What days are nonstop flights available from Chicago to Grand Cayman?

You can find nonstop flights on the following days: Friday.

How many flights depart from Chicago to Grand Cayman on average per day?

Travelers can expect 1 flight from Chicago to Grand Cayman on average per day. Morning (6am - Noon) - 100% of flight departures

How long is the flight from Chicago to Grand Cayman?

A quick flight from Chicago to Grand Cayman can take about 15h 35m. Delta provides one of the quickest options available for as low as $383. The distance between Chicago and Grand Cayman is about 1622 mi.

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

For one-way options, check prices for Delta. According to our data, you can fly for as low as $151. Users have also found prices from $279 and $857 on Air Canada and American Airlines, respectively.

What are the most popular airlines that fly from Chicago to Grand Cayman?

Before booking your flight from Chicago to Grand Cayman check out the most popular airlines for this route: American Airlines, Delta or Linear Air Taxi.

What are the cheapest flights from Chicago to Grand Cayman?

On average you can expect to pay $634 for a flight from Chicago to Grand Cayman. The cheapest flight overall is $441 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $435.

Can I find flights from Chicago to Grand Cayman for under $400 on Cheapflights?

Yes, there are multiple flights from Chicago to Grand Cayman for under $400. The cheapest flight booked recently is on Delta for just $383, but on average you can expect to pay $423.

Are there nonstop flights from Chicago to Grand Cayman for under $700 on Cheapflights?

Cheapflights has at least 7 direct flights from Chicago to Grand Cayman under $700. A good price for a nonstop flight from Chicago to Grand Cayman is less than $974.

Are there last-minute flights available from Chicago to Grand Cayman for under $700?

There are currently 5+ open flights from Chicago to Grand Cayman within the next 7 days for less than $700.

Which airlines flying from Chicago to Grand Cayman have flexible cancellations due to COVID-19?

American Airlines, United Airlines, and Delta are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

How far in advance should I book a flight from Chicago to Grand Cayman?

Find a great deal and save up to 49% by booking at least 41 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago to Grand Cayman within the next two weeks, with the cheapest ticket starting at $870.

What is the cheapest month to fly from Chicago to Grand Cayman?

Due to multiple factors, expect to potentially pay more when booking in November. For low rates, April can be a great choice for travel to Grand Cayman. Flights to Grand Cayman from Chicago in April are about $658 on average during April, but can be found for as low as $474.

When is the cheapest time to fly from Chicago to Grand Cayman (CHI - LAW)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Grand Cayman as you normally would.

Cheap Flights from Chicago, IL to Grand Cayman from $151 - Find Tickets & Airfare Deals at Cheapflights.com

Cheap flights from Chicago to Grand Cayman in March, April 2023

Apr 21 - Apr 29

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

1 stop

6h 04m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

1 stop

9h 53m

$383

Delta

Deal found 3/29

Apr 24 - Apr 27

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

5h 21m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

1 stop

10h 43m

$383

Delta

Deal found 3/29

Apr 23 - Apr 26

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

1 stop

6h 04m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

1 stop

19h 17m

$387

Delta

Deal found 3/30

Apr 21 - Apr 29

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

3 stops

29h 14m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

1 stop

10h 30m

$520

Multiple Airlines

Deal found 3/29

Apr 28 - May 5

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

2 stops

26h 05m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

1 stop

20h 40m

$522

Multiple Airlines

Deal found 3/29

Apr 21 - Apr 29

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

2 stops

11h 49m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

1 stop

10h 30m

$541

Multiple Airlines

Deal found 3/29

Apr 28 - May 5

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

2 stops

19h 46m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

2 stops

15h 39m

$553

Multiple Airlines

Deal found 3/29

Apr 24 - Apr 27

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

2 stops

31h 04m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

1 stop

9h 49m

$568

Multiple Airlines

Deal found 3/29

Apr 28 - May 5

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

2 stops

19h 46m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

3 stops

36h 35m

$581

Multiple Airlines

Deal found 3/29

Chicago to Grand Cayman 2023 flight deals

Aug 20 - Aug 31

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

1 stop

15h 35m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

1 stop

8h 27m

$383

Delta

Deal found 3/29

Jul 20 - Jul 25

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

5h 30m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

1 stop

11h 03m

$383

Delta

Deal found 3/30

May 30 - Jun 4

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

2 stops

26h 34m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

2 stops

18h 31m

$387

Delta

Deal found 3/29

May 30 - Jun 5

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

2 stops

25h 56m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

2 stops

19h 55m

$387

Delta

Deal found 3/29

Aug 16 - Aug 31

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

1 stop

28h 20m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

1 stop

11h 04m

$391

Delta

Deal found 3/29

Jul 13 - Jul 19

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

22h 23m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

1 stop

11h 03m

$391

Delta

Deal found 3/30

Aug 16 - Sep 1

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

1 stop

28h 20m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

2 stops

18h 43m

$395

Delta

Deal found 3/29

May 30 - Jun 4

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

2 stops

25h 56m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

1 stop

20h 18m

$395

Delta

Deal found 3/29

May 30 - Jun 2

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

1 stop

20h 11m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

1 stop

25h 09m

$399

Delta

Deal found 3/29

Cheap Delta flights from Chicago to Grand Cayman

Aug 20 - Aug 31

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

1 stop

15h 35m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

1 stop

8h 27m

$383

Delta

Deal found 3/29

May 30 - Jun 4

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

2 stops

26h 34m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

2 stops

18h 31m

$387

Delta

Deal found 3/29

Aug 16 - Aug 31

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

1 stop

28h 20m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

1 stop

11h 04m

$391

Delta

Deal found 3/29

Jul 13 - Jul 25

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

1 stop

21h 55m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

2 stops

18h 43m

$395

Delta

Deal found 3/30

May 30 - Jun 2

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

1 stop

20h 11m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

1 stop

25h 09m

$399

Delta

Deal found 3/29

Aug 20 - Aug 31

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

1 stop

15h 35m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

2 stops

20h 43m

$401

Delta

Deal found 3/29

Aug 16 - Aug 31

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

1 stop

28h 20m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

2 stops

20h 43m

$409

Delta

Deal found 3/29

Aug 20 - Sep 3

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

1 stop

15h 35m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

1 stop

8h 27m

$473

Delta

Deal found 3/29

Aug 16 - Sep 3

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

1 stop

28h 20m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

1 stop

8h 27m

$482

Delta

Deal found 3/29

Non-stop flights to Grand Cayman from Chicago

Jul 15 - Jul 22

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

Nonstop

3h 59m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

Nonstop

4h 06m

$608

United Airlines

Deal found 3/30

Jun 17 - Jul 1

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

Nonstop

3h 59m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

Nonstop

4h 06m

$622

United Airlines

Deal found 3/29

Jun 17 - Jun 24

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

Nonstop

3h 59m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

Nonstop

4h 06m

$698

United Airlines

Deal found 3/28

Apr 22 - Apr 29

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

Nonstop

3h 59m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

Nonstop

4h 06m

$768

United Airlines

Deal found 3/30

Apr 16 - Apr 22

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

Nonstop

3h 59m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

Nonstop

4h 06m

$968

United Airlines

Deal found 3/29

Apr 22 - Apr 29

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

Nonstop

3h 59m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

Nonstop

4h 06m

$1,551

United Airlines

Deal found 3/29

May 27 - Jun 3

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

Nonstop

3h 59m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

Nonstop

4h 06m

$1,604

United Airlines

Deal found 3/29

Last minute flights from Chicago to Grand Cayman

Apr 4 - Apr 11

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

29h 30m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

1 stop

21h 14m

$609

Multiple Airlines

Deal found 3/29

Apr 4 - Apr 11

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

1 stop

19h 43m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

2 stops

27h 00m

$651

Multiple Airlines

Deal found 3/29

Apr 4 - Apr 11

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

2 stops

10h 40m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

2 stops

20h 50m

$919

Multiple Airlines

Deal found 3/29

Apr 4 - Apr 11

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

2 stops

10h 40m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

3 stops

31h 46m

$1,019

Multiple Airlines

Deal found 3/29

Apr 4 - Apr 11

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

1 stop

19h 43m

GCM

George Town Owen Roberts Intl

ORD

Chicago O'Hare Intl

1 stop

10h 30m

$1,105

Multiple Airlines

Deal found 3/29

One-way flights to Grand Cayman from Chicago

Jul 20

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

1 stop

5h 30m

$151

Delta

Deal found 3/30

Jul 20

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

5h 30m

$151

Delta

Deal found 3/30

Aug 15

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

2 stops

39h 55m

$166

Delta

Deal found 3/30

Jul 20

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

2 stops

19h 50m

$279

Air Canada

Deal found 3/30

Apr 6

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

11h 30m

$283

Multiple Airlines

Deal found 3/29

Apr 6

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

3 stops

44h 49m

$303

Multiple Airlines

Deal found 3/29

Apr 6

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

3 stops

45h 54m

$307

Multiple Airlines

Deal found 3/29

Apr 6

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

2 stops

10h 04m

$341

Multiple Airlines

Deal found 3/29

Apr 6

ORD

Chicago O'Hare Intl

GCM

George Town Owen Roberts Intl

2 stops

19h 03m

$344

Multiple Airlines

Deal found 3/29

Find flights from Chicago to Grand Cayman within your budget

Fly from

Fly to

Budget

$383 - $469

Route

Depart

Return

Price

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

2023-08-20

1 stop15h 35m

George Town Owen Roberts Intl

2023-08-31

1 stop8h 27m

$383

Pick Dates

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

2023-04-24

1 stop5h 21m

George Town Owen Roberts Intl

2023-04-27

1 stop10h 43m

$383

Pick Dates

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

2023-05-30

2 stops26h 34m

George Town Owen Roberts Intl

2023-06-04

2 stops18h 31m

$387

Pick Dates

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

2023-05-30

2 stops25h 56m

George Town Owen Roberts Intl

2023-06-01

1 stop10h 56m

$387

Pick Dates

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

2023-08-16

1 stop28h 20m

George Town Owen Roberts Intl

2023-08-31

1 stop11h 04m

$391

Pick Dates

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

2023-05-09

2 stops18h 03m

George Town Owen Roberts Intl

2023-05-13

1 stop10h 26m

$450

Pick Dates

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

2023-05-08

2 stops26h 05m

George Town Owen Roberts Intl

2023-05-13

1 stop10h 26m

$454

Pick Dates

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

2023-05-08

1 stop24h 20m

George Town Owen Roberts Intl

2023-05-13

1 stop10h 26m

$464

Pick Dates

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

2023-05-16

1 stop23h 40m

George Town Owen Roberts Intl

2023-05-22

1 stop12h 26m

$469

Pick Dates

Flights are sorted by cheapest first

Deals found on 3/29

Reviews of Airlines Servicing Grand Cayman

Delta

8.0

Very good

2,335 reviews

Check prices

Reviews

1 / 10

I was told at the gate that my 3 hr flight from Tucson to Atlanta would offer 3 choices for a light meal/snack. None was offered. I would have planned accordingly before boarding if give the correct info

Delta

8.0

Very good

2,335 reviews

Delta

8.0

Very good

2,335 reviews

Check prices

Reviews

1 / 10

I was told at the gate that my 3 hr flight from Tucson to Atlanta would offer 3 choices for a light meal/snack. None was offered. I would have planned accordingly before boarding if give the correct info

American Airlines

7.4

Good

1,803 reviews

Delta

8.0

Very good

2,335 reviews

Check prices

Reviews

1 / 10

I was told at the gate that my 3 hr flight from Tucson to Atlanta would offer 3 choices for a light meal/snack. None was offered. I would have planned accordingly before boarding if give the correct info

Air Canada

6.7

Okay

887 reviews

Delta

8.0

Very good

2,335 reviews

Check prices

Reviews

1 / 10

I was told at the gate that my 3 hr flight from Tucson to Atlanta would offer 3 choices for a light meal/snack. None was offered. I would have planned accordingly before boarding if give the correct info

Related info for your journey

Chicago O'Hare Intl Airport is ORD and George Town Owen Roberts Intl Airport is GCM. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are some additional IATA codes for airports related to your trip.

Flights to Grand Cayman from Chicago

Flights to Chicago

Flights to Grand Cayman

Flights from Chicago

Flights from Grand Cayman

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Car Rentals at George Town

Top 4 airlines flying from Chicago to Grand Cayman

Airline	Cheapest	Average	Flexibility	On-time	COVID-19 safety
American Airlines	Cheapest$239	Average$642	FlexibilityNo cancel fee	On-time71%	COVID-19 safety	Search American Airlines flights
United Airlines	Cheapest$265	Average$670	FlexibilityNo cancel fee	On-time69%	COVID-19 safety	Search United Airlines flights
Delta	Cheapest$601	Average$670	FlexibilityNo cancel fee	On-timeN/A	COVID-19 safety	Search Delta flights
Linear Air Taxi	Cheapest$8,547	Average$51,983	FlexibilityNo cancel fee	On-timeN/A	COVID-19 safety	Search Linear Air Taxi flights

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Cheap flights from Chicago (CHI) to Grand Cayman from $151

This is the cheapest one-way flight price, found on 3/30. Prices may vary by date and flight preferences.

How far in advance should I book a flight from Chicago to Grand Cayman?

What is the cheapest month to fly from Chicago to Grand Cayman?

When is the cheapest time to fly from Chicago to Grand Cayman (CHI - LAW)?

Cheap flights from Chicago to Grand Cayman in March, April 2023

The best prices found for CHI to Grand Cayman flights for March, April

Chicago to Grand Cayman 2023 flight deals

Cheap flights to Grand Cayman from Chicago found for this year

Cheap Delta flights from Chicago to Grand Cayman

Non-stop flights to Grand Cayman from Chicago

Save time with Chicago to Grand Cayman direct flight deals

Last minute flights from Chicago to Grand Cayman

Late deals on return flights to Grand Cayman from Chicago, departing today and this week

One-way flights to Grand Cayman from Chicago

The cheapest one-way flights from Chicago to Grand Cayman

Find flights from Chicago to Grand Cayman within your budget

Use the slider to find flights from Chicago to Grand Cayman that fit your budget.

Reviews of Airlines Servicing Grand Cayman

Related info for your journey

Useful info, stats and facts about Chicago to Grand Cayman flights.

Which airlines flying from Chicago to Grand Cayman have flexible cancellations due to COVID-19?

Can I find flights from Chicago to Grand Cayman for under $400 on Cheapflights?

Are there nonstop flights from Chicago to Grand Cayman for under $700 on Cheapflights?

Are there last-minute flights available from Chicago to Grand Cayman for under $700?

What days are nonstop flights available from Chicago to Grand Cayman?

How many flights depart from Chicago to Grand Cayman on average per day?

How long is the flight from Chicago to Grand Cayman?

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

What are the most popular airlines that fly from Chicago to Grand Cayman?

What are the cheapest flights from Chicago to Grand Cayman?

What does ORD to GCM mean?

Flights to Grand Cayman from Chicago

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Top 4 airlines flying from Chicago to Grand Cayman

The chart below displays the airlines Cheapflights users traveling from Chicago to Grand Cayman choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.

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