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Cheap flights from the Cayman Islands to Chicago from $226

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 Chicago departing on 11/13. 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 the Cayman Islands to Chicago

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

Enter your travel dates to find the best prices.
Air Canada Logo
12:25 pm - 9:00 amGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
20h 35m1 stop Toronto Pearson Intl
Air Canada Logo
8:40 pm - 11:25 amORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
14h 45m1 stop Toronto Pearson Intl
$355Air Canada
Mon, Sep 21 - Wed, Sep 23
Air Canada Logo
12:25 pm - 9:00 amGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
20h 35m1 stop Toronto Pearson Intl
Air Canada Logo
3:40 pm - 11:25 amORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
19h 45m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$358Air Canada
Mon, Sep 21 - Wed, Sep 23
Air Canada Logo
12:25 pm - 12:00 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
23h 35m2 stops Toronto Pearson Intl Ottawa
Air Canada Logo
3:40 pm - 11:25 amORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
19h 45m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$376Air Canada
Mon, Sep 21 - Wed, Sep 23
Multiple Airlines Logo
7:00 am - 9:00 amGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
26h 00m2 stops Kingston Norman Manley Toronto Pearson Intl
Multiple Airlines Logo
12:30 pm - 11:25 amORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
22h 55m3 stops Quincy Regional Nashville Intl Toronto Pearson Intl
$667Multiple Airlines
Mon, Sep 21 - Wed, Sep 23
Delta Logo
1:00 pm - 11:59 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
10h 59m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:30 am - 11:40 amORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
6h 10m1 stop Atlanta Hartsfield-Jackson
$672Delta
Fri, Sep 25 - Mon, Sep 28
American Airlines Logo
12:00 pm - 10:31 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
10h 31m2 stops Miami Charlotte Douglas
American Airlines Logo
7:00 pm - 11:00 amORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
16h 00m1 stop Miami
$686American Airlines
Fri, Sep 25 - Mon, Sep 28
American Airlines Logo
12:00 pm - 10:31 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
10h 31m2 stops Miami Charlotte Douglas
American Airlines Logo
8:55 pm - 11:00 amORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
14h 05m2 stops Washington, D.C. Reagan-National Miami
$686American Airlines
Fri, Sep 25 - Mon, Sep 28
American Airlines Logo
12:36 pm - 10:31 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
9h 55m1 stop Charlotte Douglas
American Airlines Logo
6:57 pm - 11:27 amORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
16h 30m1 stop Charlotte Douglas
$761American Airlines
Mon, Sep 21 - Thu, Sep 24
American Airlines Logo
12:00 pm - 10:00 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
10h 00m2 stops Miami New York LaGuardia
American Airlines Logo
8:55 pm - 11:00 amORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
14h 05m2 stops Washington, D.C. Reagan-National Miami
$766American Airlines
Mon, Sep 21 - Thu, Sep 24
American Airlines Logo
12:00 pm - 10:00 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
10h 00m2 stops Miami New York LaGuardia
American Airlines Logo
9:01 pm - 11:27 amORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
14h 26m1 stop Charlotte Douglas
$766American Airlines
Mon, Sep 21 - Thu, Sep 24

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Air Canada flights from Cayman Islands to Chicago

Our best Air Canada deals on Cayman Islands to Chicago flight tickets
Air Canada
Sep 21
GCM12:25 pmGeorge Town Owen Roberts Intl
20h 35m
1 stop
ORD9:00 amChicago O'Hare Intl
Sep 23
ORD8:40 pmChicago O'Hare Intl
14h 45m
1 stop
GCM11:25 amGeorge Town Owen Roberts Intl
$355
Air Canada
Sep 21
GCM12:25 pmGeorge Town Owen Roberts Intl
20h 35m
1 stop
ORD9:00 amChicago O'Hare Intl
Sep 23
ORD3:40 pmChicago O'Hare Intl
19h 45m
2 stops
GCM11:25 amGeorge Town Owen Roberts Intl
$358
Air Canada
Sep 21
GCM12:25 pmGeorge Town Owen Roberts Intl
23h 35m
2 stops
ORD12:00 pmChicago O'Hare Intl
Sep 23
ORD3:40 pmChicago O'Hare Intl
19h 45m
2 stops
GCM11:25 amGeorge Town Owen Roberts Intl
$376

American Airlines flights from Cayman Islands to Chicago

Our best American Airlines deals on Cayman Islands to Chicago flight tickets
American Airlines
Sep 25
GCM12:00 pmGeorge Town Owen Roberts Intl
10h 31m
2 stops
ORD10:31 pmChicago O'Hare Intl
Sep 28
ORD8:55 pmChicago O'Hare Intl
14h 05m
2 stops
GCM11:00 amGeorge Town Owen Roberts Intl
$686
American Airlines
Sep 21
GCM12:36 pmGeorge Town Owen Roberts Intl
9h 55m
1 stop
ORD10:31 pmChicago O'Hare Intl
Sep 24
ORD6:57 pmChicago O'Hare Intl
16h 30m
1 stop
GCM11:27 amGeorge Town Owen Roberts Intl
$761
American Airlines
Sep 21
GCM12:00 pmGeorge Town Owen Roberts Intl
10h 00m
2 stops
ORD10:00 pmChicago O'Hare Intl
Sep 24
ORD8:55 pmChicago O'Hare Intl
14h 05m
2 stops
GCM11:00 amGeorge Town Owen Roberts Intl
$766

momondo Fare Finder

 
Customize your flight search to find flights from Cayman Islands to Chicago 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 August 14, 2026.
Use the filters below to find and compare flights from the Cayman Islands to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

George TownChicago

GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl

GCMORD

George Town Owen Roberts Intl

Mon 9/21

12:25 pm-9:00 am

1 stop20h 35m

Chicago O'Hare Intl

Wed 9/23

8:40 pm-11:25 am

1 stop14h 45m

$355

George TownChicago

GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl

GCMORD

George Town Owen Roberts Intl

Mon 9/21

12:25 pm-9:00 am

1 stop20h 35m

Chicago O'Hare Intl

Wed 9/23

3:40 pm-11:25 am

2 stops19h 45m

$358

George TownChicago

GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl

GCMORD

George Town Owen Roberts Intl

Mon 9/21

12:25 pm-12:00 pm

2 stops23h 35m

Chicago O'Hare Intl

Wed 9/23

3:40 pm-11:25 am

2 stops19h 45m

$376

George TownChicago

GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl

GCMORD

George Town Owen Roberts Intl

Mon 9/21

7:00 am-9:00 am

2 stops26h 00m

Chicago O'Hare Intl

Wed 9/23

12:30 pm-11:25 am

3 stops22h 55m

$667
Quickest round-trip

George TownChicago

GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl

GCMORD

George Town Owen Roberts Intl

Fri 9/25

1:00 pm-11:59 pm

1 stop10h 59m

Chicago O'Hare Intl

Mon 9/28

5:30 am-11:40 am

1 stop6h 10m

$672

George TownChicago

GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl

GCMORD

George Town Owen Roberts Intl

Fri 9/25

12:00 pm-10:31 pm

2 stops10h 31m

Chicago O'Hare Intl

Mon 9/28

7:00 pm-11:00 am

1 stop16h 00m

$686

George TownChicago

GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl

GCMORD

George Town Owen Roberts Intl

Fri 9/25

12:00 pm-10:31 pm

2 stops10h 31m

Chicago O'Hare Intl

Mon 9/28

8:55 pm-11:00 am

2 stops14h 05m

$686

George TownChicago

GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl

GCMORD

George Town Owen Roberts Intl

Mon 9/21

12:36 pm-10:31 pm

1 stop9h 55m

Chicago O'Hare Intl

Thu 9/24

6:57 pm-11:27 am

1 stop16h 30m

$761

George TownChicago

GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl

GCMORD

George Town Owen Roberts Intl

Mon 9/21

12:00 pm-10:00 pm

2 stops10h 00m

Chicago O'Hare Intl

Thu 9/24

8:55 pm-11:00 am

2 stops14h 05m

$766

George TownChicago

GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl

GCMORD

George Town Owen Roberts Intl

Mon 9/21

12:00 pm-10:00 pm

2 stops10h 00m

Chicago O'Hare Intl

Thu 9/24

9:01 pm-11:27 am

1 stop14h 26m

$766

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 Chicago from

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

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 Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Cayman Islands, with most prices found around $0. If you’re not able to fly to Chicago in September, then November is your next best option. Flight prices from Cayman Islands to Chicago during November average around $384.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $479. This is often the case because there is less demand to fly during this day of the week. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Cayman Islands to Chicago for around $2,559.

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

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Cayman Islands to Chicago during this time can be as low as $571. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $707.

What is the cheapest Cayman Islands to Chicago flight route?

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

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

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

You could potentially save up to 2% on your flight if you consider stops on a Cayman Islands to Chicago flight.

Cheap Cayman Islands to Chicago flight deals and tips

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

Best Price Found

$394

Fastest flight time

9h 32m

Direct flights

Mon, Wed, Thu and Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Cayman Islands in the past 72 hours is $394. The best round-trip flight deal from Cayman Islands to Chicago found on momondo in the last 72 hours is $601.
The fastest flight from Cayman Islands to Chicago takes 9h 32m
Direct flights go from Cayman Islands to Chicago on Monday, Wednesday, Thursday and Sunday. There are no airlines offering direct flights.
There are 3 airports in Chicago. From Cayman Islands there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from the Cayman Islands to Chicago

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

    Prices for flights from Cayman Islands to Chicago are refreshed on a daily basis.

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Cayman Islands to Chicago.

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

    The necessary travel and health documents for your Chicago 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 Cayman Islands to Chicago?

Best airlines flying from Cayman Islands to Chicago

Compare and see reviews for airlines that fly from Cayman Islands to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $571Free CancellationRating
7.1
11,927 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
Saint John

Why use momondo?

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

Finding the right flight to Chicago 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 Chicago quick and easy, saving you time and money.

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

Flights from Cayman Islands to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Cayman Islands to Chicago.

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

Yes. momondo can track prices for Cayman Islands to Chicago 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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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport