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$280+ Cheap flights from Grand Cayman 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — CHI
Feb 28 — Mar 71
Fri 2/28
Fri 3/7
1 adult, Economy
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Cheap flight deals from Grand Cayman to Chicago

Keep the following information in mind while searching for Grand Cayman to Chicago flight deals. Data was last updated February 23, 2025.

Popular in

March

Cheapest in

September
Highest demand for flights based on searches. 33% potential increase in price ($325 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($45 potential savings vs. average RT price).
Search Deals

Find flight deals from Grand Cayman to Chicago

Cheapest flights from Grand Cayman to Chicago
Explore the most affordable flight options available from Grand Cayman to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 23, 2025.

This Mytrip deal was found by Cheapflights users on 2/22. 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.
Sat 3/18:05 pmGCM - ORD
2 stops16h 37mMultiple Airlines
Sat 3/86:00 amORD - GCM
2 stops7h 50mMultiple Airlines
Deal found 2/22$823
This American Airlines deal was found by Cheapflights users on 2/22. 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.
Sat 3/15:40 pmGCM - ORD
1 stop16h 22mAmerican Airlines
Sat 3/85:40 pmORD - GCM
1 stop17h 05mAmerican Airlines
Deal found 2/22$855
This United Airlines deal was found by Cheapflights users on 2/22. 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 3/15:45 pmGCM - ORD
1 stop28h 47mUnited Airlines
Sat 3/88:39 amORD - GCM
Nonstop3h 56mUnited Airlines
Deal found 2/22$871

Find flights from Grand Cayman to Chicago within your budget

Customize your flight search to find flights from Grand Cayman 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 23, 2025.

Fly from

Grand Cayman

Fly to

Chicago

Route

Depart

Return

Price

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 4/15

11:30 am-2:26 pm

1 stop26h 56m

$280

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 4/17

2:30 pm-8:00 pm

2 stops29h 30m

$345

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Wed 4/16

11:30 am-3:29 pm

1 stop27h 59m

$363

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 4/16

1:35 pm-9:28 pm

1 stop7h 53m

$393

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 4/19

12:47 pm-10:22 pm

1 stop9h 35m

$418

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 3/12

1:03 pm-8:58 pm

1 stop7h 55m

$443

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 3/12

12:00 pm-12:12 am

2 stops12h 12m

$452

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sun 3/2

1:50 pm-9:35 am

2 stops20h 45m

$515

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sun 3/2

2:50 pm-5:43 pm

3 stops27h 53m

$722

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

Best time to book a flight from Grand Cayman to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Grand Cayman 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 Grand Cayman to Chicago

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

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

Find hourly flight availability from Grand Cayman 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 23, 2025.

When flying from Grand Cayman to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 23, 2025.
Southwest
8.1
Very good
4,387 reviews

Food

7.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Overall

8.1

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
4,387 reviews
Southwest
8.1
Very good
4,387 reviews

Food

7.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Overall

8.1

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
8,191 reviews
Southwest
8.1
Very good
4,387 reviews

Food

7.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Overall

8.1

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
8,746 reviews
Southwest
8.1
Very good
4,387 reviews

Food

7.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Overall

8.1

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
4,387 reviews

Food

7.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Overall

8.1

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.

WestJet
7.2
Good
2,796 reviews
Southwest
8.1
Very good
4,387 reviews

Food

7.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Overall

8.1

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 Grand Cayman 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 Grand Cayman to Chicago one-way?

    The cheapest airlines for a one-way flight from Grand Cayman to Chicago are Air Canada ($345), United Airlines ($393), and Delta ($418).

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

    Looking for the cheapest flight from Grand Cayman to Chicago? While on average our users pay $859, our data indicates the cheapest price to be $273. The most popular route (George Town Owen Roberts Intl - Chicago O'Hare Intl), is priced around $453.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Grand Cayman 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 Grand Cayman to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Grand Cayman to Chicago (average of $245). Flying from Grand Cayman 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 Grand Cayman?

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

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Alternative routes for Grand Cayman to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
George Town to O'Hare Intl flights
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