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$193+ Cheap flights from Cape Cod and the Islands to Illinois

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/31. Fares are subject to change and may not be available on all flights or dates of travel.
ACK — ORD
Nov 1 — Nov 81
Sat 11/1
Sat 11/8
1 adult, Economy
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Cheap flight deals from Cape Cod and the Islands to Illinois

Keep the following information in mind while searching for Cape Cod and the Islands to Illinois flight deals. Data was last updated October 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$385
(JetBlue)

One-way from

$193
(JetBlue)

Popular in

April

Cheapest in

January

Average price

$237
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
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From Cape Cod and the Islands to Illinois
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One-way flight from Cape Cod and the Islands to Illinois
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Highest demand for flights based on searches. 8% potential increase in price ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Cape Cod and the Islands to Illinois

Cheapest flights from Cape Cod and the Islands to Illinois
Explore the most affordable flight options available from Cape Cod and the Islands to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 2, 2025.

This JetBlue deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1012:07 pmHYA - ORD
1 stop6h 48mJetBlue
Tue 11/1111:20 amORD - HYA
1 stop6h 19mJetBlue
Deal found 9/30$560
This JetBlue deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/282:30 pmHYA - ORD
1 stop6h 25mJetBlue
Wed 12/311:25 amORD - HYA
1 stop6h 14mJetBlue
Deal found 10/1$615
This JetBlue deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/312:07 pmHYA - ORD
1 stop7h 15mJetBlue
Fri 11/711:20 amORD - HYA
1 stop6h 19mJetBlue
Deal found 9/30$625
This JetBlue deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1712:07 pmHYA - ORD
1 stop7h 11mJetBlue
Tue 10/2110:08 amORD - HYA
1 stop7h 31mJetBlue
Deal found 10/2$655
This JetBlue deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/212:07 pmHYA - ORD
1 stop6h 48mJetBlue
Fri 11/1411:20 amORD - HYA
1 stop6h 19mJetBlue
Deal found 9/30$665
This Priceline deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/161:47 pmPVC - ORD
1 stop5h 31mJetBlue
Mon 10/2010:08 amORD - PVC
1 stop4h 22mJetBlue
Deal found 10/1$680
This Priceline deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1612:07 pmHYA - ORD
1 stop7h 11mJetBlue
Mon 10/2010:08 amORD - HYA
1 stop7h 31mJetBlue
Deal found 10/1$705
This Expedia deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/157:58 amHYA - ORD
1 stop11h 20mJetBlue
Sun 10/1910:08 amORD - HYA
1 stop7h 31mJetBlue
Deal found 9/30$720
This Expedia deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/910:16 amHYA - ORD
1 stop11h 35mJetBlue
Sun 10/1210:08 amORD - HYA
1 stop7h 37mJetBlue
Deal found 9/30$792
This Expedia deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/288:43 amMVY - ORD
1 stop10h 12mJetBlue
Thu 10/306:45 amORD - MVY
2 stops13h 00mJetBlue
Deal found 10/2$805
This Kiwi.com deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/169:35 amHYA - ORD
1 stop28h 10mMultiple Airlines
Mon 10/207:43 pmORD - HYA
2 stops21h 56mMultiple Airlines
Deal found 10/1$819
This United deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/289:52 amMVY - ORD
1 stop6h 03mMultiple Airlines
Thu 10/307:15 amORD - MVY
1 stop7h 35mMultiple Airlines
Deal found 10/2$842

Cheapflights Fare Finder

 
Customize your flight search to find flights from Cape Cod and the Islands to Illinois 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, Cheapflights users made 2,558,603 searches. Data last updated October 2, 2025.
Use the filters below to find and compare flights from Cape Cod and the Islands to Illinois that are best for you.

Fly from

Cape Cod and the Islands

Fly to

Illinois

Route

Depart

Return

Price

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sun 2/22

12:07 pm-5:31 pm

1 stop6h 24m

Chicago O'Hare Intl

Thu 2/26

12:10 pm-6:39 pm

1 stop5h 29m

$385

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 11/10

12:07 pm-5:55 pm

1 stop6h 48m

Chicago O'Hare Intl

Tue 11/11

11:20 am-6:39 pm

1 stop6h 19m

$560

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 1/2

12:07 pm-6:46 pm

1 stop7h 39m

Chicago O'Hare Intl

Mon 1/5

6:45 am-1:10 pm

1 stop5h 25m

$600

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 11/28

2:30 pm-7:55 pm

1 stop6h 25m

Chicago O'Hare Intl

Wed 12/3

11:25 am-6:39 pm

1 stop6h 14m

$615

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 11/28

2:30 pm-7:55 pm

1 stop6h 25m

Chicago O'Hare Intl

Thu 12/4

11:25 am-6:39 pm

1 stop6h 14m

$655

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 10/17

12:07 pm-6:18 pm

1 stop7h 11m

Chicago O'Hare Intl

Tue 10/21

10:08 am-6:39 pm

1 stop7h 31m

$655

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 11/7

12:07 pm-5:55 pm

1 stop6h 48m

Chicago O'Hare Intl

Tue 11/11

11:20 am-6:39 pm

1 stop6h 19m

$665

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sun 11/2

12:07 pm-5:55 pm

1 stop6h 48m

Chicago O'Hare Intl

Fri 11/14

11:20 am-6:39 pm

1 stop6h 19m

$665

ProvincetownChicago

PVC - ORD

PVCORD

Provincetown

Thu 10/16

1:47 pm-6:18 pm

1 stop5h 31m

Chicago O'Hare Intl

Mon 10/20

10:08 am-3:30 pm

1 stop4h 22m

$680

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 10/16

12:07 pm-6:18 pm

1 stop7h 11m

Chicago O'Hare Intl

Mon 10/20

10:08 am-6:39 pm

1 stop7h 31m

$705

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/30

Showing 1-10 of 44 results
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Best time to book a flight from Cape Cod and the Islands to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Cape Cod and the Islands with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Cape Cod and the Islands to Illinois
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Cape Cod and the Islands to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Cape Cod and the Islands to Illinois?

    A quick flight from Cape Cod and the Islands to Illinois can take about 6h 24m. JetBlue provides one of the quickest options available for as low as $385. There are 905 mi between Cape Cod and the Islands and Illinois.

  • Can I find deals for flights from Cape Cod and the Islands to Illinois that include hotel bookings?

    Yes. In addition to deals on Cape Cod and the Islands to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Cape Cod and the Islands to Illinois?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Cape Cod and the Islands to Illinois.

  • Can I find deals for business class flights from Cape Cod and the Islands to Illinois?

    Yes. Cheapflights offers flight deals from Cape Cod and the Islands to Illinois by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Cape Cod and the Islands to Illinois?

    Currently, August is the cheapest month in which you can book a flight from Cape Cod and the Islands to Illinois (average of $245). Flying from Cape Cod and the Islands to Illinois in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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