United States
USD

MDW - MBJ

$167 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
$453
Typical prices: $478-$690
Frontier
Mon 11/5Fri 11/9
MDW - MBJ • 1 stop
Cheapest non-stop
$547
Typical prices: $507-$785
Southwest
Tue 1/23Tue 1/30
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 37% compared to booking last minute.
Insights
Insights
When to travel
May
Cheapest • 25% price drop
June
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Baltimore/Washington (BWI)
Cheapest • Avg $542 (round-trip)
Orlando (MCO)
Shortest trip • 6h 58m (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

Thu, Nov 5 - 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
$453Frontier
Mon, Nov 9 - Mon, Nov 16
Frontier Logo
6:08 am - 3:08 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
8h 00m1 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
$461Frontier
Thu, Nov 5 - Sun, Nov 8
Frontier Logo
6:42 pm - 3:08 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
19h 26m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
4:43 pm - 5:47 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
26h 04m1 stop Atlanta Hartsfield-Jackson
$462Frontier
Sun, Nov 15 - 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
$472Southwest
Sat, Jan 23 - Sat, Jan 30
Southwest Logo
5:20 am - 12:25 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
6h 05m1 stop Orlando
Southwest Logo
1:25 pm - 4:30 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
4h 05mnonstop
$474Southwest
Tue, Oct 27 - Thu, Oct 29
Delta Logo
6:04 am - 11:51 amMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
5h 47m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:16 pm - 10:33 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
9h 17m1 stop Atlanta Hartsfield-Jackson
$483Delta
Mon, Nov 30 - Wed, Dec 9
Southwest Logo
5:25 am - 2:45 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
8h 20m1 stop Orlando
Southwest Logo
1:50 pm - 7:30 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
6h 40m1 stop Orlando
$483Southwest
Tue, Mar 23 - Wed, Apr 7
Delta Logo
6:00 am - 3:35 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
9h 35m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:45 pm - 8:49 amMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
18h 04m1 stop Minneapolis St Paul
$484Delta
Tue, Feb 23 - Sat, Feb 27
Multiple Airlines Logo
1:18 pm - 12:45 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
22h 27m2 stops Atlanta Hartsfield-Jackson Tampa
Multiple Airlines Logo
2:01 pm - 11:46 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
10h 45m1 stop Atlanta Hartsfield-Jackson
$548Multiple Airlines
Sat, Oct 24 - Thu, Oct 29
Multiple Airlines Logo
6:21 am - 12:25 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
30h 04m3 stops Atlanta Hartsfield-Jackson Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
3:43 pm - 11:47 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 04m1 stop Atlanta Hartsfield-Jackson
$592Multiple 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 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 typically range from $478 to $690. The lowest price found in the past 5 days was $453, on Frontier.

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

Based on deals KAYAK users found in the last 12 months, Saturday is the cheapest day of the week to fly from Chicago Midway Airport to Montego Bay. It’s 12% cheaper than the average day, while Thursday is the most expensive, with prices 20% higher.

What’s 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 $432 round-trip.
•November ($924) and August ($675) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 113% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights 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 37% 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

November

Cheapest flight

$167
Beat the crowds with an average 88% drop in travelers.
The most popular month to fly with an average 95% increase in travelers.
One-way 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 answers about this route, including flight times, airports, airlines and booking tips.

  • 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.

  • 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 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.

  • 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 $478 to $690, with an average of $577 over the past 12 months. Anything below $478 counts as a good deal.

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

    Last-minute fares on this route (booked within two weeks of departure) run 2% above the $577 route average. Book 17 weeks before departure for the lowest fares.

  • 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 $542 round-trip via Baltimore/Washington (BWI), compared to $620 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 $90–$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 JetBlue. Other aircraft seen on the route include Boeing 737-800 variants.

  • 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 $453 to $4,217. That means the highest observed fare was about 9x higher than the lowest one.

  • Which airlines offer Wi-Fi on Chicago Midway Airport to Montego Bay flights?

    JetBlue is the only airline on the Chicago Midway Airport to Montego Bay route offering in-flight Wi-Fi. Pricing depends on fare class.

  • 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 in line with typical prices for this route. Average one-way fares are about $197.

  • 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

  • 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 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
    • Baltimore/Washington (BWI) - 19% of one-stop connections
    • Orlando (MCO) - 19% of one-stop connections

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

    Yes. Flexible dates can save you up to 27% on flights from Chicago Midway Airport to Montego Bay. Saturday is the cheapest departure day at $512 round-trip on average, while Thursday is the most expensive at $697, a difference of $185.

    Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • What airlines fly from Chicago Midway Airport to Montego Bay?

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

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

    Flying via Baltimore/Washington (BWI) gives the shortest average 1-stop total travel time at 6h 55m, compared with 6h 58m via Orlando (MCO) and 7h 24m via Atlanta Hartsfield-Jackson (ATL).

  • 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 AquaSol Theme Park. These are among the most viewed places in Montego Bay on KAYAK.

  • 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.

  • 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
    • JetBlue: a cabin bag in Economy Class class

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

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 are flexible, aim for a Saturday departure and avoid flying on Thursday. On this route, Saturday flights average $512, about $185 less than Thursday fares (27% 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 37% 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 $432 round-trip in that month - typically $492 less than the most expensive month, which is November (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 $542 round-trip on this route - about $78 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
    • Hotel Grand A View
    • Hotel 39 Jamaica

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