Find Cheap Flights from Chicago to Grand Cayman (CHI - GCM)

Flights overview

Useful information for finding cheap flights from Chicago to Grand Cayman and booking your next trip

Cheapest round-trip flights	$411	Air Canada 1 stop 14 hr Fri, Jun 5 — Thu, Jun 11	The cheapest round-trip flight from Chicago to Grand Cayman is currently $411
Cheapest one-way flight	$156	Air Canada 1 stop 26 hr Wed, Jun 3	The cheapest one-way flight from Chicago to Grand Cayman is currently $156
Cheapest nonstop flights	$667	United Nonstop 5 hr Sat, Aug 1 — Sat, Aug 8	The cheapest nonstop round-trip flight from Chicago to Grand Cayman is currently $667
Last-minute weekend getaway	$620	Air Canada 1 stop 14 hr Fri, May 8 — Sun, May 10	The cheapest last-minute weekend getaway from Chicago to Grand Cayman is currently $620
Cheapest business class flights	$1,186	American 1 stop 7 hr Fri, Jul 31 — Thu, Aug 6	The cheapest business class round-trip flight from Chicago to Grand Cayman is currently $1,186

Fastest flight	4 hr 1 min	The fastest nonstop flight from Chicago to Grand Cayman takes 4 hr 1 min
Nonstop flights	Some days	There are direct flights on this route 1 days a week: Sat.

When is the cheapest time to fly?

The cheapest month to fly from Chicago to Grand Cayman is typically January. The most expensive month to fly is typically June.

January Cheapest	Typical prices: $295–470
June Most expensive	Typical prices: $570–760

Popular airlines from Chicago to Grand Cayman

Southwest

from $579

Typical price: $520–1,050

855 weekly connecting flights

MDW, ORD - GCM Every day
American

from $636

Typical price: $475–860

379 weekly connecting flights

ORD - GCM Every day
Delta

from $607

Typical price: $520–1,300

162 weekly connecting flights

MDW, ORD - GCM Every day
United

Nonstop

from $642

Typical price: $475–930

1 weekly nonstop flight

ORD - GCM Every Sat

48 weekly connecting flights

ORD - GCM Every day
Air Canada

from $411

Typical price: $430–1,450

11 weekly connecting flights

ORD - GCM Every Tue, Wed, Thu, Fri, Sat, Sun
JetBlue

Typical price: $480–2,350

1 weekly connecting flight

ORD - GCM Every Fri

Popular airports near Chicago

Chicago O'Hare International Airport (ORD)

Chicago United States 26 min 16 mi
Chicago Midway International Airport (MDW)

Chicago United States 25 min 9 mi
Milwaukee Mitchell International Airport (MKE)

Milwaukee United States 1 hr 23 min 75 mi
Indianapolis International Airport (IND)

Indianapolis United States 2 hr 58 min 165 mi

Popular airports near Grand Cayman

Owen Roberts International Airport (GCM)

Grand Cayman Cayman Islands 24 min 7 mi

Frequently asked questions about flying from Chicago to Grand Cayman

The cheapest flights from Chicago to Grand Cayman are usually in January. Typical ticket prices in January range from $295 to $470.

The cheapest round-trip flight from Chicago to Grand Cayman recently found on Google Flights was with Air Canada from $411. The cheapest one-way flight was with Air Canada from $156.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest Southwest flight from Chicago to Grand Cayman is $579, flying from Jul 20 to Jul 29.
The cheapest American flight from Chicago to Grand Cayman is $636, flying from Jun 14 to Jun 23.
The cheapest Delta flight from Chicago to Grand Cayman is $607, flying from Jul 5 to Jul 14.
The cheapest United flight from Chicago to Grand Cayman is $642, flying from Aug 1 to Aug 7.
The cheapest Air Canada flight from Chicago to Grand Cayman is $411, flying from Jun 5 to Jun 11.

The cheapest round-trip flight from Chicago to Grand Cayman starts at $411 from Fri, Jun 5 to Thu, Jun 11. The cheapest one-way flight starts at $156 and departs on Wed, Jun 3.

4 hr 1 min is the shortest flight time from Chicago to Grand Cayman.

Peak travel is Dec–Apr. The weather is warm and tropical year-round, with a rainy season May–Nov and hurricane season Jun–Nov. Top annual events include Cayfest (Feb), celebrating local artists and performers, and the long-running Cayman Islands Pirates Week Festival (Nov), featuring street parties, parades, fireworks and local food and drink.

It's easy to use Google Flights to find the cheapest days to fly from Chicago to Grand Cayman.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.

What counts as the best airline for your flights from Chicago to Grand Cayman really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Chicago to Grand Cayman.

In terms of nonstop flights, United is the most popular. United offers 1 nonstop flights and 48 connecting flights per week. United flies from Chicago O'Hare International Airport (ORD) to Owen Roberts International Airport (GCM) .

In terms of flights, Southwest is the most popular. Southwest offers 855 connecting flights per week. Southwest flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Owen Roberts International Airport (GCM) .

Other popular airlines flying from Chicago to Grand Cayman are:

American offers 379 connecting flights per week. American flies from Chicago O'Hare International Airport (ORD) to Owen Roberts International Airport (GCM) .
Delta offers 162 connecting flights per week. Delta flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Owen Roberts International Airport (GCM) .
Air Canada offers 11 connecting flights per week. Air Canada flies from Chicago O'Hare International Airport (ORD) to Owen Roberts International Airport (GCM) .
JetBlue offers 1 connecting flights per week. JetBlue flies from Chicago O'Hare International Airport (ORD) to Owen Roberts International Airport (GCM) .

The number of connecting flights refers to distinct flights with at least one stop between Chicago and Grand Cayman.

The cheapest round-trip flight from Chicago to Grand Cayman recently found on Google Flights was with Air Canada from $411. The cheapest one-way flight was with Air Canada from $156.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest Southwest flight from Chicago to Grand Cayman is $579, flying from Jul 20 to Jul 29.
The cheapest American flight from Chicago to Grand Cayman is $636, flying from Jun 14 to Jun 23.
The cheapest Delta flight from Chicago to Grand Cayman is $607, flying from Jul 5 to Jul 14.
The cheapest United flight from Chicago to Grand Cayman is $642, flying from Aug 1 to Aug 7.
The cheapest Air Canada flight from Chicago to Grand Cayman is $411, flying from Jun 5 to Jun 11.

United flies direct from Chicago to Grand Cayman.

There are 1 United direct flights from Chicago to Grand Cayman per week. Flights are available on Saturday.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

The cheapest last-minute deal between Chicago and Grand Cayman at price $620 is offered by Air Canada from Fri, May 8 to Sun, May 10.

United flies direct from Chicago to Grand Cayman.

There are 1 United direct flights from Chicago to Grand Cayman per week. Flights are available on Saturday.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

Direct flights from Chicago to Grand Cayman are only available on Saturday.

The cheapest direct (nonstop) round-trip flights between Chicago and Grand Cayman start at $667 from Sat, Aug 1 to Sat, Aug 8 with United.

It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Chicago to Grand Cayman, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.

The cheapest business class round-trip flights between Chicago and Grand Cayman start at $1,186 from Fri, Jul 31 to Thu, Aug 6 with American.

The cheapest economy class round-trip flights between Chicago and Grand Cayman start at $411 from Fri, Jun 5 to Thu, Jun 11.

To book business class trips from Chicago to Grand Cayman, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.

The best last-minute getaway deal for the next weekend between Chicago and Grand Cayman starts at $620 from Fri, May 8 to Sun, May 10 with Air Canada.

The cheapest last-minute deal between Chicago and Grand Cayman at price $620 is offered by Air Canada from Fri, May 8 to Sun, May 10.

To find last-minute flight deals from Chicago to Grand Cayman, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.