MBJ - MDW

$184 Find Cheap Flights from Montego Bay to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Montego Bay to Midway departing on 10/23. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Montego Bay to Chicago, 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 Montego Bay to Chicago, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Montego Bay to Midway (MBJ-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Montego Bay to Midway 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 Montego Bay to Midway

Mon, Sep 29 - Mon, Oct 6
Frontier Logo
2:12 pm - 11:20 pmMBJ-MDW
9h 08m1 stop
Frontier Logo
6:20 am - 12:45 pmMDW-MBJ
6h 25m1 stop
$548Frontier
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Sun, Sep 28 - Sun, Oct 5
Frontier Logo
2:12 pm - 11:20 pmMBJ-MDW
9h 08m1 stop
Frontier Logo
6:20 am - 12:41 pmMDW-MBJ
6h 21m1 stop
$596Frontier
Find Deal
Sun, Sep 28 - Sun, Oct 5
Frontier Logo
2:12 pm - 7:11 amMBJ-MDW
16h 59m2 stops
Frontier Logo
6:20 am - 12:41 pmMDW-MBJ
6h 21m1 stop
$618Frontier
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Mon, Sep 29 - Mon, Oct 6
Logo
10:52 am - 6:43 pmMBJ-MDW
7h 51m1 stop
Logo
9:47 pm - 11:00 amMDW-MBJ
13h 13m2 stops
$683
Find Deal

Everything you should know

Nonstop flights
1 day a week
There are direct flights from Montego Bay to Midway 1 day a week: Sat.
Direct flights
Direct flights
Direct flights
Direct flights
Cheapest round-trip
$548
Frontier
Mon 9/29Mon 10/6
MBJ - MDW • 1 stop
Cheapest one-way
$184
Frontier
Thu 10/23
MBJ - MDW • 1 stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Booking Insights

KAYAK's insights & trends for Montego Bay to Midway flights

Get data-powered insights and trends into flights from Montego Bay to Midway 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 Montego Bay to Chicago Midway Airport?

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

Your flight ticket price will generally be cheaper if you fly to Chicago Midway Airport on a Thursday and more expensive on a Saturday. On your return trip to Montego Bay, you should consider flying back on a Friday, and avoid Wednesdays for better deals.

Can I save money by flying with a layover from Montego Bay to Chicago Midway Airport?

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $392 on average.

Find deals

Good to know

Low seasonSeptember
Cheapest flight$184
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Montego Bay to Chicago Midway Airport

When to book flights from Montego Bay to Midway

Are your dates flexible? Find out the best times to travel from Montego Bay to Midway 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 Montego Bay to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from Montego Bay to Chicago Midway Airport was $184 for a one-way ticket and $548 for a round-trip.

  • Do I need a passport to fly between Montego Bay and Chicago Midway Airport?

    Yes

  • Which airlines offer Wi-Fi service onboard planes from Montego Bay to Chicago Midway Airport?

    Only American Airlines offers inflight Wi-Fi service on the Montego Bay to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from Montego Bay to Chicago Midway Airport?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Montego Bay to Chicago Midway Airport flight route.

  • Which airline alliances offer flights from Montego Bay to Chicago Midway Airport?

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

  • How does KAYAK find such low prices on flights from Montego Bay to Chicago Midway Airport?

    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 Montego Bay to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Montego Bay to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Montego Bay 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 Montego Bay to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to Montego Bay with another airline. Booking your flights between Montego Bay and MDW 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 Montego Bay to Chicago Midway Airport?

    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 Chicago Midway Airport from Montego Bay up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Montego Bay Sangster Intl to Chicago Midway.
Find which airlines fly direct from Montego Bay Sangster Intl Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Montego Bay Sangster Intl to Chicago Midway

Saturday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Montego Bay Sangster Intl

Saturday

Southwest

Southwest

See more direct flights

Reviews of the top airline flying from Montego Bay to Midway

 
See real verified KAYAK customer reviews for airlines flying from Montego Bay to Chicago. 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 Montego Bay to Midway? 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 4242 reviews
7.5Entertainment
8.6Crew
8.0Comfort
7.0Food
8.1Boarding
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

Was good. I miss the free 2 checked bags. That was part of what made Southwest special

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

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

Information on your arrival and departure airports

Montego Bay (MBJ)
Midway (MDW)

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