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

Flights overview

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

Cheapest round-trip flights	$366	Air Canada 1 stop 21 hr Thu, Jun 11 — Wed, Jun 17	The cheapest round-trip flight from Grand Cayman to Chicago is currently $366
Cheapest one-way flight	$233	Air Canada 1 stop 25 hr Thu, Jun 11	The cheapest one-way flight from Grand Cayman to Chicago is currently $233
Cheapest nonstop flights	$651	United Nonstop 5 hr Sat, May 16 — Sat, May 23	The cheapest nonstop round-trip flight from Grand Cayman to Chicago is currently $651
Last-minute weekend getaway	$315	United 1 stop 18 hr Sat, Apr 25 — Sun, Apr 26	The cheapest last-minute weekend getaway from Grand Cayman to Chicago is currently $315
Cheapest business class flights	$1,125	American 1 stop 16 hr Fri, Jul 17 — Sun, Jul 26	The cheapest business class round-trip flight from Grand Cayman to Chicago is currently $1,125

Fastest flight	4 hr 23 min	The fastest nonstop flight from Grand Cayman to Chicago takes 4 hr 23 min
Nonstop flights	Some days	There are direct flights on this route 4 days a week: Mon, Tue, Wed, Sat.

When is the cheapest time to fly?

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

January Cheapest	Typical prices: $290–620
June Most expensive	Typical prices: $570–740

Popular airlines from Grand Cayman to Chicago

Southwest

from $579

Typical price: $530–960

728 weekly connecting flights

GCM - MDW, ORD Every day
United

Nonstop

from $631

Typical price: $470–900

7 weekly nonstop flights

GCM - ORD Every day

98 weekly connecting flights

GCM - ORD Every day
American

from $606

Typical price: $465–840

331 weekly connecting flights

GCM - ORD Every day
Delta

from $472

Typical price: $520–1,250

167 weekly connecting flights

GCM - MDW, ORD Every day
JetBlue

Typical price: $490–1,650

9 weekly connecting flights

GCM - ORD Every day
Air Canada

from $366

Typical price: $460–1,750

7 weekly connecting flights

GCM - ORD Every Mon, Thu, Fri, Sun

Popular airports near Grand Cayman

Owen Roberts International Airport (GCM)

Grand Cayman Cayman Islands 24 min 7 mi

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

Frequently asked questions about flying from Grand Cayman to Chicago

The cheapest flights from Grand Cayman to Chicago are usually in January. Typical ticket prices in January range from $290 to $620.

The cheapest round-trip flight from Grand Cayman to Chicago recently found on Google Flights was with Air Canada from $366. The cheapest one-way flight was with Air Canada from $233.

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

The cheapest Southwest flight from Grand Cayman to Chicago is $579, flying from May 28 to Jun 3.
The cheapest United flight from Grand Cayman to Chicago is $631, flying from Jul 18 to Jul 26.
The cheapest American flight from Grand Cayman to Chicago is $606, flying from May 28 to Jun 6.
The cheapest Delta flight from Grand Cayman to Chicago is $472, flying from Jul 16 to Jul 22.
The cheapest Air Canada flight from Grand Cayman to Chicago is $366, flying from Jun 11 to Jun 17.

The cheapest round-trip flight from Grand Cayman to Chicago starts at $366 from Thu, Jun 11 to Wed, Jun 17. The cheapest one-way flight starts at $233 and departs on Thu, Jun 11.

4 hr 23 min is the shortest flight time from Grand Cayman to Chicago.

Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.

It's easy to use Google Flights to find the cheapest days to fly from Grand Cayman to Chicago.
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 Grand Cayman to Chicago 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 Grand Cayman to Chicago.

In terms of nonstop flights, United is the most popular. United offers 7 nonstop flights and 98 connecting flights per week. United flies from Owen Roberts International Airport (GCM) to Chicago O'Hare International Airport (ORD) .

In terms of flights, Southwest is the most popular. Southwest offers 728 connecting flights per week. Southwest flies from Owen Roberts International Airport (GCM) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .

Other popular airlines flying from Grand Cayman to Chicago are:

American offers 331 connecting flights per week. American flies from Owen Roberts International Airport (GCM) to Chicago O'Hare International Airport (ORD) .
Delta offers 167 connecting flights per week. Delta flies from Owen Roberts International Airport (GCM) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
JetBlue offers 9 connecting flights per week. JetBlue flies from Owen Roberts International Airport (GCM) to Chicago O'Hare International Airport (ORD) .
Air Canada offers 7 connecting flights per week. Air Canada flies from Owen Roberts International Airport (GCM) to Chicago O'Hare International Airport (ORD) .

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

The cheapest round-trip flight from Grand Cayman to Chicago recently found on Google Flights was with Air Canada from $366. The cheapest one-way flight was with Air Canada from $233.

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

The cheapest Southwest flight from Grand Cayman to Chicago is $579, flying from May 28 to Jun 3.
The cheapest United flight from Grand Cayman to Chicago is $631, flying from Jul 18 to Jul 26.
The cheapest American flight from Grand Cayman to Chicago is $606, flying from May 28 to Jun 6.
The cheapest Delta flight from Grand Cayman to Chicago is $472, flying from Jul 16 to Jul 22.
The cheapest Air Canada flight from Grand Cayman to Chicago is $366, flying from Jun 11 to Jun 17.

United flies direct from Grand Cayman to Chicago.

There are 7 United direct flights from Grand Cayman to Chicago per week. Flights are available every day.

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

The cheapest last-minute deal between Grand Cayman and Chicago at price $315 is offered by United from Sat, Apr 25 to Sun, Apr 26.

United flies direct from Grand Cayman to Chicago.

There are 7 United direct flights from Grand Cayman to Chicago per week. Flights are available every day.

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

Direct flights from Grand Cayman to Chicago are only available on Monday, Tuesday, Wednesday and Saturday.

The cheapest direct (nonstop) round-trip flights between Grand Cayman and Chicago start at $651 from Sat, May 16 to Sat, May 23 with United.

It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Grand Cayman to Chicago, 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 Grand Cayman and Chicago start at $1,125 from Fri, Jul 17 to Sun, Jul 26 with American.

The cheapest economy class round-trip flights between Grand Cayman and Chicago start at $366 from Thu, Jun 11 to Wed, Jun 17.

To book business class trips from Grand Cayman to Chicago, 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 Grand Cayman and Chicago starts at $315 from Sat, Apr 25 to Sun, Apr 26 with United.

The cheapest last-minute deal between Grand Cayman and Chicago at price $315 is offered by United from Sat, Apr 25 to Sun, Apr 26.

To find last-minute flight deals from Grand Cayman to Chicago, 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.