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Cheap flights from Chicago (CHI) to Cayman Islands

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Cheap flights from Chicago to Cayman Islands in May, June 2020

The best prices found for ORD to Cayman Islands flights for May, June
25 Jun - 28 Jun
$384pp
ORD
Chicago O'Hare Intl
$self.airline
   
2 STOPS
GCM
George Town Owen Roberts Intl
GCM
George Town Owen Roberts Intl
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
29 Jun - 3 Jul
$401pp
ORD
Chicago O'Hare Intl
$self.airline
 
1 STOP
GCM
George Town Owen Roberts Intl
GCM
George Town Owen Roberts Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
25 Jun - 28 Jun
$422pp
ORD
Chicago O'Hare Intl
$self.airline
 
1 STOP
GCM
George Town Owen Roberts Intl
GCM
George Town Owen Roberts Intl
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl

Chicago to Cayman Islands 2020 flight deals

Cheap flights to Cayman Islands from Chicago found for this year
22 Aug - 25 Aug
$378pp
ORD
Chicago O'Hare Intl
JetBlue
 
1 STOP
GCM
George Town Owen Roberts Intl
GCM
George Town Owen Roberts Intl
JetBlue
 
1 STOP
ORD
Chicago O'Hare Intl
25 Jun - 28 Jun
$384pp
ORD
Chicago O'Hare Intl
$self.airline
   
2 STOPS
GCM
George Town Owen Roberts Intl
GCM
George Town Owen Roberts Intl
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
13 Jul - 17 Jul
$392pp
ORD
Chicago O'Hare Intl
$self.airline
 
1 STOP
GCM
George Town Owen Roberts Intl
GCM
George Town Owen Roberts Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Non-stop flights to Cayman Islands from Chicago

Save time with Chicago to Cayman Islands direct flight deals
31 Oct - 21 Nov
$564pp
ORD
Chicago O'Hare Intl
British Airways
Non-Stop
GCM
George Town Owen Roberts Intl
GCM
George Town Owen Roberts Intl
British Airways
Non-Stop
ORD
Chicago O'Hare Intl
31 Oct - 21 Nov
$573pp
ORD
Chicago O'Hare Intl
Interjet
Non-Stop
GCM
George Town Owen Roberts Intl
GCM
George Town Owen Roberts Intl
Interjet
Non-Stop
ORD
Chicago O'Hare Intl
31 Oct - 21 Nov
$575pp
ORD
Chicago O'Hare Intl
$self.airline
Non-Stop
GCM
George Town Owen Roberts Intl
GCM
George Town Owen Roberts Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl

One-way flights to Cayman Islands from Chicago

The cheapest one-way flights from Chicago to Cayman Islands
4:00 am - 7:00 am
Multiple Airlines
3 Stops
51h 00m
ORD - GCM
Multiple Airlines
$204
Kiwi.com
4:00 am - 7:00 am
Multiple Airlines
3 Stops
27h 00m
ORD - GCM
Multiple Airlines
$241
Kiwi.com
10:10 am - 7:30 am
Multiple Airlines
3 Stops
45h 20m
ORD - GCM
Multiple Airlines
$274
Kiwi.com

Related info for your journey

Useful info, stats and facts about Chicago to Cayman Islands flights.

Flight FAQs

From Chicago to Cayman Islands

Are flight prices decreasing from Chicago to Cayman Islands due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Chicago and Cayman Islands for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

Can I find flights from Chicago to Cayman Islands for under $400 on Cheapflights?

Yes, there are multiple flights from Chicago to Cayman Islands for under $400. The cheapest flight booked recently is on JetBlue for just $378, but on average you can expect to pay $425.

Are there nonstop flights from Chicago to Cayman Islands for under $600 on Cheapflights?

Cheapflights has at least 3 direct flights from Chicago to Cayman Islands under $600. A good price for a nonstop flight from Chicago to Cayman Islands is less than $570.

How popular is this flight route?

The Chicago to Cayman Islands flight path was viewed by 20 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

What are the most popular airlines that fly from Chicago to Cayman Islands?

Before booking your flight from Chicago to Cayman Islands check out the most popular airlines for this route: Major Airline, American Airlines or JetBlue.

What are the most popular routes from Chicago to Cayman Islands?

While some choose either Chicago Midway - George Town Owen Roberts Intl or Chicago O'Hare Intl - Cayman Brac Gerrard-Smith, Chicago O'Hare Intl - George Town Owen Roberts Intl is the most popular route from Chicago to Cayman Islands.

What are the cheapest Flights from Chicago to Cayman Islands?

Looking for the cheapest flight from Chicago to Cayman Islands? While on average our users pay $407, our data indicates the cheapest price to be $159. The most popular route (Chicago O'Hare Intl - George Town Owen Roberts Intl), is priced around $402.

Arrival points for flights from Chicago to Cayman Islands

Destination information for Cayman Islands

Things to know before you go. Useful info for your trip from Chicago to Cayman Islands
Today's exchange rate
$1 = $0.84

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Airports servicing

Grand Cayman (GCM)
Little Cayman (LYB)