$234+ Cheap flights from Chicago (CHI) to Cape Cod and the Islands
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ACK
Oct 4 — Oct 111
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Cape Cod and the Islands with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Cape Cod and the Islands
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Cheapest flights from Chicago to Cape Cod and the IslandsExplore the most affordable flight options available from Chicago to Cape Cod and the Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 4, 2026.
Explore the most affordable flight options available from Chicago to Cape Cod and the Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 4, 2026.
This Delta deal was found by Cheapflights users on 8/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:00 am -
1 stop5h 38m
Sat 9/511:53 am -
1 stop5h 22m
Deal found 8/30![Delta logo]()
$450
This American Airlines deal was found by Cheapflights users on 8/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:45 am -
Nonstop2h 49m
Tue 9/85:00 pm -
1 stop7h 37m
Deal found 8/30![American Airlines logo]()
$526
This FlightHub deal was found by Cheapflights users on 9/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/309:38 am -
1 stop24h 44m
Mon 10/53:30 pm -
1 stop18h 19m
Deal found 9/1![JetBlue logo]()
$545
This Justfly.com deal was found by Cheapflights users on 9/3. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:00 pm -
1 stop16h 19m
Wed 10/1411:00 am -
1 stop9h 14m
Deal found 9/3![JetBlue logo]()
$579
This Justfly.com deal was found by Cheapflights users on 9/3. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/228:24 pm -
1 stop15h 52m
Sat 9/262:30 pm -
1 stop5h 31m
Deal found 9/3![JetBlue logo]()
$580
This FlightHub deal was found by Cheapflights users on 8/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/277:00 am -
1 stop26h 35m
Thu 10/111:25 am -
1 stop23h 33m
Deal found 8/30![JetBlue logo]()
$594
This Justfly.com deal was found by Cheapflights users on 9/2. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/207:00 am -
1 stop26h 35m
Fri 9/253:10 pm -
1 stop18h 38m
Deal found 9/2![JetBlue logo]()
$600
This Justfly.com deal was found by Cheapflights users on 9/2. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:38 am -
1 stop26h 38m
Wed 9/233:10 pm -
1 stop18h 38m
Deal found 9/2![JetBlue logo]()
$617
This American Airlines deal was found by Cheapflights users on 8/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/45:00 am -
1 stop6h 23m
Tue 9/85:00 pm -
1 stop7h 37m
Deal found 8/30![American Airlines logo]()
$631
This FlightHub deal was found by Cheapflights users on 9/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:49 pm -
1 stop24h 06m
Tue 9/812:50 pm -
1 stop7h 35m
Deal found 9/1![Multiple Airlines logo]()
$691
This American Airlines deal was found by Cheapflights users on 9/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/49:56 am -
1 stop6h 33m
Tue 9/85:59 pm -
1 stop6h 38m
Deal found 9/1![American Airlines logo]()
$699
This KAYAK deal was found by Cheapflights users on 9/3. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:00 am -
1 stop7h 04m
Sat 10/34:00 pm -
1 stop7h 08m
Deal found 9/3![JetBlue logo]()
$709
Best flights from Chicago to Cape Cod and the IslandsDiscover carefully curated flight deals from Chicago to Cape Cod and the Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 4, 2026.
Discover carefully curated flight deals from Chicago to Cape Cod and the Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 4, 2026.
This FlightHub deal was found by Cheapflights users on 9/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/309:38 am -
1 stop24h 44m
Mon 10/53:30 pm -
1 stop18h 19m
Deal found 9/1![JetBlue logo]()
$545
This United deal was found by Cheapflights users on 8/30. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:10 am -
1 stop10h 53m
Mon 10/194:20 pm -
1 stop17h 40m
Deal found 8/30![Multiple Airlines logo]()
$742
This United Airlines deal was found by Cheapflights users on 9/3. 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 9/187:59 pm -
2 stops18h 04m
Tue 9/223:39 pm -
1 stop7h 36m
Deal found 9/3![United Airlines logo]()
$825
This FlightHub deal was found by Cheapflights users on 8/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/277:00 am -
1 stop26h 35m
Thu 10/111:25 am -
1 stop23h 33m
Deal found 8/30![JetBlue logo]()
$594
This United deal was found by Cheapflights users on 8/30. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:55 am -
2 stops10h 25m
Sun 12/65:10 pm -
1 stop6h 19m
Deal found 8/30![Multiple Airlines logo]()
$747
This FlightHub deal was found by Cheapflights users on 9/3. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:10 am -
1 stop27h 25m
Mon 10/123:28 pm -
1 stop18h 19m
Deal found 9/3![JetBlue logo]()
$734
This United deal was found by Cheapflights users on 8/30. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:55 am -
2 stops9h 44m
Sun 11/14:20 pm -
3 stops23h 34m
Deal found 8/30![Multiple Airlines logo]()
$802
This Justfly.com deal was found by Cheapflights users on 9/3. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:24 pm -
1 stop12h 09m
Tue 9/2212:50 pm -
1 stop7h 11m
Deal found 9/3![Multiple Airlines logo]()
$813
This KAYAK deal was found by Cheapflights users on 9/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:24 pm -
1 stop11h 05m
Mon 9/284:20 pm -
1 stop17h 28m
Deal found 9/2![Multiple Airlines logo]()
$814
This FlightHub deal was found by Cheapflights users on 9/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/188:24 pm -
1 stop15h 52m
Sun 9/203:10 pm -
1 stop18h 38m
Deal found 9/1![JetBlue logo]()
$896
This Priceline deal was found by Cheapflights users on 9/3. 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.
Sat 9/199:38 am -
1 stop4h 32m
Wed 9/231:41 pm -
1 stop6h 20m
Deal found 9/3![Multiple Airlines logo]()
$822
This KAYAK deal was found by Cheapflights users on 9/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:00 am -
1 stop7h 04m
Wed 9/164:00 pm -
1 stop18h 58m
Deal found 9/2![JetBlue logo]()
$919
This FlightHub deal was found by Cheapflights users on 9/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:24 pm -
1 stop12h 29m
Wed 9/234:00 pm -
1 stop18h 58m
Deal found 9/2![Multiple Airlines logo]()
$835
This JetBlue deal was found by Cheapflights users on 8/31. 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 9/257:00 am -
1 stop7h 04m
Mon 9/283:54 pm -
1 stop7h 04m
Deal found 8/31![JetBlue logo]()
$942
This FlightHub deal was found by Cheapflights users on 9/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/71:00 pm -
1 stop4h 57m
Sat 11/146:44 am -
1 stop6h 15m
Deal found 9/1![Multiple Airlines logo]()
$836
This FlightHub deal was found by Cheapflights users on 9/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/71:00 pm -
1 stop4h 57m
Thu 11/126:44 am -
1 stop6h 15m
Deal found 9/1![Multiple Airlines logo]()
$836
This United deal was found by Cheapflights users on 8/31. 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.
Thu 9/177:55 pm -
1 stop11h 34m
Sun 9/204:20 pm -
1 stop17h 43m
Deal found 8/31![Multiple Airlines logo]()
$842
This FlightHub deal was found by Cheapflights users on 8/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1112:38 pm -
1 stop25h 26m
Sat 10/173:35 pm -
1 stop4h 39m
Deal found 8/30![Multiple Airlines logo]()
$870
This FlightHub deal was found by Cheapflights users on 9/3. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:24 pm -
1 stop12h 29m
Mon 9/213:54 pm -
1 stop19h 04m
Deal found 9/3![Multiple Airlines logo]()
$984
This Priceline deal was found by Cheapflights users on 9/1. 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.
Wed 9/169:38 am -
1 stop6h 34m
Sun 9/2011:02 am -
1 stop8h 59m
Deal found 9/1![Multiple Airlines logo]()
$1,038
This KAYAK deal was found by Cheapflights users on 9/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:24 pm -
2 stops18h 16m
Mon 9/287:00 am -
2 stops26h 48m
Deal found 9/2![Multiple Airlines logo]()
$1,139
This KAYAK deal was found by Cheapflights users on 9/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/248:24 pm -
2 stops17h 07m
Mon 9/287:00 am -
2 stops26h 48m
Deal found 9/2![Multiple Airlines logo]()
$1,199
This KAYAK deal was found by Cheapflights users on 9/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:24 pm -
2 stops18h 16m
Sun 9/2711:13 am -
2 stops22h 35m
Deal found 9/2![Multiple Airlines logo]()
$1,243
Last-minute flights from Chicago to Cape Cod and the IslandsDiscover last-minute flight deals from Chicago to Cape Cod and the Islands. Data last updated September 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Cape Cod and the Islands. Data last updated September 4, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/45:00 am -
1 stop6h 23m
Tue 9/85:00 pm -
1 stop7h 37m
Deal found 8/30![American Airlines logo]()
$631
This American Airlines deal was found by Cheapflights users on 9/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/49:56 am -
1 stop6h 33m
Tue 9/85:59 pm -
1 stop6h 38m
Deal found 9/1![American Airlines logo]()
$699
This American Airlines deal was found by Cheapflights users on 8/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:45 am -
Nonstop2h 49m
Tue 9/85:00 pm -
1 stop7h 37m
Deal found 8/30![American Airlines logo]()
$526
This FlightHub deal was found by Cheapflights users on 9/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:49 pm -
1 stop24h 06m
Tue 9/812:50 pm -
1 stop7h 35m
Deal found 9/1![Multiple Airlines logo]()
$691
This American Airlines deal was found by Cheapflights users on 9/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/511:15 am -
Nonstop2h 42m
Tue 9/812:42 pm -
1 stop8h 04m
Deal found 9/1![American Airlines logo]()
$722
This Justfly.com deal was found by Cheapflights users on 9/2. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/207:00 am -
1 stop26h 35m
Fri 9/253:10 pm -
1 stop18h 38m
Deal found 9/2![JetBlue logo]()
$600
This Justfly.com deal was found by Cheapflights users on 9/3. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/228:24 pm -
1 stop15h 52m
Sat 9/262:30 pm -
1 stop5h 31m
Deal found 9/3![JetBlue logo]()
$580
This Justfly.com deal was found by Cheapflights users on 9/2. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:38 am -
1 stop26h 38m
Wed 9/233:10 pm -
1 stop18h 38m
Deal found 9/2![JetBlue logo]()
$617
This KAYAK deal was found by Cheapflights users on 9/3. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:00 am -
1 stop7h 04m
Sat 10/34:00 pm -
1 stop7h 08m
Deal found 9/3![JetBlue logo]()
$709
This FlightHub deal was found by Cheapflights users on 8/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/277:00 am -
1 stop26h 35m
Thu 10/111:25 am -
1 stop23h 33m
Deal found 8/30![JetBlue logo]()
$594
This FlightHub deal was found by Cheapflights users on 9/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/309:38 am -
1 stop24h 44m
Mon 10/53:30 pm -
1 stop18h 19m
Deal found 9/1![JetBlue logo]()
$545
This Justfly.com deal was found by Cheapflights users on 9/3. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:00 pm -
1 stop16h 19m
Wed 10/1411:00 am -
1 stop9h 14m
Deal found 9/3![JetBlue logo]()
$579
One-way flights from Chicago to Cape Cod and the IslandsSearch for one-way flight options from Chicago to Cape Cod and the Islands. Find affordable one-way fares based on user searches. Data last updated September 4, 2026.
Search for one-way flight options from Chicago to Cape Cod and the Islands. Find affordable one-way fares based on user searches. Data last updated September 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/33:50 pm -
2 stops44h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Multiple Airlines logo]()
$234
This JetBlue deal was found by Cheapflights users on 9/2. 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.
Sat 10/37:00 am -
1 stop7h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![JetBlue logo]()
$275
This JetBlue deal was found by Cheapflights users on 8/31. 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.
Sat 10/106:10 am -
1 stop7h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/31![JetBlue logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 9/1. 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.
Sat 10/33:50 pm -
3 stops37h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Multiple Airlines logo]()
$299
This Priceline deal was found by Cheapflights users on 9/3. 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.
Tue 3/211:00 am -
1 stop5h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$307
This Priceline deal was found by Cheapflights users on 9/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/211:00 am -
1 stop4h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Multiple Airlines logo]()
$307
This JetBlue deal was found by Cheapflights users on 8/31. 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 10/27:00 am -
1 stop7h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/31![JetBlue logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 9/1. 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.
Wed 12/22:31 pm -
2 stops22h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Multiple Airlines logo]()
$332
This United deal was found by Cheapflights users on 9/3. 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.
Thu 12/39:10 am -
1 stop6h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$342
This Expedia deal was found by Cheapflights users on 9/2. 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.
Thu 10/18:24 pm -
2 stops19h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![JetBlue logo]()
$351
This Expedia deal was found by Cheapflights users on 8/30. 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.
Tue 9/298:24 pm -
2 stops19h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/30![JetBlue logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Sat 10/33:50 pm -
3 stops37h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$363
Find flight deals from Chicago to Cape Cod and the Islands
Keep the following information in mind while searching for Chicago to Cape Cod and the Islands flight deals. Data was last updated September 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $545 (FlightHub) |
One-way from | $234 (Kiwi.com) |
Popular in | August |
Cheapest in | January |
Average price | $258 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Cape Cod and the Islands 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 7,457,451 searches. Data last updated September 4, 2026.
Use the filters below to find and compare flights from Chicago to Cape Cod and the Islands that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoWest Tisbury
ORD Chicago O'Hare Intl - MVY West Tisbury Martha's Vineyard
ORDMVY
Chicago O'Hare Intl
Sat 10/3
7:00 am-3:04 pm
1 stop7h 04m
West Tisbury Martha's Vineyard
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$275
ChicagoWest Tisbury
ORD Chicago O'Hare Intl - MVY West Tisbury Martha's Vineyard
ORDMVY
Chicago O'Hare Intl
Mon 9/28
7:00 am-3:04 pm
1 stop7h 04m
West Tisbury Martha's Vineyard
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$275
ChicagoWest Tisbury
ORD Chicago O'Hare Intl - MVY West Tisbury Martha's Vineyard
ORDMVY
Chicago O'Hare Intl
Sun 10/4
7:00 am-3:04 pm
1 stop7h 04m
West Tisbury Martha's Vineyard
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$275
ChicagoWest Tisbury
ORD Chicago O'Hare Intl - MVY West Tisbury Martha's Vineyard
ORDMVY
Chicago O'Hare Intl
Fri 10/2
7:00 am-3:17 pm
1 stop7h 17m
West Tisbury Martha's Vineyard
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$275
ChicagoWest Tisbury
ORD Chicago O'Hare Intl - MVY West Tisbury Martha's Vineyard
ORDMVY
Chicago O'Hare Intl
Mon 10/5
7:00 am-3:04 pm
1 stop7h 04m
West Tisbury Martha's Vineyard
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$275
ChicagoWest Tisbury
ORD Chicago O'Hare Intl - MVY West Tisbury Martha's Vineyard
ORDMVY
Chicago O'Hare Intl
Sun 9/27
7:00 am-3:04 pm
1 stop7h 04m
West Tisbury Martha's Vineyard
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$308
ChicagoWest Tisbury
ORD Chicago O'Hare Intl - MVY West Tisbury Martha's Vineyard
ORDMVY
Chicago O'Hare Intl
Sat 10/3
3:50 pm-6:30 am
3 stops37h 40m
West Tisbury Martha's Vineyard
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$322
ChicagoNantucket
ORD Chicago O'Hare Intl - ACK Nantucket Memorial
ORDACK
Chicago O'Hare Intl
Sat 10/3
3:50 pm-6:30 am
3 stops37h 40m
Nantucket Memorial
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$363
ChicagoHyannis
ORD Chicago O'Hare Intl - HYA Hyannis Barnstable
ORDHYA
Chicago O'Hare Intl
Fri 10/30
8:00 am-3:00 pm
2 stops30h 00m
Hyannis Barnstable
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$389
ChicagoNantucket
ORD Chicago O'Hare Intl - ACK Nantucket Memorial
ORDACK
Chicago O'Hare Intl
Sun 2/28
11:00 am-4:34 pm
1 stop4h 34m
Nantucket Memorial
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$402
Showing 1-10 of 53 resultsSorted by cheapest first
Best time to book a flight from Chicago to Cape Cod and the Islands
Have a flexible travel schedule? Discover the best time to fly to Cape Cod and the Islands from Chicago with our price prediction graph.
ORD-ACK
ORD-HYA
ORD-MVY
ORD-PVC
ORD-EWB
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 Chicago to Cape Cod and the Islands
CHI-zzKDT
ORD-ACK
ORD-HYA
ORD-MVY
ORD-PVC
What is the cheapest time of day to fly from CHI to KDT?
Find hourly flight availability from Chicago to Cape Cod and the Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 4, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Cape Cod and the Islands as you normally would.
Reviews of airlines servicing Cape Cod and the Islands
Get insights into the airlines that provide service to Cape Cod and the Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Cape Cod and the Islands. Reviews last updated September 4, 2026.
Read through reviews of airlines operating flights from Chicago to Cape Cod and the Islands, such as American Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.1
Entertainment
6.8
Comfort
7.2
Food
6.4
Boarding
7.5
Crew
7.9
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Overall
7.1
Entertainment
6.8
Comfort
7.2
Food
6.4
Boarding
7.5
Crew
7.9
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Related info for your journey
Find useful and relevant information for your journey from Chicago to Cape Cod and the Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Cape Cod and the Islands
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Complete your trip
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Search flights from Chicago to Cape Cod and the Islands by cabin class
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Chicago and Cape Cod and the Islands flights
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Popular flight searches
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Top 3 airlines flying from Chicago to Cape Cod and the Islands
Discover the top 3 airlines that operate flights from Chicago to Cape Cod and the Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$166 | Average$512 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$282 | Average$427 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$338 | Average$503 | FlexibilityNo cancel fee | On-time71% |