HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Grand Cayman

$125+ 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 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — GCM
Feb 11 — Feb 181
Wed 2/11
Wed 2/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Grand Cayman with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 January 12, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$384
(Kiwi.com)

One-way from

$152
(Southwest)

Popular in

December

Cheapest in

October

Average price

$575
Provider with most accurate pricing for Chicago (CHI)-George Town Owen Roberts Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-George Town Owen Roberts Intl flights.
Search Deals
From Chicago Midway to Grand Cayman
Search Deals
One-way flight from Chicago Midway to Grand Cayman
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 12, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/10. 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 2/116:15 amMDW - GCM
2 stops28h 20mMultiple Airlines
Thu 2/197:00 amGCM - MDW
1 stop7h 56mMultiple Airlines
Deal found 1/10$384
This Kiwi.com deal was found by Cheapflights users on 1/11. 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 3/166:00 amMDW - GCM
1 stop15h 15mMultiple Airlines
Sun 3/224:45 pmGCM - MDW
1 stop20h 56mMultiple Airlines
Deal found 1/11$397
This Southwest deal was found by Cheapflights users on 1/10. 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.
Tue 2/35:00 amMDW - GCM
1 stop6h 55mSouthwest
Wed 2/41:50 pmGCM - MDW
1 stop8h 10mSouthwest
Deal found 1/10$409
This Kiwi.com deal was found by Cheapflights users on 1/10. 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 2/126:15 amMDW - GCM
1 stop14h 00mMultiple Airlines
Thu 2/197:00 amGCM - MDW
1 stop7h 56mMultiple Airlines
Deal found 1/10$418
This Southwest deal was found by Cheapflights users on 1/10. 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 1/265:00 amMDW - GCM
1 stop6h 55mSouthwest
Wed 2/41:50 pmGCM - MDW
1 stop8h 10mSouthwest
Deal found 1/10$431
This Kiwi.com deal was found by Cheapflights users on 1/9. 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.
Fri 3/132:41 pmMDW - GCM
2 stops21h 39mMultiple Airlines
Thu 3/197:00 amGCM - MDW
1 stop6h 41mMultiple Airlines
Deal found 1/9$434
This Delta deal was found by Cheapflights users on 1/10. 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.
Mon 1/266:00 amMDW - GCM
1 stop5h 40mDelta
Wed 2/42:05 pmGCM - MDW
2 stops23h 41mDelta
Deal found 1/10$444
This Kiwi.com deal was found by Cheapflights users on 1/11. 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.
Sat 3/146:00 amMDW - GCM
2 stops8h 50mMultiple Airlines
Sun 3/224:45 pmGCM - MDW
1 stop20h 56mMultiple Airlines
Deal found 1/11$446
This Kiwi.com deal was found by Cheapflights users on 1/11. 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 3/236:00 amMDW - GCM
1 stop15h 15mMultiple Airlines
Sun 3/294:45 pmGCM - MDW
1 stop14h 55mMultiple Airlines
Deal found 1/11$450

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 January 12, 2026.
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

Tue 2/3

5:00 am-12:55 pm

1 stop6h 55m

George Town Owen Roberts Intl

Wed 2/4

1:50 pm-9:00 pm

1 stop8h 10m

$409

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 1/26

5:00 am-12:55 pm

1 stop6h 55m

George Town Owen Roberts Intl

Wed 2/4

1:50 pm-9:00 pm

1 stop8h 10m

$431

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 3/13

2:41 pm-12:20 pm

2 stops21h 39m

George Town Owen Roberts Intl

Thu 3/19

7:00 am-1:41 pm

1 stop6h 41m

$434

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 1/26

6:00 am-12:40 pm

1 stop5h 40m

George Town Owen Roberts Intl

Wed 2/4

2:05 pm-12:46 pm

2 stops23h 41m

$444

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 3/23

6:00 am-9:15 pm

1 stop15h 15m

George Town Owen Roberts Intl

Fri 3/27

4:45 pm-11:53 pm

1 stop7h 08m

$446

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 2/9

6:00 am-12:40 pm

1 stop5h 40m

George Town Owen Roberts Intl

Wed 2/18

1:54 pm-10:31 pm

1 stop9h 37m

$453

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 2/1

6:00 am-12:40 pm

1 stop5h 40m

George Town Owen Roberts Intl

Thu 2/5

2:05 pm-10:22 pm

1 stop9h 17m

$453

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 2/8

6:00 am-12:40 pm

1 stop5h 40m

George Town Owen Roberts Intl

Fri 2/13

1:54 pm-10:31 pm

1 stop9h 37m

$453

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 2/10

6:00 am-12:40 pm

1 stop5h 40m

George Town Owen Roberts Intl

Fri 2/13

1:54 pm-8:54 am

2 stops20h 00m

$458

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 2/18

6:00 am-12:29 pm

1 stop5h 29m

George Town Owen Roberts Intl

Sat 2/21

3:40 pm-10:31 pm

1 stop7h 51m

$483

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/12

Showing 1-10 of 18 results
1
2

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?

    Southwest can get you from Chicago Midway Airport to Grand Cayman in just under 6h 55m. Your travel time can differ by up to . The distance between Chicago Midway Airport and Grand Cayman is about 1598 mi.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.