MDW - MBJ

$165 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 7/7. 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

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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Cheap Flights from Midway to Montego Bay

 
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.

Recent round-trip flight deals from Midway to Montego Bay

KAYAK's recommended round-trip deals from the most popular airlines that fly from Midway to Montego Bay.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
8:55 pm - 11:53 amMDW-MBJ
14h 58m1 stop
Frontier Logo
9:13 am - 10:16 pmMBJ-MDW
13h 03m1 stop
$438Frontier
Find Deal
Fri, May 30 - Mon, Jun 2
Frontier Logo
6:35 am - 1:58 pmMDW-MBJ
7h 23m1 stop
Frontier Logo
9:35 am - 9:56 pmMBJ-MDW
12h 21m1 stop
$440Frontier
Find Deal
Mon, May 26 - Thu, May 29
Frontier Logo
6:40 am - 1:51 pmMDW-MBJ
7h 11m1 stop
Frontier Logo
9:38 am - 9:32 pmMBJ-MDW
11h 54m1 stop
$447Frontier
Find Deal
Wed, May 28 - Sun, Jun 1
Frontier Logo
4:46 pm - 7:50 amMDW-MBJ
15h 04m1 stop
Frontier Logo
9:08 am - 10:44 pmMBJ-MDW
13h 36m1 stop
$448Frontier
Find Deal
Tue, May 27 - Tue, Jun 3
Delta Logo
6:00 am - 3:30 pmMDW-MBJ
9h 30m1 stop
Delta Logo
1:02 pm - 9:28 pmMBJ-MDW
8h 26m1 stop
$449Delta
Find Deal
Sun, May 11 - Wed, May 14
Delta Logo
6:00 am - 3:36 pmMDW-MBJ
9h 36m1 stop
Delta Logo
1:15 pm - 9:47 pmMBJ-MDW
8h 32m1 stop
$461Delta
Find Deal
Mon, Aug 25 - Fri, Aug 29
Southwest Logo
9:00 am - 1:00 pmMDW-MBJ
4h 00mnonstop
Southwest Logo
2:20 pm - 6:30 pmMBJ-MDW
4h 10mnonstop
$462Southwest
Find Deal
Sun, Jun 8 - Tue, Jun 10
Southwest Logo
7:45 am - 2:55 pmMDW-MBJ
7h 10m1 stop
Southwest Logo
2:20 pm - 6:30 pmMBJ-MDW
4h 10mnonstop
$467Southwest
Find Deal
Sun, Jun 8 - Tue, Jun 10
 Logo
9:12 pm - 11:02 amMDW-MBJ
13h 50m2 stops
 Logo
2:02 pm - 12:55 pmMBJ-MDW
22h 53m1 stop
Fri, Jun 6 - Tue, Jun 10
 Logo
9:12 pm - 1:08 pmMDW-MBJ
15h 56m1 stop
 Logo
12:07 pm - 11:18 pmMBJ-MDW
11h 11m2 stops
Fri, Jun 13 - Mon, Jun 16
Useful Info

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, Thursday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Montego Bay back to Chicago Midway Airport, the best deals are generally found on Friday, with Saturday 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 April, where tickets cost $644 (return) on average. On the other hand, the most expensive months are December and October, where the average cost of round-trip tickets is $1,001 and $943 respectively.

Good to know

Low seasonNovember
High seasonAugust
Cheapest flight$165
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 11% 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 3 days, the lowest price for a flight from Chicago Midway Airport to Montego Bay was $165 for a one-way ticket and $438 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?

    Only American Airlines offers 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 737-800 is the aircraft model that flies most regularly on the Chicago Midway Airport to Montego Bay flight route.

  • 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 Monday, Tuesday, Wednesday, Thursday, Friday, and 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 $748 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 $821 and an overall rating of 8.0.

  • 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 $372 or less one-way and $689 or less round-trip.

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

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Montego Bay Sangster Intl to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights
See more direct flights

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.
8.0
SouthwestOverall score based on 4294 reviews
8.2Boarding
7.6Entertainment
8.6Crew
8.0Comfort
7.1Food
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Our bag was lost so that made unnecessary chaos On our trip

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

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

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