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Grand Cayman

$255+ 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 3/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — GCM
Dec 29 — Jan 51
Sun 12/29
Sun 1/5
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 December 24, 2024.

Round-trip from

$575
(Southwest)

One-way from

$255
(Southwest)
From Chicago Midway to Grand Cayman
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One-way flight from Chicago Midway to Grand Cayman
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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 December 24, 2024.

This Southwest deal was found by Cheapflights users on 12/22. 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 12/235:00 amMDW - GCM
1 stop6h 55mSouthwest
Mon 12/301:50 pmGCM - MDW
2 stops7h 45mSouthwest
Deal found 12/22$774
This Kiwi.com deal was found by Cheapflights users on 12/22. 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.
Mon 12/239:16 amMDW - GCM
1 stop25h 24mMultiple Airlines
Mon 12/302:00 pmGCM - MDW
2 stops26h 11mMultiple Airlines
Deal found 12/22$907
This Delta deal was found by Cheapflights users on 12/23. 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 12/311:52 pmGCM - MDW
1 stop9h 14mDelta
Deal found 12/23$978
This CheapOair deal was found by Cheapflights users on 12/24. 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.
Tue 12/3110:08 amMDW - GCM
2 stops50h 26mWestJet
Sun 1/52:50 pmGCM - MDW
2 stops27h 57mWestJet
Deal found 12/24$4,242

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 2,558,603 searches. Data last updated December 24, 2024.

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Route

Depart

Return

Price

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 1/9

5:35 am-12:55 pm

1 stop6h 20m

George Town Owen Roberts Intl

Tue 1/14

1:50 pm-10:40 pm

2 stops9h 50m

$575

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 2/12

4:20 pm-6:40 pm

1 stop25h 20m

George Town Owen Roberts Intl

Sat 2/15

8:50 am-6:15 pm

1 stop10h 25m

$577

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 3/25

6:00 am-11:25 am

1 stop5h 25m

George Town Owen Roberts Intl

Tue 4/1

12:50 pm-10:27 pm

1 stop9h 37m

$598

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 3/23

10:25 am-12:43 pm

2 stops26h 18m

George Town Owen Roberts Intl

Sun 3/30

1:50 pm-9:09 am

2 stops43h 19m

$3,185

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 3/14

5:55 am-11:50 am

1 stop5h 55m

$255

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 2/8

6:00 am-2:04 pm

1 stop7h 04m

$317

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 3/14

6:38 pm-4:10 pm

2 stops21h 32m

$488

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 2/8

11:25 am-1:43 pm

2 stops25h 18m

$1,191

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/24

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 December 24, 2024.
To help decide which airline to fly from Chicago to Grand Cayman, see what other customers have to say about Delta, Southwest 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
4,765 reviews

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,765 reviews
Southwest
8.1
Very good
4,765 reviews

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,580 reviews
Southwest
8.1
Very good
4,765 reviews

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

WestJet
7.3
Good
2,816 reviews
Southwest
8.1
Very good
4,765 reviews

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Grand Cayman one-way?

    One-way options have recently been found by users for as low as $255 on Southwest. Other airlines that offer cheap prices include Delta from $317 and WestJet from $1,191 one-way.

  • 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.

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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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