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Cheap Flights from Grand Cayman to O'Hare Intl

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Grand Cayman to O'Hare Intl

Wed, Dec 9 - Mon, Dec 14
Air Canada Logo
1:10 pm - 7:58 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
7h 48m1 stop Toronto Pearson Intl
Air Canada Logo
8:50 pm - 12:10 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
14h 20m1 stop Toronto Pearson Intl
$345Air Canada
Wed, Dec 9 - Mon, Dec 14
Air Canada Logo
1:10 pm - 9:08 amGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
20h 58m1 stop Toronto Pearson Intl
Air Canada Logo
1:55 pm - 12:10 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
21h 15m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$348Air Canada
Wed, Dec 9 - Mon, Dec 14
Air Canada Logo
1:10 pm - 8:00 amGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
19h 50m2 stops Toronto Pearson Intl Ottawa
Air Canada Logo
1:55 pm - 12:10 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
21h 15m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$353Air Canada
Sun, Feb 21 - Thu, Feb 25
Air Canada Logo
1:10 pm - 7:58 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
7h 48m1 stop Toronto Pearson Intl
Air Canada Logo
8:50 pm - 12:10 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
14h 20m1 stop Toronto Pearson Intl
$594Air Canada
Tue, Oct 13 - Mon, Oct 19
Multiple Airlines Logo
1:45 pm - 10:12 amGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
20h 27m3 stops Toronto Pearson Intl Ottawa Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
8:40 pm - 12:45 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
16h 05m1 stop Toronto Pearson Intl
$599Multiple Airlines
Sun, Feb 21 - Thu, Feb 25
Air Canada Logo
1:10 pm - 7:58 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
7h 48m1 stop Toronto Pearson Intl
Air Canada Logo
11:00 am - 12:10 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
24h 10m2 stops Ottawa Toronto Pearson Intl
$599Air Canada
Tue, Oct 13 - Mon, Oct 19
Multiple Airlines Logo
1:45 pm - 10:12 amGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
20h 27m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
8:40 pm - 12:45 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
16h 05m1 stop Toronto Pearson Intl
$602Multiple Airlines
Tue, Oct 13 - Mon, Oct 19
Multiple Airlines Logo
1:45 pm - 10:06 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
8h 21m1 stop Toronto Pearson Intl
Multiple Airlines Logo
8:40 pm - 12:45 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
16h 05m1 stop Toronto Pearson Intl
$610Multiple Airlines
Mon, Dec 28 - Sat, Jan 2
American Airlines Logo
5:45 pm - 9:25 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 40mnonstop
American Airlines Logo
10:40 am - 3:47 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 07mnonstop
$719American Airlines
Mon, Dec 28 - Sat, Jan 2
American Airlines Logo
5:45 pm - 9:25 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 40mnonstop
American Airlines Logo
6:00 am - 2:30 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
7h 30m1 stop Dallas/Fort Worth
$723American Airlines
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Cheapest flight

$218
Flight from George Town to Chicago

FAQs for booking Grand Cayman to Chicago flights

  • 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.

Reviews of the top airline flying from Grand Cayman to O'Hare Intl

 
Need help choosing which airline to fly with from Grand Cayman 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.
7.1
American AirlinesOverall score based on 12075 reviews
6.4Food
7.4Boarding
6.8Entertainment
7.9Crew
7.2Comfort
Airline reviews

The flight was delay roughly 90 minutes. Once we arrived at O'Hare, we sat on the tarmac for another 90 minutes. I understand that O'Hare is under construction however they need to figure out a solution as every incoming flight I have been on has been delayed coming to a gate.

2.0 MediocreSteven, Sep 2026
Read more American Airlines reviews

The flight was delay roughly 90 minutes. Once we arrived at O'Hare, we sat on the tarmac for another 90 minutes. I understand that O'Hare is under construction however they need to figure out a solution as every incoming flight I have been on has been delayed coming to a gate.

We were stuck with no gate upon landing for 90 minutes. Unacceptable.

Horrible. Flight was delayed for 4 hours first till 7pm. Then for one more hour. Then again and around 9pm we were finally boarded and waited for catering delivery for another hour. At 10pm we were not interested on food at all. Tired, sleepy we arrived after midnight. Insane.

I've never seen such poor lack of information at a gate station in 69 years. The flight from COS was to depart at 12:37pm. At boarding time, the gate agent in the microphone mumbled something completely unintelligible. I understood one word. "mechanical". Nothing else. Absolutely nothing else was reported for the next 1-1/2 hours. Past the time for departure, at 12:37pm, the gate agent simply walked away and the station was left unattended, as all of the passengers waited expectantly. The board still said that the flight was ON TIME. That was hard to believe since it was then well past 12:37pm and we all were sitting at the gate and there was absolutely no gate agent anywhere in site. I stopped an employee who was standing somewhere else and said that we can use some information. Much later, the same gate agent said that he will have information for us about 5 minutes but he "doesn't know any more than you do." Of course, five minutes came and went and he did absolutely nothing. One and a half hours after 12:37pm, he opened the door and began boarding. No explanation, no apology. Once we were boarded, the same happened on the plane. We sat. No explanation, no apology, from any flight attendants. Finally, finally, a pilot apologized and explained that there would be a delay. WELL NO KIDDING !

Our flight from Chicago to Des Moines was the problem flight due to a dismissive flight attendant. His conduct was unnecessary and unprofessional.. I will avoid using Americam Airlines again because of the situation. Very disappointing.

Mostly excellent. However, many too many gate changes. Connecting flight at ORD changed gate 6 times.

Mechanical issues and delays. I get it but bad experience. Turned my 3 hour airport experience into a 9 hours

The baggage process at the gate was terrible. Stay was not friendly at all

Flight was delayed because of mechanical. Could not get landing space which caused me to miss my connection. Messy and not organized.

We landed slightly early but then sat in holding area waiting for our gate to clear out for about an hour, so technically we arrived one hour late at the gate at ORD. The airport may be partially responsible here, but regardless of who is responsible, it was a bad experience to be so close yet unable to get off the plane.

Traveling to a place near O'Hare Intl?

Book flights to O'Hare Intl if you plan to visit one of these locations
Merrillville
Gurnee
South Haven
Oak Brook
Tinley Park
Hammond
Saint Joseph
Des Plaines
Elk Grove Village
Hoffman Estates
Portage
South Holland
Oakbrook Terrace
Willowbrook
Lansing
Alsip
Delavan
Lisle
Northbrook
Valparaiso

More options for your flight to O'Hare Intl