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.
CHI — GCM
Apr 4 — Apr 111

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.

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$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

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

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

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

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

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

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

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

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

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

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Food

7.2

Crew

8.5

Overall

8.0

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

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Food

7.2

Crew

8.5

Overall

8.0

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

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Food

7.2

Crew

8.5

Overall

8.0

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

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Food

7.2

Crew

8.5

Overall

8.0

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

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

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.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
American AirlinesCheapest$239Average$642FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
United AirlinesCheapest$265Average$670FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
DeltaCheapest$601Average$670FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
Linear Air TaxiCheapest$8,547Average$51,983FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Linear Air Taxi flights
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