MDW - MBJ

$200 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 9/28. 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

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$448
Typical prices: $452-$1,046
Delta
Sun 8/16Thu 8/27
MDW - MBJ • 1 stop
Cheapest non-stop
$1,250
Southwest
Sat 11/21Sat 11/28
MDW - MBJ • Non-stop
Nonstop flights
Sat
You can fly direct with Southwest. Average duration is 0
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top airlines
Cheapest • from $448 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top layover airports
Cheapest • Avg $585 (round-trip)
Shortest trip • 6h 24m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 28% price drop
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

Sun, Aug 16 - Thu, Aug 27
Delta Logo
6:05 am - 1:01 pm
MDW
-
MBJ
6h 56m
1 stop
Delta Logo
2:26 pm - 10:36 pm
MBJ
-
MDW
8h 10m
1 stop
$448Delta
Mon, Oct 5 - Thu, Oct 15
Delta Logo
7:01 pm - 12:07 pm
MDW
-
MBJ
17h 06m
2 stops
Delta Logo
4:49 pm - 9:18 am
MBJ
-
MDW
16h 29m
2 stops
$453Delta
Sun, Aug 2 - Wed, Aug 5
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
$472Frontier
Sun, Aug 16 - Fri, Aug 21
Southwest Logo
5:00 am - 1:30 pm
MDW
-
MBJ
8h 30m
2 stops
Southwest Logo
2:15 pm - 9:30 pm
MBJ
-
MDW
7h 15m
1 stop
$473Southwest
Sun, Aug 16 - Fri, Aug 21
Southwest Logo
5:10 am - 1:30 pm
MDW
-
MBJ
8h 20m
1 stop
Southwest Logo
2:15 pm - 10:40 pm
MBJ
-
MDW
8h 25m
1 stop
$478Southwest
Mon, Aug 17 - Fri, Aug 21
Southwest Logo
7:55 pm - 11:55 am
MDW
-
MBJ
16h 00m
2 stops
Southwest Logo
2:15 pm - 10:40 pm
MBJ
-
MDW
8h 25m
1 stop
$483Southwest
Thu, Aug 13 - Thu, Aug 20
Frontier Logo
6:05 am - 12:27 pm
MDW
-
MBJ
6h 22m
1 stop
Frontier Logo
1:32 pm - 10:47 pm
MBJ
-
MDW
9h 15m
1 stop
$485Frontier
Thu, Aug 13 - Thu, Aug 20
Frontier Logo
6:05 am - 12:27 pm
MDW
-
MBJ
6h 22m
1 stop
Frontier Logo
1:32 pm - 10:47 pm
MBJ
-
MDW
9h 15m
1 stop
$489Frontier
Wed, Aug 26 - Sat, Sep 12
Frontier Logo
11:50 am - 12:17 pm
MDW
-
MBJ
24h 27m
1 stop
Frontier Logo
2:49 pm - 9:58 pm
MBJ
-
MDW
7h 09m
1 stop
$491Frontier
Sun, Aug 16 - Sat, Aug 29
Frontier Logo
6:05 am - 12:24 pm
MDW
-
MBJ
6h 19m
1 stop
Frontier Logo
1:32 pm - 10:47 pm
MBJ
-
MDW
9h 15m
1 stop
$492Frontier
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.

Good to know

Low seasonOctober
Cheapest flight$200
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 $199 for a one-way ticket and $448 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.

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

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to Montego Bay Sangster Intl.
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

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.
7.9
SouthwestOverall score based on 4244 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.5Entertainment
7.0Food
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

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

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

It was a very good experience. No major issues at all.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

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

Information on your arrival and departure airports