Cheap flights from Chicago to Montego Bay from $123
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 to Montego Bay departing on 8/20. 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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How to get the cheapest flight ticket from Chicago to Montego Bay
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 typical price of a round-trip flight between Chicago and Montego Bay?
What is the cheapest month to fly to Montego Bay?
If you aren’t able to travel to Montego Bay during the month of January, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $526.
What is the cheapest day to depart on your flight to Montego Bay?
On average, the least expensive day to fly to Montego Bay from Chicago is on a Sunday. momondo users have found tickets for Sunday departures for as low as $534. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Thursday as prices are generally higher than usual. According to our data, the average ticket price to Montego Bay on Thursday is $672.
What is the cheapest time of day to depart on your flight to Montego Bay?
At noon is the cheapest time of day to fly from Chicago to Montego Bay when you can find flight prices for as low as $403. Flying to Montego Bay at noon is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $605.
What is the cheapest Chicago to Montego Bay Sangster Intl flight route?
Fly from Chicago Midway to Montego Bay Sangster Intl for the best Chicago - Montego Bay Sangster Intl flight prices
How far in advance should I book a flight to Montego Bay?
You are more likely to see cheaper flights to Montego Bay from Chicago when booking 16 weeks ahead of your departure date. In general, you can expect to find flights to Montego Bay for around $603 when searching 16 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 $544 on momondo.
What cabin class options are available on Chicago to Montego Bay Sangster Intl flights?
There are 3 cabin classes available to choose from on Chicago to Montego Bay Sangster Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Chicago to Montego Bay flights?
You could potentially save up to 14% on your flight if you consider stops on a Chicago to Montego Bay flight.
How have Chicago to Montego Bay flight prices changed over time?
As of June 2025, prices for Chicago to Montego Bay flights are approximately 16% more expensive when compared to flights at the same time last year.
What is the cheapest airline that flies from Chicago to Montego Bay Sangster Intl?
Spirit Airlines, Delta, and United Airlines are the most popular carriers operating from Chicago to Montego Bay Sangster Intl
What airlines fly to Montego Bay?
American Airlines, United Airlines and Spirit Airlines 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 62% 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.
How many flights depart from Chicago to Montego Bay on average per day?
As of June 2025, there are 1 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.
How many flights depart from Chicago to Montego Bay on average per week?
As of June 2025, there are 12 flights per week flying from Chicago to Montego Bay. The most common day of the week flights depart is Mon, with 17% of flights taking off on this day.
When to book flights from Chicago to Montego Bay
Cheap Chicago to Montego Bay (CHI to MBJ) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Montego Bay
Best Price Found | $123 |
|---|---|
Fastest flight time | 3h 58m |
Direct flights | Every day |
Airports in Montego Bay | 1 airport |
How far is Chicago to Montego Bay Sangster Intl by plane?
The distance between Chicago and Montego Bay Sangster Intl is about 1713.9 mi. A reasonable flight in good conditions will take 4h 00m.
When did momondo last update prices for flights from Chicago to Montego Bay Sangster Intl Airport?
Prices for flights from Chicago to Montego Bay Sangster Intl Airport refresh daily.
How many operators does momondo search for flights from Chicago to Montego Bay Sangster Intl Airport?
The number of operators available for flights from Chicago to Montego Bay Sangster Intl Airport is 6 as of June 2025.
How old do you have to be to fly from Chicago to Montego Bay Sangster Intl Airport?
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 to Montego Bay Sangster Intl Airport.
What documentation or ID do you need to fly to Montego Bay Sangster Intl Airport?
The required travel and health documents for your Montego Bay Sangster Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Montego Bay Sangster Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Chicago to Montego Bay?
momondo data reveals that the most frequently booked plane model on the route from Chicago to Montego Bay is Boeing 737-800, representing 57.13% of all bookings. The subsequent popular models are Airbus A321-100/200 at 16.65%, Boeing 737 MAX 8 at 14.16%, and Boeing 737-800 Passenger/BBJ2 (winglets) at 10.53%.
What is the most popular airline from Chicago to Montego Bay?
Based on momondo bookings for flights between Chicago and Montego Bay, the leading airline is American Airlines, making up 59% of the total bookings. Other popular airlines include United Airlines with 24%, Spirit Airlines with 8%, and Southwest with 6%.
Best airlines flying from Chicago to Montego Bay
Compare and see reviews for airlines that fly from Chicago to Montego Bay with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $276 | Free Cancellation | Rating 6.3 8,052 reviews | |||
| PriceFrom $338 | Free Cancellation | Rating 5.9 3,295 reviews | |||
| PriceFrom $410 | Free Cancellation | Rating 7.4 8,790 reviews | |||
| PriceFrom $427 | Free Cancellation | Rating 8.0 7,946 reviews | |||
| PriceFrom $427 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $579 | Free Cancellation | Rating 8.0 4,287 reviews |
Southwest Flights From Chicago to Montego Bay
Southwest flight deals from Chicago to Montego Bay start from $579 round-trip. Over the 5 Southwest flights for this route in a normal week, average airfare is usually $741 round-trip - but some users have found much cheaper deals with momondo.
American Airlines Flights From Chicago to Montego Bay
American Airlines is also a popular choice for this route. American Airlines flight deals for Chicago to Montego Bay start from as low as $427 round-trip, depending on your selected dates, with average American Airlines deals seen on momondo around $600. American Airlines operates 7 flights to Montego Bay from Chicago in an average week. Users have rated it 7.2/10 across 10,000 reviews.
Traveling to a place near Montego Bay?
Book flights to Montego Bay if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Chicago to Montego Bay?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Montego Bay. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from Chicago to Montego Bay with flexible booking policies on momondo?
Flights from Chicago to Montego Bay with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Chicago to Montego Bay?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Montego Bay from Chicago.
I’m not ready to book a flight from Chicago to Montego Bay right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Montego Bay from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.