$280+ 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 2/13. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Cayman Islands to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Cayman Islands to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Cayman Islands (KY0) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.
Round-trip from | $515 (Mytrip) |
|---|---|
One-way from | $280 (Kiwi.com) |
Good round-trip deal | $315 or less |
Good one-way deal | $412 or less |
Find flight deals from Cayman Islands to Chicago
Cheapest flights from Cayman Islands to ChicagoExplore 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 January 21, 2025.
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 January 21, 2025.
This Mytrip deal was found by Cheapflights users on 1/20. 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.
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
This Southwest deal was found by Cheapflights users on 1/20. 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.
This Southwest deal was found by Cheapflights users on 1/19. 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.
This United Airlines deal was found by Cheapflights users on 1/20. 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.
This Delta deal was found by Cheapflights users on 1/20. 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.
This Delta deal was found by Cheapflights users on 1/19. 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.
This American Airlines deal was found by Cheapflights users on 1/19. 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.
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 January 21, 2025.
Fly from
Fly to
Route
Depart
Return
Price
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Thu 3/6
11:30 am-7:44 am
2 stops21h 14m
Chicago O'Hare Intl
Thu 3/13
5:55 am-9:20 pm
2 stops15h 25m
George TownChicago
GCM - MDW
GCMMDW
George Town Owen Roberts Intl
Thu 3/6
2:00 pm-10:06 pm
2 stops9h 06m
Chicago Midway
Thu 3/13
7:25 am-9:20 pm
1 stop13h 55m
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Sat 4/12
1:10 pm-9:30 pm
1 stop8h 20m
Chicago O'Hare Intl
Sat 4/19
6:00 am-12:10 pm
1 stop6h 10m
George TownChicago
GCM - MDW
GCMMDW
George Town Owen Roberts Intl
Tue 2/25
1:50 pm-10:25 pm
2 stops9h 35m
Chicago Midway
Sat 3/1
6:30 pm-12:55 pm
2 stops17h 25m
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Thu 3/6
2:50 pm-6:06 pm
Nonstop4h 16m
Chicago O'Hare Intl
Thu 3/13
9:45 pm-3:25 pm
1 stop17h 40m
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Tue 2/25
5:20 pm-11:55 pm
1 stop7h 35m
Chicago O'Hare Intl
Sat 3/1
7:09 pm-12:00 pm
1 stop15h 51m
George TownChicago
GCM - MDW
GCMMDW
George Town Owen Roberts Intl
Sat 2/22
2:04 pm-10:20 pm
1 stop9h 16m
Chicago Midway
Sat 3/1
6:00 am-1:54 pm
1 stop6h 54m
George TownChicago
GCM - MDW
GCMMDW
George Town Owen Roberts Intl
Thu 2/13
11:30 am-6:20 pm
1 stop7h 50m
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Wed 2/5
11:30 am-12:29 pm
1 stop25h 59m
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Thu 3/13
3:00 pm-10:54 am
2 stops19h 54m
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.
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 January 21, 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 14% 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 January 21, 2025.
Food
Entertainment
Boarding
Comfort
Crew
Overall
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Food
Entertainment
Boarding
Comfort
Crew
Overall
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Food
Entertainment
Boarding
Comfort
Crew
Overall
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Food
Entertainment
Boarding
Comfort
Crew
Overall
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Food
Entertainment
Boarding
Comfort
Crew
Overall
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Food
Entertainment
Boarding
Comfort
Crew
Overall
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
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.
Traveling to a place near the Cayman Islands?
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Alternative routes for Cayman Islands to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top airline flying from Cayman Islands to Chicago
Discover the top airline that operate flights from Cayman Islands to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 21, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$451 | Average$613 | FlexibilityNo cancel fee | On-time69% |