$199 Find Cheap Flights from the Cayman Islands 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 4/30. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$286
Typical prices: $477-$489
Spirit Airlines
Thu 2/12Sun 2/15
GCM - ORD • 1 stop
Cheapest non-stop
$455
American Airlines
Fri 2/13Wed 2/18
GCM - ORD • Non-stop
Top airlines
American Airlines
Most flights • 7 per week
American Airlines
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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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!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from the Cayman Islands to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from the Cayman Islands 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 the Cayman Islands to Chicago

Thu, Feb 12 - Sun, Feb 15
Spirit Airlines Logo
2:49 pm - 11:47 pm
GCM
-
ORD
9h 58m
1 stop
Spirit Airlines Logo
5:15 am - 1:43 pm
ORD
-
GCM
7h 28m
1 stop
$286Spirit Airlines
Thu, Feb 19 - Wed, Feb 25
Spirit Airlines Logo
2:49 pm - 9:13 pm
GCM
-
ORD
7h 24m
1 stop
Spirit Airlines Logo
5:58 pm - 1:43 pm
ORD
-
GCM
18h 45m
2 stops
$316Spirit Airlines
Thu, Feb 19 - Wed, Feb 25
Spirit Airlines Logo
2:49 pm - 11:47 pm
GCM
-
ORD
9h 58m
1 stop
Spirit Airlines Logo
10:44 am - 1:43 pm
ORD
-
GCM
25h 59m
3 stops
$329Spirit Airlines
Tue, Mar 17 - Tue, Mar 24
Multiple Airlines Logo
11:30 am - 8:25 am
GCM
-
ORD
20h 55m
1 stop
Multiple Airlines Logo
4:51 pm - 4:05 pm
ORD
-
GCM
23h 14m
1 stop
$363Multiple Airlines
Thu, Feb 12 - Sun, Feb 15
Spirit Airlines Logo
2:49 pm - 12:40 am
GCM
-
ORD
10h 51m
2 stops
Spirit Airlines Logo
5:15 am - 1:43 pm
ORD
-
GCM
7h 28m
1 stop
$380Spirit Airlines
Tue, Mar 17 - Tue, Mar 24
Multiple Airlines Logo
11:30 am - 8:50 am
GCM
-
ORD
21h 20m
2 stops
Multiple Airlines Logo
4:51 pm - 4:05 pm
ORD
-
GCM
23h 14m
1 stop
$400Multiple Airlines
Fri, Feb 13 - Wed, Feb 18
Delta Logo
1:54 pm - 10:31 pm
GCM
-
MDW
9h 37m
1 stop
Delta Logo
6:00 am - 12:29 pm
MDW
-
GCM
5h 29m
1 stop
$460Delta
Thu, Feb 19 - Wed, Feb 25
Southwest Logo
1:50 pm - 10:25 pm
GCM
-
MDW
9h 35m
1 stop
Southwest Logo
5:00 am - 12:55 pm
MDW
-
GCM
6h 55m
1 stop
$495Southwest
Tue, Mar 17 - Tue, Mar 24
Delta Logo
1:12 pm - 10:31 pm
GCM
-
MDW
9h 19m
1 stop
Delta Logo
6:00 am - 11:47 am
MDW
-
GCM
5h 47m
1 stop
$496Delta
Thu, Feb 19 - Wed, Feb 25
Southwest Logo
1:50 pm - 10:25 pm
GCM
-
MDW
9h 35m
1 stop
Southwest Logo
7:50 pm - 12:55 pm
MDW
-
GCM
16h 05m
2 stops
$534Southwest
Booking Insights

KAYAK's insights & trends for flights to Chicago

Get data-powered insights and trends for flights to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is a good deal for flights to Chicago?

If you’re looking for cheap airfare to Chicago, 25% of our users found tickets to Chicago for the following prices or less: From George Town $220 one-way - $276 round-trip.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Greater Rockford Airport, with an average flight price of $134.

Good to know

Low seasonFebruary
Cheapest flight$199
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly and prices are also 22% lower on average.
Flight from George Town to Chicago

FAQs - booking Chicago flights

  • Which Chicago airport is closest to central Chicago?

    Out of the 3 airports in Chicago, Chicago Midway Airport is the nearest to the city center (9 miles). You'll travel 16 miles to reach the center of Chicago if you land in Chicago O'Hare Airport and 79 miles if you land in Chicago Greater Rockford.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $512. The cheapest price found on KAYAK in the last 2 weeks cost $218 and departed from George Town Owen Roberts Intl Airport.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Sunday where tickets can be as cheap as $373. On the other hand, the most expensive day to fly is Tuesday, where prices are $1,469 on average.

  • How does KAYAK find such low prices on flights 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 to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights 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 with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight 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 up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Chicago?

    The cheapest time of day to fly to Chicago is generally in the afternoon, when flights cost $497 on average. The most expensive time of day to fly to Chicago is generally in the evening, which is peak travel time and where the average cost of a ticket is $707.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $220 or less one-way and $276 or less round-trip.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the top airline flying from the Cayman Islands to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from the Cayman Islands to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with 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 11213 reviews
6.4Food
7.5Boarding
8.0Crew
7.2Comfort
6.9Entertainment
Airline reviews

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

2.0 MediocreManikandan, Jan 2026
DFW - ORD
Read more American Airlines reviews

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

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.

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 Chicago

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.