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Cheap flights from Illinois to Grand Cayman from $133

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 Grand Cayman departing on 6/10. 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

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Illinois to Grand Cayman

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
8:20 pm - 10:00 am
ORD
-
GCM
13h 40m
1 stop
Air Canada Logo
12:25 pm - 9:00 am
GCM
-
ORD
20h 35m
1 stop
$365Air Canada
Fri, Jun 5 - Mon, Jun 8
Air Canada Logo
8:20 pm - 10:00 am
ORD
-
GCM
13h 40m
1 stop
Air Canada Logo
12:25 pm - 10:18 am
GCM
-
ORD
21h 53m
2 stops
$368Air Canada
Fri, Jun 5 - Mon, Jun 8
United Airlines Logo
6:00 am - 12:30 pm
STL
-
GCM
6h 30m
1 stop
United Airlines Logo
1:35 pm - 10:30 pm
GCM
-
STL
8h 55m
1 stop
$461United Airlines
Wed, May 13 - Wed, May 20
United Airlines Logo
8:30 pm - 12:30 pm
STL
-
GCM
16h 00m
2 stops
United Airlines Logo
1:35 pm - 10:30 pm
GCM
-
STL
8h 55m
1 stop
$466United Airlines
Wed, May 13 - Wed, May 20
American Airlines Logo
7:25 pm - 1:36 pm
STL
-
GCM
18h 11m
1 stop
American Airlines Logo
12:10 pm - 8:04 am
GCM
-
STL
19h 54m
2 stops
$474American Airlines
Sat, Aug 1 - Wed, Aug 5
American Airlines Logo
7:25 pm - 1:36 pm
STL
-
GCM
18h 11m
1 stop
American Airlines Logo
2:10 pm - 10:58 am
GCM
-
STL
20h 48m
1 stop
$482American Airlines
Sat, Aug 1 - Wed, Aug 5
Southwest Logo
6:00 am - 12:10 pm
MDW
-
GCM
6h 10m
1 stop
Southwest Logo
1:05 pm - 12:15 am
GCM
-
MDW
11h 10m
1 stop
$492Southwest
Tue, May 5 - Fri, May 8
Southwest Logo
6:00 am - 12:10 pm
MDW
-
GCM
6h 10m
1 stop
Southwest Logo
1:05 pm - 11:55 pm
GCM
-
MDW
10h 50m
2 stops
$511Southwest
Tue, May 5 - Fri, May 8
Multiple Airlines Logo
6:00 am - 9:15 pm
MDW
-
GCM
15h 15m
2 stops
Multiple Airlines Logo
7:00 am - 10:11 pm
GCM
-
MDW
15h 11m
2 stops
$523Multiple Airlines
Thu, Jun 4 - Thu, Jun 11
Multiple Airlines Logo
6:00 am - 9:15 pm
MDW
-
GCM
15h 15m
2 stops
Multiple Airlines Logo
1:45 pm - 9:40 am
GCM
-
MDW
19h 55m
1 stop
$583Multiple Airlines
Mon, Jun 8 - Sat, Jun 13

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United Airlines flights from Illinois to Grand Cayman

Our best United Airlines deals on Illinois to Grand Cayman flight tickets
United Airlines
May 13
STL6:00 amLambert-St Louis
6h 30m
1 stop
GCM12:30 pmGeorge Town Owen Roberts Intl
May 20
GCM1:35 pmGeorge Town Owen Roberts Intl
8h 55m
1 stop
STL10:30 pmLambert-St Louis
$461
United Airlines
May 13
STL8:30 pmLambert-St Louis
16h 00m
2 stops
GCM12:30 pmGeorge Town Owen Roberts Intl
May 20
GCM1:35 pmGeorge Town Owen Roberts Intl
8h 55m
1 stop
STL10:30 pmLambert-St Louis
$466
United Airlines
May 18
STL8:30 pmLambert-St Louis
16h 00m
2 stops
GCM12:30 pmGeorge Town Owen Roberts Intl
May 22
GCM1:35 pmGeorge Town Owen Roberts Intl
9h 10m
1 stop
STL10:45 pmLambert-St Louis
$520

American Airlines flights from Illinois to Grand Cayman

Our best American Airlines deals on Illinois to Grand Cayman flight tickets
American Airlines
Aug 1
STL7:25 pmLambert-St Louis
18h 11m
1 stop
GCM1:36 pmGeorge Town Owen Roberts Intl
Aug 5
GCM12:10 pmGeorge Town Owen Roberts Intl
19h 54m
2 stops
STL8:04 amLambert-St Louis
$474
American Airlines
Aug 1
STL7:25 pmLambert-St Louis
18h 11m
1 stop
GCM1:36 pmGeorge Town Owen Roberts Intl
Aug 5
GCM2:10 pmGeorge Town Owen Roberts Intl
20h 48m
1 stop
STL10:58 amLambert-St Louis
$482
American Airlines
Aug 1
STL7:25 pmLambert-St Louis
18h 11m
1 stop
GCM1:36 pmGeorge Town Owen Roberts Intl
Aug 8
GCM4:15 pmGeorge Town Owen Roberts Intl
16h 16m
1 stop
STL8:31 amLambert-St Louis
$504

momondo Fare Finder

 
Customize your flight search to find flights from Illinois to Grand Cayman 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 April 15, 2026.
Use the filters below to find and compare flights from Illinois to Grand Cayman that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 6/5

8:20 pm-10:00 am

1 stop13h 40m

George Town Owen Roberts Intl

Mon 6/8

12:25 pm-9:00 am

1 stop20h 35m

$365

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 6/5

8:20 pm-10:00 am

1 stop13h 40m

George Town Owen Roberts Intl

Mon 6/8

12:25 pm-10:18 am

2 stops21h 53m

$368
Quickest round-trip

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Wed 5/13

6:00 am-12:30 pm

1 stop6h 30m

George Town Owen Roberts Intl

Wed 5/20

1:35 pm-10:30 pm

1 stop8h 55m

$461

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Wed 5/13

8:30 pm-12:30 pm

2 stops16h 00m

George Town Owen Roberts Intl

Wed 5/20

1:35 pm-10:30 pm

1 stop8h 55m

$466

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Sat 8/1

7:25 pm-1:36 pm

1 stop18h 11m

George Town Owen Roberts Intl

Wed 8/5

12:10 pm-8:04 am

2 stops19h 54m

$474

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Sat 8/1

7:25 pm-1:36 pm

1 stop18h 11m

George Town Owen Roberts Intl

Wed 8/5

2:10 pm-10:58 am

1 stop20h 48m

$482

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 5/5

6:00 am-12:10 pm

1 stop6h 10m

George Town Owen Roberts Intl

Fri 5/8

1:05 pm-12:15 am

1 stop11h 10m

$492

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 5/5

6:00 am-12:10 pm

1 stop6h 10m

George Town Owen Roberts Intl

Fri 5/8

1:05 pm-11:55 pm

2 stops10h 50m

$511

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 6/4

6:00 am-9:15 pm

2 stops15h 15m

George Town Owen Roberts Intl

Thu 6/11

7:00 am-10:11 pm

2 stops15h 11m

$523

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 6/8

6:00 am-9:15 pm

2 stops15h 15m

George Town Owen Roberts Intl

Sat 6/13

1:45 pm-9:40 am

1 stop19h 55m

$583

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 Grand Cayman from

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

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 Grand Cayman?

The cheapest month to fly to Grand Cayman from Illinois is in February. Flight prices, which tend to average around $527, are often lower during this time because this is during the off-season. If you don’t want to visit Grand Cayman in February, then you should wait until October to fly from Illinois, when ticket prices are also cheap, with an average price of $534.

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

The cheapest day to depart from Illinois to Grand Cayman is on a Wednesday when prices can be found for as low as $530. On the other hand, Sunday is the most expensive day to depart from Illinois because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $770.

What is the cheapest Illinois to Grand Cayman flight route?

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

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

You are more likely to see cheaper flights to Grand Cayman from Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Grand Cayman for around $671 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Grand Cayman from Illinois for as low as $492 on momondo.

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

There are 2 cabin classes available to choose from on Illinois to Grand Cayman 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 Grand Cayman flights?

No. A direct flight is the cheapest option for a flight between Illinois to Grand Cayman.

Cheap Illinois to Grand Cayman flight deals and tips

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

Fastest flight time

4h 00m

Direct flights

Mon and Sun

Airports in Grand Cayman

1 airport
The fastest flight from Illinois to Grand Cayman takes 4h 00m
Direct flights go from Illinois to Grand Cayman on Monday and Sunday. There are no airlines offering direct flights.
There is 1 airport in Grand Cayman. From Illinois there are direct flights to George Town Owen Roberts Intl (GCM).
Search flight deals

Frequently asked questions about flying from Illinois to Grand Cayman

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

    Prices for flights from Illinois to Grand Cayman refresh daily.

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

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

    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 Illinois to Grand Cayman.

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

    The necessary travel and health documents for your Grand Cayman 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 Illinois to Grand Cayman?

Best airlines flying from Illinois to Grand Cayman

Compare and see reviews for airlines that fly from Illinois to Grand Cayman with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $341Free CancellationRating
7.4
9,589 reviews
Search United Airlines flights
American AirlinesPriceFrom $429Free CancellationRating
7.1
11,580 reviews
Search American Airlines flights

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Grand Cayman from Illinois.

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

Yes. All flights to Grand Cayman 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 Grand Cayman?

Once you have performed a search for Illinois to Grand Cayman flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes. momondo can track prices for Illinois to Grand Cayman 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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