MBJ - MDW

$194 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 5/9. 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 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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Everything you should know

Cheapest round-trip
$281
Southwest
Sat 6/6Sat 6/27
MBJ - MDW • Non-stop
Cheapest one-way
$194
Southwest
Sat 5/9
MBJ - MDW • Non-stop
Nonstop flights
2 days a week
Sat, Sun
You can fly direct with Southwest. Average duration is 4h 10m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top airlines
Southwest
Cheapest • from $281 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top layover airports
Orlando (MCO)
Cheapest • Avg $555 (round-trip)
Orlando (MCO)
Shortest trip • 7h 38m (one-way)
Insights
Insights
Insights
Insights
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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!
Flight Deals
Booking Insights
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

Sat, Jun 6 - Sat, Jun 27
Southwest Logo
2:30 pm - 6:35 pm
MBJ
-
MDW
4h 05mnonstop
Southwest Logo
10:10 am - 2:00 pm
MDW
-
MBJ
3h 50mnonstop
$281Southwest
Wed, May 13 - Wed, May 27
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
$384Frontier
Sat, Jun 6 - Sat, Jun 27
Southwest Logo
2:30 pm - 6:35 pm
MBJ
-
MDW
4h 05mnonstop
Southwest Logo
6:30 am - 1:05 pm
MDW
-
MBJ
6h 35m
1 stop
$446Southwest
Wed, May 13 - Wed, May 27
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
$456Frontier
Sat, Jun 6 - Sat, Jun 27
Southwest Logo
2:30 pm - 6:35 pm
MBJ
-
MDW
4h 05mnonstop
Southwest Logo
8:10 pm - 1:30 pm
MDW
-
MBJ
17h 20m
2 stops
$459Southwest
Wed, May 13 - Wed, May 27
Southwest Logo
12:15 pm - 7:10 am
MBJ
-
MDW
18h 55m
2 stops
Southwest Logo
7:00 am - 1:55 pm
MDW
-
MBJ
6h 55m
1 stop
$491Southwest
Mon, May 11 - Wed, Sep 9
Delta Logo
1:18 pm - 9:09 pm
MBJ
-
MDW
7h 51m
1 stop
Delta Logo
6:00 am - 1:04 pm
MDW
-
MBJ
7h 04m
1 stop
$498Delta
Thu, Apr 30 - Thu, May 7
Southwest Logo
12:35 pm - 10:20 pm
MBJ
-
MDW
9h 45m
1 stop
Southwest Logo
7:30 am - 1:55 pm
MDW
-
MBJ
6h 25m
1 stop
$559Southwest
Thu, Apr 30 - Thu, May 7
Southwest Logo
12:15 pm - 7:00 pm
MBJ
-
MDW
6h 45m
1 stop
Southwest Logo
8:35 pm - 1:55 pm
MDW
-
MBJ
17h 20m
2 stops
$564Southwest
Sun, May 17 - Sat, Sep 12
Southwest Logo
2:40 pm - 11:40 pm
MBJ
-
MDW
9h 00m
1 stop
Southwest Logo
5:55 am - 12:25 pm
MDW
-
MBJ
6h 30m
1 stop
$571Southwest
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 Saturday and more expensive on a Monday. On your return trip to Montego Bay, you should consider flying back on a Sunday, and avoid Thursdays 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.

No, with an average price for the route of $281, prices are generally cheapest when you fly direct.

Find deals

Good to know

Cheapest flight$194
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 $194 for a one-way ticket and $281 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.

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

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

  • 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.

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

  • Looking for a cheap flight? 25% of our users found flights on this route for $239 or less one-way.

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

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Montego Bay Sangster Intl

Saturday

Southwest

Southwest

Sunday

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 4320 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.0Food
7.5Entertainment
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

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)