapest flights from Chicago to Boston

Cheap round-trip flights

JetBlue Logo
10:08 am - 6:39 pmORD-HYA
7h 31m1 stop
JetBlue Logo
12:07 pm - 6:18 pmHYA-ORD
7h 11m1 stop
$365JetBlue
Find Deal
vie., oct. 17 - dom., oct. 19
JetBlue Logo
12:10 pm - 6:39 pmORD-HYA
5h 29m1 stop
JetBlue Logo
12:07 pm - 5:31 pmHYA-ORD
6h 24m1 stop
$425JetBlue
Find Deal
lun., feb. 16 - vie., feb. 20
JetBlue Logo
12:10 pm - 6:39 pmORD-HYA
5h 29m1 stop
JetBlue Logo
12:07 pm - 5:31 pmHYA-ORD
6h 24m1 stop
$430JetBlue
Find Deal
jue., mar. 12 - lun., mar. 16
JetBlue Logo
9:51 am - 5:38 pmORD-HYA
6h 47m1 stop
JetBlue Logo
10:16 am - 6:23 pmHYA-ORD
9h 07m1 stop
$432JetBlue
Find Deal
mar., sep. 30 - sáb., oct. 4
JetBlue Logo
11:25 am - 6:39 pmORD-HYA
6h 14m1 stop
JetBlue Logo
12:07 pm - 6:29 pmHYA-ORD
7h 22m1 stop
$485JetBlue
Find Deal
mié., dic. 17 - mié., dic. 24
Multiple Airlines Logo
9:20 pm - 6:39 pmORD-HYA
20h 19m1 stop
Multiple Airlines Logo
4:09 pm - 11:40 amHYA-ORD
20h 31m1 stop
$583Multiple Airlines
Find Deal
jue., oct. 23 - lun., oct. 27
JetBlue Logo
6:45 am - 1:10 pmORD-HYA
5h 25m1 stop
JetBlue Logo
12:07 pm - 7:17 pmHYA-ORD
8h 10m1 stop
$585JetBlue
Find Deal
mar., dic. 23 - sáb., ene. 3
JetBlue Logo
6:45 am - 1:10 pmORD-HYA
5h 25m1 stop
JetBlue Logo
12:07 pm - 6:29 pmHYA-ORD
7h 22m1 stop
$645JetBlue
Find Deal
vie., dic. 26 - jue., ene. 1
Multiple Airlines Logo
6:00 am - 6:39 pmORD-HYA
11h 39m2 stops
Multiple Airlines Logo
9:35 am - 12:45 pmHYA-ORD
28h 10m1 stop
$769Multiple Airlines
Find Deal
jue., oct. 23 - lun., oct. 27
JetBlue Logo
6:45 am - 1:10 pmORD-HYA
5h 25m1 stop
JetBlue Logo
12:07 pm - 6:29 pmHYA-ORD
7h 22m1 stop
$770JetBlue
Find Deal
lun., dic. 22 - vie., ene. 2

JetBlue flights from Chicago to Hyannis

Our best JetBlue deals on Chicago to Hyannis flight tickets
JetBlue
Oct 17
ORD10:08 amChicago O'Hare Intl
7h 31m
1 stop
HYA6:39 pmHyannis Barnstable
Oct 19
HYA12:07 pmHyannis Barnstable
7h 11m
1 stop
ORD6:18 pmChicago O'Hare Intl
$365
Find similar
JetBlue
Feb 16
ORD12:10 pmChicago O'Hare Intl
5h 29m
1 stop
HYA6:39 pmHyannis Barnstable
Feb 20
HYA12:07 pmHyannis Barnstable
6h 24m
1 stop
ORD5:31 pmChicago O'Hare Intl
$425
Find similar
JetBlue
Mar 12
ORD12:10 pmChicago O'Hare Intl
5h 29m
1 stop
HYA6:39 pmHyannis Barnstable
Mar 16
HYA12:07 pmHyannis Barnstable
6h 24m
1 stop
ORD5:31 pmChicago O'Hare Intl
$430
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 septiembre 17, 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

vie. 10/17

10:08 am-6:39 pm

1 stop7h 31m

Hyannis Barnstable

dom. 10/19

12:07 pm-6:18 pm

1 stop7h 11m

$365

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

lun. 2/16

12:10 pm-6:39 pm

1 stop5h 29m

Hyannis Barnstable

vie. 2/20

12:07 pm-5:31 pm

1 stop6h 24m

$425

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

jue. 3/12

12:10 pm-6:39 pm

1 stop5h 29m

Hyannis Barnstable

lun. 3/16

12:07 pm-5:31 pm

1 stop6h 24m

$430

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

mar. 9/30

9:51 am-5:38 pm

1 stop6h 47m

Hyannis Barnstable

sáb. 10/4

10:16 am-6:23 pm

1 stop9h 07m

$432

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

mié. 12/17

11:25 am-6:39 pm

1 stop6h 14m

Hyannis Barnstable

mié. 12/24

12:07 pm-6:29 pm

1 stop7h 22m

$485

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

jue. 10/23

9:20 pm-6:39 pm

1 stop20h 19m

Hyannis Barnstable

lun. 10/27

4:09 pm-11:40 am

1 stop20h 31m

$583

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

mar. 12/23

6:45 am-1:10 pm

1 stop5h 25m

Hyannis Barnstable

sáb. 1/3

12:07 pm-7:17 pm

1 stop8h 10m

$585

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

vie. 12/26

6:45 am-1:10 pm

1 stop5h 25m

Hyannis Barnstable

jue. 1/1

12:07 pm-6:29 pm

1 stop7h 22m

$645

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

jue. 10/23

6:00 am-6:39 pm

2 stops11h 39m

Hyannis Barnstable

lun. 10/27

9:35 am-12:45 pm

1 stop28h 10m

$769

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

lun. 12/22

6:45 am-1:10 pm

1 stop5h 25m

Hyannis Barnstable

vie. 1/2

12:07 pm-6:29 pm

1 stop7h 22m

$770

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 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 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?

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

Direct flights

None
There are no direct flights from Chicago to Hyannis. There are no popular flight routes from Chicago to Hyannis.
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 5h 25m.

  • 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
vie. 10/17
vie. 10/24
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States