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MDW - MBJ

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

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
Mon 6/3
Mon 6/10

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 43,369,418 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
9:08 pm - 1:28 pmMDW-MBJ
16h 20m2 stops
8:07 am - 12:31 amMBJ-MDW
16h 24m2 stops
$283Frontier
Find Deal
Sat, May 18 - Tue, May 21
7:53 am - 3:35 pmMDW-MBJ
7h 42m1 stop
8:07 am - 12:31 amMBJ-MDW
16h 24m2 stops
$306Frontier
Find Deal
Sat, May 18 - Tue, May 21
7:53 am - 3:35 pmMDW-MBJ
7h 42m1 stop
8:07 am - 9:31 pmMBJ-MDW
13h 24m1 stop
$308Frontier
Find Deal
Sat, May 18 - Tue, May 21
9:44 pm - 2:46 pmMDW-MBJ
17h 02m1 stop
8:07 am - 9:10 pmMBJ-MDW
13h 03m1 stop
$327Frontier
Find Deal
Tue, Aug 6 - Tue, Aug 13
7:27 am - 2:46 pmMDW-MBJ
7h 19m1 stop
8:07 am - 9:10 pmMBJ-MDW
13h 03m1 stop
$328Frontier
Find Deal
Wed, Aug 7 - Tue, Aug 13
12:14 pm - 8:55 amMDW-MBJ
20h 41m1 stop
12:45 pm - 5:12 pmMBJ-MDW
28h 27m2 stops
Sun, May 26 - Sat, Jun 1
6:00 am - 1:05 pmMDW-MBJ
7h 05m1 stop
4:25 pm - 8:40 amMBJ-MDW
16h 15m2 stops
$472Delta
Find Deal
Wed, Jul 3 - Mon, Jul 8
3:45 pm - 11:36 amMDW-MBJ
19h 51m1 stop
2:25 pm - 9:47 pmMBJ-MDW
7h 22m1 stop
$554Delta
Find Deal
Thu, Aug 8 - Wed, Aug 14
5:50 pm - 11:22 amMDW-MBJ
17h 32m2 stops
12:50 pm - 9:44 pmMBJ-MDW
8h 54m1 stop
$588Delta
Find Deal
Sat, Oct 19 - Sat, Oct 26
6:00 am - 1:05 pmMDW-MBJ
7h 05m1 stop
12:50 pm - 9:41 pmMBJ-MDW
8h 51m1 stop
$681Delta
Find Deal
Wed, Jul 3 - Mon, Jul 8

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 Wednesday 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 $457 on average. On the other hand, the most expensive months are December and March, where the average cost of tickets is $707 and $639 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 ($389). The cheapest round-trip tickets were found on Frontier ($283) 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 7 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 8:40 am and will be landing in Montego Bay at 12:40 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 $283 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?

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

  • 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 $317 and an overall rating of 6.2.

  • 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 10838 reviews
8.2Boarding
8.0Entertainment
7.4Food
7.9Comfort
8.6Crew
Airline reviews

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

10.0 ExcellentAllan, May 2024SUN - SLC
Read more about Delta reviews

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

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

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
5/18Sat
1 stopFrontier
7h 42mMDW-MBJ
$162
6/23Sun
1 stopFrontier
7h 15mMDW-MBJ
$179
6/23Sun
2 stops
14h 48mMDW-MBJ
$182
7/7Sun
1 stopFrontier
9h 13mMDW-MBJ
$217
9/26Thu
1 stopFrontier
9h 13mMDW-MBJ
$227
7/16Tue
2 stops
13h 57mMDW-MBJ
$231
9/26Thu
2 stopsDelta
17h 23mMDW-MBJ
$389
5/14Tue
2 stopsWestJet
23h 05mMDW-MBJ
$1,909
5/14Tue
2 stopsWestJet
19h 06mMDW-MBJ
$1,913

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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.
5/7Tue
multi-stopFrontier
11h 04mMDW-MBJ
5/14Tue
multi-stopFrontier
10h 43mMBJ-MDW
$285
5/7Tue
multi-stopFrontier
7h 53mMDW-MBJ
5/9Thu
multi-stopFrontier
12h 55mMBJ-MDW
$333
5/8Wed
multi-stopFrontier
24h 20mMDW-MBJ
5/11Sat
multi-stopFrontier
10h 50mMBJ-MDW
$357
5/7Tue
multi-stopFrontier
7h 53mMDW-MBJ
5/8Wed
multi-stopFrontier
14h 58mMBJ-MDW
$408
5/7Tue
multi-stopFrontier
26h 19mMDW-MBJ
5/14Tue
multi-stopFrontier
10h 43mMBJ-MDW
$435
5/7Tue
multi-stopDelta
6h 49mMDW-MBJ
5/8Wed
multi-stopDelta
14h 56mMBJ-MDW
$669
5/8Wed
multi-stopDelta
9h 34mMDW-MBJ
5/11Sat
multi-stopDelta
16h 07mMBJ-MDW
$871
5/8Wed
multi-stopWestJet
23h 05mMDW-MBJ
5/11Sat
multi-stopWestJet
19h 45mMBJ-MDW
$3,916
5/8Wed
multi-stopWestJet
49h 45mMDW-MBJ
5/11Sat
multi-stopWestJet
21h 05mMBJ-MDW
$3,927
5/7Tue
multi-stopWestJet
21h 32mMDW-MBJ
5/9Thu
multi-stopWestJet
23h 07mMBJ-MDW
$4,117

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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: