$295 Find Cheap Flights from Grand Cayman to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 12/3. 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

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Flight Deals

Cheap Flights from Grand Cayman to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Grand Cayman to Midway 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 one-way flight deals from Grand Cayman to Midway

Wed, Dec 3
Southwest Logo
1:30 pm - 8:40 pmGCM-MDW
8h 10m1 stop
$295Southwest
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Wed, Dec 3
Southwest Logo
1:30 pm - 10:35 pmGCM-MDW
10h 05m2 stops
$299Southwest
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Wed, Dec 3
Multiple Airlines Logo
11:30 am - 1:01 pmGCM-MDW
26h 31m3 stops
$334Multiple Airlines
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Sun, Jan 4
Multiple Airlines Logo
2:40 pm - 10:15 pmGCM-MDW
56h 35m3 stops
$565Multiple Airlines
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Sun, Jan 4
Multiple Airlines Logo
7:00 am - 1:21 pmGCM-MDW
31h 21m2 stops
$566Multiple Airlines
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Fri, Jan 2
Multiple Airlines Logo
7:00 am - 1:21 pmGCM-MDW
31h 21m2 stops
$649Multiple Airlines
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Sat, Jan 3
Multiple Airlines Logo
5:56 pm - 1:21 pmGCM-MDW
44h 25m2 stops
$693Multiple Airlines
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Fri, Jan 2
Multiple Airlines Logo
5:35 pm - 1:01 pmGCM-MDW
44h 26m3 stops
$751Multiple Airlines
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Sat, Jan 3
Southwest Logo
4:10 pm - 11:20 pmGCM-MDW
8h 10m1 stop
$1,058Southwest
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Sun, Jan 4
Delta Logo
3:42 pm - 10:22 pmGCM-MDW
7h 40m1 stop
$1,088Delta
Find Deal

Everything you should know

Cheapest one-way
$295
Southwest
Wed 12/3
GCM - MDW • 1 stop
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FAQs for booking Grand Cayman to Chicago Midway Airport flights

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

    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 Grand Cayman to Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from 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 Grand Cayman to Chicago Midway Airport?

    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 to Chicago Midway Airport with an airline and back to Grand Cayman with another airline.

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

    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 to Chicago Midway Airport from Grand Cayman up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Traveling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Munster
Chesterton
Schererville
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Midway

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

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