$154 Find Cheap Flights from Chicago to Jamaica - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Jamaica departing on 9/13. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Chicago to Jamaica

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Montego Bay
Montego Bay1 stop$391
Kingston
Kingston1 stop$390
Montego Bay
Montego Bay1 stop$391
Kingston
Kingston1 stop$390

Book Cheap Chicago to Jamaica Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Jamaica that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Jamaica

Tue, Sep 22 - Wed, Sep 23
JetBlue Logo
6:00 am - 12:09 pm
ORD
-
KIN
6h 09m
1 stop
JetBlue Logo
3:05 pm - 11:31 pm
KIN
-
ORD
8h 26m
1 stop
$390JetBlue
Fri, Oct 30 - Tue, Nov 3
JetBlue Logo
7:00 am - 1:48 pm
ORD
-
MBJ
6h 48m
1 stop
JetBlue Logo
3:59 pm - 11:44 pm
MBJ
-
ORD
8h 45m
1 stop
$391JetBlue
Sat, Oct 3 - Sat, Oct 10
American Airlines Logo
7:47 am - 4:02 pm
ORD
-
KIN
8h 15m
2 stops
American Airlines Logo
5:03 pm - 12:38 am
KIN
-
ORD
7h 35m
1 stop
$391American Airlines
Fri, Sep 11 - Mon, Sep 14
American Airlines Logo
6:59 am - 4:02 pm
ORD
-
KIN
9h 03m
1 stop
American Airlines Logo
1:08 pm - 11:32 pm
KIN
-
ORD
10h 24m
1 stop
$398American Airlines
Tue, Nov 3 - Tue, Nov 10
Southwest Logo
6:05 am - 2:25 pm
MDW
-
MBJ
7h 20m
1 stop
Southwest Logo
1:50 pm - 11:05 pm
MBJ
-
MDW
10h 15m
2 stops
$453Southwest
Thu, Aug 27 - Thu, Sep 3
Delta Logo
6:42 pm - 8:13 pm
MDW
-
KIN
25h 31m
2 stops
Delta Logo
9:13 am - 6:33 pm
KIN
-
MDW
9h 20m
2 stops
$457Delta
Fri, Aug 21 - Mon, Aug 24
Delta Logo
6:05 am - 8:13 pm
MDW
-
KIN
14h 08m
1 stop
Delta Logo
9:13 am - 10:36 pm
KIN
-
MDW
13h 23m
1 stop
$464Delta
Wed, Jul 29 - Sun, Aug 16
Frontier Logo
6:05 am - 12:27 pm
MDW
-
MBJ
6h 22m
1 stop
Frontier Logo
1:39 pm - 10:03 pm
MBJ
-
MDW
8h 24m
1 stop
$472Frontier
Sun, Nov 15 - Fri, Nov 20
Southwest Logo
5:10 am - 12:50 pm
MDW
-
MBJ
6h 40m
1 stop
Southwest Logo
1:00 pm - 11:05 pm
MBJ
-
MDW
11h 05m
1 stop
$478Southwest
Mon, Oct 12 - Mon, Oct 26
Frontier Logo
6:40 am - 1:31 pm
MDW
-
MBJ
6h 51m
1 stop
Frontier Logo
2:49 pm - 9:58 pm
MBJ
-
MDW
7h 09m
1 stop
$485Frontier
Booking Insights

KAYAK's insights & trends for Chicago to Jamaica flights

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

What is the cheapest Chicago to Jamaica flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Jamaica from Chicago found in the last 5 days was to Montego Bay, at $407 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Montego Bay (MBJ), and the cheapest round-trip airline ticket found on this route in the last 5 days was $407.

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

The average price for all round-trip flights from Chicago to Jamaica depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Jamaica is generally in the morning, when round-trip flights cost $545 on average. The most expensive time of day to fly to Jamaica is generally in the morning, which is peak travel time and where the average cost of a ticket is $545.

Can I save money by flying with a layover from Chicago to Jamaica?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $495, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago to Jamaica?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Jamaica, 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 from Chicago to Jamaica is December, when tickets cost $84 (return) on average. On the other hand, the most expensive months are September and February, when the average cost of round-trip tickets is $238 and $222 respectively.

What’s the cheapest day of the week to fly from Chicago to Jamaica?

The average price of all round-trip flights from Chicago to Jamaica clicked on KAYAK for each day over the last 12 months.

For Chicago to Jamaica, Tuesday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Jamaica back to Chicago, the best deals are generally found on Wednesday, with Monday being the most expensive.

How far in advance should I book a flight from Chicago to Jamaica?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Jamaica, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Jamaica, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Find deals

Good to know

Low seasonSeptember
Cheapest flight$154
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Chicago O'Hare Airport to Kingston

FAQs - booking Jamaica flights

  • Are there airlines that offer direct flights to Jamaica from Chicago?

    If you’d like to travel to Jamaica from Chicago on a direct flight, you can travel with United Airlines or American Airlines, as these two airlines offer direct flights from Chicago’s O’Hare International Airport to Sangster International Airport.

  • Which Jamaican airport is closest to Montego Bay?

    Suppose your final destination in Jamaica is Montego Bay. In that case, you should book a flight from Chicago that lands at Sangster International Airport, given that this airport is the closest airport to the city.

  • How will I get to Montego Bay from Sangster International Airport?

    To get to Montego Bay from Sangster International Airport, you can board a taxi, van, or bus. Onboard any, you won’t spend a fortune, as these transport vehicles offer their services at pocket-friendly rates.

  • Which of the airlines that fly from Chicago to Jamaica are eco-friendly?

    If you’re an eco-conscious traveler, you should travel with American Airlines as this air travel company has taken eco-friendly steps, such as funding sustainable aviation fuel research, partnering with carbon offset companies, and investing in planes that consume less fuel and emit fewer gases.

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

    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 from Chicago to Jamaica.

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

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

  • What is the Hacker Fare option on flights from Chicago to Jamaica?

    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 from Chicago to Jamaica 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 from Chicago to Jamaica?

    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 from Chicago to Jamaica 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 Jamaica

  • Most flights from Chicago to Jamaica usually take off from Chicago’s O’Hare International Airport. However, few depart Chicago to Jamaica at Chicago Midway International Airport. Given that the flights to Jamaica from Midway International Airport are limited, you should choose O’Hare International Airport. One of the busiest transportation networks in the country, this airport has amenities like clean and accessible washrooms, large waiting lounges, payphones, and ATMs. While waiting for your flight at this airport, you’ll be able to have a meal, shop, and even appreciate art.
  • When booking a flight from Chicago to Jamaica, you should choose one that lands at an airport near the region you plan to visit. If you are traveling to Jamaica’s western region, you should book a flight that lands at Sangster International Airport. However, if you plan on visiting Jamaica’s eastern region, you should book a flight that lands at Norman Manley International Airport.
  • If you plan on renting a car that you’ll travel in with your kid while in Jamaica, it’s advisable that you carry an approved child safety seat. This is because, in Jamaica, young children are required to be seated in approved child safety seats while being transported in a car. If you don’t own one, you should see if the car rental company can provide you with one.
  • To be allowed through airport security once you land in Jamaica, you’ll need a passport with adequate blank pages and proof that you’ve got enough money to comfortably stay in the country. Kindly note that if you plan on staying in the country for more than 90 days, you’ll also have to avail your passport.
  • Jamaican airport authorities have a reputation for being extremely strict. Thus, to get cleared by them, kindly ensure that you’ve got your documents in check.
  • Norman Manley International Airport in Kingston is the airport with the most flights to other Caribbean countries. If you plan on flying to other Caribbean countries once you’ve toured Jamaican, this is the airport you should be close to.

Everything you need to know for your flight from Chicago to Jamaica

Cabin class types available on flights to Jamaica

Cabin classes available on flights to Jamaica. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights from Chicago to Jamaicafrom $1,470
Business Class flights from Chicago to Jamaicafrom $1,233
Premium Economy Class flights from Chicago to Jamaicafrom $1,447
Economy Class flights from Chicago to Jamaicafrom $407