MBJ - MDW

$170 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 2/19. 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
$351
Delta
Thu 5/14Mon 5/18
MBJ - MDW • 1 stop
Cheapest one-way
$170
Frontier
Thu 2/19
MBJ - MDW • 1 stop
Top airlines
Delta
Cheapest • from $508 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
2 days a week
There are direct flights from Montego Bay to Midway 2 days a week: Sat, Sun.
Direct flights
Direct flights
Direct flights
Direct flights
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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

Thu, May 14 - Mon, May 18
Delta Logo
2:40 pm - 9:45 pm
MBJ
-
MDW
7h 05m
1 stop
Delta Logo
6:00 am - 1:16 pm
MDW
-
MBJ
7h 16m
1 stop
$351Delta
Wed, Mar 11 - Wed, Mar 18
Delta Logo
11:15 am - 10:31 pm
MBJ
-
MDW
11h 16m
1 stop
Delta Logo
6:00 am - 3:28 pm
MDW
-
MBJ
9h 28m
1 stop
$508Delta
Sun, Jun 28 - Sat, Jul 4
Delta Logo
2:30 pm - 9:45 pm
MBJ
-
MDW
7h 15m
1 stop
Delta Logo
6:00 am - 1:05 pm
MDW
-
MBJ
7h 05m
1 stop
$982Delta
Sun, Jun 28 - Sun, Jul 5
Delta Logo
2:30 pm - 9:45 pm
MBJ
-
MDW
7h 15m
1 stop
Delta Logo
6:00 am - 3:25 pm
MDW
-
MBJ
9h 25m
1 stop
$1,061Delta
Sun, Jun 28 - Sat, Jul 4
WestJet Logo
12:45 pm - 12:30 pm
MBJ
-
MDW
23h 45m
2 stops
WestJet Logo
1:00 pm - 11:40 am
MDW
-
MBJ
22h 40m
2 stops
$1,331WestJet
Sun, Jun 28 - Sun, Jul 5
WestJet Logo
12:45 pm - 8:42 am
MBJ
-
MDW
19h 57m
2 stops
WestJet Logo
9:30 am - 11:40 am
MDW
-
MBJ
26h 10m
2 stops
$1,399WestJet
Wed, Mar 11 - Wed, Mar 18
WestJet Logo
1:55 pm - 5:22 pm
MBJ
-
MDW
27h 27m
2 stops
WestJet Logo
9:35 am - 12:49 pm
MDW
-
MBJ
27h 14m
2 stops
$1,412WestJet
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 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.

No, with an average price for the route of $445, prices are generally cheapest when you fly direct.

Find deals

Good to know

Cheapest flight$170
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

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

    There is a maximum of 1 nonstop flight a day that takes off from Montego Bay and lands in Chicago Midway Airport, with an average flight time of 4h 20m. The most common departure time is 2:00 pm and most flights take off in the afternoon. Each week, there are 1 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 $171 for a one-way ticket and $508 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.

  • 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

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 4268 reviews
7.5Entertainment
8.6Crew
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

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.

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)