MBJ - MDW

$223 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 5/29. 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 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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Flights Deals

Cheap Flights from Montego Bay to Midway

 
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.

Recent round-trip flight deals from Montego Bay to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from Montego Bay to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southwest Logo
2:20 pm - 6:30 pmMBJ-MDW
4h 10mnonstop
Southwest Logo
9:05 am - 1:05 pmMDW-MBJ
4h 00mnonstop
$437Southwest
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Wed, Jul 2 - Sat, Jul 5
Southwest Logo
2:20 pm - 6:30 pmMBJ-MDW
4h 10mnonstop
Southwest Logo
5:30 am - 12:40 pmMDW-MBJ
7h 10m1 stop
$455Southwest
Find Deal
Wed, Jul 2 - Sat, Jul 5
Frontier Logo
3:53 pm - 1:49 pmMBJ-MDW
21h 56m1 stop
Frontier Logo
6:20 am - 7:58 amMDW-MBJ
25h 38m1 stop
$462Frontier
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Sat, Jun 14 - Sat, Jun 21
Frontier Logo
3:53 pm - 1:49 pmMBJ-MDW
21h 56m1 stop
Frontier Logo
6:20 am - 2:43 pmMDW-MBJ
8h 23m1 stop
$482Frontier
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Sat, Jun 14 - Sat, Jun 21
Logo
12:07 pm - 10:28 pmMBJ-MDW
10h 21m2 stops
Logo
6:20 am - 2:43 pmMDW-MBJ
8h 23m1 stop
$486
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Sat, Jun 14 - Sat, Jun 21
Delta Logo
11:31 am - 9:13 pmMBJ-MDW
9h 42m1 stop
Delta Logo
6:00 am - 3:25 pmMDW-MBJ
9h 25m1 stop
$676Delta
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Sat, May 31 - Sun, Jun 8
Logo
12:07 pm - 10:28 pmMBJ-MDW
10h 21m2 stops
Logo
6:20 am - 2:43 pmMDW-MBJ
8h 23m1 stop
$677
Find Deal
Sat, Jun 14 - Sat, Jun 21
Delta Logo
1:02 pm - 9:13 pmMBJ-MDW
8h 11m1 stop
Delta Logo
6:00 am - 1:04 pmMDW-MBJ
7h 04m1 stop
$846Delta
Find Deal
Sat, May 31 - Sun, Jun 8
WestJet Logo
10:30 am - 5:40 pmMBJ-MDW
31h 10m2 stops
WestJet Logo
12:44 pm - 9:27 amMDW-MBJ
20h 43m2 stops
$1,054WestJet
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Sat, Jun 14 - Sat, Jun 21
WestJet Logo
12:45 pm - 1:06 pmMBJ-MDW
24h 21m2 stops
WestJet Logo
12:44 pm - 9:27 amMDW-MBJ
20h 43m2 stops
$1,062WestJet
Find Deal
Sat, Jun 14 - Sat, Jun 21
Useful Info

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 Friday and more expensive on a Saturday. On your return trip to Montego Bay, you should consider flying back on a Thursday, and avoid Sundays for better deals.

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Good to know

Low seasonMarch
High seasonMay
Cheapest flight$223
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly and prices are also 10% 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 $223 for a one-way ticket and $437 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 737-800 Passenger/BBJ2 (winglets) 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?

    There are nonstop flights from Montego Bay to Chicago Midway Airport on a daily basis.

  • 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 $287 or less one-way and $532 or less round-trip.

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

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

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

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
See more direct flights

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 4293 reviews
8.0Comfort
7.1Food
7.6Entertainment
8.6Crew
8.2Boarding
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.

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

Information on your arrival and departure airports

Midway (MDW)
Montego Bay (MBJ)

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