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Cheap flights from the Cayman Islands to Chicago from $286

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 6/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from the Cayman Islands to Chicago

Recent round-trip flight deals from the Cayman Islands to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from the Cayman Islands to Chicago.
 Logo
11:30 am - 4:03 pmGCM-ORD
28h 33m1 stop
 Logo
6:16 pm - 4:00 pmORD-GCM
21h 44m1 stop
mié., may. 28 - jue., may. 29
American Airlines Logo
12:25 pm - 7:35 pmGCM-ORD
7h 10m1 stop
American Airlines Logo
7:16 pm - 11:10 amORD-GCM
15h 54m1 stop
$660American Airlines
Find Deal
jue., may. 29 - mar., jun. 3
American Airlines Logo
12:25 pm - 11:08 pmGCM-ORD
10h 43m2 stops
American Airlines Logo
5:00 am - 11:20 amORD-GCM
6h 20m1 stop
$664American Airlines
Find Deal
jue., may. 29 - mar., jun. 3
Delta Logo
12:35 pm - 9:27 pmGCM-MDW
8h 52m1 stop
Delta Logo
6:00 am - 11:20 amMDW-GCM
5h 20m1 stop
$811Delta
Find Deal
jue., may. 29 - mar., jun. 3
American Airlines Logo
12:25 pm - 12:11 amGCM-ORD
11h 46m1 stop
American Airlines Logo
6:35 pm - 11:20 amORD-GCM
16h 45m1 stop
$815American Airlines
Find Deal
vie., may. 16 - mar., may. 20
American Airlines Logo
12:25 pm - 12:11 amGCM-ORD
11h 46m1 stop
American Airlines Logo
5:00 am - 1:10 pmORD-GCM
8h 10m2 stops
$819American Airlines
Find Deal
vie., may. 16 - mar., may. 20
 Logo
7:00 am - 11:04 pmGCM-ORD
16h 04m2 stops
 Logo
8:17 am - 9:20 pmORD-GCM
13h 03m1 stop
mié., may. 28 - jue., may. 29
American Airlines Logo
12:25 pm - 11:56 pmGCM-ORD
11h 31m2 stops
American Airlines Logo
5:00 am - 1:10 pmORD-GCM
8h 10m2 stops
$899American Airlines
Find Deal
vie., may. 16 - mar., may. 20
 Logo
11:30 am - 11:50 amGCM-ORD
24h 20m2 stops
 Logo
5:58 pm - 9:20 pmORD-GCM
27h 22m2 stops
$1,565
Find Deal
mié., may. 28 - jue., may. 29

American Airlines flights from Cayman Islands to Chicago

Our best American Airlines deals on Cayman Islands to Chicago flight tickets
American Airlines
May 29
GCM12:25 pmGeorge Town Owen Roberts Intl
7h 10m
1 stop
ORD7:35 pmChicago O'Hare Intl
Jun 3
ORD7:16 pmChicago O'Hare Intl
15h 54m
1 stop
GCM11:10 amGeorge Town Owen Roberts Intl
American Airlines
May 29
GCM12:25 pmGeorge Town Owen Roberts Intl
10h 43m
2 stops
ORD11:08 pmChicago O'Hare Intl
Jun 3
ORD5:00 amChicago O'Hare Intl
6h 20m
1 stop
GCM11:20 amGeorge Town Owen Roberts Intl
American Airlines
May 16
GCM12:25 pmGeorge Town Owen Roberts Intl
11h 46m
1 stop
ORD12:11 amChicago O'Hare Intl
May 20
ORD6:35 pmChicago O'Hare Intl
16h 45m
1 stop
GCM11:20 amGeorge Town Owen Roberts Intl

Delta flights from Cayman Islands to Chicago

Our best Delta deals on Cayman Islands to Chicago flight tickets
Delta
May 29
GCM12:35 pmGeorge Town Owen Roberts Intl
8h 52m
1 stop
MDW9:27 pmChicago Midway
Jun 3
MDW6:00 amChicago Midway
5h 20m
1 stop
GCM11:20 amGeorge Town Owen Roberts Intl
Delta
Apr 25
GCM12:47 pmGeorge Town Owen Roberts Intl
9h 35m
1 stop
MDW10:22 pmChicago Midway
Apr 28
MDW6:04 amChicago Midway
5h 18m
1 stop
GCM11:22 amGeorge Town Owen Roberts Intl

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 Sunday when prices can be found for as low as $551. This is often the case because there is less demand to fly during this day of the week. When flying out on a Wednesday, the most expensive travel day of the week, you can expect to see flight prices from Cayman Islands to Chicago for around $1,867.

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 at noon. Flights from Cayman Islands to Chicago during this time can be as low as $591. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $666.

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.

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

$286

Fastest flight time

4h 22m

Direct flights

Sun

Airports in Chicago

2 airports
The best one-way flight to Chicago from Cayman Islands in the past 72 hours is $286. The best round-trip flight deal from Cayman Islands to Chicago found on momondo in the last 72 hours is $553.
The fastest flight from Cayman Islands to Chicago takes 4h 22m
Direct flights go from Cayman Islands to Chicago on Sunday. The only airline offering direct flights is United 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 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?


Traveling to a place near Chicago?

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

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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mar. 4/22
mar. 4/29

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