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MBJ - CHI

$148 Find cheap flights from Montego Bay to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Montego Bay to Chicago departing on 5/15. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Mon 6/3
Mon 6/10

Search hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Montego Bay to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Montego Bay to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 43,369,418 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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Cheap flight deals from Montego Bay to Chicago (MBJ-CHI)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Montego Bay to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
12:45 pm - 11:29 pmMBJ-ORD
10h 44m1 stop
5:00 am - 11:41 amORD-MBJ
6h 41m1 stop
$225Spirit Airlines
Find Deal
Fri, May 31 - Mon, Jun 3
1:05 pm - 9:55 amMBJ-ORD
20h 50m2 stops
5:00 am - 11:41 amORD-MBJ
6h 41m1 stop
$260Spirit Airlines
Find Deal
Fri, May 31 - Mon, Jun 3
8:07 am - 4:31 pmMBJ-ORD
8h 24m1 stop
11:28 am - 6:57 amORD-MBJ
19h 29m1 stop
$329Frontier
Find Deal
Fri, Aug 23 - Mon, Aug 26
8:07 am - 5:12 pmMBJ-MDW
9h 05m1 stop
6:56 am - 2:11 pmMDW-MBJ
7h 15m1 stop
$330Frontier
Find Deal
Sun, Jun 2 - Sun, Jun 9
2:05 pm - 6:35 pmMBJ-ORD
4h 30mnonstop
8:45 am - 12:45 pmORD-MBJ
4h 00mnonstop
$357American Airlines
Find Deal
Wed, May 15 - Mon, Sep 2
2:05 pm - 6:35 pmMBJ-ORD
4h 30mnonstop
5:19 am - 2:04 pmORD-MBJ
8h 45m1 stop
$362American Airlines
Find Deal
Wed, May 15 - Wed, Sep 4
12:45 pm - 9:38 pmMBJ-ORD
8h 53m1 stop
11:28 am - 6:57 amORD-MBJ
19h 29m1 stop
Wed, Jul 24 - Mon, Aug 5
4:59 pm - 11:55 pmMBJ-ORD
6h 56m1 stop
7:35 pm - 11:36 amORD-MBJ
16h 01m2 stops
$423Delta
Find Deal
Wed, May 15 - Mon, Sep 2
8:07 am - 8:45 pmMBJ-ORD
12h 38m1 stop
7:59 pm - 6:57 amORD-MBJ
10h 58m1 stop
Sun, Jul 14 - Sun, Aug 25
2:25 pm - 10:01 pmMBJ-MDW
7h 36m1 stop
6:00 am - 3:34 pmMDW-MBJ
9h 34m1 stop
$786Delta
Find Deal
Fri, May 31 - Mon, Jun 3

Flights from Montego Bay to Chicago - Travel Insights & Trends

Get data-powered insights and trends into flights from Montego Bay to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Montego Bay to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Montego Bay to Chicago.
Our data shows that the cheapest route for a one-way flight from Montego Bay to Chicago cost $202 and was between Montego Bay and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $330.

What’s the cheapest day of the week to fly from Montego Bay to Chicago?

The average price of all flights from Montego Bay to Chicago clicked on KAYAK for each day over the last 12 months.
When flying from Montego Bay to Chicago, you should consider leaving on a Wednesday and avoid Mondays if you are looking for the best rates. For your return to Montego Bay, you’ll find the best rates on Tuesdays and the most expensive ones on Thursdays.

What is the cheapest month to fly from Montego Bay to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Montego Bay to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Montego Bay to Chicago is May, where tickets cost $244 on average. On the other hand, the most expensive months are February and December, where the average cost of tickets is $782 and $636 respectively.

Which airlines provide the cheapest flights from Montego Bay to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Frontier ($148) and Spirit Airlines ($163). The cheapest round-trip tickets were found on Spirit Airlines ($225) and Frontier ($329).

Which airlines fly non-stop between Montego Bay and Chicago?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Montego Bay to Chicago.
There are 3 airlines that fly nonstop from Montego Bay to Chicago. They are: American Airlines, Southwest and United Airlines. The cheapest price of all airlines flying this route was found with United Airlines at $310 for a one-way flight. On average, the best prices for this route can be found at United Airlines.

How many flights are there between Montego Bay and Chicago per day?

Each day, there are between 2 and 3 nonstop flights that take off from Montego Bay and land in Chicago, with an average flight time of 4h 20m. The most common departure time is 12:00 pm and most flights take off in the afternoon, while the most flights land at Chicago O'Hare Intl Airport. Each week, there are 17 flights. The most frequent day of departure is Sunday, when 18% of all weekly flights depart. The fewest flights depart on a Thursday.

Which cabin class options are there for flights between Montego Bay and Chicago?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 3 cabin class options for the route. These are Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Montego Bay to Chicago take?

Direct flights cover the 1,712 miles separating Montego Bay to Chicago in about 4h 24m.

What’s the earliest departure time from Montego Bay to Chicago?

Early birds can take the earliest flight from Montego Bay at 12:40 pm and will be landing in Chicago at 4:50 pm.

What’s the latest departure time from Montego Bay to Chicago?

If you prefer to fly at night, the latest flight from Montego Bay to Chicago jets off at 3:20 pm and lands at 7:25 pm.

Good to know

Low season

January

High season

July

Cheapest flight

$148
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Montego Bay to Chicago O'Hare Airport

When to book flights from Montego Bay to Chicago

Are your dates flexible? Find out the best times to travel from Montego Bay to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Montego Bay to Chicago

  • What is the cheapest flight from Montego Bay to Chicago?

    In the last 3 days, the lowest price for a flight from Montego Bay to Chicago was $148 for a one-way ticket and $225 for a round-trip.

  • Do I need a passport to fly between Montego Bay and Chicago?

    A passport is required to fly from Montego Bay to Chicago.

  • Which airports will I be using when flying from Montego Bay to Chicago?

    Montego Bay is served by only 1 airport and there are 2 airports in Chicago. You will leave Montego Bay from Montego Bay Sangster Intl and you will be arriving in Chicago at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Montego Bay to Chicago?

    American Airlines, Air Canada, and Delta offer inflight Wi-Fi service on the Montego Bay to Chicago flight route.

  • Which aircraft models fly most regularly from Montego Bay to Chicago?

    The Boeing 737-900 is the aircraft model that flies most regularly on the Montego Bay to Chicago flight route.

  • Which airline alliances offer flights from Montego Bay to Chicago?

    oneworld, and Star Alliance are the airline alliances operating flights between Montego Bay and Chicago, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Montego Bay to Chicago?

    There are nonstop flights from Montego Bay to Chicago on a daily basis.

  • Which is the best airline for flights from Montego Bay to Chicago, American Airlines or United Airlines?

    The two airlines most popular with KAYAK users for flights from Montego Bay to Chicago are American Airlines and United Airlines. With an average price for the route of $453 and an overall rating of 7.3, American Airlines is the most popular choice. United Airlines is also a great choice for the route, with an average price of $404 and an overall rating of 7.3.

  • How does KAYAK find such low prices on flights from Montego Bay to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Montego Bay to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Montego Bay to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Montego Bay is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Montego Bay to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Montego Bay with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Montego Bay to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Montego Bay up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding a cheap flight from Montego Bay to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $229 or less one-way and $357 or less round-trip.

Prefer to fly non-stop from Montego Bay to Chicago?

Find which airlines fly direct from Sangster Intl to Chicago, which days they fly and book direct flights.

Nonstop departures

Montego Bay Sangster Intl to Chicago

Monday

American Airlines, British Airways, Southwest

American Airlines, British Airways, +1 more

Tuesday

American Airlines, British Airways, Southwest

American Airlines, British Airways, +1 more

Wednesday

American Airlines, British Airways, Southwest

American Airlines, British Airways, +1 more

Thursday

American Airlines, British Airways, Southwest

American Airlines, British Airways, +1 more

Friday

American Airlines, British Airways, Southwest, +1 more

American Airlines, British Airways, +2 more

Saturday

American Airlines, British Airways, Southwest, +1 more

American Airlines, British Airways, +2 more

Sunday

American Airlines, British Airways, Southwest, +1 more

American Airlines, British Airways, +2 more

See more direct flights

Nonstop returns

Chicago to Montego Bay Sangster Intl

Monday

American Airlines, Southwest

American Airlines, Southwest

Tuesday

American Airlines, Southwest

American Airlines, Southwest

Wednesday

American Airlines, Southwest

American Airlines, Southwest

Thursday

American Airlines, Southwest

American Airlines, Southwest

Friday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Saturday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Sunday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

See more direct flights
See more direct flights

Top airlines flying from Montego Bay to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Montego Bay to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Montego Bay to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.3
United AirlinesOverall score based on 11125 reviews
7.1Entertainment
7.7Boarding
6.7Food
7.2Comfort
8.1Crew
Airline reviews

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

8.0 ExcellentAnonymous, Apr 2024YUL - ORD
Read more about United Airlines reviews

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

The plane was old and in new of a cleaning up and renovating on the interior. Seats and carpets were very worn and dirty looking. Cushioning on the seats was broken down and not as comfortable as newer jet seats. Food was a little below average but okay. Staff were friendly and hard working but did not pick up debris or food they spilled when collecting from the customers. But they were very helpful and professional.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

lounge was the highlight - seats weren't that comfortable - it was a full flight but no complaints

Book cheap flights from Montego Bay to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Montego Bay to Chicago found on KAYAK in the last 72 hours.
5/15Wed
1 stopFrontier
8h 55mMBJ-ORD
$148
5/22Wed
1 stopSpirit Airlines
10h 46mMBJ-ORD
$163
5/15Wed
nonstopAmerican Airlines
4h 30mMBJ-ORD
$221
5/12Sun
1 stopCopa Airlines
12h 11mMBJ-ORD
$222
10/13Sun
1 stopCopa Airlines
11h 57mMBJ-ORD
$262
6/25Tue
2 stops
29h 07mMBJ-ORD
$268
5/15Wed
2 stopsAmerican Airlines
11h 19mMBJ-ORD
$275
5/26Sun
2 stops
12h 00mMBJ-MDW
$275
5/12Sun
nonstopUnited Airlines
4h 24mMBJ-ORD
$341
7/7Sun
nonstopUnited Airlines
4h 24mMBJ-ORD
$462

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Last minute flights from Montego Bay to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Montego Bay to Chicago that are departing in the next 10 days.
5/8Wed
multi-stopFrontier
8h 55mMBJ-ORD
5/11Sat
multi-stopFrontier
9h 19mORD-MBJ
$334
5/8Wed
multi-stopUnited Airlines
7h 18mMBJ-ORD
5/11Sat
nonstopUnited Airlines
4h 00mORD-MBJ
$367
5/8Wed
multi-stopAmerican Airlines
9h 05mMBJ-ORD
5/11Sat
multi-stopAmerican Airlines
6h 25mORD-MBJ
$453
5/8Wed
nonstopAmerican Airlines
4h 30mMBJ-ORD
5/11Sat
nonstopAmerican Airlines
4h 00mORD-MBJ
$599
5/8Wed
multi-stopDelta
14h 56mMBJ-MDW
5/11Sat
multi-stopDelta
21h 13mMDW-MBJ
$655
5/8Wed
multi-stopFrontier
14h 58mMBJ-MDW
5/11Sat
multi-stopFrontier
8h 34mMDW-MBJ
$691

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Montego Bay - Chicago Flights

Departure:

Montego Bay (MBJ)Jamaica

Return flight deals:

Chicago - Montego Bay

Cabin classes:

$614
$2,633
$330