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Find cheap flights from the Cayman Islands to Chicago from $327

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 7/21. 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
Wed 6/5
Wed 6/12

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

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 42,830,901 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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Flights to Chicago - Travel Insights & Trends

Get data-powered insights and trends for flights to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest day to fly to Chicago?

The average price of all flights to Chicago clicked on KAYAK for each day over the last 12 months.
Based on KAYAK data, the cheapest day to fly to Chicago is Thursday where tickets can be as cheap as $465. On the other hand, the most expensive day to fly is Sunday, where prices are $702 on average.

What is the cheapest time of day to fly to Chicago?

The average price for all flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to Chicago is generally in the morning, when flights cost $546 on average. The most expensive time of day to fly to Chicago is generally in the evening, which is peak travel time and where the average cost of a ticket is $746.

What is a good deal for flights to Chicago?

If you’re looking for cheap airfare to Chicago, 25% of our users found tickets to Chicago for the following prices or less: From George Town $360 one-way - $506 round-trip.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Midway Airport, with an average flight price of $114.

Which airline offers the most flights to Chicago?

Of the 14 airlines that fly to Chicago, United Airlines offers the most flights, with around 5,233 per week, followed by American Airlines with 4,024 flights per week.

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago O'Hare Airport (ORD), Chicago Midway Airport (MDW) and Chicago Greater Rockford Airport (RFD). The busiest airport is Chicago O'Hare Airport (ORD), with 79% of all flights arriving there.

How long is the flight to Chicago?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously any flights that include a layover will also be longer. The most popular route to Chicago on KAYAK is from George Town, which takes 4h 10m.

How many direct flights to Chicago are there each day?

There are around 1,903 direct flights from within Cayman Islands to Chicago every day. Most flights depart in the morning, with 6:00 am the most common departure time and 50% of flights departing in the morning.

How many direct flights to Chicago are there each week?

Each week there are around 13,319 direct flights from within Cayman Islands to Chicago. The most common day for departures is Thursday, with 16% of flights taking off on this day.

How many long-haul flights are there to Chicago each week?

There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Chicago. Instead, there are 2 medium-haul flights (3-6 hour flight duration), with the most arriving from George Town.

How many cities have direct flights to Chicago?

From the Cayman Islands, there are direct flights to Chicago from 1 city. This city is George Town and there are 2 direct flights each week.

Good to know

Low season

November

High season

July

Cheapest flight

$327
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from George Town to Chicago

FAQs - booking Chicago flights

  • Which Chicago airport is closest to central Chicago?

    Out of the 3 airports in Chicago, Chicago Midway Airport is the nearest to the city center (9 miles). You'll travel 16 miles to reach the center of Chicago if you land in Chicago O'Hare Airport and 79 miles if you land in Chicago Greater Rockford.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $485. The cheapest price found on KAYAK in the last 2 weeks cost $263 and departed from George Town Owen Roberts Intl Airport.

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

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

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

  • What is the Hacker Fare option on flights 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 with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight 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 up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Chicago

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Prefer to fly non-stop to Chicago?

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

Nonstop departures

Cayman Islands to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 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, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Nonstop returns

Chicago to Cayman Islands

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 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, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights
See more direct flights

Top airline flying from the Cayman Islands to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from the Cayman Islands to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with 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 14713 reviews
7.1Entertainment
6.6Food
7.2Comfort
8.0Crew
7.6Boarding
Airline reviews

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

2.0 MediocreAnonymous, May 2024STL - ORD
Read more about American Airlines reviews

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

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.

Book cheap flights from the Cayman Islands to Chicago

Recent round-trip flight deals

 
These are the cheapest round-trip flights to Chicago found on KAYAK in the last 72 hours.
5/20Mon
1 stop
16h 00mGCM-ORD
6/4Tue
1 stop
18h 55mORD-GCM
$418
5/20Mon
1 stop
16h 00mGCM-ORD
6/4Tue
3 stops
29h 12mORD-GCM
$432
6/2Sun
2 stopsAir Canada
18h 16mGCM-ORD
6/8Sat
1 stopAir Canada
24h 20mORD-GCM
$505
5/19Sun
2 stopsAir Canada
18h 16mGCM-ORD
5/23Thu
1 stopAir Canada
8h 35mORD-GCM
$509
8/2Fri
1 stopDelta
8h 51mGCM-ORD
8/5Mon
1 stopDelta
5h 30mORD-GCM
$569
5/31Fri
1 stopUnited Airlines
7h 05mGCM-ORD
6/7Fri
1 stopUnited Airlines
6h 35mORD-GCM
$648
5/31Fri
2 stopsAmerican Airlines
11h 44mGCM-ORD
6/7Fri
2 stopsAmerican Airlines
7h 35mORD-GCM
$690
6/2Sun
nonstopUnited Airlines
4h 10mGCM-ORD
6/8Sat
nonstopUnited Airlines
4h 02mORD-GCM
$694
8/2Fri
2 stopsAmerican Airlines
18h 42mGCM-ORD
8/5Mon
2 stopsAmerican Airlines
28h 35mORD-GCM
$700
8/2Fri
2 stopsDelta
19h 50mGCM-MDW
8/5Mon
1 stopDelta
5h 30mMDW-GCM
$744

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best deals for one-way flights to Chicago found on KAYAK in the last 72 hours.
7/21Sun
1 stopAir Canada
18h 09mGCM-ORD
$327
7/21Sun
2 stopsAir Canada
22h 55mGCM-ORD
$352
7/21Sun
nonstopUnited Airlines
4h 10mGCM-ORD
$396
7/21Sun
3 stops
20h 33mGCM-ORD
$519

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Last minute flights to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights to Chicago that are departing in the next 10 days.
5/10Fri
multi-stopDelta
20h 00mGCM-MDW
5/14Tue
multi-stopDelta
5h 26mMDW-GCM
$943
5/10Fri
multi-stopDelta
21h 20mGCM-MDW
5/14Tue
multi-stopDelta
18h 45mMDW-GCM
$969
5/10Fri
multi-stopDelta
26h 04mGCM-MDW
5/14Tue
multi-stopDelta
17h 39mMDW-GCM
$981

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Flights to Chicago

Return flight deals:

Chicago - Cayman Islands

Cabin classes:

$1,964
$288