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Find cheap flights from Cape Cod and the Islands to Chicago from $163

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to O'Hare Intl departing on 7/23. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
wo 5/22
wo 5/29

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Good to know

Low season

January

High season

June

Cheapest flight

$163
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 25% increase in price.
Flight from West Tisbury to Chicago

FAQs for booking Cape Cod and the Islands to Chicago flights

  • How does KAYAK find such low prices on flights from Cape Cod and the Islands to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Cape Cod and the Islands to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Cape Cod and the Islands to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Cape Cod and the Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Cape Cod and the Islands to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Cape Cod and the Islands with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Cape Cod and the Islands to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Cape Cod and the Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Cape Cod and the Islands to Chicago?

Find which airlines fly direct from Cape Cod and the Islands to O'Hare Intl, which days they fly and book direct flights.

Nonstop departures

Cape Cod and the Islands to Chicago O'Hare Intl

Monday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +76 more

ANA, Aer Lingus, +77 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +76 more

ANA, Aer Lingus, +77 more

See more direct flights

Nonstop returns

Chicago O'Hare Intl to Cape Cod and the Islands

Monday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +76 more

ANA, Aer Lingus, +77 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +76 more

ANA, Aer Lingus, +77 more

See more direct flights
See more direct flights

Top airline flying from Cape Cod and the Islands to O'Hare Intl

 
Need help choosing which airline to fly with from Cape Cod and the Islands to O'Hare Intl? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.3
American AirlinesOverall score based on 14931 reviews
7.6boarding
7.2comfort
8.0crew
7.1entertainment
6.6food
Airline reviews

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

10.0 ExcellentDr. Joseph, Apr 2024DFW - ORD
Read more about American Airlines reviews

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Turn on the heat. Flight was way too cold from Arizona to Chicago.

Perfect flight. On time departure and early arrival. Smooth flight.

Overall pleasant was delayed and caused transportation issue when landing

The arriving flight was a few minutes late, but the gate crew helped to deplane and board our outgoing flight quickly and efficiently. We were able to depart quickly and arrive at ORD almost at the posted time. Great job.

Book cheap flights from Cape Cod and the Islands to Chicago

Recent round-trip flight deals

6/19wo
1 stopJetBlue
5h 14mMVY-ORD
6/25di
1 stopJetBlue
6h 24mORD-MVY
$381
6/13do
1 stopDelta
6h 37mMVY-ORD
6/17ma
1 stopDelta
4h 54mORD-MVY
$436
6/20do
1 stopJetBlue
4h 59mMVY-ORD
6/25di
1 stopJetBlue
5h 33mORD-MVY
$499
6/20do
1 stopDelta
6h 37mMVY-ORD
6/24ma
1 stopDelta
6h 43mORD-MVY
$507
6/7vr
1 stopDelta
6h 37mMVY-ORD
6/9zo
1 stopDelta
5h 48mORD-MVY
$527
7/19vr
1 stopAmerican Airlines
4h 24mMVY-ORD
7/23di
1 stopAmerican Airlines
5h 51mORD-MVY
$548
6/20do
1 stopAmerican Airlines
5h 49mHYA-ORD
6/28vr
1 stopAmerican Airlines
5h 18mORD-HYA
$554
7/22ma
1 stopAmerican Airlines
4h 24mMVY-ORD
7/23di
1 stopAmerican Airlines
4h 15mORD-MVY
$568
9/26do
1 stopJetBlue
6h 25mHYA-ORD
10/7ma
1 stopJetBlue
4h 18mORD-HYA
$612
7/22ma
1 stopAmerican Airlines
5h 52mHYA-ORD
7/23di
1 stopAmerican Airlines
4h 23mORD-HYA
$614

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Recent one-way flight deals

7/23di
1 stopAmerican Airlines
18h 19mMVY-ORD
$163
6/18di
1 stopDelta
6h 37mMVY-ORD
$188
7/23di
2 stopsAmerican Airlines
8h 28mMVY-ORD
$193
9/27vr
1 stopJetBlue
4h 51mMVY-ORD
$211
6/22za
1 stopAmerican Airlines
22h 44mACK-ORD
$226
6/21vr
1 stopDelta
23h 06mACK-ORD
$243
6/2zo
nonstopUnited Airlines
3h 17mACK-ORD
$279
9/27vr
1 stopJetBlue
6h 25mHYA-ORD
$304
6/17ma
1 stop
6h 13mPVC-ORD
$412
6/17ma
2 stops
8h 15mPVC-ORD
$497

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Last minute flights from Cape Cod and the Islands to O'Hare Intl

Last minute flight, train and bus deals

4/24wo
multi-stopJetBlue
7h 14mHYA-ORD
4/28zo
multi-stopJetBlue
5h 45mORD-HYA
$877

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Flights to Chicago