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Cheap flights from the Cayman Islands to Chicago from $287

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from the Cayman Islands to Chicago departing on 1/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from the Cayman Islands to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from the Cayman Islands to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from the Cayman Islands to Chicago.

Cheap last minute flights

Planning a quick getaway from the Cayman Islands to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals to Chicago

Find recent round-trip train or bus tickets from the Cayman Islands to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
7:00 am - 4:12 pmGCM-ORD
10h 12m1 stop
10:19 am - 4:10 pmORD-GCM
28h 51m2 stops
Tue, Dec 24 - Sun, Jan 12
7:00 am - 4:12 pmGCM-ORD
10h 12m1 stop
7:20 am - 4:10 pmORD-GCM
7h 50m1 stop
Tue, Dec 24 - Sun, Jan 12
7:00 am - 4:12 pmGCM-ORD
10h 12m1 stop
8:30 am - 4:10 pmORD-GCM
30h 40m3 stops
Tue, Dec 24 - Sun, Jan 12
7:00 am - 10:43 pmGCM-ORD
16h 43m2 stops
8:30 am - 4:10 pmORD-GCM
30h 40m3 stops
Tue, Dec 24 - Sun, Jan 12
7:00 am - 5:30 amGCM-ORD
23h 30m3 stops
8:30 am - 4:10 pmORD-GCM
30h 40m3 stops
Tue, Dec 24 - Sun, Jan 12
5:10 pm - 6:26 pmGCM-MDW
26h 16m2 stops
Wed, Jan 15
11:30 am - 12:45 pmGCM-ORD
26h 15m2 stops
Tue, Jan 21
1:50 pm - 10:00 pmGCM-ORD
9h 10m1 stop
$316Southwest
Find Deal
Fri, Dec 20
2:40 pm - 8:57 amGCM-ORD
19h 17m1 stop
$322Air Canada
Find Deal
Mon, Dec 23
4:00 pm - 8:57 amGCM-ORD
17h 57m1 stop
$328Air Canada
Find Deal
Sun, Jan 19
1:50 pm - 10:20 pmGCM-ORD
9h 30m2 stops
$334Southwest
Find Deal
Fri, Jan 10
2:50 pm - 6:06 pmGCM-ORD
4h 16mnonstop
$392United Airlines
Find Deal
Thu, Dec 19
1:52 pm - 10:06 pmGCM-MDW
9h 14m1 stop
$397Delta
Find Deal
Thu, Dec 19
1:57 pm - 9:05 pmGCM-ORD
8h 08m1 stop
$397Delta
Find Deal
Wed, Dec 18
2:40 pm - 5:56 pmGCM-ORD
4h 16mnonstop
$417United Airlines
Find Deal
Sat, Dec 21

See travel insights to Chicago from

How to get the cheapest flight ticket from Cayman Islands to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $0. This is often the case because there is less demand to fly during this day of the week. When flying out on a Thursday, the most expensive travel day of the week, you can expect to see flight prices from Cayman Islands to Chicago for around $1,059.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Cayman Islands to Chicago during this time can be as low as $0. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $758.

What is the cheapest Cayman Islands to Chicago flight route?

Fly from George Town Owen Roberts Intl to Chicago O'Hare Intl for the best Cayman Islands - Chicago flight prices

What cabin class options are available on Cayman Islands to Chicago flights?

There are 2 cabin classes available to choose from on Cayman Islands to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Cayman Islands to Chicago flights?

You could potentially save up to 26% on your flight if you consider stops on a Cayman Islands to Chicago flight.

Cheap Cayman Islands to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Cayman Islands to Chicago

Best Price Found

$287

Fastest flight time

4h 10m

Direct flights

Thu, Fri, Sat and Sun

Airports in Chicago

2 airports
The best one-way flight to Chicago from Cayman Islands in the past 72 hours is $287. The best round-trip flight deal from Cayman Islands to Chicago found on momondo in the last 72 hours is $506.
The fastest flight from Cayman Islands to Chicago takes 4h 10m
Direct flights go from Cayman Islands to Chicago on Thursday, Friday, Saturday and Sunday. Airlines offering direct flights are: United Airlines and American Airlines.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • When did momondo last update prices for flights from Cayman Islands to Chicago?

    Prices for flights from Cayman Islands to Chicago are refreshed on a daily basis.

  • How many operators does momondo search for flights from Cayman Islands to Chicago?

  • How old do you have to be to fly from Cayman Islands to Chicago?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Cayman Islands to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Cayman Islands to Chicago?


Best airlines flying from Cayman Islands to Chicago

Compare and see reviews for airlines that fly from Cayman Islands to Chicago with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $451Free CancellationRating
7.4
9,172 reviews
Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Cayman Islands to Chicago?

Finding the right flight to Chicago from Cayman Islands is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Cayman Islands to Chicago with flexible booking policies on momondo?

Flights from Cayman Islands to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Cayman Islands to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Cayman Islands to Chicago.

I’m not ready to book a flight from Cayman Islands to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Cayman Islands to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.


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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago