Flights from Grand Cayman to Chicago, United States

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Did you mean flights from Chicago to Grand Cayman?

Grand Cayman to Chicago Last modified: Jul 1, 2022 20:00 -04:00

Oops... We've scanned 19,723 round trip itineraries and didn't find any recent prices to Chicago that we think are great deals. Run an airfare search now to update and compare prices. Find Flights

How Much is a Flight from Grand Cayman to Chicago?

We have collected flight cost data from across the web for travel from Grand Cayman to Chicago, and have found the average flight price for this trip to be KYD385.

Where To Buy Cheap Flights from Grand Cayman to Chicago?

The best way to find a great deal on airfare is to search multiple sites. When you run a search on FareCompare, we search multiple sites and fare sources all at once so you don't have to - which is why we think FareCompare is the best place to find cheap tickets. Airlines can adjust prices for tickets from Grand Cayman to Chicago based on the day and time that you decide to book your flight. We have collected data from all airlines, and have found that Tuesdays, Wednesdays, and Saturdays are often the best days to book flights. If you'd like to learn more, read our article about the best time to buy airline tickets.

How far in advance should I book tickets from Grand Cayman to Chicago?

The chart below shows up-to-date information regarding how far in advance to book your flight from Grand Cayman to Chicago.

Non Stop versus Connecting
Advanced PurchaseNon StopConnecting
< 7 days KYD0 KYD0
7-14 days KYD0 KYD674
14-21 days KYD383 KYD565
21-30 days KYD451 KYD524
30-60 days KYD350 KYD499
60-90 days KYD398 KYD257
90+ days KYD403 KYD339

Cheapest Day To Fly from Grand Cayman to Chicago

We've examined 39,446 itinerary searches that we've seen for departures in the next 90 days and found that the cheapest day to fly from Grand Cayman to Chicago is Tuesday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
KYD368KYD298KYD399KYD383KYD350KYD499KYD398

Compare Flight Prices from Grand Cayman to Chicago by Month

Low priced flights are most commonly available by purchasing between one and three months in advance. International or holiday flights may need to be purchased even further in advance. The chart below shows the cheapest flight prices by month for Grand Cayman to Chicago flights.

Month Origin Destination Carrier Depart Date Return Date Stops Price
January Grand Cayman Chicago !! 1/20/22 1/24/22 0 KYD383
February Grand Cayman Chicago !! 2/11/22 2/14/22 0 KYD350
February Grand Cayman Chicago !! 2/11/22 2/14/22 0 KYD350
October Grand Cayman Chicago 00 10/21/21 10/25/21 0 KYD366
May Grand Cayman Chicago 00 5/20/22 5/25/22 0 KYD403
May Grand Cayman Chicago 00 5/20/22 5/25/22 0 KYD403
July Grand Cayman Chicago 00 7/22/22 7/25/22 0 KYD459
July Grand Cayman Chicago 00 7/22/22 7/25/22 0 KYD459

Cheap Last Minute Flights from Grand Cayman to Chicago

Looking for cheap last minute flights or a weekend getaway? We've got you covered with weekend flight deals from Grand Cayman to Chicago. The chart below shows the best last minute deals and cheap flights this weekend we could find.

Next 30 Days

SunMonTueWedThuFriSat
16 17 18 19 20 21 22
KYD383
23 24 25 26 27 28 29
KYD383

Connecting Flights vs Direct Flights from Grand Cayman to Chicago

Flights between some cities may be significantly cheaper if you choose a multi-stop airline ticket. Although these connecting flights sacrifice some convenience, on average, travelers save 20%-60% when they choose to fly multi-stop versus a direct flight.

The average price for connecting flights from Grand Cayman to Chicago is KYD499.

The average price for direct flights from Grand Cayman to Chicago is KYD398.

The chart below shows up to date information regarding non-stop flights from Grand Cayman to Chicago.

Weekly Direct Flights from Grand Cayman to Chicago - By Carrier
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
American 0 0 0 0 0 1 1 09:28 09:28
United 0 0 0 0 0 2 1 06:55 07:28

One Way Flights vs Round Trip Flights from Grand Cayman to Chicago

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 Grand Cayman to Chicago. 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 Grand Cayman to Chicago is KYD149.

The average price for round trip flights from Grand Cayman to Chicago is KYD398.

Grand Cayman to Chicago Flight Questions

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

Question: How long is the flight from Grand Cayman to Chicago?
Answer: The average Grand Cayman to Chicago flight time is 4 hours and 11 minutes.
Question: How far is Chicago from Grand Cayman?
Answer: The distance from Grand Cayman to Chicago is 2,594 kilometers (1,612 miles).
Question: How common are direct flights from Grand Cayman to Chicago?
Answer: There are 5 direct flights from Grand Cayman to Chicago.
Question: What are the most popular Grand Cayman airlines for direct flights from Grand Cayman to Chicago?
Answer: United Airlines provides 60% of the non-stop flights between Grand Cayman and Chicago.

Grand Cayman to Chicago Airports

These are the major commercial airports we're currently monitoring in Grand Cayman and Chicago. If your route includes a city with multiple airports, you may be able to find substantial savings by choosing an alternate airport.

Farecompare Research Tools

FareCompare's Flight Schedule Search Tool helps you find information about airline schedule filings, including flight numbers, depart times, and travel distance.

Cheap Flights from Grand Cayman to Chicago