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 26m , and Kingston , which takes 10h 07m.

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.

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 $150.

How much is a flight to Chicago?

On average, a flight to Chicago costs $449. The cheapest price found on KAYAK in the last 2 weeks cost $231 and departed from Montego Bay Sangster Intl Airport.

What is the cheapest day to fly to Chicago?

Based on KAYAK data, the cheapest day to fly to Chicago is Thursday where round-trip tickets can be as cheap as $416. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $547 on average.

What is the cheapest month to fly to Chicago?

The cheapest month for flights to Chicago is December , where tickets cost $370 on average for return flights. On the other hand, the most expensive months are August and July, where the average cost of tickets from Jamaica is $643 and $497 respectively. For one-way flights, the best month to travel is December with an average price of $230.

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.

Which airline offers the most flights to Chicago?

Of the 2 airlines that fly to Chicago, American Airlines offers the most flights, with around 7 per week, followed by United Airlines with 7 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 94% of all flights arriving there.

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 $464 on average. The most expensive time of day to fly to Chicago is generally in the evening, which is peak travel time and where the average cost of a ticket is $486.

How many direct flights to Chicago are there each day?

There are around 4,412 direct flights from within Jamaica to Chicago every day. Most flights depart in the morning, with 50% of flights departing in the morning.

How many direct flights to Chicago are there each week?

Each week there are around 30,882 direct flights from within Jamaica to Chicago. The most common day for departures is Sunday, with 15% of flights taking off on this day.

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 $486 round-trip.

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 and JetBlue.

$209 CHEAP FLIGHTS from Jamaica to Chicago

Save 25% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals

Cheap Flights from Jamaica to Chicago

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Direct

Recent round-trip flight deals from Jamaica to Chicago

Sat, Nov 7 - Sat, Nov 14

4:43 pm - 11:47 pmMBJ Montego Bay Sangster Intl-MDW Chicago Midway

8h 04m1 stop Atlanta Hartsfield-Jackson

7:15 am - 3:28 pmMDW Chicago Midway-MBJ Montego Bay Sangster Intl

7h 13m1 stop Atlanta Hartsfield-Jackson

$366Frontier

Thu, Nov 12 - Mon, Nov 16

4:43 pm - 11:47 pmMBJ Montego Bay Sangster Intl-MDW Chicago Midway

8h 04m1 stop Atlanta Hartsfield-Jackson

6:08 am - 3:08 pmMDW Chicago Midway-MBJ Montego Bay Sangster Intl

8h 00m1 stop Atlanta Hartsfield-Jackson

$369Frontier

Thu, Nov 5 - Thu, Nov 26

4:43 pm - 11:47 pmMBJ Montego Bay Sangster Intl-MDW Chicago Midway

8h 04m1 stop Atlanta Hartsfield-Jackson

1:16 pm - 12:56 pmMDW Chicago Midway-MBJ Montego Bay Sangster Intl

22h 40m1 stop Atlanta Hartsfield-Jackson

$384Frontier

Wed, Nov 11 - Sat, Nov 14

3:56 pm - 7:46 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 50mnonstop

4:43 pm - 10:15 amORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

16h 32m1 stop Miami

$396American Airlines

Wed, Nov 11 - Sat, Nov 14

3:22 pm - 10:30 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

8h 08m1 stop Charlotte Douglas

4:31 pm - 12:10 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

18h 39m1 stop New York John F Kennedy Intl

$406American Airlines

Thu, Nov 19 - Thu, Nov 26

3:49 pm - 7:45 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 56mnonstop

12:02 pm - 5:09 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

28h 07m1 stop Dallas/Fort Worth

$420American Airlines

Thu, Nov 12 - Mon, Nov 16

2:54 pm - 6:20 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 26mnonstop

8:40 am - 1:48 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 08mnonstop

$432United Airlines

Tue, Dec 22 - Sun, Jan 3

2:54 pm - 6:20 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 26mnonstop

8:40 am - 1:48 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 08mnonstop

$432United Airlines

Mon, Nov 23 - Mon, Nov 30

5:10 pm - 11:38 pmKIN Kingston Norman Manley-ORD Chicago O'Hare Intl

7h 28m1 stop Fort Lauderdale

7:00 am - 1:48 pmORD Chicago O'Hare Intl-KIN Kingston Norman Manley

5h 48m1 stop Fort Lauderdale

$766JetBlue

Sun, Dec 27 - Sun, Jan 10

1:15 pm - 11:33 pmKIN Kingston Norman Manley-ORD Chicago O'Hare Intl

11h 18m1 stop Fort Lauderdale

7:45 pm - 9:15 amORD Chicago O'Hare Intl-KIN Kingston Norman Manley

12h 30m1 stop Fort Lauderdale

$953JetBlue

Recent direct flight deals from Jamaica to Chicago

Tue, Dec 22 - Sun, Jan 3

2:54 pm - 6:20 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 26mnonstop

8:40 am - 1:48 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 08mnonstop

$432United Airlines

Thu, Dec 24 - Sun, Jan 3

2:54 pm - 6:20 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 26mnonstop

8:40 am - 1:48 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 08mnonstop

$432United Airlines

Fri, Dec 25 - Sun, Jan 3

2:54 pm - 6:20 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 26mnonstop

8:40 am - 1:48 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 08mnonstop

$432United Airlines

Tue, Nov 24 - Tue, Dec 1

2:54 pm - 6:20 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 26mnonstop

8:40 am - 1:48 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 08mnonstop

$432United Airlines

Thu, Nov 12 - Mon, Nov 16

2:54 pm - 6:20 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 26mnonstop

8:40 am - 1:48 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 08mnonstop

$432United Airlines

Mon, Nov 23 - Sun, Nov 29

3:49 pm - 7:45 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 56mnonstop

9:37 am - 2:49 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 12mnonstop

$442American Airlines

Tue, Dec 22 - Thu, Dec 31

3:32 pm - 7:19 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 47mnonstop

9:19 am - 2:32 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 13mnonstop

$442American Airlines

Mon, Nov 23 - Sun, Nov 29

2:54 pm - 6:20 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 26mnonstop

8:40 am - 1:48 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 08mnonstop

$442United Airlines

Thu, Dec 24 - Fri, Jan 1

2:54 pm - 6:20 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 26mnonstop

8:40 am - 1:48 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 08mnonstop

$442United Airlines

Sat, Nov 21 - Tue, Dec 1

2:54 pm - 6:20 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 26mnonstop

8:40 am - 1:48 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 08mnonstop

$442United Airlines

Booking Insights

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.

Prices

Airlines

What is the cheapest day to fly to Chicago? The average price of all round-trip flights to Chicago clicked on KAYAK for each day over the last 12 months.: Based on KAYAK data, the cheapest day to fly to Chicago is Thursday where round-trip tickets can be as cheap as $416. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $547 on average.
What is the cheapest month to fly to Chicago? To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.: The cheapest month for flights to Chicago is December, where tickets cost $370 on average for return flights. On the other hand, the most expensive months are August and July, where the average cost of tickets from Jamaica is $643 and $497 respectively. For one-way flights, the best month to travel is December with an average price of $230.
What is the cheapest time of day to fly to Chicago? The average price for all round-trip flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.: The cheapest time of day to fly to Chicago is generally in the afternoon, when round-trip flights cost $464 on average. The most expensive time of day to fly to Chicago is generally in the evening, which is peak travel time and where the average cost of a ticket is $486.
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 $486 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 $150.

Find deals

High season	December
Cheapest flight	$209

Most popular time to fly and prices are also 16% lower on average.

Flight from Montego Bay to Chicago O'Hare Airport

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 $449. The cheapest price found on KAYAK in the last 2 weeks cost $231 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.
How many direct flights to Chicago are there each week?
Each week there are around 30,882 direct flights from within Jamaica to Chicago. The most common day for departures is Sunday, with 15% of flights taking off on this day.

Looking for a cheap flight? 25% of our users found flights on this route for $327 or less one-way and $486 or less round-trip.
Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Merrillville

Hammond

Saint Joseph

Portage

Lansing

Valparaiso

Munster

Schererville

Chesterton

Porter

Monticello

Saint John

Griffith

More options for your flight to Chicago

Add a hotel or car rental

Cabin class

Direct Flights

Origins

Other airports

Other destinations

Popular routes

Return flight

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

Car rentals in Chicago

$209 Find Cheap Flights from Jamaica to Chicago - Compare and Save

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 direct flight deals from Jamaica to Chicago

KAYAK's insights & trends for flights to Chicago

What is the cheapest day to fly to Chicago?

What is the cheapest month to fly to Chicago?

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

What is a good deal for flights to Chicago?

Which is the cheapest airport to fly into in Chicago?

What are the most popular airlines flying to Chicago?

Which airline offers the most flights to Chicago?

How many airports are there in Chicago?

How long is the flight to Chicago?

How many direct flights to Chicago are there each day?

Good to know

High season

Cheapest flight

FAQs - booking Chicago flights

Top tips for finding cheap flights to Chicago

Traveling to a place near Chicago?

More options for your flight to Chicago

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

Cabin class types available on flights to Chicago

Find direct flights for Chicago

Flights from local origins to Chicago

Choose which airport to fly into in Chicago

Flights to other popular destinations

Popular routes to Chicago

Find deals for your return flight