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MBJ - MDW

$325 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 6/22. 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
0 bags
Sat 6/29
Sat 7/6

Search 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
In the last 7 days travelers have searched 42,686,544 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

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Flights from Montego Bay to Midway - Travel Insights & Trends

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 flights from Montego Bay to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
When flying from Montego Bay to Chicago Midway Airport, you should consider leaving on a Monday and avoid Wednesdays if you are looking for the best rates. For your return to Montego Bay, you’ll find the best rates on Tuesdays and the most expensive ones on Wednesdays.

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 05m. The most common departure time is 2:00 pm and most flights take off in the afternoon. Each week, there are 7 flights.

What’s the earliest departure time from Montego Bay to Chicago Midway Airport?

Early birds can take the earliest flight from Montego Bay at 2:20 pm and will be landing in Chicago Midway Airport at 6:25 pm.

What’s the latest departure time from Montego Bay to Chicago Midway Airport?

If you prefer to fly at night, the latest flight from Montego Bay to Chicago Midway Airport jets off at 3:00 pm and lands at 7:05 pm.

Good to know

Low season

May

High season

May

Cheapest flight

$325
Best time to beat the crowds with an average 54% drop in price.
Most popular time to fly and prices are also 54% 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 $325 for a one-way ticket.

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

    Yes

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

    We unfortunately don’t have that data for this specific 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.

See more FAQs

Prefer to fly non-stop from Montego Bay to Chicago Midway Airport?

Find which airlines fly direct from Sangster Intl to Midway, which days they fly and book direct flights.

Nonstop 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

Nonstop 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

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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.
6.2
FrontierOverall score based on 4016 reviews
5.1Food
4.9Entertainment
5.8Comfort
6.6Boarding
7.1Crew
Airline reviews

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

2.0 MediocreTeddy, May 2024LAS - SAN
Read more about Frontier reviews

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

My experience with frontier staff at the Denver airport was absolutely horrible. The manager on duty was even worst if was the worst experience I have ever had, I have never been treated so poorly as a customer in my life! The staff was extremely rude, eye rolls and attitude and then refusal to help me at all. I wish I could never fly frontier again that’s how horrible it was!

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Plane could have been more on time. More leg room .

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

Book cheap flights from Montego Bay to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Montego Bay to Chicago found on KAYAK in the last 72 hours.
6/22Sat
2 stops
28h 19mMBJ-MDW
$325
6/22Sat
1 stopFrontier
24h 16mMBJ-MDW
$328
6/10Mon
1 stopFrontier
25h 58mMBJ-MDW
$391
6/10Mon
2 stops
41h 42mMBJ-MDW
$419
6/30Sun
2 stops
34h 53mMBJ-MDW
$420
6/30Sun
1 stopFrontier
23h 10mMBJ-MDW
$435
6/24Mon
2 stops
29h 12mMBJ-MDW
$453
6/9Sun
1 stopDelta
7h 16mMBJ-MDW
$792
6/24Mon
2 stopsDelta
18h 18mMBJ-MDW
$798
6/9Sun
2 stopsDelta
18h 18mMBJ-MDW
$1,570

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Last minute flights from Montego Bay to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Montego Bay to Chicago that are departing in the next 10 days.
6/4Tue
multi-stopDelta
16h 07mMBJ-MDW
6/11Tue
multi-stopDelta
17h 14mMDW-MBJ
$1,920

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Montego Bay - Chicago Midway Airport Flights

Departure:

Montego Bay (MBJ)Jamaica

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Montego Bay

Cabin classes: