How to find cheap flights from Chicago to Jamaica
£294 is currently the cheapest price for a return flight from Chicago to Jamaica.
You'll be travelling from Chicago into Montego Bay in Montego Bay with that fare.
For one-way travel, the lowest available price right now is £138.
Want to let the lowest fares decide your next stop? Select 'Jamaica' in the 'To' field to find the cheapest deals by city.
Jamaica has three international airports you can touch down at.
Expand your search by choosing 'Add nearby airports.' This will compare prices across the airports closest to both your departure and destination points, which could help you save.
Book early. You'll have more times, routes and airlines to pick from. Wait until the last moment and you're likely to be left with fewer options and higher costs.
Get notified when fares change by creating a Price Alert. Download the Skyscanner app to get updates as they happen on your phone.
Best time to fly from Chicago to Jamaica
November is usually the cheapest month to hop on a flight from Chicago to Jamaica.
In general, taking a midweek flight can help you cut costs. Tuesdays and Wednesdays often mean lower prices.
January, July and December are the most popular months to travel to Jamaica. December leads the way, making it a great time to visit if you like things to feel a little more lively.
August, September and October are the quietest months. September sees the lowest overall travel demand and is a good choice if you prefer a more laid-back experience.
Flights from Chicago to Jamaica: what to expect
When flying from Chicago, you can leave from Chicago O'Hare International Airport (ORD) or Chicago Midway Airport (MDW).
At least one airport in Jamaica can be reached on a nonstop flight from Chicago.
Roughly 14 direct flights operate each week between Chicago and cities around Jamaica.
The leading airlines operating on this route are:
Montego Bay is one of the most popular routes from Chicago to Jamaica.
The average journey on this route comes in at around 4 hours 5 minutes.
Popular places to visit in Jamaica
Montego Bay
This Saint James Parish city is one of the top destinations for Chicago to Jamaica flights. Start your sightseeing at unmissable attractions like Coral Gardens Neighbourhood Beach, Harmony Beach and Fort Montego.
Montego Bay Airport (MBJ) is Montego Bay's busiest airport.
When you're ready to find somewhere comfortable to stay, explore the range of hotels in Montego Bay.
Kingston
Work your way through this Saint Andrew Parish city's biggest highlights including Bob Marley Statue, Devon House and Cascade Falls.
Kingston Norman Manley Airport (KIN) is the city's main airport.
That same magic that powers our flight search can also help you find the best-value stays around. Use it to compare availability and prices across hotels in Kingston.
Ocho Rios
Well-known sights to squeeze in while you're in this part of Saint Ann Parish include The World Famous Dunn's River Falls & Park, Ocho Rios Bay Beach and Jamaican Bobsled Rollercoaster.
Ocho Rios Airport (OCJ) is the main airport to plan your flight around.
From short city visits to longer stays, hotels in Ocho Rios cover a wide range of travel styles and budgets.
Visiting Jamaica for the first time? Here's what you need to know
Entry rules can often change, so check in advance whether you'll need a visa or other documentation before you travel. Your airline, travel agent or the local embassy or consulate should have the latest details.
The local currency is the Jamaican dollar (JMD).
Kingston is the capital of Jamaica, which has a population of around 2.8 million.
Time is the same across this destination, with a single standard time zone fixed at UTC-5.
For a warmer trip to Jamaica, consider July.
Time your visit for around January if you prefer cooler conditions.
January tends to be the driest month, while September is the wettest.
Headline events on the local calendar include Independence Day, Reggae Sumfest and Carnival celebrations. Line up your Chicago to Jamaica flight around occasions like these for an experience that goes beyond sightseeing.
Complete your trip with hotels and a car rental
With your cheap flight from Chicago to Jamaica booked, it's now time to plan what comes next. Find the best prices and exclusive rates for hotels in Jamaica. You can also check out car rental options in Jamaica and compare deals from trusted providers in seconds.
