$303 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 2/8. 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

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Everything you should know

Cheapest round-trip
$439
Southwest
Fri 2/13Wed 2/18
GCM - MDW • 1 stop
Cheapest one-way
$240
Multiple Airlines
Sun 2/8
GCM - MDW • 2 stops
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We hope you love your trip to Midway!
Flight Deals
Useful Info
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 round-trip flight deals from Grand Cayman to Midway

Fri, Feb 13 - Wed, Feb 18
Southwest Logo
1:50 pm - 7:15 pm
GCM
-
MDW
6h 25m
1 stop
Southwest Logo
5:00 am - 12:55 pm
MDW
-
GCM
6h 55m
1 stop
$439Southwest
Fri, Feb 13 - Wed, Feb 18
Delta Logo
1:54 pm - 10:31 pm
GCM
-
MDW
9h 37m
1 stop
Delta Logo
6:00 am - 12:29 pm
MDW
-
GCM
5h 29m
1 stop
$460Delta
Sat, Feb 14 - Wed, Feb 18
Southwest Logo
1:25 pm - 11:25 pm
GCM
-
MDW
11h 00m
1 stop
Southwest Logo
5:00 am - 12:55 pm
MDW
-
GCM
6h 55m
1 stop
$469Southwest
Fri, Feb 13 - Wed, Feb 18
Southwest Logo
1:50 pm - 9:40 pm
GCM
-
MDW
8h 50m
2 stops
Southwest Logo
5:00 am - 12:55 pm
MDW
-
GCM
6h 55m
1 stop
$474Southwest
Fri, Feb 13 - Wed, Feb 18
Southwest Logo
1:50 pm - 9:40 pm
GCM
-
MDW
8h 50m
2 stops
Southwest Logo
7:50 pm - 12:55 pm
MDW
-
GCM
16h 05m
2 stops
$512Southwest
Mon, Apr 27 - Thu, Apr 30
Delta Logo
1:25 pm - 10:28 pm
GCM
-
MDW
9h 03m
1 stop
Delta Logo
6:00 am - 12:00 pm
MDW
-
GCM
6h 00m
1 stop
$556Delta
Mon, Apr 27 - Thu, Apr 30
Southwest Logo
1:05 pm - 11:40 pm
GCM
-
MDW
10h 35m
1 stop
Southwest Logo
9:15 pm - 12:10 pm
MDW
-
GCM
14h 55m
2 stops
$564Southwest
Sat, Feb 14 - Wed, Feb 18
Southwest Logo
1:25 pm - 9:00 am
GCM
-
MDW
20h 35m
2 stops
Southwest Logo
4:10 pm - 12:55 pm
MDW
-
GCM
19h 45m
2 stops
$591Southwest
Mon, Apr 27 - Thu, Apr 30
Southwest Logo
1:05 pm - 10:20 pm
GCM
-
MDW
9h 15m
2 stops
Southwest Logo
9:15 pm - 12:10 pm
MDW
-
GCM
14h 55m
2 stops
$628Southwest
Sun, Mar 15 - Sun, Mar 22
Delta Logo
1:12 pm - 10:31 pm
GCM
-
MDW
9h 19m
1 stop
Delta Logo
6:00 am - 11:47 am
MDW
-
GCM
5h 47m
1 stop
$867Delta
Useful Info

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
Chesterton
Schererville
Munster
Porter
Monticello
Griffith
Saint John

Everything you need to know for your flight to Midway

Information on your arrival and departure airports

Chicago Midway Airport (MDW)