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Cheap flights from Illinois to the Cayman Islands from $174

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 8/31. 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 Illinois to the Cayman Islands

Cheap round-trip flights

American Airlines Logo
5:26 am - 1:12 pmSTL-GCM
7h 46m1 stop
American Airlines Logo
2:15 pm - 11:14 pmGCM-STL
8h 59m1 stop
$425American Airlines
Find Deal
Mon, Aug 25 - Sat, Aug 30
American Airlines Logo
2:01 pm - 11:22 amSTL-GCM
21h 21m2 stops
American Airlines Logo
3:05 pm - 11:18 pmGCM-STL
8h 13m1 stop
$427American Airlines
Find Deal
Sat, Sep 27 - Sat, Oct 11
Southwest Logo
7:55 pm - 12:55 pmMDW-GCM
16h 00m2 stops
Southwest Logo
1:50 pm - 9:00 pmGCM-MDW
8h 10m1 stop
$438Southwest
Find Deal
Mon, Jan 12 - Wed, Jan 21
Southwest Logo
6:05 am - 12:55 pmORD-GCM
5h 50m1 stop
Southwest Logo
1:50 pm - 9:50 pmGCM-ORD
9h 00m1 stop
$448Southwest
Find Deal
Mon, Jan 12 - Wed, Jan 21
Air Canada Logo
8:25 pm - 11:55 amORD-GCM
15h 30m1 stop
Air Canada Logo
12:50 pm - 9:51 amGCM-ORD
21h 01m2 stops
$451Air Canada
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Wed, Oct 15 - Mon, Oct 20
Logo
10:27 am - 9:20 pmORD-GCM
10h 53m1 stop
Logo
4:45 pm - 9:18 amGCM-ORD
16h 33m1 stop
$461
Find Deal
Fri, Sep 12 - Fri, Sep 19
Air Canada Logo
2:00 pm - 12:20 pmORD-GCM
21h 20m1 stop
Air Canada Logo
1:30 pm - 1:01 pmGCM-ORD
24h 31m1 stop
$462Air Canada
Find Deal
Sat, Nov 22 - Thu, Nov 27
Logo
10:27 am - 9:20 pmORD-GCM
10h 53m1 stop
Logo
4:45 pm - 9:18 amGCM-ORD
16h 33m1 stop
$468
Find Deal
Thu, Sep 25 - Mon, Sep 29
Delta Logo
6:00 am - 11:37 amMDW-GCM
5h 37m1 stop
Delta Logo
12:50 pm - 9:26 pmGCM-MDW
8h 36m1 stop
$477Delta
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Sat, Aug 30 - Thu, Sep 4
Delta Logo
7:59 pm - 12:30 pmORD-GCM
15h 31m1 stop
Delta Logo
1:55 pm - 11:58 pmGCM-ORD
11h 03m1 stop
$520Delta
Find Deal
Mon, Dec 22 - Tue, Dec 30

Southwest flights from Illinois to Cayman Islands

Our best Southwest deals on Illinois to Cayman Islands flight tickets
Southwest
Jan 12
MDW7:55 pmChicago Midway
16h 00m
2 stops
GCM12:55 pmGeorge Town Owen Roberts Intl
Jan 21
GCM1:50 pmGeorge Town Owen Roberts Intl
8h 10m
1 stop
MDW9:00 pmChicago Midway
$438
Find similar
Southwest
Jan 12
ORD6:05 amChicago O'Hare Intl
5h 50m
1 stop
GCM12:55 pmGeorge Town Owen Roberts Intl
Jan 21
GCM1:50 pmGeorge Town Owen Roberts Intl
9h 00m
1 stop
ORD9:50 pmChicago O'Hare Intl
$448
Find similar
Southwest
Dec 15
MDW5:05 amChicago Midway
6h 30m
1 stop
GCM12:35 pmGeorge Town Owen Roberts Intl
Dec 20
GCM4:10 pmGeorge Town Owen Roberts Intl
8h 10m
1 stop
MDW11:20 pmChicago Midway
$481
Find similar

Delta flights from Illinois to Cayman Islands

Our best Delta deals on Illinois to Cayman Islands flight tickets
Delta
Aug 30
MDW6:00 amChicago Midway
5h 37m
1 stop
GCM11:37 amGeorge Town Owen Roberts Intl
Sep 4
GCM12:50 pmGeorge Town Owen Roberts Intl
8h 36m
1 stop
MDW9:26 pmChicago Midway
$477
Find similar
Delta
Dec 22
ORD7:59 pmChicago O'Hare Intl
15h 31m
1 stop
GCM12:30 pmGeorge Town Owen Roberts Intl
Dec 30
GCM1:55 pmGeorge Town Owen Roberts Intl
11h 03m
1 stop
ORD11:58 pmChicago O'Hare Intl
$520
Find similar
Delta
Dec 22
ORD7:59 pmChicago O'Hare Intl
15h 31m
1 stop
GCM12:30 pmGeorge Town Owen Roberts Intl
Dec 27
GCM4:10 pmGeorge Town Owen Roberts Intl
17h 59m
1 stop
ORD9:09 amChicago O'Hare Intl
$545
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 July 31, 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

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Mon 8/25

5:26 am-1:12 pm

1 stop7h 46m

George Town Owen Roberts Intl

Sat 8/30

2:15 pm-11:14 pm

1 stop8h 59m

$425

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Sat 9/27

2:01 pm-11:22 am

2 stops21h 21m

George Town Owen Roberts Intl

Sat 10/11

3:05 pm-11:18 pm

1 stop8h 13m

$427

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 1/12

7:55 pm-12:55 pm

2 stops16h 00m

George Town Owen Roberts Intl

Wed 1/21

1:50 pm-9:00 pm

1 stop8h 10m

$438

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 1/12

6:05 am-12:55 pm

1 stop5h 50m

George Town Owen Roberts Intl

Wed 1/21

1:50 pm-9:50 pm

1 stop9h 00m

$448

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 10/15

8:25 pm-11:55 am

1 stop15h 30m

George Town Owen Roberts Intl

Mon 10/20

12:50 pm-9:51 am

2 stops21h 01m

$451

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 9/12

10:27 am-9:20 pm

1 stop10h 53m

George Town Owen Roberts Intl

Fri 9/19

4:45 pm-9:18 am

1 stop16h 33m

$461

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 11/22

2:00 pm-12:20 pm

1 stop21h 20m

George Town Owen Roberts Intl

Thu 11/27

1:30 pm-1:01 pm

1 stop24h 31m

$462

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 9/25

10:27 am-9:20 pm

1 stop10h 53m

George Town Owen Roberts Intl

Mon 9/29

4:45 pm-9:18 am

1 stop16h 33m

$468

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 8/30

6:00 am-11:37 am

1 stop5h 37m

George Town Owen Roberts Intl

Thu 9/4

12:50 pm-9:26 pm

1 stop8h 36m

$477

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 12/22

7:59 pm-12:30 pm

1 stop15h 31m

George Town Owen Roberts Intl

Tue 12/30

1:55 pm-11:58 pm

1 stop11h 03m

$520

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 September, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $544.

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 $668. Be sure to avoid booking your departure on a Friday as prices are generally higher than usual. According to our data, the average ticket price to Cayman Islands on Friday is $878.

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 $732 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 $689 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 $618 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 28% 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

$174

Fastest flight time

3h 46m

Direct flights

Every day

Airports in Cayman Islands

2 airports
The best one-way flight to Cayman Islands from Illinois in the past 72 hours is $174. The best round-trip flight deal from Illinois to Cayman Islands found on momondo in the last 72 hours is $425.
The fastest flight from Illinois to Cayman Islands takes 3h 46m
Direct flights go from Illinois to Cayman Islands every day.
There are 2 airports near Cayman Islands: George Town Owen Roberts Intl (GCM), Cayman Brac Gerrard-Smith (CYB)
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
DeltaPriceFrom $463Free CancellationRating
8.0
7,981 reviews
Search Delta flights
American AirlinesPriceFrom $512Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $573Free CancellationRating
7.4
8,900 reviews
Search United Airlines 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

Popular cities in the Cayman Islands

Popular flights according to clicks in the last 7 days on momondo
Flights to George Townfrom $298
Flights to Cayman Bracfrom $353
Flights to Little Caymanfrom $376