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Cheap flights from Hyannis to Chicago from $99

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Hyannis to Chicago departing on 8/4. 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 Hyannis to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
4:53 pm - 9:58 pm
HYA
-
ORD
6h 05m
1 stop
JetBlue Logo
9:37 am - 3:13 pm
ORD
-
HYA
4h 36m
1 stop
$199JetBlue
Tue, Aug 4 - Wed, Aug 5
JetBlue Logo
4:53 pm - 9:58 pm
HYA
-
ORD
6h 05m
1 stop
JetBlue Logo
6:00 am - 3:13 pm
ORD
-
HYA
8h 13m
1 stop
$227JetBlue
Tue, Jul 28 - Tue, Aug 4
JetBlue Logo
4:20 pm - 9:58 pm
HYA
-
ORD
6h 38m
1 stop
JetBlue Logo
9:35 am - 3:13 pm
ORD
-
HYA
4h 38m
1 stop
$262JetBlue
Fri, Aug 14 - Tue, Aug 18
JetBlue Logo
4:20 pm - 9:58 pm
HYA
-
ORD
6h 38m
1 stop
JetBlue Logo
6:00 am - 3:13 pm
ORD
-
HYA
8h 13m
1 stop
$306JetBlue
Wed, Sep 2 - Fri, Sep 4
JetBlue Logo
4:53 pm - 9:58 pm
HYA
-
ORD
6h 05m
1 stop
JetBlue Logo
9:41 am - 3:33 pm
ORD
-
HYA
4h 52m
1 stop
$325JetBlue
Tue, Jul 21 - Sat, Jul 25
JetBlue Logo
4:20 pm - 9:58 pm
HYA
-
ORD
6h 38m
1 stop
JetBlue Logo
6:00 am - 3:13 pm
ORD
-
HYA
8h 13m
1 stop
$369JetBlue
Thu, Sep 3 - Sat, Sep 5
JetBlue Logo
4:53 pm - 9:58 pm
HYA
-
ORD
6h 05m
1 stop
JetBlue Logo
9:41 am - 3:33 pm
ORD
-
HYA
4h 52m
1 stop
$391JetBlue
Sat, Jul 18 - Sat, Jul 25
American Airlines Logo
4:05 pm - 6:39 pm
HYA
-
ORD
3h 34mnonstop
American Airlines Logo
9:42 am - 5:19 pm
ORD
-
HYA
6h 37m
1 stop
$420American Airlines
Sat, Jul 18 - Sat, Jul 25
JetBlue Logo
4:20 pm - 9:58 pm
HYA
-
ORD
6h 38m
1 stop
JetBlue Logo
6:00 am - 3:13 pm
ORD
-
HYA
8h 13m
1 stop
$425JetBlue
Mon, Aug 10 - Thu, Aug 13
JetBlue Logo
4:20 pm - 9:58 pm
HYA
-
ORD
6h 38m
1 stop
JetBlue Logo
9:35 am - 3:13 pm
ORD
-
HYA
4h 38m
1 stop
$433JetBlue
Mon, Aug 10 - Thu, Aug 13

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JetBlue flights from Hyannis to Chicago

Our best JetBlue deals on Hyannis to Chicago flight tickets
JetBlue
Aug 4
HYA4:53 pmHyannis Barnstable
6h 05m
1 stop
ORD9:58 pmChicago O'Hare Intl
Aug 5
ORD9:37 amChicago O'Hare Intl
4h 36m
1 stop
HYA3:13 pmHyannis Barnstable
$199
JetBlue
Jul 28
HYA4:53 pmHyannis Barnstable
6h 05m
1 stop
ORD9:58 pmChicago O'Hare Intl
Aug 4
ORD6:00 amChicago O'Hare Intl
8h 13m
1 stop
HYA3:13 pmHyannis Barnstable
$227
JetBlue
Aug 14
HYA4:20 pmHyannis Barnstable
6h 38m
1 stop
ORD9:58 pmChicago O'Hare Intl
Aug 18
ORD9:35 amChicago O'Hare Intl
4h 38m
1 stop
HYA3:13 pmHyannis Barnstable
$262

American Airlines flights from Hyannis to Chicago

Our best American Airlines deals on Hyannis to Chicago flight tickets
American Airlines
Jul 18
HYA4:05 pmHyannis Barnstable
3h 34m
ORD6:39 pmChicago O'Hare Intl
Jul 25
ORD9:42 amChicago O'Hare Intl
6h 37m
1 stop
HYA5:19 pmHyannis Barnstable
$420
American Airlines
Aug 5
HYA5:59 pmHyannis Barnstable
6h 38m
1 stop
ORD11:37 pmChicago O'Hare Intl
Aug 8
ORD5:00 amChicago O'Hare Intl
6h 12m
1 stop
HYA12:12 pmHyannis Barnstable
$489
American Airlines
Jul 13
HYA6:22 pmHyannis Barnstable
6h 08m
1 stop
ORD11:30 pmChicago O'Hare Intl
Jul 20
ORD6:00 amChicago O'Hare Intl
5h 56m
1 stop
HYA12:56 pmHyannis Barnstable
$501

momondo Fare Finder

 
Customize your flight search to find flights from Hyannis to Chicago 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 7, 2026.
Use the filters below to find and compare flights from Hyannis to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 8/4

4:53 pm-9:58 pm

1 stop6h 05m

Chicago O'Hare Intl

Wed 8/5

9:37 am-3:13 pm

1 stop4h 36m

$199

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 7/28

4:53 pm-9:58 pm

1 stop6h 05m

Chicago O'Hare Intl

Tue 8/4

6:00 am-3:13 pm

1 stop8h 13m

$227

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 8/14

4:20 pm-9:58 pm

1 stop6h 38m

Chicago O'Hare Intl

Tue 8/18

9:35 am-3:13 pm

1 stop4h 38m

$262

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 9/2

4:20 pm-9:58 pm

1 stop6h 38m

Chicago O'Hare Intl

Fri 9/4

6:00 am-3:13 pm

1 stop8h 13m

$306

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 7/21

4:53 pm-9:58 pm

1 stop6h 05m

Chicago O'Hare Intl

Sat 7/25

9:41 am-3:33 pm

1 stop4h 52m

$325

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 9/3

4:20 pm-9:58 pm

1 stop6h 38m

Chicago O'Hare Intl

Sat 9/5

6:00 am-3:13 pm

1 stop8h 13m

$369

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sat 7/18

4:53 pm-9:58 pm

1 stop6h 05m

Chicago O'Hare Intl

Sat 7/25

9:41 am-3:33 pm

1 stop4h 52m

$391
Quickest round-trip

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sat 7/18

4:05 pm-6:39 pm

Nonstop3h 34m

Chicago O'Hare Intl

Sat 7/25

9:42 am-5:19 pm

1 stop6h 37m

$420

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 8/10

4:20 pm-9:58 pm

1 stop6h 38m

Chicago O'Hare Intl

Thu 8/13

6:00 am-3:13 pm

1 stop8h 13m

$425

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 8/10

4:20 pm-9:58 pm

1 stop6h 38m

Chicago O'Hare Intl

Thu 8/13

9:35 am-3:13 pm

1 stop4h 38m

$433

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 Chicago from

How to get the cheapest flight ticket from Hyannis to Chicago

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 Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $317. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Hyannis to Chicago for around $410.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Hyannis to Chicago during this time can be as low as $272. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $371.

What is the cheapest Hyannis Barnstable to Chicago flight route?

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

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

There are 2 cabin classes available to choose from on Hyannis to Chicago 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 Hyannis to Chicago flights?

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

When to book flights from Hyannis to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Hyannis to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Hyannis to Chicago (HYA to CHI) flight deals and tips

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

Fastest flight time

6h 05m

Direct flights

Sun

Airports in Chicago

3 airports
The fastest flight from Hyannis to Chicago takes 6h 05m
Direct flights go from Hyannis to Chicago on Sunday. The only airline offering direct flights is American Airlines.
There are 3 airports in Chicago. From Hyannis there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from Hyannis to Chicago

  • How far is Hyannis Barnstable to Chicago by plane?

    Chicago is 891.6 mi away from Hyannis Barnstable. A reasonable flight in good conditions will take 6h 05m.

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

    Prices for flights from Hyannis Barnstable Airport to Chicago are updated daily.

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Hyannis Barnstable Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
Saint John

Why use momondo?

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

It is quick and easy to find Hyannis to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Flights from Hyannis to Chicago 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 Hyannis to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Hyannis to Chicago.

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

Price alerts on flights to Chicago from Hyannis are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport