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Cheap flights from Illinois to Boston from $215

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to Boston departing on 9/12. 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 Illinois to Boston

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
11:15 am - 2:57 pmORD  Chicago O'Hare Intl-HYA Hyannis Barnstable
2h 42mnonstop
American Airlines Logo
5:59 pm - 11:37 pmHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
6h 38m1 stop Washington, D.C. Reagan-National
$300American Airlines
Sat, Sep 5 - Sun, Sep 6
American Airlines Logo
6:45 am - 12:12 pmORD  Chicago O'Hare Intl-HYA Hyannis Barnstable
4h 27m1 stop Philadelphia
American Airlines Logo
12:42 pm - 7:46 pmHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
8h 04m1 stop Philadelphia
$309American Airlines
Sat, Sep 5 - Sun, Sep 6
JetBlue Logo
9:35 am - 3:13 pmORD  Chicago O'Hare Intl-HYA Hyannis Barnstable
4h 38m1 stop New York John F Kennedy Intl
JetBlue Logo
4:53 pm - 9:58 pmHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
6h 05m1 stop New York John F Kennedy Intl
$323JetBlue
Wed, Sep 2 - Sat, Sep 5
American Airlines Logo
11:15 am - 2:57 pmORD  Chicago O'Hare Intl-HYA Hyannis Barnstable
2h 42mnonstop
American Airlines Logo
5:59 pm - 11:37 pmHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
6h 38m1 stop Washington, D.C. Reagan-National
$406American Airlines
Sat, Aug 29 - Wed, Sep 2
American Airlines Logo
9:57 am - 4:32 pmORD  Chicago O'Hare Intl-HYA Hyannis Barnstable
5h 35m1 stop Washington, D.C. Reagan-National
American Airlines Logo
5:59 pm - 11:37 pmHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
6h 38m1 stop Washington, D.C. Reagan-National
$415American Airlines
Sat, Aug 29 - Wed, Sep 2
Multiple Airlines Logo
7:00 am - 10:55 pmORD  Chicago O'Hare Intl-HYA Hyannis Barnstable
14h 55m2 stops New York John F Kennedy Intl West Tisbury Martha's Vineyard
Multiple Airlines Logo
2:10 pm - 7:01 pmHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
5h 51m1 stop Boston Logan Intl
$524Multiple Airlines
Sun, Sep 13 - Sat, Sep 19
JetBlue Logo
9:40 am - 3:13 pmORD  Chicago O'Hare Intl-HYA Hyannis Barnstable
4h 33m1 stop New York John F Kennedy Intl
JetBlue Logo
4:20 pm - 9:58 pmHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
6h 38m1 stop New York John F Kennedy Intl
$535JetBlue
Sat, Aug 29 - Wed, Sep 2
Multiple Airlines Logo
7:00 am - 10:55 pmORD  Chicago O'Hare Intl-HYA Hyannis Barnstable
14h 55m2 stops New York John F Kennedy Intl West Tisbury Martha's Vineyard
Multiple Airlines Logo
11:02 am - 7:01 pmHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
8h 59m1 stop Boston Logan Intl
$546Multiple Airlines
Mon, Sep 14 - Fri, Sep 18
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
11:02 am - 10:30 pmHYA  Hyannis Barnstable-ORD Chicago O'Hare Intl
12h 28m1 stop Boston Logan Intl
$556Multiple Airlines
Mon, Sep 14 - Fri, Sep 18
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
$608Multiple Airlines
Tue, Sep 22 - Sun, Sep 27

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American Airlines flights from Illinois to Hyannis

Our best American Airlines deals on Illinois to Hyannis flight tickets
American Airlines
Sep 5
ORD11:15 amChicago O'Hare Intl
2h 42m
HYA2:57 pmHyannis Barnstable
Sep 6
HYA5:59 pmHyannis Barnstable
6h 38m
1 stop
ORD11:37 pmChicago O'Hare Intl
$300
American Airlines
Sep 5
ORD6:45 amChicago O'Hare Intl
4h 27m
1 stop
HYA12:12 pmHyannis Barnstable
Sep 6
HYA12:42 pmHyannis Barnstable
8h 04m
1 stop
ORD7:46 pmChicago O'Hare Intl
$309
American Airlines
Aug 29
ORD11:15 amChicago O'Hare Intl
2h 42m
HYA2:57 pmHyannis Barnstable
Sep 2
HYA5:59 pmHyannis Barnstable
6h 38m
1 stop
ORD11:37 pmChicago O'Hare Intl
$406

JetBlue flights from Illinois to Hyannis

Our best JetBlue deals on Illinois 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
$323
JetBlue
Aug 29
ORD9:40 amChicago O'Hare Intl
4h 33m
1 stop
HYA3:13 pmHyannis Barnstable
Sep 2
HYA4:20 pmHyannis Barnstable
6h 38m
1 stop
ORD9:58 pmChicago O'Hare Intl
$535
JetBlue
Aug 28
ORD9:42 amChicago O'Hare Intl
4h 31m
1 stop
HYA3:13 pmHyannis Barnstable
Sep 1
HYA4:20 pmHyannis Barnstable
6h 38m
1 stop
ORD9:58 pmChicago O'Hare Intl
$641

momondo Fare Finder

 
Customize your flight search to find flights from Illinois 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 August 15, 2026.
Use the filters below to find and compare flights from Illinois to Hyannis that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Sat 9/5

11:15 am-2:57 pm

Nonstop2h 42m

Hyannis Barnstable

Sun 9/6

5:59 pm-11:37 pm

1 stop6h 38m

$300

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Sat 9/5

6:45 am-12:12 pm

1 stop4h 27m

Hyannis Barnstable

Sun 9/6

12:42 pm-7:46 pm

1 stop8h 04m

$309

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Wed 9/2

9:35 am-3:13 pm

1 stop4h 38m

Hyannis Barnstable

Sat 9/5

4:53 pm-9:58 pm

1 stop6h 05m

$323

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Sat 8/29

11:15 am-2:57 pm

Nonstop2h 42m

Hyannis Barnstable

Wed 9/2

5:59 pm-11:37 pm

1 stop6h 38m

$406

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Sat 8/29

9:57 am-4:32 pm

1 stop5h 35m

Hyannis Barnstable

Wed 9/2

5:59 pm-11:37 pm

1 stop6h 38m

$415

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Sun 9/13

7:00 am-10:55 pm

2 stops14h 55m

Hyannis Barnstable

Sat 9/19

2:10 pm-7:01 pm

1 stop5h 51m

$524

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Sat 8/29

9:40 am-3:13 pm

1 stop4h 33m

Hyannis Barnstable

Wed 9/2

4:20 pm-9:58 pm

1 stop6h 38m

$535

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Mon 9/14

7:00 am-10:55 pm

2 stops14h 55m

Hyannis Barnstable

Fri 9/18

11:02 am-7:01 pm

1 stop8h 59m

$546

ChicagoHyannis

ORD Chicago O'Hare Intl - HYA Hyannis Barnstable

ORDHYA

Chicago O'Hare Intl

Mon 9/14

6:10 am-12:50 pm

1 stop5h 40m

Hyannis Barnstable

Fri 9/18

11:02 am-10:30 pm

1 stop12h 28m

$556

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

$608

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 Illinois 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 Illinois to Hyannis Barnstable flight route?

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

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

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

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

Cheap Illinois to Hyannis flight deals and tips

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

Fastest flight time

4h 33m

Direct flights

Sun

Airports in Hyannis

1 airport
The fastest flight from Illinois to Hyannis takes 4h 33m
Direct flights go from Illinois to Hyannis on Sunday. There are no airlines offering direct flights.
There is 1 airport in Hyannis. From Illinois there are direct flights to Hyannis Barnstable (HYA).
Search flight deals

Frequently asked questions about flying from Illinois to Hyannis

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

    Prices for flights from Illinois to Hyannis Barnstable Airport were last updated today.

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Illinois to Hyannis Barnstable Airport.

  • What documentation or ID do you need to fly to Hyannis Barnstable Airport?

    The travel and health documents required for your trip to Hyannis Barnstable Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Hyannis Barnstable Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Illinois to Hyannis?

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Hyannis from Illinois.

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

Flights from Illinois to Hyannis with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once all potential Illinois to Hyannis flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Illinois to Hyannis right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Hyannis, momondo offers a useful price alert feature which will track prices for flights to Hyannis from Illinois and alert you when they change.

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