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$105+ 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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
ACK — ORD
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 August 14, 2025.

Round-trip from

$278
(American Airlines)

One-way from

$105
(JetBlue)

Popular in

March

Cheapest in

September

Average price

$223
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 ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 14, 2025.

This American Airlines deal was found by Cheapflights users on 8/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/285:16 pmACK - ORD
1 stop7h 09mAmerican Airlines
Mon 9/16:06 amORD - ACK
1 stop4h 47mAmerican Airlines
Deal found 8/13$278
This Delta deal was found by Cheapflights users on 8/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/223:26 pmACK - ORD
1 stop7h 27mDelta
Tue 8/267:00 amORD - ACK
1 stop6h 46mDelta
Deal found 8/12$318
This American Airlines deal was found by Cheapflights users on 8/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2712:10 pmHYA - ORD
1 stop6h 10mAmerican Airlines
Sun 8/316:55 amORD - HYA
1 stop5h 07mAmerican Airlines
Deal found 8/12$343
This JetBlue deal was found by Cheapflights users on 8/12. 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 11/1410:29 amHYA - ORD
1 stop8h 26mJetBlue
Sun 11/1611:20 amORD - HYA
1 stop6h 26mJetBlue
Deal found 8/12$347
This American Airlines deal was found by Cheapflights users on 8/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/291:44 pmHYA - ORD
1 stop5h 08mAmerican Airlines
Sun 8/316:06 amORD - HYA
1 stop6h 45mAmerican Airlines
Deal found 8/12$381
This American Airlines deal was found by Cheapflights users on 8/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1612:10 pmHYA - ORD
1 stop6h 10mAmerican Airlines
Mon 8/186:06 amORD - HYA
1 stop6h 58mAmerican Airlines
Deal found 8/14$413
This American Airlines deal was found by Cheapflights users on 8/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/261:44 pmHYA - ORD
1 stop6h 18mAmerican Airlines
Wed 8/276:00 amORD - HYA
1 stop6h 13mAmerican Airlines
Deal found 8/12$481
This JetBlue deal was found by Cheapflights users on 8/12. 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.
Wed 8/275:15 pmHYA - ORD
1 stop6h 13mJetBlue
Sun 8/318:40 amORD - HYA
1 stop7h 58mJetBlue
Deal found 8/12$512
This United Airlines deal was found by Cheapflights users on 8/14. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/124:31 pmACK - ORD
1 stop7h 54mUnited Airlines
Mon 9/156:10 pmORD - ACK
2 stops14h 45mUnited Airlines
Deal found 8/14$532
This Mytrip deal was found by Cheapflights users on 8/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2710:29 amHYA - ORD
2 stops12h 53mMultiple Airlines
Sun 8/3110:12 amORD - HYA
2 stops9h 15mMultiple Airlines
Deal found 8/12$561
This American Airlines deal was found by Cheapflights users on 8/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/282:03 pmMVY - ORD
1 stop8h 08mAmerican Airlines
Mon 9/16:06 amORD - MVY
1 stop8h 31mAmerican Airlines
Deal found 8/13$590
This United deal was found by Cheapflights users on 8/12. 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 8/2610:29 amHYA - ORD
1 stop7h 36mMultiple Airlines
Wed 8/278:50 amORD - HYA
2 stops10h 37mMultiple Airlines
Deal found 8/12$606

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 August 14, 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

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Thu 8/28

5:16 pm-11:25 pm

1 stop7h 09m

Chicago O'Hare Intl

Mon 9/1

6:06 am-11:53 am

1 stop4h 47m

$278

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 8/27

12:10 pm-5:20 pm

1 stop6h 10m

Chicago O'Hare Intl

Sun 8/31

6:55 am-1:02 pm

1 stop5h 07m

$343

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 11/14

10:29 am-5:55 pm

1 stop8h 26m

Chicago O'Hare Intl

Sun 11/16

11:20 am-6:46 pm

1 stop6h 26m

$347

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 8/29

1:44 pm-5:52 pm

1 stop5h 08m

Chicago O'Hare Intl

Sun 8/31

6:06 am-1:51 pm

1 stop6h 45m

$381

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 8/26

1:44 pm-7:02 pm

1 stop6h 18m

Chicago O'Hare Intl

Wed 8/27

6:00 am-1:13 pm

1 stop6h 13m

$481

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 8/27

5:15 pm-10:28 pm

1 stop6h 13m

Chicago O'Hare Intl

Sun 8/31

8:40 am-5:38 pm

1 stop7h 58m

$512

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Fri 9/12

4:31 pm-11:25 pm

1 stop7h 54m

Chicago O'Hare Intl

Mon 9/15

6:10 pm-9:55 am

2 stops14h 45m

$532

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 8/27

10:29 am-10:22 pm

2 stops12h 53m

Chicago O'Hare Intl

Sun 8/31

10:12 am-8:27 pm

2 stops9h 15m

$561

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Thu 8/28

2:03 pm-9:11 pm

1 stop8h 08m

Chicago O'Hare Intl

Mon 9/1

6:06 am-3:37 pm

1 stop8h 31m

$590

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 8/26

10:29 am-5:05 pm

1 stop7h 36m

Chicago O'Hare Intl

Wed 8/27

8:50 am-8:27 pm

2 stops10h 37m

$606

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

Showing 1-10 of 53 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

What is the cheapest time of day to fly from KDT to IL?

Find hourly flight availability from Cape Cod and the Islands to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Cape Cod and the Islands to Illinois as you normally would.

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.

  • 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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