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$272+ Cheap flights from the Cayman Islands to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — CHI
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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Cheap flight deals from Cayman Islands to Chicago

Keep the following information in mind while searching for Cayman Islands to Chicago flight deals. Data was last updated February 20, 2025.

Round-trip from

$453
(Kiwi.com)

One-way from

$272
(Mytrip)

Popular in

March

Cheapest in

September

Good round-trip deal

$457 or less

Good one-way deal

$572 or less
From Cayman Islands to Chicago (CHI)
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One-way flight from Cayman Islands to Chicago (CHI)
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Highest demand for flights based on searches. 33% potential increase in price ($325 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($45 potential savings vs. average RT price).
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Price to beat on a round-trip flight from Cayman Islands to Chicago (CHI).
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Price to beat on a one-way flight from Cayman Islands to Chicago (CHI).
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Find flight deals from Cayman Islands to Chicago

Cheapest flights from Cayman Islands to Chicago
Explore the most affordable flight options available from Cayman Islands to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/304:45 pmGCM - ORD
1 stop16h 06mMultiple Airlines
Mon 6/27:00 amORD - GCM
1 stop9h 10mMultiple Airlines
Deal found 2/19$453
This JetBlue deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/2012:10 pmGCM - ORD
1 stop22h 49mJetBlue
Wed 3/2611:44 amORD - GCM
1 stop23h 26mJetBlue
Deal found 2/19$525
This Gotogate deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/203:00 pmGCM - ORD
2 stops19h 54mAir Canada
Wed 3/268:30 pmORD - GCM
1 stop17h 30mAir Canada
Deal found 2/19$556
This Southwest deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/2012:40 pmGCM - MDW
1 stop7h 25mSouthwest
Wed 3/266:30 pmMDW - GCM
2 stops17h 15mSouthwest
Deal found 2/19$600
This American Airlines deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3012:45 pmGCM - ORD
1 stop11h 14mAmerican Airlines
Sun 11/25:01 amORD - GCM
2 stops8h 54mAmerican Airlines
Deal found 2/19$600
This Delta deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2612:56 pmGCM - ORD
1 stop8h 25mDelta
Mon 9/296:00 amORD - GCM
1 stop5h 31mDelta
Deal found 2/19$601
This Kiwi.com deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/511:25 amGCM - MDW
1 stop11h 11mMultiple Airlines
Sat 4/124:10 pmMDW - GCM
1 stop24h 00mMultiple Airlines
Deal found 2/18$619
This United Airlines deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/191:45 pmGCM - ORD
Nonstop4h 22mUnited Airlines
Sun 4/209:50 pmORD - GCM
1 stop14h 40mUnited Airlines
Deal found 2/19$670

Find flights from Cayman Islands to Chicago within your budget

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, Cheapflights users made 2,558,603 searches. Data last updated February 20, 2025.

Fly from

Cayman Islands

Fly to

Chicago

Route

Depart

Return

Price

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 5/30

4:45 pm-8:51 am

1 stop16h 06m

Chicago O'Hare Intl

Mon 6/2

7:00 am-4:10 pm

1 stop9h 10m

$453

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 3/20

12:10 pm-10:59 am

1 stop22h 49m

Chicago O'Hare Intl

Wed 3/26

11:44 am-11:10 am

1 stop23h 26m

$525

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 3/20

3:00 pm-10:54 am

2 stops19h 54m

Chicago O'Hare Intl

Wed 3/26

8:30 pm-2:00 pm

1 stop17h 30m

$556

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 3/20

12:40 pm-8:05 pm

1 stop7h 25m

Chicago Midway

Wed 3/26

6:30 pm-11:45 am

2 stops17h 15m

$600

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 4/5

11:25 am-10:36 pm

1 stop11h 11m

Chicago Midway

Sat 4/12

4:10 pm-4:10 pm

1 stop24h 00m

$619

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 4/19

1:45 pm-6:07 pm

Nonstop4h 22m

Chicago O'Hare Intl

Sun 4/20

9:50 pm-12:30 pm

1 stop14h 40m

$670

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 3/28

12:00 pm-10:16 pm

2 stops10h 16m

Chicago O'Hare Intl

Mon 3/31

6:05 am-2:34 pm

2 stops8h 29m

$1,142

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 5/29

11:30 am-8:51 am

1 stop21h 21m

$272

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 5/19

12:50 pm-8:02 am

2 stops19h 12m

$310

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 3/19

1:50 pm-6:06 pm

Nonstop4h 16m

$387

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 12 results
1
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Best time to book a flight from Cayman Islands to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Cayman Islands with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Cayman Islands to Chicago

Get recent, data-driven insights about flights from Cayman Islands to Chicago including ideal travel times, pricing trends, and more.

What is the cheapest time of day to fly from KY to CHI?

Find hourly flight availability from Cayman Islands to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 20, 2025.

One of the essential ways to save on airfare from Cayman Islands to Chicago is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 17% on airfare.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated February 20, 2025.
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Cayman Islands to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Cayman Islands to Chicago one-way?

    The cheapest airlines for a one-way flight from Cayman Islands to Chicago are Air Canada ($310), United Airlines ($387), and Delta ($393).

  • What are the cheapest flights from Cayman Islands to Chicago?

    On average you can expect to pay $859 for a flight from Cayman Islands to Chicago. The cheapest flight overall is $273 while the most popular route, (George Town Owen Roberts Intl - Chicago O'Hare Intl) is currently priced at $453.

  • Can I find deals for flights from Cayman Islands to Chicago that include hotel bookings?

    Yes. In addition to deals on Cayman Islands to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Cayman Islands to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Cayman Islands to Chicago.

  • Can I find deals for business class flights from Cayman Islands to Chicago?

    Yes. Cheapflights offers flight deals from Cayman Islands to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Cayman Islands to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Cayman Islands to Chicago (average of $245). Flying from Cayman Islands to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near the Cayman Islands?

Book flights to the Cayman Islands if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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