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Cheap flights from Grand Cayman to Chicago from $283

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Grand Cayman to Chicago departing on 5/24. 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 Grand Cayman to Chicago

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Grand Cayman to Chicago.
Southwest Logo
1:10 pm - 8:25 pmGCM-MDW
7h 15m1 stop
Southwest Logo
7:50 pm - 11:50 amMDW-GCM
16h 00m2 stops
$556Southwest
Find Deal
Sat, May 17 - Mon, May 19
Southwest Logo
3:50 pm - 7:25 amGCM-MDW
15h 35m2 stops
Southwest Logo
5:15 pm - 11:50 amMDW-GCM
18h 35m2 stops
$576Southwest
Find Deal
Sat, May 17 - Mon, May 19
Southwest Logo
1:10 pm - 8:25 pmGCM-MDW
7h 15m1 stop
Southwest Logo
5:50 am - 11:50 amMDW-GCM
6h 00m1 stop
$736Southwest
Find Deal
Sat, May 17 - Mon, May 19
Delta Logo
12:35 pm - 9:27 pmGCM-MDW
8h 52m1 stop
Delta Logo
6:00 am - 11:20 amMDW-GCM
5h 20m1 stop
$776Delta
Find Deal
Thu, May 29 - Tue, Jun 3
Delta Logo
12:35 pm - 9:20 pmGCM-ORD
8h 45m1 stop
Delta Logo
5:30 am - 11:20 amORD-GCM
5h 50m1 stop
$976Delta
Find Deal
Fri, May 16 - Tue, May 20
American Airlines Logo
12:25 pm - 11:56 pmGCM-ORD
11h 31m2 stops
American Airlines Logo
5:00 am - 11:10 amORD-GCM
6h 10m1 stop
$1,187American Airlines
Find Deal
Fri, May 16 - Tue, May 20
American Airlines Logo
12:10 pm - 9:58 pmGCM-ORD
9h 48m2 stops
American Airlines Logo
5:00 am - 1:10 pmORD-GCM
8h 10m2 stops
$2,513American Airlines
Find Deal
Fri, May 16 - Tue, May 20

American Airlines flights from Grand Cayman to Chicago

Our best American Airlines deals on Grand Cayman to Chicago flight tickets
American Airlines
Apr 25
GCM12:35 pmGeorge Town Owen Roberts Intl
10h 41m
2 stops
ORD11:16 pmChicago O'Hare Intl
Apr 28
ORD7:00 amChicago O'Hare Intl
5h 59m
1 stop
GCM12:59 pmGeorge Town Owen Roberts Intl
American Airlines
Apr 25
GCM12:35 pmGeorge Town Owen Roberts Intl
8h 46m
2 stops
ORD9:21 pmChicago O'Hare Intl
Apr 28
ORD5:10 amChicago O'Hare Intl
7h 49m
2 stops
GCM12:59 pmGeorge Town Owen Roberts Intl
American Airlines
May 16
GCM12:25 pmGeorge Town Owen Roberts Intl
11h 31m
2 stops
ORD11:56 pmChicago O'Hare Intl
May 20
ORD5:00 amChicago O'Hare Intl
6h 10m
1 stop
GCM11:10 amGeorge Town Owen Roberts Intl

Delta flights from Grand Cayman to Chicago

Our best Delta deals on Grand Cayman 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
May 16
GCM12:35 pmGeorge Town Owen Roberts Intl
8h 45m
1 stop
ORD9:20 pmChicago O'Hare Intl
May 20
ORD5:30 amChicago O'Hare Intl
5h 50m
1 stop
GCM11:20 amGeorge Town Owen Roberts Intl
Delta
Apr 25
GCM12:47 pmGeorge Town Owen Roberts Intl
8h 03m
1 stop
ORD8:50 pmChicago O'Hare Intl
Apr 28
ORD5:30 amChicago O'Hare Intl
5h 52m
1 stop
GCM11:22 amGeorge Town Owen Roberts Intl

See travel insights to Chicago from

How to get the cheapest flight ticket from Grand Cayman 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 Grand Cayman 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 Grand Cayman 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 Grand Cayman to Chicago flight route?

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

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

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

Cheap Grand Cayman to Chicago flight deals and tips

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

Best Price Found

$283

Fastest flight time

4h 22m

Direct flights

Sun

Airports in Chicago

2 airports
The best one-way flight to Chicago from Grand Cayman in the past 72 hours is $283. The best round-trip flight deal from Grand Cayman to Chicago found on momondo in the last 72 hours is $556.
The fastest flight from Grand Cayman to Chicago takes 4h 22m
Direct flights go from Grand Cayman 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 Grand Cayman to Chicago?

    Prices for flights from Grand Cayman to Chicago were last updated today.

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Grand Cayman 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 Grand Cayman 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 Grand Cayman to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Grand Cayman to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

Flights from Grand Cayman 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 Grand Cayman 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 Grand Cayman to Chicago.

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

Yes. momondo can track prices for Grand Cayman 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