$161 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 2/12. 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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Everything you should know

Cheapest round-trip
$368
Typical prices: $477-$489
Multiple Airlines
Sun 2/15Wed 2/18
GCM - ORD • 2 stops
Cheapest non-stop
$455
American Airlines
Fri 2/13Wed 2/18
GCM - ORD • Non-stop
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Flight Deals
Useful Info
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

Sun, Feb 15 - Wed, Feb 18
Multiple Airlines Logo
2:49 pm - 7:54 am
GCM
-
ORD
18h 05m
2 stops
Multiple Airlines Logo
4:43 pm - 1:43 pm
ORD
-
GCM
20h 00m
1 stop
$368Multiple Airlines
Sun, Feb 15 - Wed, Feb 18
Spirit Airlines Logo
2:49 pm - 9:13 pm
GCM
-
ORD
7h 24m
1 stop
Spirit Airlines Logo
4:43 pm - 1:43 pm
ORD
-
GCM
20h 00m
1 stop
$371Spirit Airlines
Thu, Apr 30 - Fri, May 1
Air Canada Logo
12:30 pm - 6:16 pm
GCM
-
ORD
29h 46m
1 stop
Air Canada Logo
9:15 pm - 11:30 am
ORD
-
GCM
14h 15m
1 stop
$376Air Canada
Thu, Apr 30 - Fri, May 1
Air Canada Logo
12:30 pm - 12:17 pm
GCM
-
ORD
23h 47m
2 stops
Air Canada Logo
8:20 pm - 11:30 am
ORD
-
GCM
15h 10m
1 stop
$394Air Canada
Sat, Feb 14 - Wed, Feb 18
Multiple Airlines Logo
11:25 am - 11:47 pm
GCM
-
ORD
13h 22m
2 stops
Multiple Airlines Logo
4:43 pm - 1:43 pm
ORD
-
GCM
20h 00m
1 stop
$419Multiple Airlines
Sat, Feb 14 - Wed, Feb 18
Multiple Airlines Logo
11:25 am - 11:47 pm
GCM
-
ORD
13h 22m
2 stops
Multiple Airlines Logo
4:43 pm - 1:43 pm
ORD
-
GCM
20h 00m
1 stop
$425Multiple Airlines
Fri, Feb 13 - Wed, Feb 18
Southwest Logo
1:50 pm - 9:00 pm
GCM
-
MDW
8h 10m
1 stop
Southwest Logo
5:00 am - 12:55 pm
MDW
-
GCM
6h 55m
1 stop
$439Southwest
Fri, Feb 13 - Wed, Feb 18
Delta Logo
1:54 pm - 10:31 pm
GCM
-
MDW
9h 37m
1 stop
Delta Logo
6:20 pm - 12:29 pm
MDW
-
GCM
17h 09m
2 stops
$460Delta
Sat, Feb 14 - Wed, Feb 18
Southwest Logo
1:25 pm - 11:25 pm
GCM
-
MDW
11h 00m
1 stop
Southwest Logo
5:00 am - 12:55 pm
MDW
-
GCM
6h 55m
1 stop
$469Southwest
Sat, Feb 14 - Wed, Feb 18
Delta Logo
1:54 pm - 8:54 am
GCM
-
MDW
20h 00m
2 stops
Delta Logo
6:00 am - 12:29 pm
MDW
-
GCM
5h 29m
1 stop
$490Delta
Useful Info

Good to know

Low seasonDecember
Cheapest flight$161
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly and prices are also 24% 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.
7.2
American AirlinesOverall score based on 11205 reviews
7.5Boarding
8.0Crew
6.4Food
7.2Comfort
6.9Entertainment
Airline reviews

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

10.0 Excellentaras, Jan 2026
PIT - ORD
Read more American Airlines reviews

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Flight, food and crew were all good, friendly and very satisfactory.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Griffith
Saint John

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.