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$283+ 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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — CHI
abr. 27 — may. 41
dom. 4/27
dom. 5/4
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 abril 22, 2025.

Round-trip from

$542
(Southwest)

One-way from

$283
(JetBlue)

Popular in

March

Cheapest in

September

Average price

$908

Good round-trip deal

$392 or less

Good one-way deal

$357 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. 31% potential increase in price ($297 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($39 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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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 abril 22, 2025.

This Southwest deal was found by Cheapflights users on 4/21. 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.
vie. 6/1312:45 pmGCM - MDW
2 stops12h 10mSouthwest
lun. 6/167:05 pmMDW - GCM
2 stops16h 45mSouthwest
Deal found 4/21$542
This Southwest deal was found by Cheapflights users on 4/21. 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.
vie. 6/1312:45 pmGCM - ORD
2 stops20h 40mSouthwest
lun. 6/165:25 pmORD - GCM
2 stops18h 25mSouthwest
Deal found 4/21$556
This Mytrip deal was found by Cheapflights users on 4/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 6/134:45 pmGCM - ORD
2 stops29h 34mMultiple Airlines
lun. 6/161:43 pmORD - GCM
1 stop26h 27mMultiple Airlines
Deal found 4/21$558
This American Airlines deal was found by Cheapflights users on 4/21. 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.
mar. 9/212:45 pmGCM - ORD
1 stop6h 31mAmerican Airlines
lun. 9/85:15 amORD - GCM
1 stop5h 50mAmerican Airlines
Deal found 4/21$610
This United Airlines deal was found by Cheapflights users on 4/21. 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.
sáb. 5/174:09 pmGCM - ORD
1 stop16h 32mUnited Airlines
lun. 5/199:50 pmORD - GCM
1 stop14h 40mUnited Airlines
Deal found 4/21$671
This Delta deal was found by Cheapflights users on 4/21. 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.
vie. 4/2512:47 pmGCM - MDW
1 stop9h 35mDelta
lun. 4/286:04 amMDW - GCM
1 stop5h 18mDelta
Deal found 4/21$916
This Delta deal was found by Cheapflights users on 4/21. 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.
vie. 4/2512:47 pmGCM - ORD
1 stop8h 03mDelta
lun. 4/285:30 amORD - GCM
1 stop5h 52mDelta
Deal found 4/21$916

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated abril 22, 2025.
Use the filters below to find and compare flights from the Cayman Islands to Chicago that are best for you.

Fly from

Cayman Islands

Fly to

Chicago

Route

Depart

Return

Price

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

vie. 6/13

12:45 pm-12:55 am

2 stops12h 10m

Chicago Midway

lun. 6/16

7:05 pm-11:50 am

2 stops16h 45m

$542

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

vie. 6/13

12:45 pm-9:25 am

2 stops20h 40m

Chicago O'Hare Intl

lun. 6/16

5:25 pm-11:50 am

2 stops18h 25m

$556

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

vie. 6/13

4:45 pm-10:19 pm

2 stops29h 34m

Chicago O'Hare Intl

lun. 6/16

1:43 pm-4:10 pm

1 stop26h 27m

$558

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

mar. 9/2

12:45 pm-7:16 pm

1 stop6h 31m

Chicago O'Hare Intl

lun. 9/8

5:15 am-11:05 am

1 stop5h 50m

$610

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

sáb. 5/17

4:09 pm-8:41 am

1 stop16h 32m

Chicago O'Hare Intl

lun. 5/19

9:50 pm-12:30 pm

1 stop14h 40m

$671

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

sáb. 5/24

11:40 am-9:54 pm

1 stop10h 14m

$283

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

mar. 7/22

11:30 am-8:51 am

1 stop21h 21m

$286

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

lun. 7/21

12:50 pm-9:52 am

2 stops21h 02m

$308

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

lun. 8/4

12:45 pm-10:10 pm

1 stop9h 25m

$385

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

mar. 5/20

1:35 pm-9:30 pm

1 stop7h 55m

$393

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/20

Showing 1-10 of 12 results
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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.

Cheapflights Insights

Everything you need to know about your flight from the Cayman Islands to Chicago

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 abril 22, 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 at noon tend to be the most expensive. A flight in the morning could potentially save you up to 4% 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 abril 22, 2025.
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,286 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,683 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,923 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
WestJet
7.2
Good
2,813 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 JetBlue ($283), Air Canada ($308), and Southwest ($385).

  • What are the most reliable airlines from Cayman Islands to Chicago?

    Consider American Airlines (86%), United Airlines (72%) or Qatar Airways (67%) when booking your flight. These represent the most reliable airlines when flying from Cayman Islands to Chicago.

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

    On average you can expect to pay $454 for a flight from Cayman Islands to Chicago. The cheapest flight overall is $212 while the most popular route, (George Town Owen Roberts Intl - Chicago O'Hare Intl) is currently priced at $544.

  • 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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