MDW - MBJ

$154 Find Cheap Flights from Chicago Midway Airport to Montego Bay - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$429
Typical prices: $474-$688
Frontier
Tue 10/2Thu 10/4
MDW - MBJ • 1 stop
Cheapest non-stop
$750
Typical prices: $486-$748
Southwest
Tue 2/20Tue 2/27
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
Baltimore/Washington (BWI)
Cheapest • Avg $561 (round-trip)
Orlando (MCO)
Shortest trip • 6h 56m (one-way)
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Montego Bay!
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

Sun, Nov 1 - Mon, Nov 9
Frontier Logo
6:42 pm - 3:08 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
19h 26m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
4:23 pm - 11:47 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 24m1 stop Atlanta Hartsfield-Jackson
$433Frontier
Thu, Nov 12 - Mon, Nov 16
Frontier Logo
6:42 pm - 3:08 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
19h 26m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
4:23 pm - 5:47 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
26h 24m1 stop Atlanta Hartsfield-Jackson
$441Frontier
Fri, Nov 13 - Sun, Nov 15
Frontier Logo
6:16 am - 3:08 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
7h 52m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
4:43 pm - 11:25 amMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
19h 42m2 stops Atlanta Hartsfield-Jackson Dallas/Fort Worth
$447Frontier
Wed, Dec 2 - Wed, Dec 9
Southwest Logo
5:20 am - 12:50 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
6h 30m1 stop Orlando
Southwest Logo
3:25 pm - 9:25 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
7h 00m1 stop Baltimore/Washington
$462Southwest
Sat, Oct 31 - Tue, Nov 3
Delta Logo
6:04 am - 3:35 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
9h 31m1 stop Atlanta Hartsfield-Jackson
Delta Logo
3:26 pm - 10:33 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 07m1 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
2:16 pm - 10:54 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
9h 38m1 stop Atlanta Hartsfield-Jackson
$462Delta
Sat, Jan 23 - Sat, Jan 30
Delta Logo
6:00 am - 2:10 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
7h 10m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:20 pm - 10:10 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 50m1 stop Atlanta Hartsfield-Jackson
$463Delta
Wed, Dec 2 - Wed, Dec 9
Southwest Logo
5:20 am - 12:50 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
6h 30m1 stop Orlando
Southwest Logo
1:50 pm - 9:30 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 40m2 stops Orlando Lambert-St Louis
$467Southwest
Fri, Oct 16 - Sat, Oct 24
Multiple Airlines Logo
3:20 pm - 6:30 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
27h 10m1 stop Toronto Island
Multiple Airlines Logo
3:48 pm - 11:43 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
7h 55m1 stop Atlanta Hartsfield-Jackson
$651Multiple Airlines
Sat, Oct 17 - Tue, Oct 20
Multiple Airlines Logo
3:20 pm - 11:45 amMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
20h 25m1 stop Toronto Island
Multiple Airlines Logo
12:45 pm - 11:00 amMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
22h 15m1 stop Toronto Pearson Intl
$679Multiple 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 $429. 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 $429 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.

Find deals

Key details for Chicago Midway Airport to Montego Bay flights

Low season

December

Cheapest flight

$154
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 $561 round-trip via Baltimore/Washington (BWI), 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 family is used most often on this route, operated mainly by Southwest and American Airlines. Other aircraft seen on the route include Boeing 737 MAX 8 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) - 20% of one-stop connections
    • Baltimore/Washington (BWI) - 16% of one-stop connections
    • Houston Hobby (HOU) - 1% 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 7:45 am and lands at 11:40 am
    • 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 $430 to $3,868. That means the highest observed fare was about 9x 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 $212, which is 7% 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 6h 56m, compared with 6h 57m via Baltimore/Washington (BWI) and 7h 27m 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 Baltimore/Washington Airport (BWI) can be cheaper than flying direct. The cheapest layover option averages $561 round-trip on this route - about $40 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

Prefer to fly direct from Chicago Midway Airport to Montego Bay?

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

Direct departures

Chicago Midway to Montego Bay Sangster Intl

Saturday

Southwest

Southwest

See more direct flights

Direct returns

Montego Bay Sangster Intl to Chicago Midway

Saturday

Southwest

Southwest

See more direct flights

More options for your flight from Midway to Montego Bay

Complete your trip to Montego Bay with a hotel stay or car rental

Car rentals in Montego Bay
Hotels in Montego Bay
Vacations in Montego Bay