Cheap flights from Jamaica to Chicago from $174
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 8/6. 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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American Airlines flights from Jamaica to Chicago
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Frontier flights from Jamaica to Chicago
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How to get the cheapest flight ticket from Jamaica to Chicago
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 month to fly to Chicago?
The month of September is, on average, the cheapest month to fly to Chicago from Jamaica, with most prices found around $330. If you’re not able to fly to Chicago in September, then April is your next best option. Flight prices from Jamaica to Chicago during April average around $406.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $488. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Jamaica to Chicago for around $634.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Jamaica to Chicago during this time can be as low as $448. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $518.
What is the cheapest Jamaica to Chicago flight route?
Fly from Montego Bay Sangster Intl to Chicago O'Hare Intl for the best Jamaica - Chicago flight prices
What is the cheapest airline that flies from Jamaica to Chicago?
Spirit Airlines, Delta, and American Airlines are the most popular carriers operating from Jamaica to Chicago
What airlines fly to Chicago?
American Airlines, Spirit Airlines and Delta are the top three most popular airlines that fly to Chicago from Jamaica according to our data. American Airlines is the first choice among our users, with 43% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Jamaica to Chicago on average per day?
The number of flights available between Jamaica and Chicago is 2 per day as of June 2025. The most frequent departure time is 2:00PM, with 100% of daily flights leaving in the afternoon.
How many flights depart from Jamaica to Chicago on average per week?
The number of flights available between Jamaica and Chicago is 19 per week as of June 2025. The most frequent departure day is Mon, with 16% of weekly flights leaving on this day.
Cheap Jamaica to Chicago flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Jamaica to Chicago
When did momondo last update prices for flights from Jamaica to Chicago?
Prices for flights from Jamaica to Chicago refresh daily.
How many operators does momondo search for flights from Jamaica to Chicago?
The number of operators available for flights from Jamaica to Chicago is 5 as of June 2025.
How old do you have to be to fly from Jamaica to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Jamaica to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago 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. 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?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Jamaica to Chicago is Boeing 737 MAX 8 (21.01% of total bookings). The next most popular plane models are Airbus A321-100/200 (15.94%), Boeing 737-800 Passenger/BBJ2 (winglets) (11.59%), and Airbus A321neo (9.42%).
Best airlines flying from Jamaica to Chicago
Compare and see reviews for airlines that fly from Jamaica to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $251 | Free Cancellation | Rating 6.3 8,052 reviews | |||
| PriceFrom $255 | Free Cancellation | Rating 7.4 8,790 reviews | |||
| PriceFrom $322 | Free Cancellation | Rating 8.0 7,950 reviews | |||
| PriceFrom $357 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $509 | Free Cancellation | Rating 8.0 4,287 reviews |
Traveling to a place near Chicago?
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Why should I use momondo to find a flight deal from Jamaica to Chicago?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Jamaica to Chicago. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from Jamaica to Chicago with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for Jamaica to Chicago flights to just show those with flexible booking policies.
How can momondo help me find flights from Jamaica to Chicago?
momondo provides multiple filters to help you find the best flight to Chicago from Jamaica. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Jamaica to Chicago right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Jamaica to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.