Cheap Flights from Chicago to Montego Bay from $157

Frequently Asked Questions

• What are the cheapest flights from Chicago to Montego Bay (CHI-MBJ)?

  Based on Trip.com data, Air Canada offers one-way fares as low as $157 on Cheapest nonstop routes (e.g. ORD to MBJ on Sun, Dec 6), while Air Canada offers Cheapest nonstop round-trips from $364 departing on Tue, Nov 17 and returning on Sat, Nov 21.

• Which airlines offer direct flights from Chicago to Montego Bay?

  At the moment, you can catch a nonstop flight from Chicago to Montego Bay with the following airlines, including: American Airlines Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.

• When is the best time to book flights from Chicago to Montego Bay?

  By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Chicago to Montego Bay is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.

• How many flights are there per week from Chicago to Montego Bay?

  Based on Trip.com data in the past 4 weeks, there is 2 flight per week flying from Chicago to Montego Bay. You can check the weekly schedule for popular airlines on this route below: American Airlines: -/-/-/-/-/-/- -- AA3228 (09:10)

• How can I find the best deals on flights from Chicago to Montego Bay?

  To find best deals on flights from Chicago to Montego Bay, you can use various tools on Trip.com:
  · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Sun, Dec 6, with one-way flights priced at just $157.
  · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is American Airlines.
  · Set up price alerts to easily monitor ticket prices without having to check every day.
  · Check Trip.com flight deals and promo codes frequently.
  · Avoid peak season unless you book very early. It seems the peak season for Montego Bay travel is around January.
  · Get exclusive promo codes for Trip.com app users.

• When are flight tickets from Chicago (CHI) to Montego Bay (MBJ) the cheapest?

  The cheapest months to fly from Chicago to Montego Bay is October, when demand for travel is lower.

• Which upcoming date is cheapest to fly from Chicago to Montego Bay on?

  After crunching the numbers on our October flight calendar, it's currently cheapest to fly from Chicago to Montego Bay on October 24, 2026 with Air Canada, with prices starting at $357.

• Which airports can I fly into Montego Bay from Chicago?

  You can arrive at any of the following airports in Montego Bay: Sangster International Airport (MBJ). Flights from O'Hare International Airport to Sangster International Airport (ORD-MBJ) are by far the most popular option for this route.

• Is there any time difference between Chicago and Montego Bay?

  The time difference between Montego Bay and Chicago is 1h.

• How do I change or cancel my ticket from Chicago to Montego Bay?

  Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.

• What is the average cost of a one-way flight from Chicago to Montego Bay?

  Based on Trip.com data for flights departing in the next 30 days, the average one-way fare from Chicago to Montego Bay is $336. Fares vary by travel date, airline and availability.

• What is the average cost of a round-trip flight from Chicago to Montego Bay?

  Based on Trip.com data for travel in the next 30 days, the average round-trip fare from Chicago to Montego Bay is $580. The final price depends on the outbound and return dates, airline and fare conditions.

• How do I book flights from Chicago to Montego Bay on Trip.com?

  Enter Chicago and Montego Bay, choose your travel dates and passengers, then compare flights by price, duration and baggage. Select a fare, review the change and cancellation rules, enter traveler details and complete payment to receive your confirmation.

• Are there budget airlines on the Chicago to Montego Bay route?

  Jetblue Airwaysare the most popular budget airlines flying from Chicago to Montego Bay. Check baggage, seat and payment fees before comparing the final price.