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Grand Cayman

$311+ 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 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — GCM
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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Cheap flight deals from Midway to Grand Cayman

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

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 November 21, 2024.

This Southwest deal was found by Cheapflights users on 11/19. 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.
Mon 12/96:00 amMDW - GCM
1 stop5h 55mSouthwest
Thu 12/121:50 pmGCM - MDW
2 stops9h 30mSouthwest
Deal found 11/19$575
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/246:00 amMDW - GCM
1 stop7h 32mDelta
Tue 12/313:47 pmGCM - MDW
1 stop7h 19mDelta
Deal found 11/21$618
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.
Thu 12/196:00 amMDW - GCM
1 stop14h 20mMultiple Airlines
Thu 12/264:45 pmGCM - MDW
2 stops21h 39mMultiple Airlines
Deal found 11/20$669
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/112:15 pmMDW - GCM
2 stops22h 34mWestJet
Sun 12/152:50 pmGCM - MDW
2 stops23h 41mWestJet
Deal found 11/20$3,094

Find flights from Midway to Grand Cayman within your budget

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

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Route

Depart

Return

Price

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 2/19

7:25 am-4:10 pm

1 stop7h 45m

George Town Owen Roberts Intl

Fri 2/28

4:45 pm-8:44 am

1 stop16h 59m

$488

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 2/25

5:45 am-12:55 pm

1 stop6h 10m

George Town Owen Roberts Intl

Sat 3/1

2:10 pm-11:15 pm

2 stops10h 05m

$532

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 2/23

6:00 am-12:44 pm

1 stop5h 44m

George Town Owen Roberts Intl

Fri 2/28

2:09 pm-10:20 pm

1 stop9h 11m

$588

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 1/5

11:48 am-1:49 pm

2 stops25h 01m

George Town Owen Roberts Intl

Sun 1/12

2:50 pm-5:47 pm

2 stops27h 57m

$1,630

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 11/27

8:35 pm-12:55 pm

2 stops15h 20m

$311

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 11/27

6:05 am-1:49 pm

3 stops30h 44m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

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.

Travel insights for flights from Midway to Grand Cayman

Get recent, data-driven insights about flights from Midway to Grand Cayman including ideal travel times, pricing trends, and more.
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 November 21, 2024.
To help decide which airline to fly from Chicago to Grand Cayman, see what other customers have to say about Delta and WestJet. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,005 reviews

Comfort

8.1

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

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

Comfort

8.1

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

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

Comfort

8.1

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Reviews

1 / 10

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

WestJet
7.3
Good
2,811 reviews
Southwest
8.1
Very good
5,005 reviews

Comfort

8.1

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

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 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 June is currently the most expensive (average of $560). 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.
O'Hare Intl to George Town flights
Midway to George Town flights
O'Hare Intl to Cayman Brac flights
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