$237 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 6/15. 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, 0 bags

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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

Thu, Apr 9 - Sun, Apr 12
Spirit Airlines Logo
1:52 pm - 11:17 pm
GCM
-
ORD
9h 25m
1 stop
Spirit Airlines Logo
5:05 am - 12:57 pm
ORD
-
GCM
7h 52m
1 stop
$351Spirit Airlines
Thu, Apr 9 - Sun, Apr 12
Multiple Airlines Logo
1:52 pm - 11:36 pm
GCM
-
ORD
9h 44m
2 stops
Multiple Airlines Logo
5:05 am - 12:57 pm
ORD
-
GCM
7h 52m
1 stop
$394Multiple Airlines
Thu, Apr 23 - Sun, Apr 26
Air Canada Logo
11:55 am - 9:10 am
GCM
-
ORD
21h 15m
1 stop
Air Canada Logo
6:40 pm - 10:15 am
ORD
-
GCM
15h 35m
1 stop
$416Air Canada
Thu, Apr 23 - Sun, Apr 26
Air Canada Logo
11:55 am - 5:50 pm
GCM
-
ORD
29h 55m
1 stop
Air Canada Logo
8:40 am - 10:15 am
ORD
-
GCM
25h 35m
2 stops
$419Air Canada
Thu, Apr 23 - Sun, Apr 26
Air Canada Logo
11:55 am - 7:58 am
GCM
-
ORD
20h 03m
2 stops
Air Canada Logo
2:00 pm - 10:15 am
ORD
-
GCM
20h 15m
2 stops
$429Air Canada
Thu, Apr 30 - Mon, May 4
Multiple Airlines Logo
4:45 pm - 11:59 pm
GCM
-
ORD
7h 14m
1 stop
Multiple Airlines Logo
11:51 am - 4:05 pm
ORD
-
GCM
28h 14m
2 stops
$460Multiple Airlines
Sat, Apr 4 - Thu, Apr 9
Multiple Airlines Logo
1:15 pm - 12:38 am
GCM
-
ORD
35h 23m
2 stops
Multiple Airlines Logo
5:05 am - 12:57 pm
ORD
-
GCM
7h 52m
1 stop
$479Multiple Airlines
Thu, Apr 9 - Sun, Apr 12
Spirit Airlines Logo
1:52 pm - 2:16 pm
GCM
-
ORD
24h 24m
3 stops
Spirit Airlines Logo
5:05 am - 12:57 pm
ORD
-
GCM
7h 52m
1 stop
$482Spirit Airlines
Thu, Apr 23 - Sun, Apr 26
Southwest Logo
1:05 pm - 8:40 pm
GCM
-
MDW
7h 35m
1 stop
Southwest Logo
5:05 am - 11:55 am
MDW
-
GCM
6h 50m
1 stop
$498Southwest
Thu, Apr 23 - Sun, Apr 26
Southwest Logo
1:05 pm - 10:45 pm
GCM
-
MDW
9h 40m
2 stops
Southwest Logo
5:05 am - 11:55 am
MDW
-
GCM
6h 50m
1 stop
$503Southwest
Useful Info

Good to know

Low seasonNovember
Cheapest flight$237
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly and prices are also 16% lower on average.
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.
7.1
American AirlinesOverall score based on 11468 reviews
7.9Crew
6.9Entertainment
7.5Boarding
7.2Comfort
6.4Food
Airline reviews

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

2.0 MediocreMarianne, Mar 2026
DFW - ORD
Read more American Airlines reviews

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

I understand that there is a catering issue - water should be the minimum stock. During the flight, not once that the attendants came through with water. The conversations in the kitchen were very loud and they were swearing. I do not expect any white glove service, at the minimum, we should be cordial. It was almost an inconveniece that we were on the flight. And it made us feel if you even dare question us, we'll make you deplane.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Saint Joseph
Hammond
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Lansing
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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.