Cheap flights from Chicago Midway Airport to Jamaica from $109
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Jamaica departing on 9/20. 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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Southwest flights from Chicago Midway Airport to Jamaica
Our best Southwest deals on Chicago Midway Airport to Jamaica flight tickets
Delta flights from Chicago Midway Airport to Jamaica
Our best Delta deals on Chicago Midway Airport to Jamaica flight tickets
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How to get the cheapest flight ticket from Chicago Midway Airport to Jamaica
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 Jamaica?
The cheapest month to fly to Jamaica from Chicago Midway Airport is in July. Flight prices, which tend to average around $620, are often lower during this time because this is during the off-season. If you aren’t able to travel to Jamaica during the month of July, then flying in November is also cheap. Prices for this month can be found on momondo for an average of $625.
What is the cheapest day to depart on your flight to Jamaica?
The cheapest day to depart on your flight to Jamaica is on a Friday when prices can be found for as low as $579. This is often the case because there is less demand to fly during this day of the week. On the other hand, Wednesday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $832.
What is the cheapest time of day to depart on your flight to Jamaica?
Our most recent data shows that the best time of day to fly to Jamaica is in the afternoon. Flights from Chicago Midway Airport to Jamaica during this time can be as low as $436. In the morning is when there is more demand to fly to Jamaica, so prices are often more expensive at around $733 per ticket.
What is the cheapest Chicago Midway to Jamaica flight route?
Fly from Chicago Midway to Montego Bay Sangster Intl for the best Chicago Midway - Jamaica flight prices
How far in advance should I book a flight to Jamaica?
You are more likely to see cheaper flights to Jamaica from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Jamaica for around $741 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Jamaica from Chicago Midway Airport for as low as $507 on momondo.
What cabin class options are available on Chicago Midway to Jamaica flights?
There are 1 cabin classes available to choose from on Chicago Midway to Jamaica flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Chicago Midway to Jamaica?
Frontier, Delta, and Southwest are the most popular carriers operating from Chicago Midway to Jamaica
What airlines fly to Jamaica?
Southwest, Delta and Frontier are the top three most popular airlines that fly to Jamaica from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 69% of people opting to fly with this airline when traveling to Jamaica. Keep in mind that there are 3 different airlines that fly to Jamaica on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago Midway Airport to Jamaica on average per week?
As of July 2025, 5 flights take off from Chicago Midway Airport and land in Jamaica each week. The most common flight departure day for this route is Mon, with 20% of weekly flights taking off on this day.
Cheap Chicago Midway Airport to Jamaica flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Jamaica
Best Price Found | $109 |
|---|---|
Fastest flight time | 5h 48m |
Direct flights | Mon, Tue, Wed, Fri, Sat and Sun |
Airports in Jamaica | 2 airports |
When did momondo last update prices for flights from Chicago Midway Airport to Jamaica?
Prices for flights from Chicago Midway Airport to Jamaica were last updated today.
How many operators does momondo search for flights from Chicago Midway Airport to Jamaica?
As of July 2025, there are 3 operators available to choose from for flights from Chicago Midway Airport to Jamaica.
How old do you have to be to fly from Chicago Midway Airport to Jamaica?
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 Chicago Midway Airport to Jamaica.
What documentation or ID do you need to fly to Jamaica?
The necessary travel and health documents for your Jamaica trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago Midway Airport to Jamaica?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago Midway Airport to Jamaica is Boeing 737-800 Passenger/BBJ2 (winglets) (42.06% of total bookings). The next most popular plane models are Airbus A321-100/200 (29.91%), Boeing 737-800 (15.89%), and Boeing 737 MAX 8 (9.35%).
Best airlines flying from Chicago Midway Airport to Jamaica
Compare and see reviews for airlines that fly from Chicago Midway Airport to Jamaica with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $338 | Free Cancellation | Rating 5.9 3,286 reviews | |||
| PriceFrom $452 | Free Cancellation | Rating 8.0 7,982 reviews | |||
| PriceFrom $555 | Free Cancellation | Rating 8.0 4,266 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Jamaica?
It is quick and easy to find Chicago to Jamaica flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Jamaica that suits you.
Can I find flights from Chicago to Jamaica with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Jamaica from Chicago with this policy.
How can momondo help me find flights from Chicago to Jamaica?
momondo helps you find the best flight between Chicago and Jamaica by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
I’m not ready to book a flight from Chicago to Jamaica right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Chicago to Jamaica 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.