August is the cheapest month to fly this route, with average fares around $355 round trip.
Average round-trip fares by departure month, based on current availability.
| Month | Avg Price | Lowest | Relative Cost | |
|---|---|---|---|---|
| May 2026 | $375 | $342 | ||
| June 2026 | $380 | $338 | Peak | |
| July 2026 | $357 | $338 | ||
| August 2026 | $355 | $352 | Best |
Departing on Tuesday offers the lowest average fares at $351. Thursday departures are the most expensive at $425, a difference of $74.
The best time to fly is August. Set up an alert and we'll notify you when prices drop.
Get Started Free →The cheapest month to fly from Chicago to Montego Bay is August, with average round-trip fares around $355. The lowest fare found in August is $352.
Tuesday departures are the cheapest, averaging $351 round trip. The most expensive day is Thursday at $425.
Based on current pricing trends, booking for August travel offers the best value. Avoid June if possible, as fares average $380 compared to $355 in the cheapest month. May is a solid middle-ground option at $375.
Flying in August instead of June can save you approximately $25 per round trip. The cheapest month averages $355 while the most expensive averages $380.
Airlines, flight times, price calendar, and more for Chicago to Montego Bay
View ORD → MBJ Details