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Find cheap flights from Cayman Islands to Chicago O'Hare Airport from $258

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 5/14. 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
lun. 6/3
lun. 6/10

Search hundreds of travel sites at once for deals on flights to Chicago O'Hare Airport

 
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 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.

Flights to O'Hare Intl - Travel Insights & Trends

Get data-powered insights and trends for flights to O'Hare Intl 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 O'Hare Intl Airport 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 O'Hare Intl Airport?

The average price for all flights to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport is generally in the morning, when flights cost $513 on average. The most expensive time of day to fly to Chicago O'Hare Intl Airport is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $529.

What is a good deal for flights to Chicago O'Hare Intl Airport?

If you’re looking for cheap airfare to Chicago O'Hare Intl Airport, 25% of our users found tickets to Chicago O'Hare Intl Airport for the following prices or less: From George Town $371 one-way - $389 round-trip.

Which airline offers the most flights to Chicago O'Hare Intl Airport?

Of the 12 airlines that fly to Chicago O'Hare Intl Airport, United Airlines offers the most flights, with around 5,222 per week, followed by American Airlines with 2,596 flights per week.

How long is the flight to Chicago O'Hare Intl Airport?

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 O'Hare Intl Airport are there each day?

There are around 1,267 direct flights from within Cayman Islands to Chicago O'Hare Intl Airport every day. Most flights depart in the morning, with 6:00 am the most common departure time and 52% of flights departing in the morning.

How many direct flights to Chicago O'Hare Intl Airport are there each week?

Each week there are around 8,868 direct flights from within Cayman Islands to Chicago O'Hare Intl Airport. The most common day for departures is Thursday, with 15% of flights taking off on this day.

How many long-haul flights are there to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport. 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 O'Hare Intl Airport?

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

Good to know

Low season

February

High season

August

Cheapest flight

$258
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly and prices are also 17% lower on average.
Flight from George Town to Chicago

FAQs - booking Chicago O'Hare Airport flights

  • How far is Chicago O'Hare Airport from central Chicago?

    The city center of Chicago is 16 miles from Chicago O'Hare Airport.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $451. The cheapest price found on KAYAK in the last 2 weeks cost $239 and departed from George Town Owen Roberts Intl Airport.

  • How does KAYAK find such low prices on flights to Chicago O'Hare Airport?

    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 O'Hare Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport 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 O'Hare Airport?

    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 O'Hare Airport 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 O'Hare Airport?

    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 O'Hare Airport 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 O'Hare Airport

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

Prefer to fly non-stop to Chicago O'Hare Intl?

Find which airlines fly direct to O'Hare Intl, which days they fly and book direct flights.

Nonstop departures

Cayman 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 Cayman 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 the Cayman Islands to O'Hare Intl

 
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 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
United AirlinesOverall score based on 11125 reviews
7.7Boarding
7.1Entertainment
7.2Comfort
8.1Crew
6.7Food
Airline reviews

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

8.0 ExcellentAnonymous, Apr 2024YUL - ORD
Read more about United Airlines reviews

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

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 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.
5/23jue.
1 stopAir Canada
18h 09mGCM-ORD
6/6jue.
1 stopAir Canada
8h 35mORD-GCM
$513
5/19dom.
1 stopAir Canada
18h 09mGCM-ORD
6/1sáb.
1 stopAir Canada
22h 35mORD-GCM
$530
5/23jue.
2 stopsAir Canada
18h 16mGCM-ORD
6/6jue.
1 stopAir Canada
8h 35mORD-GCM
$537
5/24vie.
1 stopUnited Airlines
7h 20mGCM-ORD
6/9dom.
nonstopUnited Airlines
4h 02mORD-GCM
$619
5/23jue.
2 stopsAir Canada
18h 16mGCM-ORD
6/9dom.
1 stopAir Canada
8h 35mORD-GCM
$620
5/24vie.
1 stopUnited Airlines
9h 19mGCM-ORD
6/9dom.
1 stopUnited Airlines
6h 35mORD-GCM
$623
5/24vie.
2 stopsAmerican Airlines
11h 44mGCM-ORD
6/7vie.
2 stopsAmerican Airlines
14h 17mORD-GCM
$690
5/21mar.
2 stopsAmerican Airlines
9h 14mGCM-ORD
6/5mié.
1 stopAmerican Airlines
6h 35mORD-GCM
$711
5/20lun.
2 stops
13h 44mGCM-ORD
6/6jue.
1 stop
10h 53mORD-GCM
$752
5/20lun.
2 stops
13h 44mGCM-ORD
6/5mié.
2 stops
31h 39mORD-GCM
$762

Search by stops

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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.
5/14mar.
1 stop
21h 15mGCM-ORD
$258
5/13lun.
1 stop
23h 15mGCM-ORD
$259
9/26jue.
1 stopAir Canada
7h 48mGCM-ORD
$302
9/29dom.
2 stopsAir Canada
23h 42mGCM-ORD
$303
9/25mié.
2 stopsAmerican Airlines
10h 16mGCM-ORD
$385
9/23lun.
2 stopsDelta
18h 36mGCM-ORD
$408
5/24vie.
1 stopDelta
11h 04mGCM-ORD
$422
9/24mar.
2 stopsAmerican Airlines
10h 16mGCM-ORD
$445
5/20lun.
1 stopUnited Airlines
10h 32mGCM-ORD
$472
5/11sáb.
nonstopUnited Airlines
4h 12mGCM-ORD
$531

Search by stops

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Search by price

Flights to Chicago O'Hare Airport

Destination:

Chicago O'Hare Airport (ORD)United States

Return flight deals:

Chicago O'Hare Airport - Cayman Islands

Cabin classes:

$1,964
$288

Popular routes

The most searched flights to Chicago O'Hare Airport by KAYAK users.