Can I find flights from Chicago Midway Airport to Cayman Islands for under $400 on Cheapflights?

Yes, there are multiple flights from Chicago Midway Airport to Cayman Islands for under $400. The cheapest flight booked recently is on Delta for just $391, but on average you can expect to pay $568.

What is the cheapest month to fly from Chicago Midway Airport to Cayman Islands?

Flights from Chicago Midway Airport to Cayman Islands lean towards being more expensive in November. Prices are generally better when you fly from Chicago Midway Airport to Cayman Islands in April, with the cheapest ticket starting at $474.

When is the cheapest time to fly from Chicago Midway Airport to Cayman Islands (MDW - KY)?

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

Cheap Flights from Chicago Midway Airport (MDW) to the Cayman Islands from $161 - Find Tickets & Airfare Deals at Cheapflights.com

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MDW — GCM

Jun 6 — Jun 131

Round-tripOne-way

1 adult, Economy

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When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 41 days in advance, which can save you up to 49% on flights from Chicago Midway Airport to Cayman Islands compared to booking the week you need them. Waiting 41 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $870. For sooner than that we have options available in the next 3 days from $1,069.

Cheap flights from Midway to Cayman Islands in June, July 2023

Jun 23 - Jun 26

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

5h 24m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

1 stop

11h 07m

$403

Delta

Deal found 6/1

Jun 23 - Jun 26

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

5h 24m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

1 stop

11h 07m

$432

Delta

Deal found 6/1

Jun 23 - Jun 26

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

5h 24m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

2 stops

19h 55m

$451

Delta

Deal found 6/1

Jun 16 - Jun 23

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

5h 24m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

1 stop

11h 07m

$487

Delta

Deal found 5/31

Jun 23 - Jun 26

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

5h 24m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

2 stops

19h 55m

$501

Delta

Deal found 6/1

Jun 29 - Jul 3

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

25h 42m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

1 stop

17h 00m

$514

Multiple Airlines

Deal found 6/1

Jun 29 - Jul 3

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

16h 02m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

1 stop

17h 00m

$520

Multiple Airlines

Deal found 5/31

Jul 23 - Jul 29

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

20h 18m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

1 stop

7h 54m

$548

Multiple Airlines

Deal found 5/31

Jun 29 - Jul 2

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

16h 02m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

1 stop

18h 30m

$557

Multiple Airlines

Deal found 5/31

Midway to Cayman Islands 2023 flight deals

Sep 11 - Sep 15

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

5h 54m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

1 stop

8h 29m

$391

Delta

Deal found 5/31

Sep 11 - Sep 15

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

5h 54m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

2 stops

19h 16m

$395

Delta

Deal found 5/31

Jun 23 - Jun 26

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

5h 24m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

1 stop

11h 07m

$403

Delta

Deal found 6/1

Jun 23 - Jun 26

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

5h 24m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

1 stop

11h 07m

$432

Delta

Deal found 6/1

Jun 23 - Jun 26

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

5h 24m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

2 stops

19h 55m

$451

Delta

Deal found 6/1

Nov 10 - Nov 14

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

2 stops

18h 56m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

1 stop

6h 57m

$455

Multiple Airlines

Deal found 5/30

Aug 17 - Aug 21

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

5h 30m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

1 stop

10h 57m

$481

Delta

Deal found 5/31

Jun 16 - Jun 23

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

5h 24m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

1 stop

11h 07m

$487

Delta

Deal found 5/31

Aug 27 - Sep 3

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

5h 30m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

2 stops

19h 47m

$491

Delta

Deal found 5/30

Cheap Delta flights from Midway to Cayman Islands

Sep 11 - Sep 15

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

5h 54m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

1 stop

8h 29m

$391

Delta

Deal found 5/31

Sep 11 - Sep 15

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

5h 54m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

2 stops

19h 16m

$395

Delta

Deal found 5/31

Aug 17 - Aug 21

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

5h 30m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

1 stop

10h 57m

$481

Delta

Deal found 5/31

Jun 16 - Jun 23

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

5h 24m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

1 stop

11h 07m

$487

Delta

Deal found 5/31

Aug 27 - Sep 3

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

5h 30m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

2 stops

19h 47m

$491

Delta

Deal found 5/30

Aug 17 - Aug 21

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

5h 30m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

2 stops

20h 00m

$529

Delta

Deal found 5/31

Nov 4 - Nov 10

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

5h 55m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

2 stops

20h 18m

$560

Delta

Deal found 6/1

Aug 27 - Sep 3

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

2 stops

16h 15m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

2 stops

19h 47m

$575

Delta

Deal found 5/30

Aug 17 - Aug 21

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

2 stops

16h 15m

GCM

George Town Owen Roberts Intl

MDW

Chicago Midway

2 stops

20h 00m

$594

Delta

Deal found 5/31

One-way flights to Cayman Islands from Midway

Sep 22

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

1 stop

5h 54m

$161

Delta

Deal found 5/31

Sep 22

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

2 stops

19h 56m

$203

Multiple Airlines

Deal found 5/31

Sep 23

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

2 stops

26h 47m

$247

Multiple Airlines

Deal found 5/31

Sep 22

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

2 stops

17h 54m

$304

Delta

Deal found 6/1

Sep 23

MDW

Chicago Midway

GCM

George Town Owen Roberts Intl

3 stops

25h 38m

$1,008

Multiple Airlines

Deal found 5/31

Find flights from Midway to Cayman Islands within your budget

Fly from

Fly to

Budget

$391 - $557

Route

Depart

Return

Price

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Mon 9/11

1 stop5h 54m

George Town Owen Roberts Intl

Fri 9/15

1 stop8h 29m

$391

Pick Dates

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Mon 9/11

1 stop5h 54m

George Town Owen Roberts Intl

Fri 9/15

2 stops19h 16m

$395

Pick Dates

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Fri 11/10

2 stops18h 56m

George Town Owen Roberts Intl

Tue 11/14

1 stop6h 57m

$455

Pick Dates

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Thu 8/17

1 stop5h 30m

George Town Owen Roberts Intl

Mon 8/21

1 stop10h 57m

$481

Pick Dates

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Fri 6/16

1 stop5h 24m

George Town Owen Roberts Intl

Fri 6/23

1 stop11h 07m

$487

Pick Dates

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Sun 8/27

1 stop5h 30m

George Town Owen Roberts Intl

Sun 9/3

2 stops19h 47m

$491

Pick Dates

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Thu 6/29

1 stop16h 02m

George Town Owen Roberts Intl

Mon 7/3

1 stop17h 00m

$520

Pick Dates

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Sun 7/23

1 stop20h 18m

George Town Owen Roberts Intl

Sat 7/29

1 stop7h 54m

$548

Pick Dates

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Thu 6/29

1 stop16h 02m

George Town Owen Roberts Intl

Sun 7/2

1 stop18h 30m

$557

Pick Dates

Flights are sorted by cheapest first

Deals found on 5/31

Reviews of Airlines Servicing Cayman Islands

Delta

8.0

Very good

2,382 reviews

Check prices

Reviews

1 / 10

I really enjoyed my Virgin Atlantic flight from New York JFK to London. The boarding started early and was very well organized. The team made us feel welcomed and comfortable.

Delta

8.0

Very good

2,382 reviews

Delta

8.0

Very good

2,382 reviews

Check prices

Reviews

1 / 10

I really enjoyed my Virgin Atlantic flight from New York JFK to London. The boarding started early and was very well organized. The team made us feel welcomed and comfortable.

WestJet

7.1

Good

630 reviews

Delta

8.0

Very good

2,382 reviews

Check prices

Reviews

1 / 10

I really enjoyed my Virgin Atlantic flight from New York JFK to London. The boarding started early and was very well organized. The team made us feel welcomed and comfortable.

Related info for your journey

These are just IATA (International Air Transport Association) codes. They are used in aviation to identify and differentiate airports. That’s why a Chicago Midway Airport to George Town Owen Roberts Intl Airport flight would often be abbreviated as a MDW to GCM flight. Cayman Brac Gerrard-Smith Airport (CYB), Little Cayman Airport (LYB) are some additional IATA codes for airports related to your trip.

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Cheap flights from Midway (MDW) to the Cayman Islands from $161

This is the cheapest one-way flight price, found on 5/31. Prices may vary by date and flight preferences.

How far in advance should I book a flight from Chicago Midway Airport to Cayman Islands?

What is the cheapest month to fly from Chicago Midway Airport to Cayman Islands?

When is the cheapest time to fly from Chicago Midway Airport to Cayman Islands (MDW - KY)?

Cheap flights from Midway to Cayman Islands in June, July 2023

The best prices found for MDW to Cayman Islands flights for June, July

Midway to Cayman Islands 2023 flight deals

Cheap flights to Cayman Islands from Midway found for this year

Cheap Delta flights from Midway to Cayman Islands

One-way flights to Cayman Islands from Midway

The cheapest one-way flights from Midway to Cayman Islands

Find flights from Midway to Cayman Islands within your budget

Use the slider to find flights from Midway to Cayman Islands that fit your budget.

Reviews of Airlines Servicing Cayman Islands

Related info for your journey

Useful info, stats and facts about Midway to Cayman Islands flights.

Can I find flights from Chicago Midway Airport to Cayman Islands for under $400 on Cheapflights?

What does MDW to GCM mean?

Flights to Cayman Islands from Midway

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