What airlines fly to Chicago?

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Chicago from Hyannis according to our data. United Airlines is the first choice among our users, with 38% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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.

$250 Cheap Flights from Hyannis to Chicago in 2026

Find the cheapest flights from Hyannis to Chicago

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One-way

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Cheap round-trip flights

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2:10 pm - 9:03 amHYA Hyannis Barnstable-ORD Chicago O'Hare Intl

19h 53m1 stop Boston Logan Intl

9:24 pm - 7:40 pmORD Chicago O'Hare Intl-HYA Hyannis Barnstable

21h 16m1 stop Boston Logan Intl

$622Multiple Airlines

Sat, Sep 19 - Sat, Sep 26

2:10 pm - 12:28 amHYA Hyannis Barnstable-ORD Chicago O'Hare Intl

11h 18m2 stops Boston Logan Intl Newark

9:24 pm - 7:40 pmORD Chicago O'Hare Intl-HYA Hyannis Barnstable

21h 16m1 stop Boston Logan Intl

$627Multiple Airlines

Sat, Sep 19 - Sat, Sep 26

11:02 am - 7:01 pmHYA Hyannis Barnstable-ORD Chicago O'Hare Intl

8h 59m1 stop Boston Logan Intl

9:38 am - 2:45 pmORD Chicago O'Hare Intl-HYA Hyannis Barnstable

4h 07m1 stop Boston Logan Intl

$812Multiple Airlines

Tue, Sep 15 - Sat, Sep 19

2:10 pm - 12:28 amHYA Hyannis Barnstable-ORD Chicago O'Hare Intl

11h 18m2 stops Boston Logan Intl Newark

6:00 am - 2:45 pmORD Chicago O'Hare Intl-HYA Hyannis Barnstable

7h 45m2 stops Newark Boston Logan Intl

$813Multiple Airlines

Sat, Sep 19 - Sat, Sep 26

1:20 pm - 9:00 amHYA Hyannis Barnstable-ORD Chicago O'Hare Intl

20h 40m1 stop Boston Logan Intl

6:10 am - 3:00 pmORD Chicago O'Hare Intl-HYA Hyannis Barnstable

7h 50m1 stop Boston Logan Intl

$822Multiple Airlines

Thu, Oct 15 - Sat, Oct 17

1:20 pm - 9:00 amHYA Hyannis Barnstable-ORD Chicago O'Hare Intl

20h 40m1 stop Boston Logan Intl

6:00 am - 3:00 pmORD Chicago O'Hare Intl-HYA Hyannis Barnstable

8h 00m2 stops Newark Boston Logan Intl

$827Multiple Airlines

Thu, Oct 15 - Sat, Oct 17

11:02 am - 10:29 pmHYA Hyannis Barnstable-ORD Chicago O'Hare Intl

12h 27m1 stop Boston Logan Intl

8:50 am - 7:40 pmORD Chicago O'Hare Intl-HYA Hyannis Barnstable

9h 50m2 stops Washington, D.C. Dulles Intl Boston Logan Intl

$843Multiple Airlines

Thu, Sep 24 - Sun, Sep 27

1:20 pm - 9:00 amHYA Hyannis Barnstable-ORD Chicago O'Hare Intl

20h 40m1 stop Boston Logan Intl

6:10 am - 3:00 pmORD Chicago O'Hare Intl-HYA Hyannis Barnstable

7h 50m1 stop Boston Logan Intl

$852Multiple Airlines

Thu, Oct 15 - Sun, Oct 18

1:20 pm - 2:54 pmHYA Hyannis Barnstable-ORD Chicago O'Hare Intl

26h 34m3 stops Boston Logan Intl Newark Cleveland Hopkins Intl

3:40 pm - 3:00 pmORD Chicago O'Hare Intl-HYA Hyannis Barnstable

22h 20m1 stop Boston Logan Intl

$937Multiple Airlines

Tue, Nov 24 - Fri, Nov 27

2:15 pm - 7:01 pmHYA Hyannis Barnstable-ORD Chicago O'Hare Intl

5h 46m1 stop Boston Logan Intl

9:38 am - 5:12 pmORD Chicago O'Hare Intl-HYA Hyannis Barnstable

6h 34m1 stop Boston Logan Intl

$953Multiple Airlines

Mon, Sep 14 - Fri, Sep 18

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JetBlue flights from Hyannis to Chicago

Our best JetBlue deals on Hyannis to Chicago flight tickets

JetBlue

Sep 3

HYA4:20 pmHyannis Barnstable

6h 38m

1 stop

ORD9:58 pmChicago O'Hare Intl

Sep 5

ORD9:41 amChicago O'Hare Intl

4h 33m

1 stop

HYA3:14 pmHyannis Barnstable

$1,106

JetBlue

Sep 3

HYA4:20 pmHyannis Barnstable

6h 38m

1 stop

ORD9:58 pmChicago O'Hare Intl

Sep 6

ORD6:00 amChicago O'Hare Intl

8h 13m

1 stop

HYA3:13 pmHyannis Barnstable

$1,251

JetBlue

Sep 3

HYA4:20 pmHyannis Barnstable

6h 38m

1 stop

ORD9:58 pmChicago O'Hare Intl

Sep 5

ORD9:41 amChicago O'Hare Intl

4h 33m

1 stop

HYA3:14 pmHyannis Barnstable

$1,339

American Airlines flights from Hyannis to Chicago

Our best American Airlines deals on Hyannis to Chicago flight tickets

American Airlines

Sep 2

HYA1:47 pmHyannis Barnstable

6h 42m

1 stop

ORD7:29 pmChicago O'Hare Intl

Sep 5

ORD11:15 amChicago O'Hare Intl

2h 42m

HYA2:57 pmHyannis Barnstable

$426

American Airlines

Sep 2

HYA12:42 pmHyannis Barnstable

8h 04m

1 stop

ORD7:46 pmChicago O'Hare Intl

Sep 5

ORD5:00 amChicago O'Hare Intl

6h 12m

1 stop

HYA12:12 pmHyannis Barnstable

$435

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HyannisChicago

HYA Hyannis Barnstable - ORD Chicago O'Hare Intl

HYAORD

Hyannis Barnstable

Sat 9/19

2:10 pm-9:03 am

1 stop19h 53m

Chicago O'Hare Intl

Sat 9/26

9:24 pm-7:40 pm

1 stop21h 16m

$622

HyannisChicago

HYA Hyannis Barnstable - ORD Chicago O'Hare Intl

HYAORD

Hyannis Barnstable

Sat 9/19

2:10 pm-12:28 am

2 stops11h 18m

Chicago O'Hare Intl

Sat 9/26

9:24 pm-7:40 pm

1 stop21h 16m

$627

HyannisChicago

HYA Hyannis Barnstable - ORD Chicago O'Hare Intl

HYAORD

Hyannis Barnstable

Tue 9/15

11:02 am-7:01 pm

1 stop8h 59m

Chicago O'Hare Intl

Sat 9/19

9:38 am-2:45 pm

1 stop4h 07m

$812

HyannisChicago

HYA Hyannis Barnstable - ORD Chicago O'Hare Intl

HYAORD

Hyannis Barnstable

Sat 9/19

2:10 pm-12:28 am

2 stops11h 18m

Chicago O'Hare Intl

Sat 9/26

6:00 am-2:45 pm

2 stops7h 45m

$813

HyannisChicago

HYA Hyannis Barnstable - ORD Chicago O'Hare Intl

HYAORD

Hyannis Barnstable

Thu 10/15

1:20 pm-9:00 am

1 stop20h 40m

Chicago O'Hare Intl

Sat 10/17

6:10 am-3:00 pm

1 stop7h 50m

$822

HyannisChicago

HYA Hyannis Barnstable - ORD Chicago O'Hare Intl

HYAORD

Hyannis Barnstable

Thu 10/15

1:20 pm-9:00 am

1 stop20h 40m

Chicago O'Hare Intl

Sat 10/17

6:00 am-3:00 pm

2 stops8h 00m

$827

HyannisChicago

HYA Hyannis Barnstable - ORD Chicago O'Hare Intl

HYAORD

Hyannis Barnstable

Thu 9/24

11:02 am-10:29 pm

1 stop12h 27m

Chicago O'Hare Intl

Sun 9/27

8:50 am-7:40 pm

2 stops9h 50m

$843

HyannisChicago

HYA Hyannis Barnstable - ORD Chicago O'Hare Intl

HYAORD

Hyannis Barnstable

Thu 10/15

1:20 pm-9:00 am

1 stop20h 40m

Chicago O'Hare Intl

Sun 10/18

6:10 am-3:00 pm

1 stop7h 50m

$852

HyannisChicago

HYA Hyannis Barnstable - ORD Chicago O'Hare Intl

HYAORD

Hyannis Barnstable

Tue 11/24

1:20 pm-2:54 pm

3 stops26h 34m

Chicago O'Hare Intl

Fri 11/27

3:40 pm-3:00 pm

1 stop22h 20m

$937

Quickest round-trip

HyannisChicago

HYA Hyannis Barnstable - ORD Chicago O'Hare Intl

HYAORD

Hyannis Barnstable

Mon 9/14

2:15 pm-7:01 pm

1 stop5h 46m

Chicago O'Hare Intl

Fri 9/18

9:38 am-5:12 pm

1 stop6h 34m

$953

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

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 $320. 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 $418.

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 $284. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $370.

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 is only 1 cabin class 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

Best Price Found	$250
Fastest flight time	6h 38m
Direct flights	None

The best one-way flight to Chicago from Hyannis in the past 72 hours is $250. The best round-trip flight deal from Hyannis to Chicago found on momondo in the last 72 hours is $622.

The fastest flight from Hyannis to Chicago takes 6h 38m

There are no direct flights from Hyannis to Chicago. There are no popular flight routes from Hyannis to Chicago.

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 38m.
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?
Based on momondo bookings for flights between Hyannis and Chicago, the leading plane model is Airbus A220-300, making up 18.18% of the total bookings. Other popular models include Boeing 737-800 with 18.18%, Embraer 175 with 18.18%, and Boeing 737 MAX 8 with 9.09%.

Merrillville

New Buffalo

Hammond

Portage

Benton Harbor

Lansing

Saint Joseph

Valparaiso

Schererville

Munster

Chesterton

Monticello

Porter

Crown Point

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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Cheap flights from Hyannis to Chicago from $250

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 10/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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JetBlue flights from Hyannis to Chicago

Our best JetBlue deals on Hyannis to Chicago flight tickets

American Airlines flights from Hyannis to Chicago

Our best American Airlines deals on Hyannis to Chicago flight tickets

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How to get the cheapest flight ticket from Hyannis to Chicago

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

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

What is the cheapest Hyannis Barnstable to Chicago flight route?

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

Can stopping save me money on Hyannis to Chicago flights?

What airlines fly to Chicago?

When to book flights from Hyannis to Chicago

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

Best Price Found

Fastest flight time

Direct flights

Frequently asked questions about flying from Hyannis to Chicago

Traveling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago 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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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Popular flights according to clicks in the last 7 days on momondo

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According to popular flight searches on momondo this year

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