MDW - MBJ

$119 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 2/14. 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

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
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Everything you should know

Cheapest round-trip
$376
Overall average: $643
Delta
Sun 2/22Thu 2/26
MDW - MBJ • 1 stop
Cheapest non-stop
$523
Southwest
Tue 6/9Fri 6/12
MDW - MBJ • Non-stop
Top airlines
Delta
Cheapest • from $376 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
October
Cheapest • 17% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Nonstop flights
2 days a week
There are direct flights from Midway to Montego Bay 2 days a week: Sat, Sun.
Direct flights
Direct flights
Direct flights
Direct flights
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, Feb 22 - Thu, Feb 26
Delta Logo
6:00 am - 3:19 pm
MDW
-
MBJ
8h 19m
1 stop
Delta Logo
4:44 pm - 10:31 pm
MBJ
-
MDW
6h 47m
1 stop
$376Delta
Thu, Apr 9 - Mon, Apr 13
Frontier Logo
9:20 am - 12:42 pm
MDW
-
MBJ
27h 22m
2 stops
Frontier Logo
1:57 pm - 10:19 pm
MBJ
-
MDW
8h 22m
1 stop
$391Frontier
Sat, Feb 28 - Wed, Mar 4
Delta Logo
6:00 am - 3:19 pm
MDW
-
MBJ
8h 19m
1 stop
Delta Logo
2:19 pm - 10:31 pm
MBJ
-
MDW
9h 12m
1 stop
$394Delta
Tue, Mar 17 - Thu, Mar 26
Delta Logo
7:20 pm - 1:27 pm
MDW
-
MBJ
18h 07m
1 stop
Delta Logo
2:42 pm - 8:50 am
MBJ
-
MDW
18h 08m
1 stop
$396Delta
Fri, Feb 20 - Fri, Feb 27
Multiple Airlines Logo
6:48 pm - 9:25 am
MDW
-
MBJ
13h 37m
1 stop
Multiple Airlines Logo
1:00 pm - 3:19 pm
MBJ
-
MDW
27h 19m
2 stops
$397Multiple Airlines
Tue, Mar 17 - Wed, Mar 25
Delta Logo
6:34 pm - 11:21 am
MDW
-
MBJ
16h 47m
2 stops
Delta Logo
4:49 pm - 8:53 am
MBJ
-
MDW
16h 04m
2 stops
$401Delta
Fri, Apr 3 - Mon, Apr 6
Frontier Logo
2:56 pm - 7:56 am
MDW
-
MBJ
17h 00m
1 stop
Frontier Logo
1:57 pm - 10:19 pm
MBJ
-
MDW
8h 22m
1 stop
$403Frontier
Sun, Feb 15 - Thu, Feb 19
Multiple Airlines Logo
9:04 pm - 12:02 pm
MDW
-
MBJ
13h 58m
2 stops
Multiple Airlines Logo
3:08 pm - 10:37 pm
MBJ
-
MDW
8h 29m
1 stop
$404Multiple Airlines
Sun, Feb 8 - Sat, Feb 14
Delta Logo
6:00 am - 3:20 pm
MDW
-
MBJ
8h 20m
1 stop
Delta Logo
4:44 pm - 10:31 pm
MBJ
-
MDW
6h 47m
1 stop
$406Delta
Fri, Apr 17 - Wed, Apr 22
Delta Logo
6:30 am - 3:29 pm
MDW
-
MBJ
8h 59m
1 stop
Delta Logo
2:40 pm - 10:29 pm
MBJ
-
MDW
7h 49m
1 stop
$409Delta
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.

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

The average price of all round-trip flights from Chicago Midway Airport to Montego Bay clicked on KAYAK for each day over the last 12 months.

For Chicago Midway Airport to Montego Bay, Friday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Montego Bay back to Chicago Midway Airport, the best deals are generally found on Saturday, with Monday being the most expensive.

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 October, where tickets cost $549 (return) on average. On the other hand, the most expensive months are August and June, where the average cost of round-trip tickets is $799 and $783 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 $507, prices are generally cheapest when you fly direct.

Good to know

Low seasonOctober
Cheapest flight$119
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly and prices are also 7% lower on average.
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

  • How many flights are there between Chicago Midway Airport and Montego Bay per day?

    There is a maximum of 1 nonstop flight a day that takes off from Chicago Midway Airport and lands in Montego Bay, with an average flight time of 3h 55m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 1 flights.

  • What is the cheapest flight from Chicago Midway Airport to Montego Bay?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Montego Bay was $119 for a one-way ticket and $376 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 airline alliances offer flights from Chicago Midway Airport to Montego Bay?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Montego Bay.

  • On which days can I fly direct from Chicago Midway Airport to Montego Bay?

    You can catch a nonstop flight from Chicago Midway Airport to Montego Bay on Saturday.

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

    The two airlines most popular with KAYAK users for flights from Chicago to Montego Bay are Southwest and Delta. With an average price for the route of $724 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $630 and an overall rating of 7.9.

  • 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.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to Montego Bay

  • Looking for a cheap flight? 25% of our users found flights on this route for $509 or less round-trip.

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

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Montego Bay Sangster Intl to Chicago Midway

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top 3 airlines serving 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.
8.0
SouthwestOverall score based on 4268 reviews
7.0Food
8.1Boarding
7.5Entertainment
8.6Crew
8.0Comfort
Airline reviews

Great flight but super high price. Glad it was a business trip and not personal

10.0 ExcellentPieter, Jan 2026
LGB - DAL
Read more Southwest reviews

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

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

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

We got exit row seats both flights. Everything was running on time

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Pretty seamless, just a tad bit late in taking off and landing.

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

There was no wifi available on this flight. And there were no screens, no onboard entertainment, no entertainment options at all. It was like travelling in the 1990s again, except without even a main screen for options. Seats, as usual, were tight and uncomfortable.

Good seat comfort ORF to ATL. Bad seat ATL to SEA (terrible lumbar support, hard, ouch)..

Because I was moved to an exit row, the snacks in economy comfort, the selection of snacks was better.

I upgraded to first. Quick and easy boarding. Comfortable seat with power and a nice IPA.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

Plane and crew on board were fine. Everything else was terrible.

The third party booking with cheapflightsfares was awful. Kayak should NOT partner with them. They sold me a bundle including seat selection and carry-on, but did not book the carry-ons with Frontier, so I’m out of pocket for $414 more while I await resolution.

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

Information on your arrival and departure airports