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Grand Cayman

$155+ 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 12/22. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — GCM
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
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 November 20, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$354
(Delta)

One-way from

$155
(Southwest)

Popular in

December

Cheapest in

October

Average price

$764
Provider with most accurate pricing for Chicago (CHI)-George Town Owen Roberts Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-George Town Owen Roberts Intl flights.
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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. 7% potential increase in price ($54 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 20, 2025.

This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:00 amMDW - GCM
1 stop5h 36mDelta
Wed 12/313:42 pmGCM - MDW
1 stop7h 40mDelta
Deal found 11/19$354
This Southwest deal was found by Cheapflights users on 11/18. 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.
Sun 12/75:50 amMDW - GCM
1 stop5h 45mSouthwest
Wed 12/101:30 pmGCM - MDW
2 stops10h 05mSouthwest
Deal found 11/18$389
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/276:00 amMDW - GCM
1 stop5h 35mDelta
Thu 12/41:50 pmGCM - MDW
1 stop10h 57mDelta
Deal found 11/19$405
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/276:00 amMDW - GCM
1 stop5h 35mDelta
Wed 12/31:50 pmGCM - MDW
1 stop10h 57mDelta
Deal found 11/20$414
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/286:00 amMDW - GCM
1 stop5h 35mDelta
Mon 12/11:50 pmGCM - MDW
2 stops23h 44mDelta
Deal found 11/20$419
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:00 amMDW - GCM
1 stop5h 36mDelta
Thu 1/13:42 pmGCM - MDW
1 stop7h 40mDelta
Deal found 11/19$482
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/265:57 pmMDW - GCM
1 stop16h 38mMultiple Airlines
Sat 12/68:50 amGCM - MDW
1 stop14h 40mMultiple Airlines
Deal found 11/19$501
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/236:00 amMDW - GCM
1 stop5h 35mDelta
Thu 12/41:50 pmGCM - MDW
1 stop10h 57mDelta
Deal found 11/19$505
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:00 amMDW - GCM
1 stop5h 36mDelta
Mon 1/53:45 pmGCM - MDW
1 stop7h 22mDelta
Deal found 11/20$507

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 November 20, 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

Fri 12/12

6:00 am-12:35 pm

1 stop5h 35m

George Town Owen Roberts Intl

Fri 12/19

1:50 pm-11:47 pm

1 stop10h 57m

$354

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 12/7

6:00 am-12:35 pm

1 stop5h 35m

George Town Owen Roberts Intl

Wed 12/10

1:50 pm-11:47 pm

1 stop10h 57m

$354

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 4/19

1:00 pm-11:24 am

2 stops22h 24m

George Town Owen Roberts Intl

Thu 4/23

12:45 pm-9:45 pm

1 stop9h 00m

$359

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 4/19

5:59 pm-11:24 am

2 stops17h 25m

George Town Owen Roberts Intl

Fri 4/24

12:45 pm-9:45 pm

1 stop9h 00m

$359

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 1/7

5:10 pm-1:53 pm

2 stops19h 43m

George Town Owen Roberts Intl

Mon 1/12

7:00 am-2:06 pm

1 stop8h 06m

$384

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 4/17

6:00 am-11:24 am

1 stop5h 24m

George Town Owen Roberts Intl

Fri 4/24

12:45 pm-9:45 pm

1 stop9h 00m

$384

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 4/17

6:00 am-11:24 am

1 stop5h 24m

George Town Owen Roberts Intl

Wed 4/22

12:45 pm-9:45 pm

1 stop9h 00m

$384

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 1/25

6:00 am-12:40 pm

1 stop5h 40m

George Town Owen Roberts Intl

Thu 1/29

2:05 pm-10:22 pm

1 stop9h 17m

$386

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 1/6

1:28 pm-12:40 pm

2 stops22h 12m

George Town Owen Roberts Intl

Sat 1/10

3:25 pm-8:52 am

2 stops18h 27m

$389

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 1/6

6:14 pm-12:40 pm

2 stops17h 26m

George Town Owen Roberts Intl

Mon 1/12

2:05 pm-12:48 pm

2 stops23h 43m

$389

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

Showing 1-10 of 20 results
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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.

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.

  • How long is the flight from Chicago Midway Airport to Grand Cayman?

    Delta can get you from Chicago Midway Airport to Grand Cayman in just under 5h 35m. Your travel time can differ by up to . The distance between Chicago Midway Airport and Grand Cayman is about 1598 mi.

  • 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 $155 on Southwest. Other airlines that offer cheap prices include WestJet from $309 and Delta from $338 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.

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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