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$287+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — CHI
nov. 26 — dic. 31
mar. 11/26
mar. 12/3
1 adult, Economy
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Cheap flight deals from Grand Cayman to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Grand Cayman (zzLAW) 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 noviembre 21, 2024.

Find flight deals from Grand Cayman to Chicago

One-way flights from Grand Cayman to Chicago
Search for one-way flight options from Grand Cayman to Chicago. Find affordable one-way fares based on user searches. Data last updated noviembre 21, 2024.

This eDestinos deal was found by Cheapflights users on 11/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 1/155:10 pmGCM - MDW
2 stops26h 16mMultiple Airlines
Deal found 11/20$287
This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
mar. 1/2111:30 amGCM - ORD
2 stops26h 15mMultiple Airlines
Deal found 11/20$294
This Southwest deal was found by Cheapflights users on 11/21. 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.
sáb. 12/212:15 pmGCM - ORD
1 stop9h 20mSouthwest
Deal found 11/21$316
This Air Canada deal was found by Cheapflights users on 11/21. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/224:00 pmGCM - ORD
1 stop17h 57mAir Canada
Deal found 11/21$322
This United Airlines deal was found by Cheapflights users on 11/21. 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.
jue. 12/192:50 pmGCM - ORD
Nonstop4h 16mUnited Airlines
Deal found 11/21$392
This Delta deal was found by Cheapflights users on 11/20. 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.
jue. 12/191:52 pmGCM - MDW
1 stop9h 14mDelta
Deal found 11/20$397
This Delta deal was found by Cheapflights users on 11/20. 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.
mié. 12/181:57 pmGCM - ORD
1 stop8h 08mDelta
Deal found 11/20$397
This American Airlines deal was found by Cheapflights users on 11/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 1/151:00 pmGCM - ORD
2 stops9h 42mAmerican Airlines
Deal found 11/20$408
This Justfly.com deal was found by Cheapflights users on 11/21. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/286:50 pmGCM - ORD
2 stops20h 55mBritish Airways
Deal found 11/21$3,710

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 2,612,795 searches. Data last updated noviembre 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

mié. 1/15

5:10 pm-6:26 pm

2 stops26h 16m

$287

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

mar. 1/21

11:30 am-12:45 pm

2 stops26h 15m

$294

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

sáb. 12/21

2:15 pm-10:35 pm

1 stop9h 20m

$316

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

dom. 12/22

4:00 pm-8:57 am

1 stop17h 57m

$322

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

jue. 12/19

2:50 pm-6:06 pm

Nonstop4h 16m

$392

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

jue. 12/19

1:52 pm-10:06 pm

1 stop9h 14m

$397

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

mié. 12/18

1:57 pm-9:05 pm

1 stop8h 08m

$397

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

mié. 1/15

1:00 pm-9:42 pm

2 stops9h 42m

$408

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

sáb. 12/28

6:50 pm-2:45 pm

2 stops20h 55m

$3,710

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

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 month to book a flight from Grand Cayman to Chicago?

Currently, September is the cheapest month in which you can book a flight from Grand Cayman to Chicago (average of $232). Flying from Grand Cayman to Chicago in June is currently the most expensive (average of $308). 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.

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 noviembre 21, 2024.

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 noviembre 21, 2024.
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,005 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,755 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,172 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Air Canada
7.0
Good
8,246 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 Southwest ($316), Air Canada ($322), and United Airlines ($392).

  • 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 $573, our data indicates the cheapest price to be $177. The most popular route (George Town Owen Roberts Intl - Chicago O'Hare Intl), is priced around $506.

  • 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, September is the cheapest month in which you can book a flight from Grand Cayman to Chicago (average of $232). Flying from Grand Cayman to Chicago in June is currently the most expensive (average of $308). 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

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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

Top airline flying from Grand Cayman to Chicago

Discover the top airline that operate flights from Grand Cayman 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 2,612,795 searches. Data last updated noviembre 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$451Average$558FlexibilityNo cancel feeOn-time69%
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