Cheap flights from Montego Bay to Chicago from $166
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Montego Bay to Chicago departing on 9/4. 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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American Airlines flights from Montego Bay to Chicago
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Spirit Airlines flights from Montego Bay to Chicago
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How to get the cheapest flight ticket from Montego Bay to Chicago
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 cheapest month to fly to Chicago?
The month of September is, on average, the cheapest month to fly to Chicago from Montego Bay, with most prices found around $330. If you’re not able to fly to Chicago in September, then April is your next best option. Flight prices from Montego Bay to Chicago during April average around $406.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $462. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Montego Bay to Chicago for around $634.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Montego Bay to Chicago during this time can be as low as $489. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $504.
What is the cheapest Montego Bay Sangster Intl to Chicago flight route?
Fly from Montego Bay Sangster Intl to Chicago O'Hare Intl for the best Montego Bay Sangster Intl - Chicago flight prices
What cabin class options are available on Montego Bay Sangster Intl to Chicago flights?
There are 4 cabin classes available to choose from on Montego Bay Sangster Intl to Chicago 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 Montego Bay to Chicago flights?
No. A direct flight is the cheapest option for a flight between Montego Bay to Chicago.
What is the cheapest airline that flies from Montego Bay Sangster Intl to Chicago?
Spirit Airlines, American Airlines, and Delta are the most popular carriers operating from Montego Bay Sangster Intl to Chicago
What airlines fly to Chicago?
American Airlines, Spirit Airlines and Delta are the top three most popular airlines that fly to Chicago from Montego Bay according to our data. American Airlines is the first choice among our users, with 42% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Montego Bay to Chicago on average per day?
2 flights are operational daily from Montego Bay to Chicago as of July 2025. The most popular departure time for this route is 2:00PM, with 100% of flights per day taking off in the afternoon.
How many flights depart from Montego Bay to Chicago on average per week?
The number of flights available between Montego Bay and Chicago is 15 per week as of July 2025. The most frequent departure day is Mon, with 20% of weekly flights leaving on this day.
When to book flights from Montego Bay to Chicago
Cheap Montego Bay to Chicago (MBJ to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Montego Bay to Chicago
How far is Montego Bay Sangster Intl to Chicago by plane?
The distance between Montego Bay Sangster Intl and Chicago is about 1713.9 mi. 4h 10m is a normal flight duration for this route.
When did momondo last update prices for flights from Montego Bay Sangster Intl Airport to Chicago?
Prices for flights from Montego Bay Sangster Intl Airport to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from Montego Bay Sangster Intl Airport to Chicago?
The number of operators available for flights from Montego Bay Sangster Intl Airport to Chicago is 4 as of July 2025.
How old do you have to be to fly from Montego Bay Sangster Intl Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Montego Bay Sangster Intl Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Montego Bay to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Montego Bay to Chicago is Boeing 737 MAX 8 (24.68% of total bookings). The next most popular plane models are Airbus A321neo (18.35%), Boeing 737-800 (Scimitar Winglets) (17.09%), and Boeing 737-800 Passenger/BBJ2 (winglets) (10.13%).
What is the most popular airline from Montego Bay to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Montego Bay to Chicago is American Airlines (51% of total bookings). The next most popular airline is United Airlines (49%).
Best airlines flying from Montego Bay to Chicago
Compare and see reviews for airlines that fly from Montego Bay to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $251 | Free Cancellation | Rating 6.3 8,064 reviews | |||
| PriceFrom $255 | Free Cancellation | Rating 7.4 8,844 reviews | |||
| PriceFrom $376 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $509 | Free Cancellation | Rating 8.0 4,258 reviews |
Southwest Flights From Montego Bay to Chicago
Across 5 Southwest flights from Montego Bay to Chicago this week, the average price was $608, with the best Southwest deals starting from $509 round-trip. 4,256 users have rated Southwest on momondo, with an average score of 8.0/10.
American Airlines Flights From Montego Bay to Chicago
Across 10,000 American Airlines reviews on momondo, the average score is 7.2/10. American Airlines flies from Montego Bay to Chicago about 3 times each week, with ticket deals ranging from $376 to $491. Price data is based on momondo searches in the last 72 hours.
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Why should I use momondo to find a flight deal from Montego Bay to Chicago?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Montego Bay to Chicago. momondo saves you time and could save you money on your trip.
Can I find flights from Montego Bay to Chicago with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Chicago from Montego Bay with this policy.
How can momondo help me find flights from Montego Bay to Chicago?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Montego Bay to Chicago.
I’m not ready to book a flight from Montego Bay to Chicago right now. Can momondo alert me if prices change?
If you are not ready to book a flight from Montego Bay to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.