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Grand Cayman

$354+ 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 3/23. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — GCM
nov. 12 — nov. 191
1 adult
mar. 11/12
mar. 11/19
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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 noviembre 7, 2024.

This Southwest deal was found by Cheapflights users on 11/5. 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.
dom. 12/155:10 amMDW - GCM
1 stop6h 45mSouthwest
dom. 12/221:50 pmGCM - MDW
1 stop9h 05mSouthwest
Deal found 11/5$590
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
lun. 12/169:57 pmMDW - GCM
1 stop17h 13mMultiple Airlines
dom. 12/222:00 pmGCM - MDW
1 stop19h 21mMultiple Airlines
Deal found 11/5$604
This Delta deal was found by Cheapflights users on 11/7. 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.
mar. 12/246:00 amMDW - GCM
1 stop5h 27mDelta
mar. 12/313:47 pmGCM - MDW
1 stop7h 19mDelta
Deal found 11/7$608
This Mytrip deal was found by Cheapflights users on 11/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/49:30 amMDW - GCM
3 stops27h 19mWestJet
dom. 12/82:50 pmGCM - MDW
2 stops28h 42mWestJet
Deal found 11/6$779

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 2,537,365 searches. Data last updated noviembre 7, 2024.

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Route

Depart

Return

Price

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

sáb. 11/16

6:00 am-12:37 pm

1 stop5h 37m

$392

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

vie. 1/3

6:00 am-3:45 pm

1 stop8h 45m

George Town Owen Roberts Intl

mar. 1/7

11:30 am-5:57 pm

2 stops31h 27m

$573

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

dom. 12/15

5:10 am-12:55 pm

1 stop6h 45m

George Town Owen Roberts Intl

dom. 12/22

1:50 pm-9:55 pm

1 stop9h 05m

$590

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

sáb. 1/18

6:00 am-12:44 pm

1 stop5h 44m

George Town Owen Roberts Intl

mié. 1/22

2:09 pm-10:20 pm

1 stop9h 11m

$603

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

mié. 12/4

9:30 am-1:49 pm

3 stops27h 19m

George Town Owen Roberts Intl

dom. 12/8

2:50 pm-6:32 pm

2 stops28h 42m

$779

Flights are sorted by cheapest first

Deals found on 11/6

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 noviembre 7, 2024.
Southwest
8.1
Very good
5,083 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Entertainment

7.7

Boarding

8.3

Food

7.2

Reviews

1 / 10

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

Southwest
8.1
Very good
5,083 reviews
Southwest
8.1
Very good
5,083 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Entertainment

7.7

Boarding

8.3

Food

7.2

Reviews

1 / 10

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

Delta
8.0
Very good
8,828 reviews
Southwest
8.1
Very good
5,083 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Entertainment

7.7

Boarding

8.3

Food

7.2

Reviews

1 / 10

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

WestJet
7.3
Good
2,804 reviews
Southwest
8.1
Very good
5,083 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Entertainment

7.7

Boarding

8.3

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

Top airline flying from Midway to Grand Cayman

Discover the top airline that operate flights from Midway to Grand Cayman. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,537,365 searches. Data last updated noviembre 7, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$398Average$603FlexibilityNo cancel feeOn-timeN/A
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