Cheap flights from Jamaica to Chicago from $214
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Jamaica to Chicago departing on 6/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Recent round-trip flight deals from Jamaica to Chicago
Recent one-way flight deals from Jamaica to Chicago
Southwest flights from Jamaica to Chicago Midway Airport
Our best Southwest deals on Jamaica to Chicago Midway Airport flight tickets
Frontier flights from Jamaica to Chicago Midway Airport
Our best Frontier deals on Jamaica to Chicago Midway Airport flight tickets
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How to get the cheapest flight ticket from Jamaica to Chicago Midway Airport
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Jamaica at noon is the least expensive time of day to depart. momondo users have found prices as low as $568 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $763. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Jamaica to Chicago Midway flight route?
Fly from Montego Bay Sangster Intl to Chicago Midway for the best Jamaica - Chicago Midway flight prices
How long does it take to fly to Chicago Midway Airport?
On average, it takes 4h 29m to fly from Jamaica to Chicago Midway Airport if you fly out of Montego Bay (the most popular airport in Jamaica) and into Chicago O'Hare Intl Airport (the most popular airport in Chicago Midway Airport). If you’re flying out of Kingston and into Chicago O'Hare Intl Airport, then the flight time is around 9h 26m.
Cheap Jamaica to Chicago Midway Airport flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Jamaica to Chicago Midway Airport
When did momondo last update prices for flights from Jamaica to Chicago Midway Airport?
Prices for flights from Jamaica to Chicago Midway Airport refresh daily.
How many operators does momondo search for flights from Jamaica to Chicago Midway Airport?
As of May 2025, there is 1 operator available to choose from for flights from Jamaica to Chicago Midway Airport.
How old do you have to be to fly from Jamaica to Chicago Midway Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Jamaica to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Jamaica to Chicago Midway Airport?
Based on momondo bookings for flights between Jamaica and Chicago Midway Airport, the leading plane model is Boeing 737-800 Passenger/BBJ2 (winglets), making up 50.00% of the total bookings. Other popular models include Boeing 737 MAX 8 with 20.00%, Airbus A321-100/200 with 10.00%, and Boeing 737-800 with 10.00%.
Best airlines flying from Jamaica to Chicago Midway Airport
Compare and see reviews for airlines that fly from Jamaica to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $332 | Free Cancellation | Rating 8.0 7,944 reviews | |||
| PriceFrom $509 | Free Cancellation | Rating 8.0 4,292 reviews |
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Jamaica to Chicago?
Finding the right flight to Chicago from Jamaica is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.
Can I find flights from Jamaica to Chicago with flexible booking policies on momondo?
Flights from Jamaica to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Jamaica to Chicago?
Once all potential Jamaica to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Jamaica to Chicago right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Chicago from Jamaica. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.