Cheap Flight Tickets from Chicago (MDW) to Montego Bay (MBJ), Starting at $522

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

$522

WN Southwest Airlines • 1 stop • 12h 5m

Dec 01 – Jan 09

The cheapest round trip flight from Chicago to Montego Bay (MDW-MBJ-MDW) is currently $522

🔍 Search Flights

Cheapest Direct Flight

$637

UA United Airlines • nonstop • 6h 48m

Nov 28

The cheapest nonstop flight from Chicago to Montego Bay (MDW-MBJ) is currently $637

🔍 Search Flights

Fastest Flight

5h 55m

The fastest nonstop flight from Chicago to Montego Bay (MDW-MBJ) takes 5h 55m

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 01 - Jan 09, Economy
WN
Chicago → Montego Bay
12h 5m
6:00 AM - 2:25 PM • 1 stop
WN
Chicago → Montego Bay
6h 50m
12:45 PM - 3:55 PM • nonstop
$522
Southwest Airlines
Dec 01 - Jan 09, Economy
WN
Chicago → Montego Bay
8h 55m
8:10 AM - 2:45 PM • 1 stop
WN
Chicago → Montego Bay
6h 50m
12:45 PM - 3:55 PM • nonstop
$522
Southwest Airlines
Nov 29 - Jan 07, Economy
WN
Chicago → Montego Bay
23h 55m
11:10 PM - 2:45 PM • 2 stops
WN
Chicago → Montego Bay
13h 25m
2:00 PM - 9:05 PM • 1 stop
$852
Southwest Airlines
Dec 01 - Jan 06, Economy
WN
Chicago → Montego Bay
27h 20m
8:45 PM - 2:25 PM • 2 stops
WN
Chicago → Montego Bay
14h
1:10 PM - 8:50 PM • 1 stop
$1001
Southwest Airlines
Dec 02 - Jan 06, Economy
WN
Chicago → Montego Bay
12h 5m
6:00 AM - 2:25 PM • 1 stop
WN
Chicago → Montego Bay
28h 25m
3:10 PM - 7:15 AM • 2 stops
$1056
Southwest Airlines
Dec 02 - Jan 06, Economy
WN
Chicago → Montego Bay
8h 55m
8:10 AM - 2:45 PM • 1 stop
WN
Chicago → Montego Bay
28h 25m
3:10 PM - 7:15 AM • 2 stops
$1165
Southwest 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?
Yes, you can fly MDW to MBJ non-stop on
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 6:00 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 852
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 10:500 pm

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

More Flight Options for Chicago (MDW) and Montego Bay (MBJ)

Why Fareleaders for MDW to MBJ Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on Chicago to Montego Bay flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on MDW to MBJ flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of Chicago to Montego Bay flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the Chicago (MDW) to Montego Bay (MBJ)
Terms and Conditions*