MBJ - MDW

$172 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 5/13. 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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$336
Frontier
Sun 5/10Mon 6/1
MBJ - MDW • 1 stop
Cheapest one-way
$172
Frontier
Wed 5/13
MBJ - MDW • 1 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
Frontier
Cheapest • from $336 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top layover airports
Atlanta (ATL)
Cheapest • Avg $445 (round-trip)
Orlando (MCO)
Shortest trip • 7h 00m (one-way)
Insights
Insights
Insights
Insights
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 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

Sun, May 10 - Mon, Jun 1
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
$336Frontier
Wed, Aug 26 - Sat, Aug 29
Frontier Logo
1:26 pm - 10:11 pm
MBJ
-
MDW
8h 45m
1 stop
Frontier Logo
6:00 am - 12:21 pm
MDW
-
MBJ
6h 21m
1 stop
$348Frontier
Thu, May 14 - Mon, Aug 31
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
Frontier Logo
6:00 am - 12:21 pm
MDW
-
MBJ
6h 21m
1 stop
$369Frontier
Tue, Jun 2 - Fri, Jun 5
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
Frontier Logo
12:04 pm - 12:11 pm
MDW
-
MBJ
24h 07m
1 stop
$374Frontier
Tue, Jun 2 - Fri, Jun 5
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
$376Frontier
Thu, May 14 - Sun, Aug 30
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
Frontier Logo
6:00 am - 12:21 pm
MDW
-
MBJ
6h 21m
1 stop
$396Frontier
Fri, Jun 12 - Fri, Jun 19
Frontier Logo
1:26 pm - 11:04 am
MBJ
-
MDW
21h 38m
1 stop
Frontier Logo
12:04 pm - 12:21 pm
MDW
-
MBJ
24h 17m
1 stop
$402Frontier
Thu, May 14 - Wed, Sep 2
Delta Logo
2:21 pm - 8:43 am
MBJ
-
MDW
18h 22m
2 stops
Delta Logo
6:00 am - 3:34 pm
MDW
-
MBJ
9h 34m
1 stop
$411Delta
Mon, May 11 - Fri, May 15
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
$432Frontier
Thu, May 14 - Sat, Sep 12
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
Frontier Logo
12:03 pm - 1:31 pm
MDW
-
MBJ
25h 28m
1 stop
$439Frontier
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 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 $214 on average.

Find deals

Good to know

Cheapest flight$172
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 $172 for a one-way ticket and $336 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 $417 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 4314 reviews
7.0Food
8.6Crew
8.0Comfort
8.1Boarding
7.5Entertainment
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

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)