MDW - MBJ

$177 Find Cheap Flights from Chicago Midway Airport to Montego Bay - Compare and Save

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Everything you should know

Cheapest round-trip
$422
Typical prices: $474-$688
Frontier
Wed 11/7Mon 11/12
MDW - MBJ • 1 stop
Cheapest non-stop
$775
Typical prices: $486-$748
Southwest
Tue 2/13Tue 2/20
MDW - MBJ • Non-stop
Nonstop flights
Not available
There are currently no direct flights between Chicago Midway Airport and Montego Bay. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to book
17 weeks
in advance
Our data shows that travelers who book at least 17 weeks in advance save around 38% compared to booking last minute.
Insights
Insights
When to travel
May
Cheapest • 21% price drop
June
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Fort Lauderdale (FLL)
Cheapest • Avg $447 (round-trip)
Orlando (MCO)
Shortest trip • 7h 00m (one-way)
Insights
Insights
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Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Montego Bay (MDW-MBJ)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Montego Bay

Sat, Nov 7 - Thu, Nov 12
Frontier Logo
7:25 am - 3:28 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
7h 03m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
4:43 pm - 11:47 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 04m1 stop Atlanta Hartsfield-Jackson
$422Frontier
Thu, Oct 29 - Sun, Nov 8
Frontier Logo
6:42 pm - 2:08 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
19h 26m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
4:43 pm - 11:47 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 04m1 stop Atlanta Hartsfield-Jackson
$433Frontier
Wed, Nov 11 - Sat, Nov 14
Frontier Logo
6:42 pm - 3:29 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
19h 47m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
4:43 pm - 11:47 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 04m1 stop Atlanta Hartsfield-Jackson
$433Frontier
Mon, Nov 9 - Sat, Nov 21
Southwest Logo
5:05 am - 2:25 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
8h 20m1 stop Baltimore/Washington
Southwest Logo
2:25 pm - 5:35 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
4h 10mnonstop
$452Southwest
Tue, Sep 29 - Sat, Oct 3
Southwest Logo
6:15 am - 11:55 amMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
5h 40m1 stop Orlando
Southwest Logo
12:55 pm - 10:15 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
9h 20m1 stop Houston Hobby
$462Southwest
Sun, Nov 8 - Wed, Nov 11
Delta Logo
6:04 am - 4:27 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
9h 23m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:16 pm - 10:54 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
9h 38m1 stop Atlanta Hartsfield-Jackson
$462Delta
Sun, Nov 8 - Wed, Nov 11
Delta Logo
6:04 am - 4:27 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
9h 23m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:20 pm - 10:56 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
9h 36m1 stop Atlanta Hartsfield-Jackson
$462Delta
Sun, Sep 27 - Thu, Oct 1
Southwest Logo
6:10 am - 11:45 amMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
5h 35m1 stop Orlando
Southwest Logo
12:00 pm - 11:05 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
11h 05m2 stops Orlando Lambert-St Louis
$467Southwest
Sat, Oct 10 - Tue, Nov 3
Multiple Airlines Logo
6:15 am - 2:33 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
8h 18m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:20 pm - 6:00 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
24h 40m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County
$791Multiple Airlines
Sat, Oct 10 - Tue, Oct 13
Multiple Airlines Logo
6:15 am - 2:33 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
8h 18m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
12:45 pm - 9:17 amMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
20h 32m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County
$964Multiple Airlines
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to Montego Bay flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Chicago Midway Airport to Montego Bay with more confidence.

How much is a round-trip flight from Chicago Midway Airport to Montego Bay?

Round-trip flights from Chicago Midway Airport to Montego Bay start at $422. Prices are below average for this route right now, with typical round-trip fares ranging from $474 to $688. The lowest price found in the past 5 days was $422 on Frontier.

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

Saturday is the cheapest day of the week to fly from Chicago Midway Airport to Montego Bay, it is 11% cheaper than the average day. Thursday is the most expensive day with flight prices 33% higher than average. Based on deals found by KAYAK users in the last 12 months.

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

  • May is the cheapest month to fly from Chicago Midway Airport to Montego Bay at $452 round-trip.
  • August ($675) and June ($672) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 49% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices from Chicago Midway Airport to Montego Bay the cheapest?

Flights from Chicago Midway Airport to Montego Bay are cheapest 17 weeks before departure. Booking in this window typically costs about 38% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

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Key details for Chicago Midway Airport to Montego Bay flights

Low season

December

Cheapest flight

$175
Best time to beat the crowds but there is an average 15% increase in price.
Most popular time to fly with an average 17% 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

Your Chicago Midway Airport to Montego Bay flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Which airlines offer extra legroom and free seat selection on Chicago Midway Airport to Montego Bay flights?

    Among airlines operating Chicago Midway Airport to Montego Bay flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • What airlines are available from Chicago Midway Airport to Montego Bay?

    Only Southwest operates flights between Chicago Midway Airport and Montego Bay.

  • Which airports can I use when flying from Chicago Midway Airport to Montego Bay?

    Flights from Chicago Midway Airport to Montego Bay usually depart from Chicago Midway (MDW) and arrive at Montego Bay Sangster Intl (MBJ).

  • Which airlines include bags at no extra cost on Chicago Midway Airport to Montego Bay flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

  • What cabin classes can I book on flights from Chicago Midway Airport to Montego Bay?

    Only Economy Class is available on flights from Chicago Midway Airport to Montego Bay.

  • How much can I save by taking a layover when flying from Chicago Midway Airport to Montego Bay?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $447 round-trip via Fort Lauderdale (FLL), compared to $601 for nonstop.

  • What is the standard checked-bag allowance on flights from Chicago Midway Airport to Montego Bay?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Chicago Midway Airport to Montego Bay?

    The Boeing 737 MAX 8 family is used most often on this route, operated mainly by American Airlines and Southwest. Other aircraft seen on the route include Boeing 737 variants.

  • Which airports do connecting flights from Chicago Midway Airport to Montego Bay pass through?

    One-stop flights from Chicago Midway Airport to Montego Bay most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 63% of one-stop connections
    • Orlando (MCO) - 22% of one-stop connections
    • Baltimore/Washington (BWI) - 13% of one-stop connections
    • Fort Lauderdale (FLL) - 2% of one-stop connections

    Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Chicago Midway Airport to Montego Bay?

    On the Chicago Midway Airport to Montego Bay route, being flexible with your departure day can save you up to 34%. Saturday is the cheapest day at $512 round-trip on average, while Thursday is the most expensive at $769: a $257 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • What popular places can I visit in Montego Bay?

    Some of the most popular sights in Montego Bay are Doctor's Cave Bathing Club, Cornwall Beach and Montego Bay Cruise Port. These are among the most viewed places in Montego Bay on KAYAK.

  • What are the earliest and latest flights from Chicago Midway Airport to Montego Bay?

    These are the earliest and latest flight times available from Chicago Midway Airport to Montego Bay:

    • Earliest: departs at 8:05 am and lands at 12:00 pm
    • Latest: departs at 8:05 am and lands at 12:00 pm.

    The flight takes about 3h 55m.

  • How expensive are last-minute Chicago Midway Airport to Montego Bay flights?

    Last-minute fares on this route - booked within 2 weeks of departure - run 3% above the route average of $575. Book 17 weeks before departure for the lowest fares.

  • How long is a flight from Chicago Midway Airport to Montego Bay?

    A nonstop flight from Chicago Midway Airport to Montego Bay takes 3h 55m, covering 1,709 miles.

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

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • Have flight prices from Chicago Midway Airport to Montego Bay changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $422 to $4,055. That means the highest observed fare was about 10x higher than the lowest one.

  • How are flight prices from Chicago Midway Airport to Montego Bay looking right now?

    One-way fares from Chicago Midway Airport to Montego Bay are currently higher than usual. Average one-way flight prices are about $220, which is 11% above the typical average for this route.

  • How much time can I save by choosing a different layover airport from Chicago Midway Airport to Montego Bay?

    Flying via Orlando (MCO) gives the shortest average 1-stop total travel time at 7h 00m, compared with 7h 12m via Baltimore/Washington (BWI) and 7h 23m via Atlanta Hartsfield-Jackson (ATL).

  • What car rental options are available at Montego Bay Sangster Intl Airport (MBJ)?

    Montego Bay Sangster Intl Airport (MBJ) hosts 5 major car rental companies, with daily rates starting from around $4 for economy cars. Top options include:
    · Timeless Car Rental
    · Classique Car Rentals
    · Epic Car Rental Limited
    · Chalis
    · Island Car Rentals

  • How much should I expect to pay for a Chicago Midway Airport to Montego Bay flight?

    Round-trip flights from Chicago Midway Airport to Montego Bay range from $474 to $688, with an average of $575 over the past 12 months. Anything below $474 counts as a good deal.

Your guide to booking Chicago Midway Airport to Montego Bay flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Saturday departure instead of Thursday. On this route, Saturday flights average $512 - about $257 less than Thursday (33% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 17 weeks before you fly. On this route, that window historically saves about 38% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago Midway Airport to Montego Bay trip for May. Fares historically average $452 round-trip in that month - typically $223 less than the most expensive month, which is August (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Fort Lauderdale Airport (FLL) can be cheaper than flying direct. The cheapest layover option averages $447 round-trip on this route - about $154 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Montego Bay Sangster Intl Airport.
    - S Hotel Jamaica
    - Riu Reggae
    - Hotel Grand A View

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Montego Bay (MBJ)