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Find cheap flights from Grand Cayman to Chicago from $415

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 5/22. 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
sáb. 6/1
sáb. 6/8

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Good to know

Low season

November

High season

July
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly and prices are also 8% lower on average.

FAQs for booking flights from Grand Cayman to Chicago

  • How does KAYAK find such low prices on flights from Grand Cayman 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 Grand Cayman to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Grand Cayman to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Grand Cayman 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 Grand Cayman 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 Grand Cayman with another airline.

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

Find which airlines fly direct from Grand Cayman to Chicago, which days they fly and book direct flights.

Nonstop departures

Grand Cayman to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

See more direct flights

Nonstop returns

Chicago to Grand Cayman

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

See more direct flights
See more direct flights

Top airline flying from Grand Cayman to Chicago

 
Need help choosing which airline to fly with from Grand Cayman to Chicago? 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 14788 reviews
7.1Entertainment
7.6Boarding
7.2Comfort
8.0Crew
6.6Food
Airline reviews

The plane was old and in new of a cleaning up and renovating on the interior. Seats and carpets were very worn and dirty looking. Cushioning on the seats was broken down and not as comfortable as newer jet seats. Food was a little below average but okay. Staff were friendly and hard working but did not pick up debris or food they spilled when collecting from the customers. But they were very helpful and professional.

8.0 ExcellentMichael, Apr 2024AMM - ORD
Read more about American Airlines reviews

The plane was old and in new of a cleaning up and renovating on the interior. Seats and carpets were very worn and dirty looking. Cushioning on the seats was broken down and not as comfortable as newer jet seats. Food was a little below average but okay. Staff were friendly and hard working but did not pick up debris or food they spilled when collecting from the customers. But they were very helpful and professional.

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.

lounge was the highlight - seats weren't that comfortable - it was a full flight but no complaints

Book cheap flights from Grand Cayman to Chicago

Recent round-trip flight deals

5/22mié.
1 stop
6h 57mGCM-MDW
6/3lun.
1 stop
20h 47mMDW-GCM
$415
5/22mié.
1 stop
6h 57mGCM-MDW
6/5mié.
1 stop
7h 43mMDW-GCM
$423
5/19dom.
1 stopAir Canada
18h 09mGCM-ORD
6/1sáb.
1 stopAir Canada
24h 20mORD-GCM
$530
8/2vie.
1 stopAmerican Airlines
8h 50mGCM-ORD
8/5lun.
1 stopAmerican Airlines
5h 59mORD-GCM
$575
8/2vie.
2 stopsDelta
20h 31mGCM-ORD
8/5lun.
1 stopDelta
5h 30mORD-GCM
$579
10/8mar.
1 stopAmerican Airlines
8h 43mGCM-ORD
10/15mar.
2 stopsAmerican Airlines
8h 06mORD-GCM
$580
5/22mié.
1 stopUnited Airlines
10h 32mGCM-ORD
6/2dom.
nonstopUnited Airlines
4h 02mORD-GCM
$619
5/23jue.
2 stopsAir Canada
18h 16mGCM-ORD
6/2dom.
1 stopAir Canada
8h 35mORD-GCM
$620
5/22mié.
1 stopUnited Airlines
7h 15mGCM-ORD
6/5mié.
1 stopUnited Airlines
6h 35mORD-GCM
$623
5/22mié.
1 stopDelta
9h 10mGCM-MDW
6/4mar.
1 stopDelta
5h 31mMDW-GCM
$664

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Recent one-way flight deals

5/22mié.
1 stopUnited Airlines
15h 25mGCM-ORD
$637
5/22mié.
2 stopsAmerican Airlines
11h 44mGCM-ORD
$665
5/22mié.
3 stops
55h 19mGCM-ORD
$2,049

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Flights to Chicago

Return flight deals:

Chicago - Grand Cayman

Cabin classes:

$274
$293
$219
$38

Browse origins: