MDW - MBJ

$142 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 9/26. 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
1 adult, Economy

KAYAK searches 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
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Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Montego Bay

Thu, Sep 18 - Sat, Sep 20
 Logo
4:56 pm - 9:47 amMDW-MBJ
16h 51m2 stops
 Logo
2:05 pm - 11:17 pmMBJ-MDW
9h 12m1 stop
Fri, Oct 3 - Mon, Oct 6
 Logo
1:49 pm - 10:17 amMDW-MBJ
20h 28m1 stop
 Logo
10:55 am - 6:43 pmMBJ-MDW
7h 48m1 stop
Sat, Sep 13 - Sat, Sep 20
Frontier Logo
6:15 am - 12:45 pmMDW-MBJ
6h 30m1 stop
Frontier Logo
2:05 pm - 12:44 pmMBJ-MDW
22h 39m2 stops
$397Frontier
Find Deal
Sat, Sep 13 - Sat, Sep 20
Frontier Logo
6:15 am - 12:45 pmMDW-MBJ
6h 30m1 stop
Frontier Logo
2:05 pm - 11:17 pmMBJ-MDW
9h 12m1 stop
$409Frontier
Find Deal
Sat, Oct 18 - Thu, Oct 23
Delta Logo
6:00 am - 12:07 pmMDW-MBJ
6h 07m1 stop
Delta Logo
2:45 pm - 10:14 pmMBJ-MDW
7h 29m1 stop
$410Delta
Find Deal
Fri, Oct 3 - Mon, Oct 6
 Logo
1:49 pm - 11:05 amMDW-MBJ
21h 16m2 stops
 Logo
10:55 am - 6:43 pmMBJ-MDW
7h 48m1 stop
Fri, Sep 19 - Sat, Sep 20
Frontier Logo
6:20 am - 12:45 pmMDW-MBJ
6h 25m1 stop
Frontier Logo
2:05 pm - 12:44 pmMBJ-MDW
22h 39m2 stops
$417Frontier
Find Deal
Sat, Dec 6 - Sun, Dec 14
Frontier Logo
6:00 am - 3:33 pmMDW-MBJ
8h 33m1 stop
Frontier Logo
4:53 pm - 11:05 pmMBJ-MDW
7h 12m1 stop
$419Frontier
Find Deal
Mon, Oct 20 - Wed, Oct 29
Southwest Logo
5:50 am - 1:35 pmMDW-MBJ
7h 45m1 stop
Southwest Logo
1:00 pm - 10:35 pmMBJ-MDW
9h 35m1 stop
$425Southwest
Find Deal
Sun, Sep 21 - Tue, Sep 23
Southwest Logo
5:45 am - 11:45 amMDW-MBJ
6h 00m1 stop
Southwest Logo
12:55 pm - 9:40 pmMBJ-MDW
8h 45m1 stop
$435Southwest
Find Deal
Booking Insights

KAYAK's insights & trends for Midway to Montego Bay flights

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 round-trip flights from Chicago Midway Airport to Montego Bay clicked on KAYAK for each day over the last 12 months.

For Chicago Midway Airport to Montego Bay, Friday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Montego Bay back to Chicago Midway Airport, the best deals are generally found on Thursday, with Saturday being 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 round-trip 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 July, where tickets cost $616 (return) on average. On the other hand, the most expensive months are October and August, where the average cost of round-trip tickets is $943 and $845 respectively.

Can I save money by flying with a layover from Chicago Midway Airport to Montego Bay?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $482 on average.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip 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 week.

To get a below average price on the flight from Chicago Midway Airport to Montego Bay, you should book around 5 weeks before departure, which saves you about 6% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$142
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 5% increase in price.
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 $142 for a one-way ticket and $393 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 airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Montego Bay?

    Only American Airlines offers inflight Wi-Fi service on the Chicago Midway Airport to Montego Bay flight route.

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

    The Boeing 737-800 Passenger/BBJ2 (winglets) is the aircraft model that flies most regularly on the Chicago Midway Airport to Montego Bay flight route.

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

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Montego Bay.

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

    The two airlines most popular with KAYAK users for flights from Chicago to Montego Bay are Southwest and Delta. With an average price for the route of $730 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $645 and an overall rating of 7.9.

  • 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.

Reviews of the 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
SouthwestOverall score based on 4242 reviews
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
8.1Boarding
Airline reviews

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

2.0 MediocreMike, Aug 2025AUS - BWI
Read more Southwest reviews

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

Everything you need to know for your flight from Midway to Montego Bay

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