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MDW - MBJ

Find cheap flights from Chicago Midway Airport to Montego Bay from $99

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Montego Bay departing on 5/14. 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
Thu 5/23
Thu 5/30

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Montego Bay, 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 Chicago to Montego Bay, as well as popular online travel agencies
In the last 7 days travelers have searched 44,632,927 times on KAYAK, and here is why:

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Cheap flight deals from Midway to Montego Bay (MDW-MBJ)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Montego Bay 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
6:45 am - 3:19 pmMDW-MBJ
8h 34m1 stop
3:34 pm - 1:53 pmMBJ-MDW
22h 19m1 stop
$238Frontier
Find Deal
Sat, May 4 - Wed, May 8
8:16 pm - 7:20 amMDW-MBJ
11h 04m1 stop
3:34 pm - 1:53 pmMBJ-MDW
22h 19m1 stop
$242Frontier
Find Deal
Tue, May 7 - Wed, May 8
6:45 am - 1:59 pmMDW-MBJ
7h 14m1 stop
8:07 am - 9:36 pmMBJ-MDW
13h 29m1 stop
$259Frontier
Find Deal
Sun, May 12 - Sat, May 18
6:55 am - 7:20 amMDW-MBJ
24h 25m1 stop
11:51 am - 10:41 pmMBJ-MDW
10h 50m1 stop
$266Frontier
Find Deal
Mon, May 6 - Sat, May 11
6:45 am - 3:19 pmMDW-MBJ
8h 34m1 stop
11:51 am - 10:41 pmMBJ-MDW
10h 50m1 stop
$276Frontier
Find Deal
Sat, May 4 - Sat, May 11
7:00 am - 2:53 pmMDW-MBJ
7h 53m1 stop
1:01 pm - 1:53 pmMBJ-MDW
24h 52m2 stops
Tue, May 7 - Wed, May 8
5:59 pm - 11:22 amMDW-MBJ
17h 23m2 stops
4:25 pm - 8:45 amMBJ-MDW
16h 20m2 stops
$472Delta
Find Deal
Sat, Sep 7 - Thu, Sep 12
6:00 am - 3:33 pmMDW-MBJ
9h 33m1 stop
4:59 pm - 7:55 amMBJ-MDW
14h 56m1 stop
$543Delta
Find Deal
Sat, May 4 - Sat, May 11
6:00 am - 3:33 pmMDW-MBJ
9h 33m1 stop
4:59 pm - 9:06 amMBJ-MDW
16h 07m2 stops
$547Delta
Find Deal
Sat, May 4 - Sat, May 11
6:00 am - 3:34 pmMDW-MBJ
9h 34m1 stop
4:59 pm - 7:55 amMBJ-MDW
14h 56m1 stop
$553Delta
Find Deal
Sat, May 11 - Wed, May 15

Flights from Midway to Montego Bay - Travel Insights & Trends

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

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

The average price of all flights from Chicago Midway Airport to Montego Bay clicked on KAYAK for each day over the last 12 months.
If you are looking for a flight deal from Chicago Midway Airport to Montego Bay, look for departures on Tuesdays and avoid leaving on a Wednesday, as it's usually the priciest day. When flying back from Montego Bay, Monday is the cheapest day to fly and Friday is the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to Montego Bay, 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 Chicago Midway Airport to Montego Bay is August, where tickets cost $472 on average. On the other hand, the most expensive months are December and June, where the average cost of tickets is $734 and $627 respectively.

How far in advance should I book a flight from Chicago Midway Airport to Montego Bay?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to Montego Bay, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to Montego Bay, you should book around 4 days before departure. For the absolute cheapest price, our data suggests you should book 86 days before departure.

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

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 ($99) and Delta ($287). The cheapest round-trip tickets were found on Frontier ($238) and Delta ($472).

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

There is a maximum of 1 nonstop flight a day that takes off from Chicago Midway Airport and lands in Montego Bay, with an average flight time of 3h 55m. The most common departure time is 9:00 am and most flights take off in the morning. Each week, there are 4 flights.

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

Early birds can take the earliest flight from Chicago Midway Airport at 9:05 am and will be landing in Montego Bay at 1:00 pm.

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

If you prefer to fly at night, the latest flight from Chicago Midway Airport to Montego Bay jets off at 10:25 am and lands at 2:20 pm.

Good to know

Low season

October

High season

June

Cheapest flight

$99
Best time to beat the crowds but there is an average 34% increase in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Chicago Midway Airport to Montego Bay

When to book flights from Midway to Montego Bay

Are your dates flexible? Find out the best times to travel from Midway to Montego Bay 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 Chicago Midway Airport to Montego Bay flights

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Montego Bay was $99 for a one-way ticket and $238 for a round-trip.

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

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

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

    We unfortunately don’t have that data for this specific route.

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

    You can catch a nonstop flight from Chicago Midway Airport to Montego Bay on Tuesday, Thursday, Saturday, and Sunday.

  • Which is the best airline for flights from Chicago to Montego Bay, Delta or Frontier?

    The two airlines most popular with KAYAK users for flights from Chicago to Montego Bay are Delta and Frontier. With an average price for the route of $755 and an overall rating of 8.0, Delta is the most popular choice. Frontier is also a great choice for the route, with an average price of $340 and an overall rating of 6.3.

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

    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 Chicago Midway Airport to Montego Bay.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Montego Bay from Chicago Midway Airport 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 Chicago Midway Airport to Montego Bay?

    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 Montego Bay with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and MBJ can sometimes prove cheaper using this method.

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

    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 Montego Bay from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

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

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

Nonstop departures

Chicago Midway to Montego Bay Sangster Intl

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Nonstop returns

Montego Bay Sangster Intl to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights
See more direct flights

Top airlines flying from Midway to Montego Bay

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Montego Bay. 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 Midway to Montego Bay? 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.
8.0
DeltaOverall score based on 11028 reviews
8.2boarding
7.5food
8.6crew
7.9comfort
8.0entertainment
Airline reviews

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

2.0 MediocreMarisol, Apr 2024DFW - ATL
Read more about Delta reviews

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive.

They did a fine job. Can't wait to use Delta in the future.

There was a loud squeaky sound the whole time we were flying.

Had a broken tray in business class. Crew just shrugged it off.

Seat back monitors and outlets were dead and not working.

Everything was great except for the seat. The backrest would not stay in the upright position.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

Flight delayed about 2 hrs so it made it a VERY late night

The crew, food, and entertainment were all good. But my screen had some sort of bug where if I turned it off, it would turn back on after 2-5 minutes. At full brightness. It made it very hard to get any shut-eye on the overnight flight. Also, the older Boeing plane, while nicely cared for (and no doors fell off 😅👏) doesn't have the nice air quality of newer planes. So I felt a bit greasy by the time we landed in Sweden.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Not have to pay for every single item to take a flight. Seating and delays sucked.

Flight was cancelled and I had to spend the night in the airport lugging my suitcase around

If you don’t check in 24 hours in advance, they will charge you $110 to check your bag instead of the $30. I did not get an email with this information and did not check in. In addition, my flight home was cancelled at layover and I had to spend the night in the airport, and then have another layover at another airport before making it home. Will not fly frontier again.

Terrible. Seats are bad and the baggage policy is inconsistent

Book cheap flights from Chicago to Montego Bay

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Montego Bay found on KAYAK in the last 72 hours.
5/14Tue
1 stopFrontier
7h 53mMDW-MBJ
$99
5/2Thu
1 stopFrontier
9h 03mMDW-MBJ
$103
5/1Wed
1 stopFrontier
24h 20mMDW-MBJ
$115
4/30Tue
1 stopFrontier
11h 04mMDW-MBJ
$120
5/7Tue
2 stops
15h 25mMDW-MBJ
$137
5/5Sun
2 stops
29h 24mMDW-MBJ
$167
5/3Fri
2 stopsDelta
16h 21mMDW-MBJ
$287
6/5Wed
1 stopDelta
9h 34mMDW-MBJ
$361
6/6Thu
3 stopsWestJet
22h 36mMDW-MBJ
$455
5/3Fri
3 stopsWestJet
23h 49mMDW-MBJ
$641

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Last minute flights from Midway to Montego Bay

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 Chicago to Montego Bay that are departing in the next 10 days.
4/26Fri
multi-stopFrontier
16h 30mMDW-MBJ
4/28Sun
multi-stopFrontier
12h 06mMBJ-MDW
$360
4/25Thu
multi-stopFrontier
9h 03mMDW-MBJ
4/30Tue
multi-stopFrontier
10h 43mMBJ-MDW
$430
4/27Sat
multi-stopFrontier
8h 34mMDW-MBJ
4/28Sun
multi-stopFrontier
32h 41mMBJ-MDW
$445
4/25Thu
multi-stopFrontier
9h 03mMDW-MBJ
4/29Mon
multi-stopFrontier
27h 41mMBJ-MDW
$447
4/27Sat
multi-stopDelta
7h 10mMDW-MBJ
5/1Wed
multi-stopDelta
16h 12mMBJ-MDW
$468
4/25Thu
multi-stopFrontier
50h 37mMDW-MBJ
4/30Tue
multi-stopFrontier
10h 43mMBJ-MDW
$506
4/25Thu
multi-stopFrontier
42h 38mMDW-MBJ
4/29Mon
multi-stopFrontier
22h 19mMBJ-MDW
$513
4/27Sat
multi-stopFrontier
8h 34mMDW-MBJ
5/1Wed
multi-stopFrontier
14h 58mMBJ-MDW
$567
4/27Sat
multi-stopWestJet
20h 02mMDW-MBJ
4/28Sun
multi-stopWestJet
16h 25mMBJ-MDW
$4,039
4/25Thu
multi-stopWestJet
20h 59mMDW-MBJ
4/30Tue
multi-stopWestJet
23h 00mMBJ-MDW
$4,725

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Chicago Midway Airport - Montego Bay Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

Montego Bay (MBJ)Jamaica

Return flight deals:

Montego Bay - Chicago Midway Airport

Cabin classes: