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 routes to Chicago on KAYAK are from Montego Bay, which takes 4h 39m, and Kingston, which takes 7h 39m.

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 routes to Chicago on KAYAK are from Montego Bay, which takes 4h 39m, and Kingston, which takes 7h 39m.

Question 3

What is the cheapest flight to Chicago?

Accepted Answer

In the last 3 days, the cheapest flight deal to Chicago was found on the route from Montego Bay, at $301 return. The most popular connection is from New York to Chicago and KAYAK users have found round-trip deals for as low as $160 in the last 3 days. Visit our flight page for the latest deals!>/a>

Question 4

What is the cheapest flight to Chicago?

Accepted Answer

In the last 3 days, the cheapest flight deal to Chicago was found on the route from Montego Bay, at $301 return. The most popular connection is from New York to Chicago and KAYAK users have found round-trip deals for as low as $160 in the last 3 days. Visit our flight page for the latest deals!>/a>

Question 5

Which airlines fly to Chicago?

Accepted Answer

Many airlines fly to Chicago, the most common ones being American Airlines, Southwest, and United Airlines. See the amount of flights per week for popular airlines flying to Chicago. Visit our flight page for the latest deals!>/a>

Question 6

Which airlines fly to Chicago?

Accepted Answer

Many airlines fly to Chicago, the most common ones being American Airlines, Southwest, and United Airlines. See the amount of flights per week for popular airlines flying to Chicago. Visit our flight page for the latest deals!>/a>

Question 7

Which Chicago airport is closest to central Chicago?

Accepted Answer

9 miles away from Chicago’s city center, Chicago Midway Airport is the closest of the 3 major airports in the city. There are 16 miles separating Chicago city center to Chicago O'Hare Airport, and 79 miles to Chicago Greater Rockford. <a href='/flight-routes/Jamaica-JM0/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 8

How many cities have direct flights to Chicago?

Accepted Answer

From Jamaica, there are direct flights to Chicago from 1 city. This city is Montego Bay and there are 9 direct flights each week.

Question 9

How many cities have direct flights to Chicago?

Accepted Answer

From Jamaica, there are direct flights to Chicago from 1 city. This city is Montego Bay and there are 9 direct flights each week.

Question 10

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 $132.

Question 11

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 $132.

Question 12

How much is a flight to Chicago?

Accepted Answer

On average, a flight to Chicago costs $364. The cheapest price found on KAYAK in the last 2 weeks cost $182 and departed from Montego Bay Sangster Intl Airport.

Question 13

What is the cheapest day to fly to Chicago?

Accepted Answer

Based on KAYAK data, the cheapest day to fly to Chicago is Wednesday where round-trip tickets can be as cheap as $410. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $550 on average.

Question 14

What is the cheapest day to fly to Chicago?

Accepted Answer

Based on KAYAK data, the cheapest day to fly to Chicago is Wednesday where round-trip tickets can be as cheap as $410. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $550 on average.

Question 15

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/Jamaica-JM0/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 16

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/Jamaica-JM0/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 17

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/Jamaica-JM0/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 18

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/Jamaica-JM0/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 19

Which airline offers the most flights to Chicago?

Accepted Answer

Of the 3 airlines that fly to Chicago, American Airlines offers the most flights, with around 7 per week, followed by Southwest with 2 flights per week.

Question 20

Which airline offers the most flights to Chicago?

Accepted Answer

Of the 3 airlines that fly to Chicago, American Airlines offers the most flights, with around 7 per week, followed by Southwest with 2 flights per week.

Question 21

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 95% of all flights arriving there.

Question 22

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 95% of all flights arriving there.

Question 23

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 evening, when round-trip flights cost $454 on average. The most expensive time of day to fly to Chicago is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $466.

Question 24

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 evening, when round-trip flights cost $454 on average. The most expensive time of day to fly to Chicago is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $466.

Question 25

How many direct flights to Chicago are there each day?

Accepted Answer

There are around 5,634 direct flights from within Jamaica to Chicago every day. Most flights depart in the morning, with 49% of flights departing in the morning.

Question 26

How many direct flights to Chicago are there each day?

Accepted Answer

There are around 5,634 direct flights from within Jamaica to Chicago every day. Most flights depart in the morning, with 49% of flights departing in the morning.

Question 27

How many direct flights to Chicago are there each week?

Accepted Answer

Each week there are around 39,434 direct flights from within Jamaica to Chicago. The most common day for departures is Sunday, with 16% of flights taking off on this day.

Question 28

How many direct flights to Chicago are there each week?

Accepted Answer

Each week there are around 39,434 direct flights from within Jamaica to Chicago. The most common day for departures is Sunday, with 16% of flights taking off on this day.

Question 29

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 Montego Bay $316 round-trip.

Question 30

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 Montego Bay $316 round-trip.

Question 31

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 9 medium-haul flights (3-6 hour flight duration), with the most arriving from Montego Bay.

Question 32

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 9 medium-haul flights (3-6 hour flight duration), with the most arriving from Montego Bay.

Question 33

What are the most popular airlines flying to Chicago?

Accepted Answer

The most popular airline among KAYAK users flying to Chicago is American Airlines, followed by United Airlines.

Low season	March
High season	May
Cheapest flight	$194

$194 Find Cheap Flights from Jamaica to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

Cheap Flights from Jamaica to Chicago

Recent round-trip flight deals from Jamaica to Chicago

Recent one-way flight deals from Jamaica to Chicago

Recent last minute flight deals from Jamaica to Chicago

Recent direct flight deals from Jamaica to Chicago

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 the cheapest flight to Chicago?

In the last 3 days, the cheapest flight deal to Chicago was found on the route from Montego Bay, at $301 return. The most popular connection is from New York to Chicago and KAYAK users have found round-trip deals for as low as $160 in the last 3 days.

What is the cheapest day to fly to Chicago?

Based on KAYAK data, the cheapest day to fly to Chicago is Wednesday where round-trip tickets can be as cheap as $410. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $550 on average.

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

The cheapest time of day to fly to Chicago is generally in the evening, when round-trip flights cost $454 on average. The most expensive time of day to fly to Chicago is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $466.

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 Montego Bay $316 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 $132.

What are the most popular airlines flying to Chicago?

The most popular airline among KAYAK users flying to Chicago is American Airlines, followed by United Airlines.

Which airline offers the most flights to Chicago?

Of the 3 airlines that fly to Chicago, American Airlines offers the most flights, with around 7 per week, followed by Southwest with 2 flights per week.

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 95% 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 routes to Chicago on KAYAK are from Montego Bay, which takes 4h 39m, and Kingston, which takes 7h 39m.

How many direct flights to Chicago are there each day?

There are around 5,634 direct flights from within Jamaica to Chicago every day. Most flights depart in the morning, with 49% of flights departing in the morning.

How many direct flights to Chicago are there each week?

Each week there are around 39,434 direct flights from within Jamaica to Chicago. The most common day for departures is Sunday, with 16% of flights taking off on this day.

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 9 medium-haul flights (3-6 hour flight duration), with the most arriving from Montego Bay.

How many cities have direct flights to Chicago?

From Jamaica, there are direct flights to Chicago from 1 city. This city is Montego Bay and there are 9 direct flights each week.

Good to know

FAQs - booking Chicago flights

What is the cheapest flight to Chicago?

In the last 3 days, the cheapest flight deal to Chicago was found on the route from Montego Bay, at $301 return. The most popular connection is from New York to Chicago and KAYAK users have found round-trip deals for as low as $160 in the last 3 days.

Which Chicago airport is closest to central Chicago?

9 miles away from Chicago’s city center, Chicago Midway Airport is the closest of the 3 major airports in the city. There are 16 miles separating Chicago city center to Chicago O'Hare Airport, and 79 miles to Chicago Greater Rockford.

How much is a flight to Chicago?

On average, a flight to Chicago costs $364. The cheapest price found on KAYAK in the last 2 weeks cost $182 and departed from Montego Bay Sangster Intl Airport.

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.

Top tips for finding cheap flights to Chicago

Traveling to a place near Chicago?

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Find direct flights for Chicago

Flights to other popular destinations

Flights from local origins to Chicago

Choose which airport to fly into in Chicago

Popular routes to Chicago

Find deals for your return flight