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$183+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
ACK — ORD
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
1 adult, Economy
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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 November 20, 2025.

This Expedia deal was found by Cheapflights users on 11/20. 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.
Fri 12/56:00 amHYA - ORD
2 stops14h 43mJetBlue
Mon 12/811:25 amORD - HYA
1 stop4h 55mJetBlue
Deal found 11/20$535
This JetBlue deal was found by Cheapflights users on 11/20. 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 12/51:34 pmMVY - ORD
1 stop7h 09mJetBlue
Tue 12/911:25 amORD - MVY
1 stop6h 25mJetBlue
Deal found 11/20$579
This JetBlue deal was found by Cheapflights users on 11/18. 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.
Thu 12/111:28 pmMVY - ORD
1 stop7h 15mJetBlue
Sun 12/1411:25 amORD - MVY
1 stop6h 25mJetBlue
Deal found 11/18$589
This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
Mon 11/249:35 amHYA - ORD
1 stop9h 24mMultiple Airlines
Wed 11/2612:17 pmORD - HYA
2 stops45h 13mMultiple Airlines
Deal found 11/20$806

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 November 20, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$535
(Expedia)

One-way from

$183
(JetBlue)

Popular in

March

Cheapest in

September

Average price

$247
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
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($19 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 November 2025
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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 November 20, 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

Fri 12/5

6:00 am-7:43 pm

2 stops14h 43m

Chicago O'Hare Intl

Mon 12/8

11:25 am-5:20 pm

1 stop4h 55m

$535

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Fri 12/5

1:34 pm-7:43 pm

1 stop7h 09m

Chicago O'Hare Intl

Tue 12/9

11:25 am-6:50 pm

1 stop6h 25m

$579

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Thu 12/11

1:28 pm-7:43 pm

1 stop7h 15m

Chicago O'Hare Intl

Sun 12/14

11:25 am-6:50 pm

1 stop6h 25m

$589

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sat 1/17

12:07 pm-5:44 pm

1 stop6h 37m

$183

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 1/20

12:07 pm-5:44 pm

1 stop6h 37m

$183

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sun 1/18

7:05 am-5:44 pm

1 stop11h 39m

$188

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 1/22

12:07 pm-5:44 pm

1 stop6h 37m

$193

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 1/23

12:07 pm-5:44 pm

1 stop6h 37m

$193

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Sat 1/17

1:30 pm-5:44 pm

1 stop5h 14m

$202

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sun 1/11

12:07 pm-5:44 pm

1 stop6h 37m

$203

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 26 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 14h 43m. JetBlue provides one of the quickest options available for as low as $535. 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.

See more FAQs

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