$214 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 10/29. 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

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

Sun, Jan 4 - Fri, Jan 16
Delta Logo
6:00 am - 12:37 pmMDW-GCM
5h 37m1 stop
Delta Logo
2:00 pm - 9:46 pmGCM-MDW
8h 46m1 stop
$340Delta
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Sun, Jan 4 - Tue, Jan 13
Delta Logo
6:08 pm - 2:20 pmMDW-GCM
19h 12m2 stops
Delta Logo
2:00 pm - 12:35 pmGCM-MDW
23h 35m2 stops
$345Delta
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Wed, Nov 26 - Thu, Dec 4
Delta Logo
9:34 am - 12:35 pmMDW-GCM
26h 01m2 stops
Delta Logo
1:50 pm - 11:49 pmGCM-MDW
10h 59m1 stop
$357Delta
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Tue, Jan 6 - Sat, Jan 17
Delta Logo
6:00 am - 12:35 pmMDW-GCM
5h 35m1 stop
Delta Logo
3:07 pm - 9:46 pmGCM-MDW
7h 39m1 stop
$365Delta
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Sun, Jan 4 - Sun, Jan 11
Delta Logo
6:08 pm - 12:30 pmMDW-GCM
17h 22m2 stops
Delta Logo
2:00 pm - 12:35 pmGCM-MDW
23h 35m2 stops
$370Delta
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Thu, Nov 27 - Wed, Dec 3
Delta Logo
6:00 am - 12:35 pmMDW-GCM
5h 35m1 stop
Delta Logo
1:50 pm - 11:49 pmGCM-MDW
10h 59m1 stop
$377Delta
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Wed, Jan 7 - Wed, Jan 14
Southwest Logo
5:00 am - 12:55 pmMDW-GCM
6h 55m1 stop
Southwest Logo
1:50 pm - 10:05 pmGCM-MDW
9h 15m2 stops
$409Southwest
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Wed, Dec 3 - Tue, Dec 9
Southwest Logo
5:05 am - 12:35 pmMDW-GCM
6h 30m1 stop
Southwest Logo
1:30 pm - 8:40 pmGCM-MDW
8h 10m1 stop
$418Southwest
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Wed, Dec 3 - Tue, Dec 9
Southwest Logo
5:05 am - 12:35 pmMDW-GCM
6h 30m1 stop
Southwest Logo
1:30 pm - 5:05 amGCM-MDW
16h 35m2 stops
$423Southwest
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Tue, Oct 28 - Mon, Nov 3
Multiple Airlines Logo
5:56 pm - 11:35 amMDW-GCM
41h 39m2 stops
Multiple Airlines Logo
12:40 pm - 12:30 amGCM-MDW
12h 50m1 stop
$528Multiple Airlines
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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 $344, prices are generally cheapest when you fly direct.

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Good to know

Cheapest flight$226
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)

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