What is the cheapest airline that flies from Grand Cayman to Chicago Midway?

Southwest is the most popular carrier operating from Grand Cayman to Chicago Midway

How old do you have to be to fly from Grand Cayman to Chicago Midway Airport?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Grand Cayman to Chicago Midway Airport.

What documentation or ID do you need to fly to Chicago Midway Airport?

The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$270 Cheap Flights from Grand Cayman to Chicago Midway Airport in 2026

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Find the cheapest flights from Grand Cayman to Chicago

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

1:05 pm - 12:05 am

GCM

MDW

11h 00m

1 stop

5:35 am - 12:10 pm

MDW

GCM

6h 35m

1 stop

$422Southwest

Thu, Apr 23 - Mon, Apr 27

1:05 pm - 11:30 pm

GCM

MDW

10h 25m

2 stops

5:35 am - 12:10 pm

MDW

GCM

6h 35m

1 stop

$427Southwest

Thu, Apr 23 - Mon, Apr 27

1:05 pm - 10:45 pm

GCM

MDW

9h 40m

2 stops

6:25 pm - 12:10 pm

MDW

GCM

17h 45m

2 stops

$478Southwest

Thu, Apr 23 - Mon, Apr 27

1:05 pm - 12:05 am

GCM

MDW

11h 00m

1 stop

5:35 am - 12:10 pm

MDW

GCM

6h 35m

1 stop

$510Southwest

Mon, Apr 13 - Mon, Apr 20

1:05 pm - 10:45 pm

GCM

MDW

9h 40m

2 stops

5:35 am - 12:10 pm

MDW

GCM

6h 35m

1 stop

$515Southwest

Mon, Apr 13 - Mon, Apr 20

1:05 pm - 10:45 pm

GCM

MDW

9h 40m

2 stops

5:30 am - 12:10 pm

MDW

GCM

6h 40m

2 stops

$527Southwest

Mon, Apr 13 - Mon, Apr 20

11:50 am - 7:05 pm

GCM

MDW

7h 15m

1 stop

9:40 pm - 12:10 pm

MDW

GCM

14h 30m

2 stops

$558Southwest

Mon, Mar 30 - Mon, Apr 6

1:15 pm - 10:19 pm

GCM

MDW

33h 04m

2 stops

12:55 pm - 12:44 pm

MDW

GCM

23h 49m

1 stop

$570Multiple Airlines

Sat, Mar 28 - Sat, Apr 4

11:50 am - 12:05 am

GCM

MDW

12h 15m

2 stops

6:25 pm - 12:10 pm

MDW

GCM

17h 45m

2 stops

$598Southwest

Mon, Mar 30 - Mon, Apr 6

12:40 pm - 11:35 pm

GCM

MDW

10h 55m

2 stops

6:20 pm - 12:00 pm

MDW

GCM

17h 40m

2 stops

$652Southwest

Fri, Mar 27 - Sat, Apr 4

Delta flights from Grand Cayman to Chicago Midway Airport

Our best Delta deals on Grand Cayman to Chicago Midway Airport flight tickets

Delta

Apr 14

GCM1:25 pmGeorge Town Owen Roberts Intl

19h 22m

2 stops

MDW8:47 amChicago Midway

Apr 21

MDW6:00 amChicago Midway

6h 00m

1 stop

GCM12:00 pmGeorge Town Owen Roberts Intl

$510

Delta

Apr 14

GCM1:25 pmGeorge Town Owen Roberts Intl

19h 22m

2 stops

MDW8:47 amChicago Midway

Apr 23

MDW1:24 pmChicago Midway

22h 36m

2 stops

GCM12:00 pmGeorge Town Owen Roberts Intl

$540

Delta

Mar 30

GCM1:12 pmGeorge Town Owen Roberts Intl

9h 19m

1 stop

MDW10:31 pmChicago Midway

Apr 6

MDW6:00 amChicago Midway

5h 47m

1 stop

GCM11:47 amGeorge Town Owen Roberts Intl

$1,146

Southwest flights from Grand Cayman to Chicago Midway Airport

Our best Southwest deals on Grand Cayman to Chicago Midway Airport flight tickets

Southwest

Apr 23

GCM1:05 pmGeorge Town Owen Roberts Intl

11h 00m

1 stop

MDW12:05 amChicago Midway

Apr 27

MDW5:35 amChicago Midway

6h 35m

1 stop

GCM12:10 pmGeorge Town Owen Roberts Intl

$422

Southwest

Apr 23

GCM1:05 pmGeorge Town Owen Roberts Intl

10h 25m

2 stops

MDW11:30 pmChicago Midway

Apr 27

MDW5:35 amChicago Midway

6h 35m

1 stop

GCM12:10 pmGeorge Town Owen Roberts Intl

$427

Southwest

May 4

GCM1:05 pmGeorge Town Owen Roberts Intl

11h 00m

1 stop

MDW12:05 amChicago Midway

May 5

MDW6:00 amChicago Midway

6h 10m

1 stop

GCM12:10 pmGeorge Town Owen Roberts Intl

$459

momondo Fare Finder

Use the filters below to find and compare flights from Grand Cayman to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 4/23

1:05 pm-12:05 am

1 stop11h 00m

Chicago Midway

Mon 4/27

5:35 am-12:10 pm

1 stop6h 35m

$422

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 4/23

1:05 pm-11:30 pm

2 stops10h 25m

Chicago Midway

Mon 4/27

5:35 am-12:10 pm

1 stop6h 35m

$427

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 4/23

1:05 pm-10:45 pm

2 stops9h 40m

Chicago Midway

Mon 4/27

6:25 pm-12:10 pm

2 stops17h 45m

$478

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Mon 4/13

1:05 pm-12:05 am

1 stop11h 00m

Chicago Midway

Mon 4/20

5:35 am-12:10 pm

1 stop6h 35m

$510

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Mon 4/13

1:05 pm-10:45 pm

2 stops9h 40m

Chicago Midway

Mon 4/20

5:35 am-12:10 pm

1 stop6h 35m

$515

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Mon 4/13

1:05 pm-10:45 pm

2 stops9h 40m

Chicago Midway

Mon 4/20

5:30 am-12:10 pm

2 stops6h 40m

$527

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Mon 3/30

11:50 am-7:05 pm

1 stop7h 15m

Chicago Midway

Mon 4/6

9:40 pm-12:10 pm

2 stops14h 30m

$558

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 3/28

1:15 pm-10:19 pm

2 stops33h 04m

Chicago Midway

Sat 4/4

12:55 pm-12:44 pm

1 stop23h 49m

$570

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Mon 3/30

11:50 am-12:05 am

2 stops12h 15m

Chicago Midway

Mon 4/6

6:25 pm-12:10 pm

2 stops17h 45m

$598

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 3/27

12:40 pm-11:35 pm

2 stops10h 55m

Chicago Midway

Sat 4/4

6:20 pm-12:00 pm

2 stops17h 40m

$652

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Grand Cayman to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Can stopping save me money on Grand Cayman to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Grand Cayman to Chicago Midway Airport.

Cheap Grand Cayman to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Grand Cayman to Chicago Midway Airport

Fastest flight time	7h 56m
Direct flights	None

The fastest flight from Grand Cayman to Chicago Midway Airport takes 7h 56m

There are no direct flights from Grand Cayman to Chicago Midway Airport. There are no popular flight routes from Grand Cayman to Chicago Midway Airport.

Search flight deals

When did momondo last update prices for flights from Grand Cayman to Chicago Midway Airport?
Prices for flights from Grand Cayman to Chicago Midway Airport refresh daily.
How old do you have to be to fly from Grand Cayman to Chicago Midway Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Grand Cayman to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Grand Cayman to Chicago Midway Airport?
momondo data reveals that the most frequently booked plane model on the route from Grand Cayman to Chicago Midway Airport is Boeing 737 MAX 8, representing 16.46% of all bookings. The subsequent popular models are Boeing 737-800 at 10.71%, Boeing 737-800 Passenger/BBJ2 (winglets) at 10.50%, and Airbus A321neo at 8.36%.

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Chesterton

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Why use momondo?

Why should I use momondo to find a flight deal from Grand Cayman to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Grand Cayman to Chicago for you.

Can I find flights from Grand Cayman to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Grand Cayman on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Grand Cayman to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Grand Cayman. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Grand Cayman to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Grand Cayman to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.