When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 49 days in advance, which can save you up to 3% on flights from Chicago Midway to Jamaica compared to booking the week you need them. Waiting 49 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $441. For sooner than that we have options available in the next 3 days from $445.
August is one of the best times of the year to fly to Jamaica from Chicago Midway. Prices for August average $452 per person but you can even find prices for as low as $210. The most expensive prices can be found in the month of December. Opting for a August flight can save you 29% on your journey compared to booking in August