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Cheap flights from Illinois to Grand Cayman from $143

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 6/17. 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
1 adult, Economy, 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.
American Airlines Logo
5:00 am - 11:00 am
STL
-
GCM
6h 00m
1 stop
American Airlines Logo
2:10 pm - 10:40 pm
GCM
-
STL
8h 30m
1 stop
$424American Airlines
Wed, Aug 19 - Tue, Aug 25
American Airlines Logo
5:00 am - 1:10 pm
STL
-
GCM
8h 10m
1 stop
American Airlines Logo
12:00 pm - 11:34 pm
GCM
-
STL
11h 34m
2 stops
$429American Airlines
Wed, Aug 19 - Tue, Aug 25
Southwest Logo
5:10 am - 11:55 am
MDW
-
GCM
6h 45m
1 stop
Southwest Logo
12:50 pm - 10:05 pm
GCM
-
MDW
9h 15m
1 stop
$438Southwest
Tue, Jul 14 - Wed, Jul 22
Multiple Airlines Logo
2:15 pm - 11:25 am
ORD
-
GCM
21h 10m
1 stop
Multiple Airlines Logo
7:00 am - 9:00 am
GCM
-
ORD
26h 00m
2 stops
$465Multiple Airlines
Sun, Sep 6 - Fri, Sep 11
Southwest Logo
7:35 pm - 11:55 am
MDW
-
GCM
16h 20m
2 stops
Southwest Logo
12:50 pm - 8:10 pm
GCM
-
MDW
7h 20m
1 stop
$470Southwest
Tue, Jul 14 - Wed, Jul 22
Air Canada Logo
3:45 pm - 9:45 am
ORD
-
GCM
18h 00m
1 stop
Air Canada Logo
12:25 pm - 3:51 pm
GCM
-
ORD
27h 26m
1 stop
$485Air Canada
Fri, Sep 4 - Mon, Sep 7
Air Canada Logo
4:15 pm - 12:00 pm
STL
-
GCM
19h 45m
1 stop
Air Canada Logo
1:10 pm - 3:30 pm
GCM
-
STL
27h 20m
1 stop
$499Air Canada
Sat, Oct 31 - Sat, Nov 7
Multiple Airlines Logo
5:35 pm - 11:25 am
ORD
-
GCM
17h 50m
1 stop
Multiple Airlines Logo
2:10 pm - 8:45 am
GCM
-
ORD
18h 35m
1 stop
$540Multiple Airlines
Wed, Jun 24 - Sat, Jul 4
United Airlines Logo
5:42 pm - 4:30 pm
MLI
-
GCM
21h 48m
2 stops
United Airlines Logo
5:45 pm - 10:14 am
GCM
-
MLI
17h 29m
2 stops
$676United Airlines
Mon, Dec 7 - Thu, Dec 10
United Airlines Logo
6:30 am - 1:30 pm
MLI
-
GCM
7h 00m
1 stop
United Airlines Logo
1:50 pm - 10:04 am
GCM
-
MLI
20h 14m
1 stop
$678United Airlines
Sat, Jul 4 - Sat, Jul 11

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Delta flights from Illinois to Grand Cayman

Our best Delta deals on Illinois to Grand Cayman flight tickets
Delta
Sep 12
MDW6:00 amChicago Midway
5h 40m
1 stop
GCM11:40 amGeorge Town Owen Roberts Intl
Sep 25
GCM12:55 pmGeorge Town Owen Roberts Intl
9h 30m
1 stop
MDW10:25 pmChicago Midway
$646
Delta
Aug 9
MDW6:05 amChicago Midway
5h 34m
1 stop
GCM11:39 amGeorge Town Owen Roberts Intl
Aug 18
GCM1:04 pmGeorge Town Owen Roberts Intl
9h 32m
1 stop
MDW10:36 pmChicago Midway
$661
Delta
Aug 22
MDW6:05 amChicago Midway
5h 34m
1 stop
GCM11:39 amGeorge Town Owen Roberts Intl
Aug 26
GCM1:04 pmGeorge Town Owen Roberts Intl
9h 32m
1 stop
MDW10:36 pmChicago Midway
$671

American Airlines flights from Illinois to Grand Cayman

Our best American Airlines deals on Illinois to Grand Cayman flight tickets
American Airlines
Aug 19
STL5:00 amLambert-St Louis
6h 00m
1 stop
GCM11:00 amGeorge Town Owen Roberts Intl
Aug 25
GCM2:10 pmGeorge Town Owen Roberts Intl
8h 30m
1 stop
STL10:40 pmLambert-St Louis
$424
American Airlines
Aug 19
STL5:00 amLambert-St Louis
8h 10m
1 stop
GCM1:10 pmGeorge Town Owen Roberts Intl
Aug 25
GCM12:00 pmGeorge Town Owen Roberts Intl
11h 34m
2 stops
STL11:34 pmLambert-St Louis
$429
American Airlines
Aug 19
STL5:00 amLambert-St Louis
8h 10m
1 stop
GCM1:10 pmGeorge Town Owen Roberts Intl
Aug 25
GCM12:30 pmGeorge Town Owen Roberts Intl
10h 25m
1 stop
STL10:55 pmLambert-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 June 12, 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
Quickest round-trip

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Wed 8/19

5:00 am-11:00 am

1 stop6h 00m

George Town Owen Roberts Intl

Tue 8/25

2:10 pm-10:40 pm

1 stop8h 30m

$424

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Wed 8/19

5:00 am-1:10 pm

1 stop8h 10m

George Town Owen Roberts Intl

Tue 8/25

12:00 pm-11:34 pm

2 stops11h 34m

$429

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 7/14

5:10 am-11:55 am

1 stop6h 45m

George Town Owen Roberts Intl

Wed 7/22

12:50 pm-10:05 pm

1 stop9h 15m

$438

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 9/6

2:15 pm-11:25 am

1 stop21h 10m

George Town Owen Roberts Intl

Fri 9/11

7:00 am-9:00 am

2 stops26h 00m

$465

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 7/14

7:35 pm-11:55 am

2 stops16h 20m

George Town Owen Roberts Intl

Wed 7/22

12:50 pm-8:10 pm

1 stop7h 20m

$470

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 9/4

3:45 pm-9:45 am

1 stop18h 00m

George Town Owen Roberts Intl

Mon 9/7

12:25 pm-3:51 pm

1 stop27h 26m

$485

St. LouisGeorge Town

STL - GCM

STLGCM

Lambert-St Louis

Sat 10/31

4:15 pm-12:00 pm

1 stop19h 45m

George Town Owen Roberts Intl

Sat 11/7

1:10 pm-3:30 pm

1 stop27h 20m

$499

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 6/24

5:35 pm-11:25 am

1 stop17h 50m

George Town Owen Roberts Intl

Sat 7/4

2:10 pm-8:45 am

1 stop18h 35m

$540

MolineGeorge Town

MLI - GCM

MLIGCM

Moline Quad-City

Mon 12/7

5:42 pm-4:30 pm

2 stops21h 48m

George Town Owen Roberts Intl

Thu 12/10

5:45 pm-10:14 am

2 stops17h 29m

$676

MolineGeorge Town

MLI - GCM

MLIGCM

Moline Quad-City

Sat 7/4

6:30 am-1:30 pm

1 stop7h 00m

George Town Owen Roberts Intl

Sat 7/11

1:50 pm-10:04 am

1 stop20h 14m

$678

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 December. Flight prices, which tend to average around $172, are often lower during this time because this is during the off-season. If you don’t want to visit Grand Cayman in December, then you should wait until February to fly from Illinois, when ticket prices are also cheap, with an average price of $231.

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 Thursday 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 from Illinois 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 $674 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?

You could potentially save up to 8% on your flight if you consider stops on a Illinois to Grand Cayman flight.

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

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 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
9,810 reviews
Search United Airlines flights
American AirlinesPriceFrom $429Free CancellationRating
7.1
11,644 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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