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Cheap Flights from Chicago to Grand Cayman, KY, Cayman Islands - CHI to GCM

Popular flights from Chicago to Grand Cayman

We’ve got the inside scoop on finding the best time to fly for the best price. Not sure when to travel for your next vacation? Find details below on when-to-fly and when-to-buy.

American Airlines
Departure Date Return Date Lowest Price
Aug 2, 2016 Aug 11, 2016 $436
Aug 2, 2016 Aug 11, 2016 $436
Aug 6, 2016 Aug 13, 2016 $436
Cayman Airways
Departure Date Return Date Lowest Price
Jul 3, 2016 Jul 10, 2016 $558
JetBlue Airways
Departure Date Return Date Lowest Price
Jun 16, 2016 Jun 21, 2016 $679
United Airlines
Departure Date Return Date Lowest Price
Jun 9, 2016 Jun 12, 2016 $497
Jun 14, 2016 Jun 23, 2016 $497
Jun 18, 2016 Jun 25, 2016 $497
Jun 23, 2016 Jun 26, 2016 $497
Jul 2, 2016 Jul 9, 2016 $497

How Much Does it Cost to Fly from Chicago to Grand Cayman (CHI to GCM)?

We have collected flight cost data from across the web for travel from Chicago to Grand Cayman, and have found the average flight price for this trip to be $442.

When Can I Buy the Cheapest Flight from Chicago to Grand Cayman (CHI to GCM)?

Airlines can adjust prices for plane tickets from Chicago to Grand Cayman based on the day and time that you decide to book your flight. We have collected data from all airlines, and have discovered that the best days to book flights are Tuesdays, Wednesdays, and Saturdays. Read our article to find more information about the best time to buy airline tickets.

Cheapest Day To Fly from Chicago to Grand Cayman

The chart below shows up-to-date information regarding the cheapest days to fly from Chicago to Grand Cayman.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$445 $436 $445 $445 $438 $438 $445

Lowest Fares Chart By Month from Chicago to Grand Cayman

The chart below shows the lowest fare by month when flying from Chicago to Grand Cayman.

Month Origin Destination Carrier Depart Date Return Date Stops Price
May Chicago Grand Cayman American 5/31/16 6/5/16 1 $445
June Chicago Grand Cayman American 6/1/16 6/6/16 1 $445
July Chicago Grand Cayman American 7/1/16 7/8/16 2 $438
August Chicago Grand Cayman American 8/2/16 8/11/16 1 $436
September Chicago Grand Cayman American 9/5/16 9/12/16 1 $445
October Chicago Grand Cayman American 10/2/16 10/9/16 1 $445
November Chicago Grand Cayman American 11/6/16 11/13/16 1 $436
December Chicago Grand Cayman American 12/2/16 12/7/16 1 $435

Round Trip vs One Way Flights from Chicago to Grand Cayman (CHI to GCM)

We have found that there is often no price difference between buying a round trip flight versus a one way flight. Increased flexibility is the main benefit when it comes to buying a one way flight from Chicago to Grand Cayman. However, booking a round trip flight can be a simpler process. You can compare round trip and one way flights by using our flight comparison.

The average price for one way flights from Chicago to Grand Cayman is $227.

The average price for round trip flights from Chicago to Grand Cayman is $543.

Chicago to Grand Cayman Flight Questions

Below are some common questions that asked about this flight route:

Question: What are the most popular connecting cities when flying from Chicago to Grand Cayman?
Answer: Atlanta, GA

Airlines Flying from Chicago to Grand Cayman (CHI to GCM)

Below are the different airlines that fly from Chicago to Grand Cayman with the average price of their plane tickets. Just remember that different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary of the next 30 days for flights from Chicago to Grand Cayman.

Chicago to Grand Cayman
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American CLT X X X X X X X
American IND / MIA X X X X X
Air Canada YYZ X
JetBlue JFK X X X X X
Delta ATL X X X X X X X
United IAH X X X X X X X

Airports for Your Route

These pages contain information about the major airports in Chicago and Grand Cayman, so you can feel comfortable knowing how to get around whether you are about to take off or you just landed.

Cheap Domestic Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to New York American, Alaska, JetBlue, Spirit, United $109
Chicago to Orlando American, JetBlue, Frontier, Spirit, United $137
Chicago to Miami American, Alaska, Frontier, United $108
Chicago to Los Angeles American, Alaska, Frontier, Spirit, United, Virgin America $167
Chicago to Las Vegas American, Alaska, Frontier, Spirit, United, Virgin America $107
Chicago to Atlanta American, Spirit, United $71
Chicago to Ft Lauderdale American, Alaska, JetBlue, Spirit, United $107
Chicago to Dallas - Ft Worth American, Alaska, Frontier, Spirit, United $87
Chicago to Tampa American, Alaska, Spirit, United $126
Chicago to Houston American, Spirit, United $127
Chicago to Ft Myers American, Spirit, United $177
Chicago to Washington American, Alaska, Frontier, United $88
Chicago to San Francisco American, Alaska, Frontier, United, Virgin America $147
Chicago to Denver American, Alaska, Frontier, Spirit, United $81
Chicago to Phoenix American, Alaska, Frontier, Spirit, United $127
Chicago to Boston American, JetBlue, Spirit, United $87
Chicago to New Orleans American, Spirit, United $87

Cheap International Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Cancun Silver, Interjet, American, AeroMexico, Alaska, JetBlue, Frontier, Spirit, Sun Country, United, Virgin America, Volaris, Great Lakes $283
Chicago to Montego Bay Silver, American, Alaska, JetBlue, Frontier, Spirit, United $308
Chicago to Toronto Air Choice One, American, Air Canada, Alaska, JetBlue, Frontier, Spirit, Public Charters, Porter, United, WestJet, Great Lakes $227

Cheap International Flights to Grand Cayman - GCM

FlightsAirlineLowest Price
Indianapolis to Grand Cayman American, Cayman, United $576
Milwaukee to Grand Cayman American, Cayman, United $656
Grand Rapids to Grand Cayman American, Cayman, United $625
Madison to Grand Cayman American, Cayman, United $725
Moline to Grand Cayman American, Cayman, United $716
Ft Wayne to Grand Cayman American, Cayman, United $684
Bloomington - Normal to Grand Cayman American, Cayman, United Check Dates
Lansing to Grand Cayman American, Cayman, United $750
South Bend to Grand Cayman American, Cayman, United $661
Peoria to Grand Cayman American, Cayman, United $783
Cheap Flights from Chicago to Grand Cayman, KY, Cayman Islands, from $436 Round trip from CHI to GCM