Cheap Flight Tickets from Chicago (MDW) to Montego Bay (MBJ), Starting at $500

Good to Know: Cheapest and Fastest MDW - MBJ Flights

Useful information for finding best airline tickets from Chicago Midway International to Sangster International on your next trip.

Cheapest Round Trip Flight

$500

WN Southwest Airlines • 1 stop • 10h 40m

Dec 13 – Dec 13

The cheapest round trip flight from Chicago to Montego Bay (MDW-MBJ-MDW) is currently $500

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Fastest Flight

9h 14m

The fastest nonstop flight from Chicago to Montego Bay (MDW-MBJ) takes 9h 14m

Top Airlines Flying from Chicago to Montego Bay

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

WestJet Airlines

WestJet Airlines

American Airlines, AA

American Airlines

Latest Flight Deals from Chicago (MDW) to Montego Bay (MBJ)

Compare and book low fare round-trip air tickets from Chicago to Montego Bay. Ideal for travelers with confirmed return itineraries.

Dec 13 - Dec 13, Economy
WN
Chicago → Montego Bay
10h 40m
5:10 AM - 12:50 PM • 1 stop
WN
Chicago → Montego Bay
14h 5m
3:25 PM - 11:10 PM • 1 stop
$500
Southwest Airlines
Dec 13 - Dec 13, Economy
WN
Chicago → Montego Bay
10h 40m
5:10 AM - 12:50 PM • 1 stop
WN
Chicago → Montego Bay
27h 30m
3:25 PM - 7:15 AM • 2 stops
$505
Southwest Airlines
Dec 13 - Dec 13, Economy
DL
Chicago → Montego Bay
9h 14m
6:00 AM - 12:54 PM • 1 stop
DL
Chicago → Montego Bay
13h 46m
3:28 PM - 10:54 PM • 1 stop
$545
Delta Airlines
Dec 13 - Dec 13, Economy
DL
Chicago → Montego Bay
9h 14m
6:00 AM - 12:54 PM • 1 stop
DL
Chicago → Montego Bay
31h 49m
3:28 PM - 9:37 AM • 2 stops
$550
Delta Airlines
Dec 13 - Dec 13, Economy
DL
Chicago → Montego Bay
11h 43m
6:00 AM - 2:03 PM • 1 stop
DL
Chicago → Montego Bay
32h 29m
6:12 PM - 1:01 PM • 2 stops
$550
Delta Airlines
Dec 13 - Dec 13, Economy
DL
Chicago → Montego Bay
11h 43m
6:00 AM - 2:03 PM • 1 stop
DL
Chicago → Montego Bay
28h 36m
6:12 PM - 10:28 AM • 1 stop
$760
Delta Airlines

Fly from Chicago to Montego Bay with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Chicago to Montego Bay? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Chicago to Montego Bay Flights

What are the airports in Chicago?
ORD,MDW
What’s the most popular airline flying from MDW to MBJ?
The most popular airline flying from Chicago to Montego Bay are
Can I fly from MDW to MBJ non-stop?
NO
Which airlines fly nonstop between Chicago and Montego Bay?
The non-stop flights between Chicago and Montego Bay are .
What’s the earliest departure time from MDW to MBJ Airport?
The earliest flight leaves MDW at 5:10 am and lands in MBJ - Sangster International
What are the airports in Montego Bay?
MBJ
Can I make changes to my Chicago to Montego Bay flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from MDW to MBJ?
Read the fare rules of the Chicago to Montego Bay air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Chicago and Montego Bay?
operate flights between Chicago and Montego Bay
How long does a flight from Chicago to Montego Bay take?
It takes approximately 4 hour to fly non-stop from MDW to MBJ, which is 1705.68 miles by air.
Which airlines provide the cheapest flights from Chicago (MDW) to Montego Bay (MBJ) ?
In the past couple of days, the cheapest tickets to MBJ from MDW were found on WN : USD 505
Do I need a passport to fly between MDW and MBJ?
Yes
What’s the latest departure time from MDW to MBJ ?
The last flight leaves MDW at 6:00 am

Chicago (MDW) to Montego Bay (MBJ): Airport Information

Origin Airport Chicago Midway International , Chicago, US
Destination Airport Sangster International , Montego Bay, JM
Distance 1706 miles

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