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Grand Cayman

$267+ Cheap flights from Midway (MDW) to Grand Cayman

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 7/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — GCM
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
1 adult, Economy
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Cheap flight deals from Midway to Grand Cayman

Keep the following information in mind while searching for Midway to Grand Cayman flight deals. Data was last updated June 18, 2025.

Round-trip from

$595
(Delta)

One-way from

$267
(Southwest)

Popular in

March

Cheapest in

September

Average price

$657
From Chicago Midway to Grand Cayman
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One-way flight from Chicago Midway to Grand Cayman
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Highest demand for flights based on searches. 11% potential increase in price ($81 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Find flight deals from Midway to Grand Cayman

Cheapest flights from Midway to Grand Cayman
Explore the most affordable flight options available from Midway to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 18, 2025.

This Delta deal was found by Cheapflights users on 6/15. 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.
Sun 10/126:00 amMDW - GCM
1 stop5h 42mDelta
Sun 10/191:02 pmGCM - MDW
1 stop8h 42mDelta
Deal found 6/15$545
This Southwest deal was found by Cheapflights users on 6/17. 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.
Sat 9/66:15 amMDW - GCM
1 stop5h 55mSouthwest
Sat 9/131:10 pmGCM - MDW
1 stop7h 10mSouthwest
Deal found 6/17$626
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Thu 6/194:06 pmMDW - GCM
1 stop23h 54mMultiple Airlines
Sun 6/2212:40 pmGCM - MDW
1 stop9h 52mMultiple Airlines
Deal found 6/16$742
This WestJet deal was found by Cheapflights users on 6/17. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/261:05 pmMDW - GCM
2 stops23h 44mWestJet
Sun 11/302:50 pmGCM - MDW
2 stops23h 19mWestJet
Deal found 6/17$3,382

Cheapflights Fare Finder

Customize your flight search to find flights from Midway to Grand Cayman 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 June 18, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Grand Cayman that are best for you.

Fly from

Midway

Fly to

Grand Cayman

Route

Depart

Return

Price

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 8/30

6:00 am-11:37 am

1 stop5h 37m

George Town Owen Roberts Intl

Thu 9/4

12:50 pm-9:26 pm

1 stop8h 36m

$595

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 9/6

6:15 am-12:10 pm

1 stop5h 55m

George Town Owen Roberts Intl

Sat 9/13

1:10 pm-8:20 pm

1 stop7h 10m

$626

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 7/11

1:46 pm-12:45 pm

2 stops22h 59m

George Town Owen Roberts Intl

Tue 7/15

1:45 pm-5:39 pm

2 stops27h 54m

$3,498

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 7/3

9:45 pm-11:50 am

2 stops14h 05m

$267

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 7/31

6:00 am-11:22 am

1 stop5h 22m

$318

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 8/2

9:12 pm-9:45 pm

3 stops24h 33m

$618

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/17

Best time to book a flight from Midway to Grand Cayman

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

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Grand Cayman
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Grand Cayman

Get insights into the airlines that provide service to Grand Cayman. 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 Grand Cayman. Reviews last updated June 18, 2025.
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,964 reviews
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
WestJet
7.2
Good
2,876 reviews
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

Find useful and relevant information for your journey from Midway to Grand Cayman. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Grand Cayman (average of $467). Flying from Chicago Midway Airport to Grand Cayman in March is currently the most expensive (average of $594). 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 Midway to Grand Cayman

See prices for flight routes from nearby airports that may be better suited for you.
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