MDW - MBJ

$167 Find Cheap Flights from Chicago Midway Airport to Montego Bay - Compare and Save

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 9/14. 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
1 adult, Economy, 0 bags

Save 20% 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
$421
Typical prices: $452-$1,046
Southwest
Sat 8/22Fri 8/28
MDW - MBJ • 1 stop
Cheapest non-stop
$1,004
Southwest
Sat 11/21Sat 11/28
MDW - MBJ • Non-stop
Top layover airports
Baltimore (BWI)
Cheapest • Avg $587 (round-trip)
Orlando (MCO)
Shortest trip • 6h 24m (one-way)
Insights
Insights
Insights
Insights
When to travel
August
Cheapest • 29% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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)

 
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

Sat, Aug 22 - Fri, Aug 28
Southwest Logo
5:00 am - 12:50 pm
MDW
-
MBJ
7h 50m
1 stop
Southwest Logo
2:15 pm - 10:20 pm
MBJ
-
MDW
8h 05m
2 stops
$421Southwest
Sun, Dec 6 - Wed, Dec 9
Southwest Logo
5:05 am - 2:25 pm
MDW
-
MBJ
8h 20m
1 stop
Southwest Logo
1:00 pm - 7:00 pm
MBJ
-
MDW
7h 00m
1 stop
$459Southwest
Sat, Sep 19 - Wed, Sep 23
Southwest Logo
5:55 am - 12:25 pm
MDW
-
MBJ
6h 30m
1 stop
Southwest Logo
1:55 pm - 8:45 pm
MBJ
-
MDW
6h 50m
1 stop
$460Southwest
Mon, Aug 17 - Thu, Aug 20
Southwest Logo
5:55 am - 1:15 pm
MDW
-
MBJ
7h 20m
2 stops
Southwest Logo
2:15 pm - 9:30 pm
MBJ
-
MDW
7h 15m
1 stop
$463Southwest
Sun, Dec 6 - Wed, Dec 9
Southwest Logo
8:40 pm - 2:25 pm
MDW
-
MBJ
16h 45m
2 stops
Southwest Logo
1:00 pm - 9:20 pm
MBJ
-
MDW
9h 20m
1 stop
$464Southwest
Mon, Aug 17 - Thu, Aug 20
Southwest Logo
7:25 am - 1:15 pm
MDW
-
MBJ
5h 50m
1 stop
Southwest Logo
2:15 pm - 9:30 pm
MBJ
-
MDW
7h 15m
1 stop
$468Southwest
Tue, Aug 11 - Sat, Aug 15
Frontier Logo
6:05 am - 12:27 pm
MDW
-
MBJ
6h 22m
1 stop
Frontier Logo
1:32 pm - 10:03 pm
MBJ
-
MDW
8h 31m
1 stop
$472Frontier
Tue, Sep 15 - Fri, Sep 18
Southwest Logo
6:15 am - 11:55 am
MDW
-
MBJ
5h 40m
1 stop
Southwest Logo
2:15 pm - 10:20 pm
MBJ
-
MDW
8h 05m
2 stops
$473Southwest
Fri, Oct 23 - Mon, Oct 26
Delta Logo
6:00 am - 3:34 pm
MDW
-
MBJ
9h 34m
1 stop
Delta Logo
1:32 pm - 10:25 pm
MBJ
-
MDW
8h 53m
1 stop
$478Delta
Sun, Aug 2 - Thu, Aug 6
Frontier Logo
6:05 am - 12:24 pm
MDW
-
MBJ
6h 19m
1 stop
Frontier Logo
1:32 pm - 10:03 pm
MBJ
-
MDW
8h 31m
1 stop
$482Frontier
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.

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

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Montego Bay departing in August.

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 August, where tickets cost $472 (return) on average. On the other hand, the most expensive months are March and November, where the average cost of round-trip tickets is $1,144 and $738 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.

No, with an average price for the route of $467, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonOctober
Cheapest flight$167
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 1% 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 5 days, the lowest price for a flight from Chicago Midway Airport to Montego Bay was $167 for a one-way ticket and $421 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?

    American Airlines, and JetBlue offer 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 MAX 8 is the aircraft model that flies most regularly on the Chicago Midway Airport to Montego Bay flight route.

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

    The two airlines most popular with KAYAK users for flights from Chicago to Montego Bay are Southwest and Frontier. With an average price for the route of $653 and an overall rating of 7.9, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $493 and an overall rating of 5.6.

  • 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.

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)