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Cheap flights from Midway (MDW) to Grand Cayman from $163

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 6/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
MDW — GCM
May 1 — May 81
From?
To?
Wed 5/1
Wed 5/8
1 adult, Economy
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How far in advance should I book a flight from Chicago Midway Airport to Grand Cayman?

To save up to 50% on this flight, we recommend booking at least 34 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Chicago Midway Airport to Grand Cayman from $655 1-2 weeks out and tickets from $655 for flights departing within the next 72 hours.

What is the cheapest month to fly from Chicago Midway Airport to Grand Cayman?

The best pricing can be found in the month of January. Prices to Grand Cayman from Chicago Midway Airport average $629. You can even find prices in January for less than $629, as users have found deals to Grand Cayman from as low as $230. The month of December appears to be one of the more expensive times to travel to Grand Cayman from Chicago Midway Airport. Flying in the targeted month can save you up to 41%.

When is the cheapest time to fly from Chicago Midway Airport to Grand Cayman (MDW - LAW)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Grand Cayman as you normally would.

Cheap Delta flights from Midway to Grand Cayman

Explore cheap flight options specifically provided by Delta for the route between Midway and Grand Cayman. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 3,068,117 searches. Data last updated April 26, 2024.
Peruse some of the lowest-priced Delta flights we've found from Chicago to Grand Cayman. It's recommended that users confirm their flight details before booking.
Sun 7/76:49 pmMDW - GCM
1 stop16h 41mDelta
Tue 7/1612:50 pmGCM - MDW
1 stop8h 51mDelta
Deal found 4/25$578
Mon 7/81:24 pmMDW - GCM
2 stops22h 06mDelta
Tue 7/1612:50 pmGCM - MDW
2 stops19h 50mDelta
Deal found 4/25$583
Fri 7/56:00 amMDW - GCM
1 stop5h 35mDelta
Thu 7/1112:50 pmGCM - MDW
1 stop8h 51mDelta
Deal found 4/25$603
Thu 7/49:29 amMDW - GCM
2 stops26h 06mDelta
Thu 7/1112:50 pmGCM - MDW
1 stop8h 51mDelta
Deal found 4/25$608
Thu 5/306:00 amMDW - GCM
1 stop5h 26mDelta
Mon 6/312:51 pmGCM - MDW
1 stop9h 10mDelta
Deal found 4/25$628
Tue 7/96:00 amMDW - GCM
1 stop5h 30mDelta
Wed 7/1012:50 pmGCM - MDW
1 stop8h 51mDelta
Deal found 4/25$658
Fri 7/56:00 amMDW - GCM
1 stop5h 35mDelta
Fri 7/1212:50 pmGCM - MDW
2 stops19h 50mDelta
Deal found 4/25$708
Sun 9/86:00 amMDW - GCM
1 stop5h 30mDelta
Sun 9/1512:50 pmGCM - MDW
2 stops19h 55mDelta
Deal found 4/24$712
Sun 7/216:00 amMDW - GCM
1 stop5h 30mDelta
Sat 7/2712:50 pmGCM - MDW
2 stops19h 50mDelta
Deal found 4/25$778

Cheap WestJet flights from Midway to Grand Cayman

Explore cheap flight options specifically provided by WestJet for the route between Midway and Grand Cayman. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 3,068,117 searches. Data last updated April 26, 2024.
Have a look at some of the cheapest available WestJet flights departing from Chicago and landing in Grand Cayman. Check back soon if you're not seeing flights that suit your needs.
Sat 6/2212:07 pmMDW - GCM
2 stops24h 32mWestJet
Sat 6/291:45 pmGCM - MDW
2 stops21h 42mWestJet
Deal found 4/25$2,951
Sat 6/2912:07 pmMDW - GCM
2 stops24h 32mWestJet
Sat 7/61:45 pmGCM - MDW
2 stops23h 59mWestJet
Deal found 4/25$2,969
Mon 6/242:24 pmMDW - GCM
2 stops22h 15mWestJet
Sun 6/301:45 pmGCM - MDW
2 stops21h 43mWestJet
Deal found 4/25$3,047
Sun 7/217:06 pmMDW - GCM
2 stops41h 33mWestJet
Sat 7/271:45 pmGCM - MDW
2 stops31h 56mWestJet
Deal found 4/25$3,059

Cheap Midway to Grand Cayman flights in April & May 2024

Find cheap flight options from Midway to Grand Cayman specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,068,117 searches. Prices were last updated on April 26, 2024.
These are some of the most attractive deals on flights from Chicago to Grand Cayman in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Fri 5/317:23 pmMDW - GCM
1 stop20h 47mMultiple Airlines
Fri 6/711:05 amGCM - MDW
1 stop12h 32mMultiple Airlines
Deal found 4/24$538
Sat 5/185:45 pmMDW - GCM
1 stop22h 25mMultiple Airlines
Sat 5/2511:30 amGCM - MDW
1 stop12h 39mMultiple Airlines
Deal found 4/24$556
Fri 5/3112:04 pmMDW - GCM
2 stops9h 16mMultiple Airlines
Fri 6/74:45 pmGCM - MDW
1 stop15h 51mMultiple Airlines
Deal found 4/24$570
Thu 5/306:00 amMDW - GCM
1 stop5h 26mDelta
Mon 6/312:51 pmGCM - MDW
1 stop9h 10mDelta
Deal found 4/25$628
Thu 5/235:01 amMDW - GCM
2 stops40h 19mMultiple Airlines
Mon 5/279:30 amGCM - MDW
1 stop8h 57mMultiple Airlines
Deal found 4/25$630
Fri 5/247:23 pmMDW - GCM
2 stops19h 27mMultiple Airlines
Fri 5/317:00 amGCM - MDW
1 stop11h 27mMultiple Airlines
Deal found 4/24$651
Fri 5/1010:37 amMDW - GCM
1 stop29h 33mMultiple Airlines
Sun 5/1211:30 amGCM - MDW
1 stop10h 39mMultiple Airlines
Deal found 4/26$708
Fri 5/104:51 pmMDW - GCM
2 stops23h 19mMultiple Airlines
Sun 5/1211:30 amGCM - MDW
1 stop10h 39mMultiple Airlines
Deal found 4/26$712
Thu 5/236:22 pmMDW - GCM
1 stop21h 23mMultiple Airlines
Mon 5/279:30 amGCM - MDW
1 stop8h 57mMultiple Airlines
Deal found 4/25$765

Midway to Grand Cayman 2024 flight deals

Discover exclusive flight deals for travel between Midway and Grand Cayman in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,068,117 searches. Data last updated April 26, 2024.
These are some of the most attractive deals on flights from Chicago to Grand Cayman in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Sat 8/108:13 pmMDW - GCM
1 stop22h 27mMultiple Airlines
Wed 8/1411:30 amGCM - MDW
1 stop7h 48mMultiple Airlines
Deal found 4/24$483
Sat 9/217:48 amMDW - GCM
1 stop8h 22mMultiple Airlines
Fri 9/277:00 amGCM - MDW
1 stop12h 18mMultiple Airlines
Deal found 4/25$517
Mon 7/88:13 pmMDW - GCM
1 stop19h 57mMultiple Airlines
Sat 7/1311:30 amGCM - MDW
1 stop7h 48mMultiple Airlines
Deal found 4/25$536
Sun 7/78:13 pmMDW - GCM
1 stop19h 57mMultiple Airlines
Sat 7/1311:30 amGCM - MDW
1 stop7h 48mMultiple Airlines
Deal found 4/25$537
Fri 5/317:23 pmMDW - GCM
1 stop20h 47mMultiple Airlines
Fri 6/711:05 amGCM - MDW
1 stop12h 32mMultiple Airlines
Deal found 4/24$538
Mon 7/88:13 pmMDW - GCM
1 stop19h 57mMultiple Airlines
Wed 7/1011:30 amGCM - MDW
1 stop7h 48mMultiple Airlines
Deal found 4/25$541
Sun 7/78:13 pmMDW - GCM
1 stop19h 57mMultiple Airlines
Wed 7/1011:30 amGCM - MDW
1 stop7h 48mMultiple Airlines
Deal found 4/25$542
Sat 6/299:31 amMDW - GCM
1 stop6h 39mMultiple Airlines
Sat 7/69:10 amGCM - MDW
1 stop10h 08mMultiple Airlines
Deal found 4/25$543
Sat 6/299:31 amMDW - GCM
1 stop6h 39mMultiple Airlines
Sat 7/69:10 amGCM - MDW
1 stop10h 08mMultiple Airlines
Deal found 4/25$544

One-way flights to Grand Cayman from Midway

Search for one-way flight options from Midway to Grand Cayman. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,068,117 searches. Data last updated April 26, 2024.
Some of the best available deals we've found on one-way flights from Chicago to Grand Cayman. Users needing a return flight from Chicago to Grand Cayman should utilize the search form above.
Wed 6/58:27 amMDW - GCM
1 stop7h 43mMultiple Airlines
Deal found 4/25$163
Wed 6/51:43 pmMDW - GCM
2 stops28h 57mMultiple Airlines
Deal found 4/25$256
Wed 6/58:50 pmMDW - GCM
3 stops24h 30mMultiple Airlines
Deal found 4/24$542

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 3,068,117 searches. Data last updated April 26, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$483 - $608

Route

Depart

Return

Price

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Sat 8/10

1 stop22h 27m

George Town Owen Roberts Intl

Wed 8/14

1 stop7h 48m

$483

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Sat 9/21

1 stop8h 22m

George Town Owen Roberts Intl

Fri 9/27

1 stop12h 18m

$517

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Mon 7/8

1 stop19h 57m

George Town Owen Roberts Intl

Sat 7/13

1 stop7h 48m

$536

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Sun 7/7

1 stop19h 57m

George Town Owen Roberts Intl

Sat 7/13

1 stop7h 48m

$537

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Fri 5/31

1 stop20h 47m

George Town Owen Roberts Intl

Fri 6/7

1 stop12h 32m

$538

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Sun 7/7

1 stop16h 41m

George Town Owen Roberts Intl

Tue 7/16

1 stop8h 51m

$578

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Mon 7/8

2 stops22h 06m

George Town Owen Roberts Intl

Tue 7/16

2 stops19h 50m

$583

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Fri 7/5

1 stop5h 35m

George Town Owen Roberts Intl

Thu 7/11

1 stop8h 51m

$603

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Thu 7/4

2 stops26h 06m

George Town Owen Roberts Intl

Thu 7/11

1 stop8h 51m

$608

Flights are sorted by cheapest first

Deals found on 4/24

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 April 26, 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.
Delta
8.1
Very good
10,966 reviews
Check prices

Comfort

7.9

Entertainment

8.0

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.4

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

Delta
8.1
Very good
10,966 reviews
Delta
8.1
Very good
10,966 reviews
Check prices

Comfort

7.9

Entertainment

8.0

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.4

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

WestJet
7.5
Good
2,985 reviews
Delta
8.1
Very good
10,966 reviews
Check prices

Comfort

7.9

Entertainment

8.0

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.4

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

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 flights from Chicago Midway Airport to Grand Cayman for under $500 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to Grand Cayman for under $500. The cheapest flight booked recently is on Multiple Airlines for just $483, but on average you can expect to pay $555.

  • What does MDW to GCM mean?

    MDW and GCM are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. MDW to GCM refers to a flight route from Chicago Midway Airport to George Town Owen Roberts Intl Airport.

  • Can I find deals for flights from Midway to Grand Cayman that include extra baggage allowance?

    The amount of baggage you can bring on your Midway to Grand Cayman flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Midway to Grand Cayman with specific airlines?

    Yes, Cheapflights allows you to browse and filter Midway to Grand Cayman flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Midway to Grand Cayman that allow pets onboard?

    Many airlines flying from Midway to Grand Cayman offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Midway to Grand Cayman?

    Yes, you can often find last-minute deals on Midway to Grand Cayman flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago Midway Airport to Grand Cayman flight deals updated?

    The Chicago Midway Airport to Grand Cayman flight deals you see on this page were last updated on 4/25.

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
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 3,068,117 searches. Data last updated April 26, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$408Average$635FlexibilityNo cancel feeOn-timeN/A
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Search flights from Midway to Grand Cayman by cabin class

Find flights from Midway to Grand Cayman, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Midway to Grand Cayman?

When you search for this flight from Midway to Grand Cayman, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Midway to Grand Cayman?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Grand Cayman from Midway.

Can Cheapflights find flights from Midway to Grand Cayman with no change fees?

Yes, we can. To see specific flights from Midway to Grand Cayman with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Midway to Grand Cayman become cheaper?

Yes! Start tracking prices for Midway to Grand Cayman flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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