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Cheap flights from the Cayman Islands to Illinois from $235

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from the Cayman Islands to Illinois departing on 10/26. 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 the Cayman Islands to Illinois

Recent round-trip flight deals from the Cayman Islands to Illinois

Delta Logo
2:00 pm - 10:14 pmGCM-MDW
9h 14m1 stop
Delta Logo
6:00 am - 12:35 pmMDW-GCM
5h 35m1 stop
$383Delta
Find Deal
Fri, Nov 7 - Mon, Nov 10
Delta Logo
2:00 pm - 11:58 pmGCM-ORD
10h 58m1 stop
Delta Logo
5:23 am - 12:35 pmORD-GCM
6h 12m1 stop
$383Delta
Find Deal
Fri, Nov 7 - Mon, Nov 10
Air Canada Logo
1:30 pm - 9:13 amGCM-ORD
20h 43m1 stop
Air Canada Logo
8:15 pm - 12:25 pmORD-GCM
15h 10m1 stop
$391Air Canada
Find Deal
Thu, Nov 6 - Thu, Nov 13
Air Canada Logo
1:30 pm - 12:51 pmGCM-ORD
24h 21m2 stops
Air Canada Logo
8:15 pm - 12:25 pmORD-GCM
15h 10m1 stop
$396Air Canada
Find Deal
Thu, Nov 6 - Thu, Nov 13
American Airlines Logo
4:01 pm - 7:11 pmGCM-ORD
4h 10mnonstop
American Airlines Logo
7:07 pm - 12:13 pmORD-GCM
16h 06m1 stop
$407American Airlines
Find Deal
Sat, Nov 8 - Mon, Nov 10
American Airlines Logo
1:20 pm - 12:37 amGCM-ORD
12h 17m1 stop
American Airlines Logo
7:07 pm - 12:13 pmORD-GCM
16h 06m1 stop
$417American Airlines
Find Deal
Sat, Nov 8 - Sat, Nov 15
Southwest Logo
1:40 pm - 12:10 amGCM-MDW
11h 30m2 stops
Southwest Logo
5:50 am - 12:35 pmMDW-GCM
5h 45m1 stop
$446Southwest
Find Deal
Fri, Nov 7 - Mon, Nov 10
Southwest Logo
1:55 pm - 7:55 pmGCM-MDW
7h 00m1 stop
Southwest Logo
5:50 am - 12:35 pmMDW-GCM
5h 45m1 stop
$544Southwest
Find Deal
Sat, Nov 8 - Mon, Nov 10
Multiple Airlines Logo
8:50 am - 12:30 pmGCM-ORD
28h 40m1 stop
Multiple Airlines Logo
6:00 am - 11:35 amORD-GCM
28h 35m2 stops
$564Multiple Airlines
Find Deal
Sat, Nov 8 - Sat, Nov 15
Multiple Airlines Logo
8:50 am - 5:08 pmGCM-ORD
33h 18m3 stops
Multiple Airlines Logo
8:00 am - 12:25 pmORD-GCM
27h 25m1 stop
$639Multiple Airlines
Find Deal
Sat, Nov 8 - Sat, Nov 15

American Airlines flights from Cayman Islands to Illinois

Our best American Airlines deals on Cayman Islands to Illinois flight tickets
American Airlines
Nov 8
GCM4:01 pmGeorge Town Owen Roberts Intl
4h 10m
ORD7:11 pmChicago O'Hare Intl
Nov 10
ORD7:07 pmChicago O'Hare Intl
16h 06m
1 stop
GCM12:13 pmGeorge Town Owen Roberts Intl
$407
Find similar
American Airlines
Nov 8
GCM1:20 pmGeorge Town Owen Roberts Intl
12h 17m
1 stop
ORD12:37 amChicago O'Hare Intl
Nov 15
ORD7:07 pmChicago O'Hare Intl
16h 06m
1 stop
GCM12:13 pmGeorge Town Owen Roberts Intl
$417
Find similar
American Airlines
Nov 8
GCM4:01 pmGeorge Town Owen Roberts Intl
4h 10m
ORD7:11 pmChicago O'Hare Intl
Nov 15
ORD10:15 amChicago O'Hare Intl
3h 45m
GCM3:00 pmGeorge Town Owen Roberts Intl
$427
Find similar

Air Canada flights from Cayman Islands to Illinois

Our best Air Canada deals on Cayman Islands to Illinois flight tickets
Air Canada
Nov 6
GCM1:30 pmGeorge Town Owen Roberts Intl
20h 43m
1 stop
ORD9:13 amChicago O'Hare Intl
Nov 13
ORD8:15 pmChicago O'Hare Intl
15h 10m
1 stop
GCM12:25 pmGeorge Town Owen Roberts Intl
$391
Find similar
Air Canada
Nov 6
GCM1:30 pmGeorge Town Owen Roberts Intl
24h 21m
2 stops
ORD12:51 pmChicago O'Hare Intl
Nov 13
ORD8:15 pmChicago O'Hare Intl
15h 10m
1 stop
GCM12:25 pmGeorge Town Owen Roberts Intl
$396
Find similar
Air Canada
Nov 6
GCM1:30 pmGeorge Town Owen Roberts Intl
54h 25m
2 stops
ORD6:55 pmChicago O'Hare Intl
Nov 13
ORD7:20 amChicago O'Hare Intl
28h 05m
2 stops
GCM12:25 pmGeorge Town Owen Roberts Intl
$411
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Cayman Islands to Illinois 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 September 24, 2025.
Use the filters below to find and compare flights from the Cayman Islands to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 11/7

2:00 pm-10:14 pm

1 stop9h 14m

Chicago Midway

Mon 11/10

6:00 am-12:35 pm

1 stop5h 35m

$383

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 11/7

2:00 pm-11:58 pm

1 stop10h 58m

Chicago O'Hare Intl

Mon 11/10

5:23 am-12:35 pm

1 stop6h 12m

$383

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 11/6

1:30 pm-9:13 am

1 stop20h 43m

Chicago O'Hare Intl

Thu 11/13

8:15 pm-12:25 pm

1 stop15h 10m

$391

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 11/6

1:30 pm-12:51 pm

2 stops24h 21m

Chicago O'Hare Intl

Thu 11/13

8:15 pm-12:25 pm

1 stop15h 10m

$396

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 11/8

4:01 pm-7:11 pm

Nonstop4h 10m

Chicago O'Hare Intl

Mon 11/10

7:07 pm-12:13 pm

1 stop16h 06m

$407

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 11/8

1:20 pm-12:37 am

1 stop12h 17m

Chicago O'Hare Intl

Sat 11/15

7:07 pm-12:13 pm

1 stop16h 06m

$417

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 11/7

1:40 pm-12:10 am

2 stops11h 30m

Chicago Midway

Mon 11/10

5:50 am-12:35 pm

1 stop5h 45m

$446

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 11/8

1:55 pm-7:55 pm

1 stop7h 00m

Chicago Midway

Mon 11/10

5:50 am-12:35 pm

1 stop5h 45m

$544

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 11/8

8:50 am-12:30 pm

1 stop28h 40m

Chicago O'Hare Intl

Sat 11/15

6:00 am-11:35 am

2 stops28h 35m

$564

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 11/8

8:50 am-5:08 pm

3 stops33h 18m

Chicago O'Hare Intl

Sat 11/15

8:00 am-12:25 pm

1 stop27h 25m

$639

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 Illinois from

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

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 Illinois?

The cheapest day to depart from Cayman Islands to Illinois is on a Sunday when prices can be found for as low as $295. Flights from Cayman Islands to Illinois on a Wednesday will generally be more expensive and average around $1,867. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

Our most recent data shows that the best time of day to fly to Illinois is at noon. Flights from Cayman Islands to Illinois during this time can be as low as $593. Flights in the morning are often more expensive with an average ticket price of $666.

What is the cheapest Cayman Islands to Illinois flight route?

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

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

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

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

Cheap Cayman Islands to Illinois flight deals and tips

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

Fastest flight time

4h 10m

Direct flights

Mon, Tue, Wed, Sat and Sun

Airports in Illinois

1 airport
The fastest flight from Cayman Islands to Illinois takes 4h 10m
Direct flights go from Cayman Islands to Illinois on Monday, Tuesday, Wednesday, Saturday and Sunday. There are no airlines offering direct flights.
There is 1 airport near Illinois: Chicago O'Hare Intl (ORD)
Search flight deals

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

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Cayman Islands to Illinois.

  • What documentation or ID do you need to fly to Illinois?

    The required travel and health documents for your Illinois trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Illinois. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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

Why use momondo?

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

Finding the right flight to Illinois from Cayman Islands is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Illinois quick and easy, saving you time and money.

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

Yes. momondo allows you to filter the results for Cayman Islands to Illinois flights to just show those with flexible booking policies.

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

momondo helps you find the best flight between Cayman Islands and Illinois by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Of course. momondo tracks the price of Cayman Islands to Illinois flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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