$208 Find Cheap Flights from Grand Cayman 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 Chicago departing on 12/14. 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
1 adult, Economy

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Cheap Flights from Grand Cayman to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Grand Cayman to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Grand Cayman to Chicago

Sat, Oct 4 - Sat, Oct 11
American Airlines Logo
12:25 pm - 8:27 pmGCM-ORD
8h 02m1 stop
American Airlines Logo
7:05 pm - 11:10 amORD-GCM
16h 05m1 stop
$471American Airlines
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Sat, Oct 4 - Sat, Oct 11
Delta Logo
12:52 pm - 8:05 amGCM-ORD
19h 13m2 stops
Delta Logo
5:20 am - 11:35 amORD-GCM
6h 15m1 stop
$487Delta
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Tue, Mar 10 - Wed, Mar 11
United Airlines Logo
1:50 pm - 6:04 pmGCM-ORD
4h 14mnonstop
United Airlines Logo
9:35 pm - 3:30 pmORD-GCM
17h 55m1 stop
$578United Airlines
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Sat, Oct 4 - Sat, Oct 11
Multiple Airlines Logo
8:50 am - 8:24 amGCM-ORD
23h 34m2 stops
Multiple Airlines Logo
7:43 pm - 5:20 pmORD-GCM
21h 37m2 stops
$598Multiple Airlines
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Sat, Oct 4 - Sat, Oct 11
Multiple Airlines Logo
8:50 am - 8:24 amGCM-ORD
23h 34m2 stops
Multiple Airlines Logo
11:55 am - 11:35 amORD-GCM
23h 40m3 stops
$602Multiple Airlines
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Tue, Mar 10 - Wed, Mar 11
American Airlines Logo
1:00 pm - 5:10 pmGCM-ORD
4h 10mnonstop
American Airlines Logo
8:10 am - 11:56 amORD-GCM
3h 46mnonstop
$615American Airlines
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Sat, Oct 4 - Sat, Oct 11
Multiple Airlines Logo
8:50 am - 2:05 pmGCM-ORD
29h 15m3 stops
Multiple Airlines Logo
11:55 am - 11:35 amORD-GCM
23h 40m3 stops
$627Multiple Airlines
Find Deal
Tue, Mar 10 - Wed, Mar 11
American Airlines Logo
1:00 pm - 5:10 pmGCM-ORD
4h 10mnonstop
American Airlines Logo
8:04 pm - 10:45 amORD-GCM
14h 41m2 stops
$655American Airlines
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Tue, Mar 10 - Wed, Mar 11
American Airlines Logo
12:40 pm - 7:31 pmGCM-ORD
6h 51m1 stop
American Airlines Logo
8:04 pm - 10:45 amORD-GCM
14h 41m2 stops
$659American Airlines
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Everything you should know

Cheapest round-trip
$471
American Airlines
Sat 10/4Sat 10/11
GCM - ORD • 1 stop
Cheapest non-stop
$615
American Airlines
Tue 3/10Wed 3/11
GCM - ORD • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Useful Info

Good to know

Cheapest flight$208
Flight from George Town to Chicago

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.

Reviews of the 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.
7.2
American AirlinesOverall score based on 10000 reviews
7.5Boarding
6.4Food
7.2Comfort
8.0Crew
6.9Entertainment
Airline reviews

The flight was on time and crew were nice, seats were tight and there was entertainment available

8.0 ExcellentJohn, Sep 2025YUL - ORD
Read more American Airlines reviews

The flight was on time and crew were nice, seats were tight and there was entertainment available

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

They should have MSNBC available on board. A 4- hour flight should provide more than a cookie.

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

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Everything you need to know for your flight to Chicago

Cabin class types available on flights to Grand Cayman

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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