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Cheap flights from Illinois to the Cayman Islands from $85

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to the Cayman Islands departing on 12/7. 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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0 bags

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Find the cheapest flights from Illinois to the Cayman Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
3:26 pm - 1:45 pmORD-GCM
21h 19m1 stop
Spirit Airlines Logo
5:56 pm - 12:09 amGCM-ORD
7h 13m1 stop
$319Spirit Airlines
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Wed, Dec 10 - Sat, Dec 13
Spirit Airlines Logo
4:38 pm - 1:45 pmORD-GCM
20h 07m2 stops
Spirit Airlines Logo
5:56 pm - 12:09 amGCM-ORD
7h 13m1 stop
$320Spirit Airlines
Find Deal
Wed, Dec 10 - Sat, Dec 13
Multiple Airlines Logo
5:00 am - 4:55 pmORD-GCM
10h 55m1 stop
Multiple Airlines Logo
11:30 am - 6:36 pmGCM-ORD
8h 06m1 stop
$337Multiple Airlines
Find Deal
Sat, Dec 6 - Wed, Dec 10
Delta Logo
6:00 am - 12:40 pmSTL-GCM
5h 40m1 stop
Delta Logo
2:05 pm - 11:39 pmGCM-STL
10h 34m1 stop
$338Delta
Find Deal
Mon, Jan 26 - Mon, Feb 2
Multiple Airlines Logo
5:32 pm - 1:43 pmORD-GCM
19h 11m1 stop
Multiple Airlines Logo
2:40 pm - 11:35 pmGCM-ORD
9h 55m2 stops
$338Multiple Airlines
Find Deal
Sat, Feb 21 - Thu, Feb 26
American Airlines Logo
9:47 am - 2:51 pmORD-GCM
4h 04mnonstop
American Airlines Logo
3:51 pm - 6:59 pmGCM-ORD
4h 08mnonstop
$340American Airlines
Find Deal
Sat, Jan 24 - Sat, Jan 31
American Airlines Logo
6:05 am - 2:26 pmORD-GCM
7h 21m1 stop
American Airlines Logo
3:51 pm - 6:59 pmGCM-ORD
4h 08mnonstop
$344American Airlines
Find Deal
Sat, Jan 24 - Sat, Jan 31
Delta Logo
6:00 am - 12:40 pmSTL-GCM
5h 40m1 stop
Delta Logo
2:05 pm - 11:39 pmGCM-STL
10h 34m1 stop
$346Delta
Find Deal
Mon, Jan 19 - Mon, Jan 26
United Airlines Logo
8:45 am - 1:45 pmORD-GCM
4h 00mnonstop
United Airlines Logo
5:30 pm - 11:39 pmGCM-ORD
7h 09m1 stop
$350United Airlines
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Sat, Jan 3 - Sat, Jan 10
United Airlines Logo
8:45 am - 1:45 pmORD-GCM
4h 00mnonstop
United Airlines Logo
2:50 pm - 6:04 pmGCM-ORD
4h 14mnonstop
$376United Airlines
Find Deal
Thu, Feb 12 - Sun, Feb 15

Delta flights from Illinois to Cayman Islands

Our best Delta deals on Illinois to Cayman Islands flight tickets
Delta
Jan 26
STL6:00 amLambert-St Louis
5h 40m
1 stop
GCM12:40 pmGeorge Town Owen Roberts Intl
Feb 2
GCM2:05 pmGeorge Town Owen Roberts Intl
10h 34m
1 stop
STL11:39 pmLambert-St Louis
$338
Find similar
Delta
Jan 19
STL6:00 amLambert-St Louis
5h 40m
1 stop
GCM12:40 pmGeorge Town Owen Roberts Intl
Jan 26
GCM2:05 pmGeorge Town Owen Roberts Intl
10h 34m
1 stop
STL11:39 pmLambert-St Louis
$346
Find similar
Delta
Jan 24
ORD5:33 amChicago O'Hare Intl
7h 27m
1 stop
GCM2:00 pmGeorge Town Owen Roberts Intl
Jan 29
GCM2:05 pmGeorge Town Owen Roberts Intl
10h 52m
1 stop
ORD11:57 pmChicago O'Hare Intl
$354
Find similar

United Airlines flights from Illinois to Cayman Islands

Our best United Airlines deals on Illinois to Cayman Islands flight tickets
United Airlines
Jan 3
ORD8:45 amChicago O'Hare Intl
4h 00m
GCM1:45 pmGeorge Town Owen Roberts Intl
Jan 10
GCM5:30 pmGeorge Town Owen Roberts Intl
7h 09m
1 stop
ORD11:39 pmChicago O'Hare Intl
$350
Find similar
United Airlines
Feb 12
ORD8:45 amChicago O'Hare Intl
4h 00m
GCM1:45 pmGeorge Town Owen Roberts Intl
Feb 15
GCM2:50 pmGeorge Town Owen Roberts Intl
4h 14m
ORD6:04 pmChicago O'Hare Intl
$376
Find similar
United Airlines
Dec 6
STL6:30 amLambert-St Louis
9h 05m
2 stops
GCM4:35 pmGeorge Town Owen Roberts Intl
Dec 13
GCM5:30 pmGeorge Town Owen Roberts Intl
19h 45m
2 stops
STL12:15 pmLambert-St Louis
$382
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Illinois to Cayman Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated November 10, 2025.
Use the filters below to find and compare flights from Illinois to the Cayman Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 12/10

3:26 pm-1:45 pm

1 stop21h 19m

George Town Owen Roberts Intl

Sat 12/13

5:56 pm-12:09 am

1 stop7h 13m

$319

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 12/10

4:38 pm-1:45 pm

2 stops20h 07m

George Town Owen Roberts Intl

Sat 12/13

5:56 pm-12:09 am

1 stop7h 13m

$320

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 12/6

5:00 am-4:55 pm

1 stop10h 55m

George Town Owen Roberts Intl

Wed 12/10

11:30 am-6:36 pm

1 stop8h 06m

$337

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Mon 1/26

6:00 am-12:40 pm

1 stop5h 40m

George Town Owen Roberts Intl

Mon 2/2

2:05 pm-11:39 pm

1 stop10h 34m

$338

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 2/21

5:32 pm-1:43 pm

1 stop19h 11m

George Town Owen Roberts Intl

Thu 2/26

2:40 pm-11:35 pm

2 stops9h 55m

$338

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/24

9:47 am-2:51 pm

Nonstop4h 04m

George Town Owen Roberts Intl

Sat 1/31

3:51 pm-6:59 pm

Nonstop4h 08m

$340

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/24

6:05 am-2:26 pm

1 stop7h 21m

George Town Owen Roberts Intl

Sat 1/31

3:51 pm-6:59 pm

Nonstop4h 08m

$344

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Mon 1/19

6:00 am-12:40 pm

1 stop5h 40m

George Town Owen Roberts Intl

Mon 1/26

2:05 pm-11:39 pm

1 stop10h 34m

$346

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/3

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Sat 1/10

5:30 pm-11:39 pm

1 stop7h 09m

$350

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 2/12

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Sun 2/15

2:50 pm-6:04 pm

Nonstop4h 14m

$376

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to the Cayman Islands from

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

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 month to fly to Cayman Islands?

If you aren’t able to travel to Cayman Islands during the month of October, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $569.

What is the cheapest day to depart on your flight to Cayman Islands?

Our data shows that Monday is the least expensive day to fly to Cayman Islands. Tickets to fly out on this day can be as low as $593. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Cayman Islands on Sunday is $780.

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

According to our data, the cheapest time of day to fly to Cayman Islands is in the afternoon. momondo users have found flights departing from Illinois to Cayman Islands in the afternoon for as low as $507. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $718 on average. Flights to Cayman Islands from Illinois in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Illinois to Cayman Islands flight route?

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

How far in advance should I book a flight to Cayman Islands?

You are more likely to see cheaper flights to Cayman Islands from Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Cayman Islands for around $708 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Cayman Islands from Illinois for as low as $540 on momondo.

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

There are 3 cabin classes available to choose from on Illinois to Cayman Islands 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 Illinois to Cayman Islands flights?

You could potentially save up to 1% on your flight if you consider stops on a Illinois to Cayman Islands flight.

Cheap Illinois to Cayman Islands flight deals and tips

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

Best Price Found

$582

Fastest flight time

3h 46m

Direct flights

Every day

Airports in Cayman Islands

1 airport
The best one-way flight to Cayman Islands from Illinois in the past 72 hours is $582. The best round-trip flight deal from Illinois to Cayman Islands found on momondo in the last 72 hours is $448.
The fastest flight from Illinois to Cayman Islands takes 3h 46m
Direct flights go from Illinois to Cayman Islands every day.
There is 1 airport near Cayman Islands: George Town Owen Roberts Intl (GCM)
Search flight deals

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

    Prices for flights from Illinois to Cayman Islands were last updated today.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Illinois to Cayman Islands.

  • What documentation or ID do you need to fly to Cayman Islands?

    The travel and health documents you'll need for your trip to Cayman Islands may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Cayman Islands. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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

Best airlines flying from Illinois to Cayman Islands

Compare and see reviews for airlines that fly from Illinois to Cayman Islands with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $434Free CancellationRating
7.4
9,012 reviews
Search United Airlines flights
American AirlinesPriceFrom $488Free CancellationRating
7.2
11,045 reviews
Search American Airlines flights
DeltaPriceFrom $564Free CancellationRating
7.9
8,007 reviews
Search Delta flights

Why use momondo?

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

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

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

Yes. All flights to Cayman Islands from Illinois on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once all potential Illinois to Cayman Islands flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Price alerts on flights to Cayman Islands from Illinois are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Cayman Islands trip

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Find better results for your trip to the Cayman Islands

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