$282 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 7/25. 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
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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

Wed, Jun 10 - Wed, Jun 24
Multiple Airlines Logo
7:00 am - 1:25 pm
GCM
-
ORD
30h 25m
2 stops
Multiple Airlines Logo
8:40 pm - 11:25 am
ORD
-
GCM
14h 45m
1 stop
$440Multiple Airlines
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
Sat, Jun 13 - Sat, Jun 20
Multiple Airlines Logo
10:55 am - 9:00 am
GCM
-
ORD
22h 05m
1 stop
Multiple Airlines Logo
5:10 am - 11:35 am
ORD
-
GCM
30h 25m
3 stops
$528Multiple 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
6:55 am - 9:15 pm
ORD
-
GCM
14h 20m
2 stops
$534Multiple Airlines
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
Sat, May 16 - Wed, May 20
Southwest Logo
1:05 pm - 10:35 pm
GCM
-
MDW
9h 30m
2 stops
Southwest Logo
6:00 am - 12:10 pm
MDW
-
GCM
6h 10m
1 stop
$672Southwest
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 the cheapest day to fly to Chicago?

The average price of all round-trip flights to Chicago clicked on KAYAK for each day over the last 12 months.

Based on KAYAK data, the cheapest day to fly to Chicago is Sunday where round-trip tickets can be as cheap as $381. On the other hand, the most expensive day to fly is Friday, where round-trip prices are $2,559 on average.

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

The average price for all round-trip flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Chicago is generally in the afternoon, when round-trip flights cost $599 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.

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 $470 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 (RFD), with an average flight price of $132.

Good to know

Low seasonNovember
Cheapest flight$282
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 - 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 $505. The cheapest price found on KAYAK in the last 2 weeks cost $262 and departed from George Town Owen Roberts Intl Airport.

  • 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.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $273 or less one-way and $470 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.
7.1
American AirlinesOverall score based on 11674 reviews
6.9Entertainment
7.9Crew
6.4Food
7.5Boarding
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
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Saint John
Griffith

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.