Cheap flights from Chicago to Montego Bay from $208

If you aren’t able to travel to Montego Bay during the month of April, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $504.

On average, the least expensive day to fly to Montego Bay from Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $486. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Montego Bay on Saturday is $642.

Fly from Chicago O'Hare Intl to Montego Bay Sangster Intl for the best Chicago - Montego Bay Sangster Intl flight prices

You are more likely to see cheaper flights to Montego Bay from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Montego Bay for around $569 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Montego Bay from Chicago for as low as $479 on momondo.

There are 3 cabin classes available to choose from on Chicago to Montego Bay flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

No. A direct flight is the cheapest option for a flight between Chicago to Montego Bay.

Air Canada, Southwest, and United Airlines are the most popular carriers operating from Chicago to Montego Bay Sangster Intl

American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Montego Bay from Chicago according to our data. American Airlines is the first choice among our users, with 61% of people opting to fly with this airline when traveling to Montego Bay. Keep in mind that there are 6 different airlines that fly to Montego Bay on a routine basis, so you have a few additional options to choose from.

Orlando (MCO) was the most common stop: 30% of momondo users choosing 1-stop flights on this route connected there.

Flights via Toronto (YYZ) offer the lowest average round-trip price of $453.

Flights connecting via Orlando (MCO) have the shortest average one-way travel time: 6h 27m.

Atlanta (ATL) has the shortest average layover time for this route: 2h 30m.

As of November 2026, there are 2 flights per day flying from Chicago to Montego Bay. The most common time of day flights depart is 8:00AM, with 100% of flights taking off at noon.

As of November 2026, there are 14 flights per week flying from Chicago to Montego Bay. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.