$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 6/22. 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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Flight Deals

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, May 28 - Thu, Jun 4
Multiple Airlines Logo
7:00 am - 7:41 pm
GCM
-
ORD
12h 41m
2 stops
Multiple Airlines Logo
9:20 am - 9:15 pm
ORD
-
GCM
11h 55m
1 stop
$487Multiple Airlines
Thu, May 28 - Thu, Jun 4
Multiple Airlines Logo
7:00 am - 11:56 pm
GCM
-
ORD
16h 56m
1 stop
Multiple Airlines Logo
9:20 am - 9:15 pm
ORD
-
GCM
11h 55m
1 stop
$489Multiple Airlines
Thu, May 28 - Thu, Jun 4
Multiple Airlines Logo
7:00 am - 10:02 pm
GCM
-
MDW
15h 02m
2 stops
Multiple Airlines Logo
6:00 am - 9:15 pm
MDW
-
GCM
15h 15m
2 stops
$491Multiple Airlines
Wed, Sep 9 - Sun, Sep 13
Multiple Airlines Logo
7:00 am - 7:48 pm
GCM
-
ORD
36h 48m
2 stops
Multiple Airlines Logo
10:43 am - 11:30 am
ORD
-
GCM
24h 47m
1 stop
$500Multiple Airlines
Thu, Jun 11 - Thu, Jun 18
Multiple Airlines Logo
12:25 pm - 9:00 am
GCM
-
ORD
20h 35m
1 stop
Multiple Airlines Logo
7:07 am - 9:15 pm
ORD
-
GCM
14h 08m
2 stops
$513Multiple Airlines
Thu, Jun 11 - Thu, Jun 18
Multiple Airlines Logo
12:25 pm - 9:00 am
GCM
-
ORD
20h 35m
1 stop
Multiple Airlines Logo
7:10 am - 9:15 pm
ORD
-
GCM
14h 05m
1 stop
$521Multiple Airlines
Thu, May 21 - Sat, May 23
Air Canada Logo
12:25 pm - 2:55 pm
GCM
-
ORD
26h 30m
1 stop
Air Canada Logo
6:22 pm - 11:25 am
ORD
-
GCM
41h 03m
2 stops
$556Air Canada
Thu, May 28 - Thu, Jun 4
Southwest Logo
1:05 pm - 8:40 pm
GCM
-
MDW
7h 35m
1 stop
Southwest Logo
6:30 am - 11:55 am
MDW
-
GCM
5h 25m
1 stop
$653Southwest
Thu, May 28 - Thu, Jun 4
Southwest Logo
1:05 pm - 10:45 pm
GCM
-
MDW
9h 40m
2 stops
Southwest Logo
6:30 am - 11:55 am
MDW
-
GCM
5h 25m
1 stop
$658Southwest
Sat, Jun 13 - Sat, Jun 20
Delta Logo
12:59 pm - 10:17 pm
GCM
-
MDW
9h 18m
1 stop
Delta Logo
6:00 am - 11:34 am
MDW
-
GCM
5h 34m
1 stop
$668Delta
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Good to know

Low seasonNovember
Cheapest flight$237
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly and prices are also 14% 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 11678 reviews
7.5Boarding
6.4Food
6.9Entertainment
7.9Crew
7.2Comfort
Airline reviews

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

10.0 ExcellentDeepa, Apr 2026
DFW - ORD
Read more American Airlines reviews

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Didn't make it back on American Airlines due to a maintenance issue. The communication and updates were terrible. I ended up returning on Aero Mexico which had a much nicer aircraft with a large entertainment screen with movies and shows AND they had a nice inflight meal. That was a treat after being delayed 26 hours! I think some additional flight miles, or something should be offered for that long of a delay ---it was not pleasant at all---very physical and emotional experience.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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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.