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

ORD

$168 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 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
Tue 6/4
Tue 6/11

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

In the last 7 days travelers have searched 43,369,418 times on KAYAK, and here is why:

Save 22% 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

$168
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 24% 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 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 14728 reviews
7.2Comfort
6.6Food
7.1Entertainment
7.6Boarding
8.0Crew
Airline reviews

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.

6.0 GoodAnonymous, Apr 2024SPI - ORD
Read more about American Airlines reviews

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.

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

Book cheap flights from Cape Cod and the Islands to Chicago

Recent round-trip flight deals

7/12Fri
1 stopDelta
6h 36mACK-ORD
7/16Tue
1 stopDelta
7h 17mORD-ACK
$263
7/12Fri
1 stopDelta
6h 36mACK-ORD
7/16Tue
2 stopsDelta
7h 12mORD-ACK
$268
5/25Sat
nonstopUnited Airlines
3h 17mACK-ORD
5/27Mon
nonstopUnited Airlines
2h 53mORD-ACK
$270
6/25Tue
1 stopAmerican Airlines
6h 11mHYA-ORD
6/26Wed
1 stopAmerican Airlines
4h 14mORD-HYA
$306
7/12Fri
1 stopDelta
7h 47mMVY-ORD
7/16Tue
1 stopDelta
15h 37mORD-MVY
$314
5/25Sat
1 stopUnited Airlines
7h 45mACK-ORD
5/27Mon
nonstopUnited Airlines
2h 53mORD-ACK
$319
7/12Fri
1 stopDelta
6h 31mMVY-ORD
7/16Tue
2 stopsDelta
19h 56mORD-MVY
$330
6/25Tue
2 stopsAmerican Airlines
10h 40mHYA-ORD
6/26Wed
1 stopAmerican Airlines
4h 19mORD-HYA
$388
5/23Thu
1 stopJetBlue
8h 20mHYA-ORD
5/26Sun
1 stopJetBlue
4h 59mORD-HYA
$607
9/20Fri
1 stopJetBlue
6h 25mHYA-ORD
9/23Mon
1 stopJetBlue
4h 18mORD-HYA
$632

Search by stops

Search by airline

Search by price

Recent one-way flight deals

7/23Tue
1 stopAmerican Airlines
18h 19mMVY-ORD
$168
6/4Tue
1 stopDelta
5h 16mMVY-ORD
$193
7/23Tue
2 stopsAmerican Airlines
10h 04mMVY-ORD
$198
6/22Sat
1 stopJetBlue
5h 47mACK-ORD
$217
6/22Sat
nonstopAmerican Airlines
2h 58mACK-ORD
$220
6/2Sun
nonstopUnited Airlines
3h 17mACK-ORD
$255
8/18Sun
1 stopJetBlue
7h 39mACK-ORD
$278
6/22Sat
2 stopsAmerican Airlines
9h 34mACK-ORD
$298
5/26Sun
1 stopJetBlue
4h 42mHYA-ORD
$303
8/17Sat
2 stopsUnited Airlines
16h 37mACK-ORD
$334

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

5/8Wed
multi-stopJetBlue
8h 30mHYA-ORD
5/9Thu
multi-stopJetBlue
4h 59mORD-HYA
$867
5/8Wed
multi-stop
10h 43mEWB-ORD
5/9Thu
multi-stop
7h 12mORD-EWB
$1,269

Search by stops

Search by airline

Search by price

Flights to Chicago