Cheap flights from Grand Cayman to Chicago from $248

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1 stop
Sun, Nov 23
Grand Cayman GCMChicago ORD
$248
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1 stop
Mon, Nov 24
Grand Cayman GCMChicago MDW
$268
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1 stop
Sun, Nov 23
Grand Cayman GCMChicago ORD
$274
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1 stop
Sun, Nov 23
Grand Cayman GCMChicago ORD
$285
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1 stop
Mon, Nov 24
Grand Cayman GCMChicago ORD
$302
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1 stop
Wed, Nov 26
Grand Cayman GCMChicago MDW
$412
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1 stop
Sun, Nov 23 – Fri, Nov 28
Grand Cayman GCMChicago ORD
$392
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1 stop
Sun, Nov 23 – Fri, Nov 28
Grand Cayman GCMChicago ORD
$398
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1 stop
Sun, Nov 23 – Fri, Nov 28
Grand Cayman GCMChicago ORD
$418
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1 stop
Sun, Nov 23 – Fri, Nov 28
Grand Cayman GCMChicago ORD
$423
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1 stop
Sun, Nov 23 – Fri, Nov 28
Grand Cayman GCMChicago ORD
$517
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1 stop
Sun, Nov 23 – Fri, Nov 28
Grand Cayman GCMChicago ORD
$542
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How much do flights to Chicago cost?

Cheapest one-way trip

$248

Cheapest round-trip

$392

Average round-trip

$503

Includes rare itinerary

Travel hack

Nonstop flights in November

$382 – $485

Key info about flying to Chicago

Depart from
Owen Roberts International
Arrive to
O Hare International
Average flights per week
220
Flight distance
2600 km
Worth visiting
Art Institute of Chicago

Weekly direct flights

Discover the top airlines offering direct flights from Grand Cayman to Chicago in the next month. You’ll find the number of daily direct flights per airline in the chart.

AirlineSun 02.11Mon 03.11Tue 04.11Wed 05.11Thu 06.11Fri 07.11Sat 08.11
United Airlines
------------------2
Weekly flights: 2 totalDaily flights: 0.29 averageMost flights: Saturday 2 flights
AirlineSun 09.11Mon 10.11Tue 11.11Wed 12.11Thu 13.11Fri 14.11Sat 15.11
United Airlines
------------------2
Weekly flights: 2 totalDaily flights: 0.29 averageMost flights: Saturday 2 flights
AirlineSun 16.11Mon 17.11Tue 18.11Wed 19.11Thu 20.11Fri 21.11Sat 22.11
United Airlines
------------------2
Weekly flights: 2 totalDaily flights: 0.29 averageMost flights: Saturday 2 flights
AirlineSun 23.11Mon 24.11Tue 25.11Wed 26.11Thu 27.11Fri 28.11Sat 29.11
United Airlines
------------------1
Weekly flights: 1 totalDaily flights: 0.14 averageMost flights: Saturday 1 flights

Check-in for a flight from Grand Cayman to Chicago

NameCarrier codeIATA CodePassport needed during booking
Cayman AirwaysCAYKXNo
Frontier AirlinesFFTF9No
United AirlinesUALUANo
Spirit AirlinesNKSNKNo
JetBlue AirwaysJBUB6No

Online check-in is not available for these airlines.

Weather in Chicago

Average Weather

MonthAverage monthly max temperatureAverage monthly min temperature
January-1°C-6°C
February0°C-5°C
March6°C0°C
April11°C4°C
May17°C10°C
June22°C16°C
July26°C20°C
August25°C19°C
September22°C16°C
October15°C10°C
November8°C3°C
December2°C-1°C
Hottest Month
26°C
July
Coldest month
-6°C
January
Sunny days
256
days per year
Snow days
16
days per year

14 day forecast

Saturday
8 Nov
88%
8°C5°C
15 Nov
18°C10°C
Sunday
9 Nov
87%
3°C-1°C
16 Nov
87%
16°C9°C
Monday
10 Nov
78%
4°C-2°C
17 Nov
14°C7°C
Tuesday
11 Nov
5°C-2°C
18 Nov
14°C8°C
Wednesday
12 Nov
10°C3°C
19 Nov
89%
14°C10°C
Thursday
13 Nov
11°C4°C
20 Nov
12°C9°C
Friday
14 Nov
12°C6°C
21 Nov
83%
9°C7°C
Book your trip to arrive at O Hare International, Chicago Midway International, or Chicago Rockford International. The distance between Grand Cayman and Chicago is 2600 km. The most popular airlines for this route are Cayman Airways, Frontier Airlines, United Airlines, Spirit Airlines, and JetBlue Airways. Grand Cayman and Chicago have 220 direct flights per week.

Frequently asked questions

How long does it take to travel from Grand Cayman to Chicago?
A one-way nonstop (direct) flight between Grand Cayman and Chicago takes around 4.2 hours.
What is the flight distance between Grand Cayman and Chicago?
The flight distance between Grand Cayman and Chicago is 2600 km.
What airlines offer nonstop (direct) flights between Grand Cayman and Chicago?
Several carriers operate flights between Grand Cayman and Chicago. Airlines offering nonstop (direct) flights include United Airlines.
What are the most popular routes to and from Grand Cayman?
Travelers frequently search for route combinations, such as Grand Cayman and Toronto, Berlin, Mexico City, Dublin, Charlotte, Orlando, Houston, Guadalajara, Rome, Dallas, Atlanta, San José, Detroit, Paris, Port of Spain, Amsterdam, Cancún, Tampa, Madrid, Split.
What are the most popular routes to and from Chicago?
Travelers frequently search for route combinations, such as Chicago and Mexico City, New York, Guadalajara, Dallas, Houston, Atlanta, Los Angeles, Morelia, Orlando, Philadelphia, León, Tampa, San Francisco, Miami, Denver, Phoenix, Seattle, Monterrey, Las Vegas, Washington, D.C..
What airports are near Grand Cayman?
The main airport in Grand Cayman is Owen Roberts International. It is also served by Owen Roberts International.
What airports are near Chicago?
The main airport in Chicago is O Hare International. It is also served by Gerald R. Ford International, General Mitchell International, South Bend International, Dane County Regional, General Wayne A. Downing Peoria International, Fort Wayne International, Quad City International, Central Illinois Regional, Muskegon County, University of Illinois Willard.
Which airlines fly between Grand Cayman and Chicago?
Currently, you can fly between Grand Cayman and Chicago with Cayman Airways, Frontier Airlines, United Airlines, Spirit Airlines, JetBlue Airways.
When’s the best time to travel between Grand Cayman and Chicago?
If you don’t have specific dates for your trip between Grand Cayman and Chicago, you can enter a date range into the departure and return fields. Most carriers on the Kiwi.com website allow you to search and book up to six months from the day of your search. Order the search results by the best, cheapest, or fastest route, or find the cheapest outbound and return combination in the pricing table.
What flights operate between Grand Cayman and Chicago?
How many airports are there near Grand Cayman?
How many airports are there near Chicago?
What time do nonstop (direct) flights between Grand Cayman and Chicago depart?
What time do nonstop (direct) flights between Grand Cayman and Chicago arrive?
What time do flights between Grand Cayman and Chicago depart?
What time do flights between Grand Cayman and Chicago arrive?

Planning a trip? Thanks to our Virtual Interlining algorithm, we offer billions of route combinations between any origin and destination in the world by plane. Find the cheapest routes and best deals, as well as the best dates to travel.

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