Question 1

How long is the flight to Chicago?

Accepted Answer

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously, any flights that include a layover will also be longer. The most popular route to Chicago on KAYAK is from George Town, which takes 4h 22m.

Question 2

How long is the flight to Chicago?

Accepted Answer

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously, any flights that include a layover will also be longer. The most popular route to Chicago on KAYAK is from George Town, which takes 4h 22m.

Question 3

Which Chicago airport is closest to central Chicago?

Accepted Answer

Out of the 3 airports in Chicago, Chicago Midway Airport is the nearest to the city center (9 miles). You'll travel 16 miles to reach the center of Chicago if you land in Chicago O'Hare Airport and 79 miles if you land in Chicago Greater Rockford. <a href='/flight-routes/Cayman-Islands-KY0/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 4

How many cities have direct flights to Chicago?

Accepted Answer

From the Cayman Islands, there are direct flights to Chicago from 1 city. This city is George Town and there are 1 direct flights each week.

Question 5

How many cities have direct flights to Chicago?

Accepted Answer

From the Cayman Islands, there are direct flights to Chicago from 1 city. This city is George Town and there are 1 direct flights each week.

Question 6

Which is the cheapest airport to fly into in Chicago?

Accepted Answer

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Greater Rockford Airport (RFD), with an average flight price of $108.

Question 7

Which is the cheapest airport to fly into in Chicago?

Accepted Answer

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Greater Rockford Airport (RFD), with an average flight price of $108.

Question 8

How much is a flight to Chicago?

Accepted Answer

On average, a flight to Chicago costs $924. The cheapest price found on KAYAK in the last 2 weeks cost $295 and departed from George Town Owen Roberts Intl Airport.

Question 9

What is the cheapest day to fly to Chicago?

Accepted Answer

Based on KAYAK data, the cheapest day to fly to Chicago is Sunday where round-trip tickets can be as cheap as $295. On the other hand, the most expensive day to fly is Wednesday, where round-trip prices are $1,867 on average.

Question 10

How does KAYAK find such low prices on flights to Chicago?

Accepted Answer

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago. <a href='/flight-routes/Cayman-Islands-KY0/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 11

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

Accepted Answer

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travelers know whether to wait or book now. <a href='/flight-routes/Cayman-Islands-KY0/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 12

What is the Hacker Fare option on flights to Chicago?

Accepted Answer

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back with another airline. <a href='/flight-routes/Cayman-Islands-KY0/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 13

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago?

Accepted Answer

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best. <a href='/flight-routes/Cayman-Islands-KY0/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 14

How many airports are there in Chicago?

Accepted Answer

There are 3 airports in Chicago: Chicago O'Hare Airport (ORD), Chicago Midway Airport (MDW) and Chicago Greater Rockford Airport (RFD). The busiest airport is Chicago O'Hare Airport (ORD), with 94% of all flights arriving there.

Question 15

How many airports are there in Chicago?

Accepted Answer

There are 3 airports in Chicago: Chicago O'Hare Airport (ORD), Chicago Midway Airport (MDW) and Chicago Greater Rockford Airport (RFD). The busiest airport is Chicago O'Hare Airport (ORD), with 94% of all flights arriving there.

Question 16

What is the cheapest time of day to fly to Chicago?

Accepted Answer

The cheapest time of day to fly to Chicago is generally in the afternoon, when round-trip flights cost $618 on average. The most expensive time of day to fly to Chicago is generally in the morning, which is peak travel time and where the average cost of a ticket is $666.

Question 17

How many direct flights to Chicago are there each day?

Accepted Answer

There are around 1,584 direct flights from within Cayman Islands to Chicago every day. Most flights depart in the morning, with 6:00 am the most common departure time and 52% of flights departing in the morning.

Question 18

How many direct flights to Chicago are there each day?

Accepted Answer

There are around 1,584 direct flights from within Cayman Islands to Chicago every day. Most flights depart in the morning, with 6:00 am the most common departure time and 52% of flights departing in the morning.

Question 19

How many direct flights to Chicago are there each week?

Accepted Answer

Each week there are around 11,085 direct flights from within Cayman Islands to Chicago. The most common day for departures is Sunday, with 15% of flights taking off on this day.

Question 20

What is a good deal for flights to Chicago?

Accepted Answer

If you’re looking for cheap airfare to Chicago, 25% of our users found tickets to Chicago for the following prices or less: From George Town $660 round-trip.

Question 21

What is a good deal for flights to Chicago?

Accepted Answer

If you’re looking for cheap airfare to Chicago, 25% of our users found tickets to Chicago for the following prices or less: From George Town $660 round-trip.

Question 22

How many long-haul flights are there to Chicago each week?

Accepted Answer

There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Chicago. Instead, there are 1 medium-haul flights (3-6 hour flight duration), with the most arriving from George Town.

Question 23

How many long-haul flights are there to Chicago each week?

Accepted Answer

There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Chicago. Instead, there are 1 medium-haul flights (3-6 hour flight duration), with the most arriving from George Town.

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Cheap Flights from the Cayman Islands to Chicago

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KAYAK's insights & trends for flights to Chicago

Get data-powered insights and trends for flights to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is a good deal for flights to Chicago?

If you’re looking for cheap airfare to Chicago, 25% of our users found tickets to Chicago for the following prices or less: From George Town $660 round-trip.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Greater Rockford Airport (RFD), with an average flight price of $108.

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago O'Hare Airport (ORD), Chicago Midway Airport (MDW) and Chicago Greater Rockford Airport (RFD). The busiest airport is Chicago O'Hare Airport (ORD), with 94% of all flights arriving there.

How long is the flight to Chicago?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously, any flights that include a layover will also be longer. The most popular route to Chicago on KAYAK is from George Town, which takes 4h 22m.

How many direct flights to Chicago are there each day?

There are around 1,584 direct flights from within Cayman Islands to Chicago every day. Most flights depart in the morning, with 6:00 am the most common departure time and 52% of flights departing in the morning.

How many long-haul flights are there to Chicago each week?

There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Chicago. Instead, there are 1 medium-haul flights (3-6 hour flight duration), with the most arriving from George Town.

How many cities have direct flights to Chicago?

From the Cayman Islands, there are direct flights to Chicago from 1 city. This city is George Town and there are 1 direct flights each week.

Good to know

FAQs - booking Chicago flights

Which Chicago airport is closest to central Chicago?

Out of the 3 airports in Chicago, Chicago Midway Airport is the nearest to the city center (9 miles). You'll travel 16 miles to reach the center of Chicago if you land in Chicago O'Hare Airport and 79 miles if you land in Chicago Greater Rockford.

How much is a flight to Chicago?

On average, a flight to Chicago costs $924. The cheapest price found on KAYAK in the last 2 weeks cost $295 and departed from George Town Owen Roberts Intl Airport.

What is the cheapest day to fly to Chicago?

Based on KAYAK data, the cheapest day to fly to Chicago is Sunday where round-trip tickets can be as cheap as $295. On the other hand, the most expensive day to fly is Wednesday, where round-trip prices are $1,867 on average.

How does KAYAK find such low prices on flights to Chicago?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

What is the Hacker Fare option on flights to Chicago?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

What is the cheapest time of day to fly to Chicago?

The cheapest time of day to fly to Chicago is generally in the afternoon, when round-trip flights cost $618 on average. The most expensive time of day to fly to Chicago is generally in the morning, which is peak travel time and where the average cost of a ticket is $666.

How many direct flights to Chicago are there each week?

Each week there are around 11,085 direct flights from within Cayman Islands to Chicago. The most common day for departures is Sunday, with 15% of flights taking off on this day.

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