$153 Find Cheap Flights from Chicago Midway Airport to Grand Cayman

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Grand Cayman departing on 12/15. 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.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Grand Cayman

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Grand Cayman, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Grand Cayman, as well as popular online travel agencies
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Flight Deals

Book Cheap Midway to Grand Cayman Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Grand Cayman that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Grand Cayman

ح, فبراير 15 - ح, فبراير 22
Multiple Airlines Logo
6:30 am - 11:35 amMDW-GCM
28h 05m1 stop
Multiple Airlines Logo
2:40 pm - 11:25 pmGCM-MDW
9h 45m2 stops
$376Multiple Airlines
Find Deal
ن, ديسمبر 15 - ر, يناير 14
Southwest Logo
5:05 am - 12:35 pmMDW-GCM
6h 30m1 stop
Southwest Logo
1:50 pm - 9:00 pmGCM-MDW
8h 10m1 stop
$429Southwest
Find Deal
ن, ديسمبر 15 - ر, يناير 14
Southwest Logo
5:05 am - 12:35 pmMDW-GCM
6h 30m1 stop
Southwest Logo
1:50 pm - 10:05 pmGCM-MDW
9h 15m2 stops
$434Southwest
Find Deal
خ, يناير 29 - ث, فبراير 3
Southwest Logo
5:00 am - 12:55 pmMDW-GCM
6h 55m1 stop
Southwest Logo
1:50 pm - 9:00 pmGCM-MDW
8h 10m1 stop
$446Southwest
Find Deal
خ, مارس 5 - ح, مارس 8
Multiple Airlines Logo
6:30 am - 9:15 pmMDW-GCM
13h 45m1 stop
Multiple Airlines Logo
4:45 pm - 3:33 pmGCM-MDW
22h 48m1 stop
$450Multiple Airlines
Find Deal
خ, يناير 29 - ر, فبراير 4
Southwest Logo
7:50 pm - 12:55 pmMDW-GCM
16h 05m2 stops
Southwest Logo
1:50 pm - 10:05 pmGCM-MDW
9h 15m2 stops
$451Southwest
Find Deal
ر, ديسمبر 24 - ر, ديسمبر 31
Delta Logo
6:00 am - 12:36 pmMDW-GCM
5h 36m1 stop
Delta Logo
1:52 pm - 10:22 pmGCM-MDW
9h 30m1 stop
$452Delta
Find Deal
ح, فبراير 15 - ح, فبراير 22
Multiple Airlines Logo
6:30 am - 11:35 amMDW-GCM
28h 05m1 stop
Multiple Airlines Logo
7:00 am - 2:05 pmGCM-MDW
8h 05m1 stop
$455Multiple Airlines
Find Deal
ح, يناير 25 - خ, يناير 29
Delta Logo
1:26 pm - 12:40 pmMDW-GCM
22h 14m2 stops
Delta Logo
2:05 pm - 8:52 amGCM-MDW
19h 47m2 stops
$457Delta
Find Deal
س, مايو 2 - ر, مايو 6
Southwest Logo
9:20 am - 2:40 pmMDW-GCM
5h 20m1 stop
Southwest Logo
1:05 pm - 9:25 pmGCM-MDW
8h 20m1 stop
$459Southwest
Find Deal
Booking Insights

KAYAK's insights & trends for Midway to Grand Cayman flights

Get data-powered insights and trends into flights from Midway to Grand Cayman to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Chicago Midway Airport to Grand Cayman?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $400, prices are generally cheapest when you fly direct.

Find deals

Good to know

Cheapest flight$153
Flight from Chicago Midway Airport to George Town

FAQs - booking Grand Cayman flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Grand Cayman?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Grand Cayman.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Grand Cayman?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to Grand Cayman is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Grand Cayman?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago Midway Airport to Grand Cayman with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Grand Cayman?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago Midway Airport to Grand Cayman up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Grand Cayman?

    The cheapest time of day to fly to Grand Cayman is generally in the morning, when round-trip flights cost $615 on average. The most expensive time of day to fly to Grand Cayman is generally in the morning, which is peak travel time and where the average cost of a ticket is $615.

Everything you need to know for your flight to Grand Cayman

Information on your arrival and departure airports

Chicago Midway Airport (MDW)