Find flights
When to book
FAQs & Tips
Direct Flights
Airlines
Deals

ORD

$130 Find cheap flights from Cape Cod and the Islands to Chicago

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 6/14. 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
Fri 6/21
Fri 6/28

Search hundreds of travel sites at once for deals on flights to Chicago

In the last 7 days travelers have searched 43,423,329 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Good to know

Low season

January

High season

June

Cheapest flight

$130
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 17% 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, +77 more

ANA, Aer Lingus, +78 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, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 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, +77 more

ANA, Aer Lingus, +78 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, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

See more direct flights
See more direct flights

Top airlines 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.
8.0
DeltaOverall score based on 10585 reviews
7.4Food
8.2Boarding
8.6Crew
7.9Comfort
8.0Entertainment
Airline reviews

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

8.0 ExcellentEric, May 2024BOS - CUN
Read more about Delta reviews

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

They did a fine job. Can't wait to use Delta in the future.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

Seats in first class on the E175 recline too far back. I was in 2A, and the man in 1A fully reclined almost the entire flight. It took 6-7 inches of space away from me and made it very difficult to work on my laptop.

Mario was great. Made a night flight on a small aircraft pleasant and memorable.

Crew were exceptional. Plane was quiet and quite empty, so I had a row to sleep across.

The seat could use more support or cushion. I'm in my 50's and have back issues so the seats are a bit hard for longer flights.

The plane was in bad condition. We were taxied for mode than an hour because a light panel had feel off. The bathroom in first class had broken panels as well. Overall poor aircraft maintenance

My only real complaint was how much turbulence there was-and that probably can't be avoided. I felt really sick getting off the plane. But boarding was super easy, the flight attendants were friendly, the bathroom was clean. Everything else about the flight was perfectly fine. Thanks!

Caroline (Supervisor) was great! Salute to the employees like her!

The CX617 from HK to BKK was delayed more than 1.5 hours.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

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.

Book cheap flights from Cape Cod and the Islands to Chicago

Recent round-trip flight deals

6/18Tue
1 stopAmerican Airlines
19h 40mHYA-ORD
6/25Tue
1 stopAmerican Airlines
5h 18mORD-HYA
$273
6/18Tue
2 stopsAmerican Airlines
10h 40mHYA-ORD
6/25Tue
1 stopAmerican Airlines
4h 19mORD-HYA
$290
6/13Thu
1 stopJetBlue
5h 14mMVY-ORD
6/18Tue
1 stopJetBlue
5h 33mORD-MVY
$304
6/18Tue
2 stopsAmerican Airlines
10h 40mHYA-ORD
6/25Tue
2 stopsAmerican Airlines
14h 51mORD-HYA
$350
9/27Fri
1 stopJetBlue
5h 42mACK-ORD
9/30Mon
1 stopJetBlue
6h 17mORD-ACK
$368
6/1Sat
1 stopDelta
4h 56mACK-ORD
6/5Wed
1 stopDelta
4h 11mORD-ACK
$418
6/1Sat
1 stopDelta
4h 56mACK-ORD
6/5Wed
2 stopsDelta
9h 07mORD-ACK
$423
6/1Sat
nonstopUnited Airlines
3h 17mACK-ORD
6/5Wed
1 stopUnited Airlines
5h 43mORD-ACK
$524
9/26Thu
2 stops
7h 02mACK-ORD
9/29Sun
2 stops
8h 43mORD-ACK
$1,134
9/27Fri
2 stops
9h 39mACK-ORD
9/29Sun
2 stops
8h 43mORD-ACK
$1,224

Search by stops

Search by airline

Search by price

Recent one-way flight deals

6/14Fri
1 stopJetBlue
5h 14mMVY-ORD
$130
7/23Tue
2 stopsAmerican Airlines
9h 27mMVY-ORD
$158
6/13Thu
1 stopJetBlue
7h 33mACK-ORD
$164
6/17Mon
1 stopJetBlue
5h 14mMVY-ORD
$171
6/15Sat
1 stopJetBlue
4h 59mMVY-ORD
$201
9/1Sun
1 stopAmerican Airlines
8h 06mACK-ORD
$208
8/2Fri
1 stopDelta
5h 09mACK-ORD
$229
9/1Sun
2 stopsDelta
7h 31mACK-ORD
$234
7/14Sun
nonstopUnited Airlines
3h 17mACK-ORD
$244
6/20Thu
2 stopsUnited Airlines
16h 17mACK-ORD
$252

Search by stops

Search by airline

Search by price

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

Last minute flight, train and bus deals

5/24Fri
multi-stopJetBlue
8h 20mHYA-ORD
5/27Mon
multi-stopJetBlue
4h 59mORD-HYA
$750
5/24Fri
multi-stopDelta
6h 14mMVY-ORD
5/27Mon
multi-stopDelta
4h 43mORD-MVY
$823
5/24Fri
multi-stopJetBlue
8h 20mHYA-ORD
5/27Mon
multi-stopJetBlue
5h 20mORD-HYA
$975

Search by stops

Search by airline

Search by price

Flights to Chicago