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Flights from Chicago to Little Cayman, Cayman Islands Last modified: Sep 29, 2016 1:00 AM

Chicago to Little Cayman Last modified: Sep 19, 2016 4:36 AM

We've scanned 18,984,511,576 round trip itineraries and found the cheapest flights from Chicago to Little Cayman. United & Cayman frequently offer the best deals on Chicago to Little Cayman flights, or select your preferred carrier below to see the cheapest days to fly.

United
CHILYB
Sat 10/8
2 stops
LYBCHI
Sat 10/15
2 stops
$527
Select
Cayman
CHILYB
Fri 11/25
3 stops
LYBCHI
Fri 12/2
3 stops
$720
Select
Major Airlines
CHILYB
Sat 12/10
2 stops
LYBCHI
Sat 12/17
2 stops
$1,342
Select
American
CHILYB
Fri 12/23
2 stops
LYBCHI
Mon 12/26
2 stops
$1,609
Select
American
CHILYB
Fri 12/23
3 stops
LYBCHI
Mon 12/26
3 stops
$1,609
Select

How Much is a Flight from Chicago to Little Cayman?

Unfortunately we weren't able to find enough recent prices to provide a meaningful average. Running an airfare search now will update and compare prices. Find Flights

Where To Buy Cheap Flights from Chicago to Little Cayman?

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 thinking FareCompare is the best place to find cheap tickets. Airlines can adjust prices for tickets from Chicago to Little Cayman 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 Chicago to Little Cayman?

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

Non Stop versus Connecting
Advanced PurchaseNon StopConnecting
< 7 days $0 $726
7-14 days $0 $833
14-21 days $0 $527
21-30 days $0 $728
30-60 days $0 $657
60-90 days $0 $558
90+ days $0 $620

Cheapest Day To Fly from Chicago to Little Cayman

We've examined 18,991,239,476 itinerary searches that we've seen for departures in the next 90 days and found that the cheapest day to fly from Chicago to Little Cayman is Saturday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$726 $901 $761 $731 $558 $527 $731

Compare Flight Prices from Chicago to Little Cayman 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 Chicago to Little Cayman flights.

Month Origin Destination Carrier Depart Date Return Date Stops Price
September Chicago Little Cayman United 9/19/16 9/24/16 2 $726
October Chicago Little Cayman United 10/8/16 10/15/16 2 $527
November Chicago Little Cayman United 11/25/16 12/3/16 2 $558
December Chicago Little Cayman United 12/29/16 1/4/17 3 $691
January Chicago Little Cayman United 1/7/17 1/14/17 3 $620
February Chicago Little Cayman Cayman 2/27/17 3/4/17 3 $647
March Chicago Little Cayman United 3/11/17 3/18/17 2 $700
April Chicago Little Cayman United 4/28/17 5/3/17 3 $626

Cheap Last Minute Flights from Chicago to Little Cayman

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

Next 30 Days

SunMonTueWedThuFriSat
18 19 20 21 22 23 24
$785
25 26 27 28 29 30 1
$785 $914
2 3 4 5 6 7 8
$914 $775
9 10 11 12 13 14 15
$775 $728
16 17 18 19 20 21 22
$728 $767
23 24 25 26 27 28 29
$767

Connecting Flights vs Direct Flights from Chicago to Little Cayman

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 Chicago to Little Cayman is $1,653.

The average price for direct flights from Chicago to Little Cayman is not available.

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

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 Little 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 Little Cayman is not available.

The average price for round trip flights from Chicago to Little Cayman is $1,653.

Chicago to Little 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 Little Cayman?
Answer: Grand Cayman, KY

Airlines in Chicago flying to Little Cayman Last modified: Sep 29, 2016 1:00 AMNumber of routes searched: 2Number of itineraries searched: 278

Wondering which airlines fly out of Chicago to Little Cayman? We've gathered the average price of Chicago airlines with flights to Little Cayman. Different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary showing which days of the week individual carriers offer flights for the next 30 days.

Chicago to Little Cayman
Airline Connections Mon Tue Wed Thu Fri Sat Sun
Cayman GCM
Cayman GCM / CYB

Chicago to Little Cayman Airports

These are the major commercial airports we're currently monitoring in Chicago and Little Cayman. 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 Domestic Flights from Chicago - CHI

FlightsAirlineLowest Price
Flights from Chicago to Key West American, Delta, United $322
Flights from Chicago to San Juan American, JetBlue, Delta, Spirit, United $100
Flights from Chicago to Sarasota - Bradenton American, Delta, United $201
Flights from Chicago to Jacksonville American, JetBlue, Delta, United $272
Flights from Chicago to Charleston American, JetBlue, Delta, United $257
Flights from Chicago to Daytona Beach American, Delta $181
Flights from Chicago to Panama CityCheck Dates

Cheap International Flights from Chicago - CHI

FlightsAirlineLowest Price
Flights from Chicago to Montego Bay American, Air Canada, JetBlue, British Airways, Delta, Spirit, United, WestJet $408
Flights from Chicago to Grand Cayman American, JetBlue, Delta, Cayman, United, WestJet $466
Flights from Chicago to Kingston American, Air Canada, JetBlue, Copa, Delta, Cayman, Spirit, United $520
Flights from Chicago to Punta Cana American, Air Canada, JetBlue, British Airways, Copa, Delta, Frontier, Spirit, United, WestJet $318
Flights from Chicago to Nassau American, Air Berlin, Air Canada, JetBlue, British Airways, Copa, Delta, United, WestJet $373
Flights from Chicago to Cozumel American, Air Canada, AeroMexico, Delta, United, WestJet $402
Flights from Chicago to Guadalajara Interjet, American, AeroMexico, Alaska, Copa, Delta, United, Volaris $298
Flights from Chicago to St Thomas Island American, Delta, Spirit, United $317
Flights from Chicago to Belize City American, British Airways, Delta, United $362
Flights from Chicago to Aruba American, Air Canada, Avianca, JetBlue, British Airways, Delta, Spirit, United $376
Flights from Chicago to Puerto Plata American, Air Canada, JetBlue, United, WestJet $508
Flights from Chicago to Guatemala City Interjet, American, AeroMexico, Avianca, Copa, Delta, Spirit, United, Volaris $393
Flights from Chicago to Puerto Vallarta Interjet, American, Air Canada, AeroMexico, Alaska, Delta, Frontier, United, WestJet $227

Cheap Domestic Flights to Little Cayman - LYB

FlightsAirlineLowest Price
Flights from Indianapolis to Miami American, Delta $181
Flights from Milwaukee to Miami American, Delta, United $263
Flights from Indianapolis to Orlando American, Delta, Frontier, United $87
Flights from Milwaukee to Orlando American, Delta, Frontier, United $107
Flights from Indianapolis to Ft Lauderdale American, Delta, United $181
Flights from Milwaukee to Ft Lauderdale American, Alaska, Delta, United $270

Cheap International Flights to Little Cayman - LYB

FlightsAirlineLowest Price
Flights from Indianapolis to Grand Cayman American, Air Canada, British Airways, Delta, United $547
Flights from Milwaukee to Grand Cayman American, Air Canada, British Airways, Delta, United $519
Flights from Indianapolis to Montego Bay American, Air Canada, Copa, Delta, United $433
Flights from Milwaukee to Montego Bay American, Air Canada, Copa, Delta, United, WestJet $439
Cheap Flights from Chicago to Little Cayman