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Uncover the best deals on Chicago to Montego Bay flights by comparing fares from hundreds of airlines and agencies.
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
$808
Delta Airlines
• 1 stop
• 7h 17m
Sep 24 – Dec 17
The cheapest round trip flight from Chicago to Montego Bay (MDW-MBJ-MDW) is currently $808
Fastest Flight
7h 17m
The fastest nonstop flight from Chicago to Montego Bay (MDW-MBJ) takes 7h 17m
Top Airlines Flying from Chicago to Montego Bay
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.
Sep 24 - Dec 17, Economy
Chicago → Montego Bay
7h 17m
6:05 AM - 3:35 PM • 1 stop
Chicago → Montego Bay
6h 55m
6:12 PM - 11:52 PM • 1 stop
Delta Airlines
Sep 24 - Dec 17, Economy
Chicago → Montego Bay
7h 23m
6:05 AM - 1:01 PM • 1 stop
Chicago → Montego Bay
6h 55m
6:12 PM - 11:52 PM • 1 stop
Delta Airlines
Sep 24 - Dec 17, Economy
Chicago → Montego Bay
7h 24m
6:05 AM - 11:48 AM • 1 stop
Chicago → Montego Bay
6h 55m
6:12 PM - 11:52 PM • 1 stop
Delta Airlines
Sep 24 - Dec 17, Economy
Chicago → Montego Bay
40h 57m
10:48 AM - 11:45 AM • 2 stops
Chicago → Montego Bay
23h 22m
8:35 PM - 9:37 AM • 2 stops
WestJet Airlines
Sep 24 - Dec 17, Economy
Chicago → Montego Bay
37h 6m
1:19 PM - 11:45 AM • 2 stops
Chicago → Montego Bay
25h 24m
8:35 PM - 10:59 AM • 2 stops
WestJet Airlines
Flying to Montego Bay soon? We've surfaced some of the most affordable last-minute flights from Chicago to Montego Bay, ideal for urgent plans or spontaneous trips.
Sep 24 - Dec 17, Economy
Chicago → Montego Bay
7h 17m
6:05 AM - 3:35 PM • 1 stop
Chicago → Montego Bay
6h 55m
6:12 PM - 11:52 PM • 1 stop
Delta Airlines
Sep 24 - Dec 17, Economy
Chicago → Montego Bay
7h 23m
6:05 AM - 1:01 PM • 1 stop
Chicago → Montego Bay
6h 55m
6:12 PM - 11:52 PM • 1 stop
Delta Airlines
Sep 24 - Dec 17, Economy
Chicago → Montego Bay
7h 24m
6:05 AM - 11:48 AM • 1 stop
Chicago → Montego Bay
6h 55m
6:12 PM - 11:52 PM • 1 stop
Delta Airlines
Sep 24 - Dec 17, Economy
Chicago → Montego Bay
40h 57m
10:48 AM - 11:45 AM • 2 stops
Chicago → Montego Bay
23h 22m
8:35 PM - 9:37 AM • 2 stops
WestJet Airlines
Sep 24 - Dec 17, Economy
Chicago → Montego Bay
37h 6m
1:19 PM - 11:45 AM • 2 stops
Chicago → Montego Bay
25h 24m
8:35 PM - 10:59 AM • 2 stops
WestJet Airlines
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 6:05 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 DL : USD 808
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 1:19 pm
Hotels in Montego Bay (MBJ)
5 hotels near Sangster International — compare rates from top booking sites.
5-star hotel
Grand Palladium Lady Hamilton Resort & Spa All Inclusive
📍 The Point, Lucea, Hanover 00000
Compare booking sites
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5-star hotel
Grand Palladium Jamaica Resort Spa All Inclusive
📍 The Point Lucea, Montego Bay
Compare booking sites
Search Deals →
5-star hotel
Half Moon
📍 Rosehall Main Road, Montego Bay
Compare booking sites
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5-star hotel
Hyatt Zilara Rose Hall Adults Only - All Inclusive
📍 Rose Hall Road, Montego Bay
Compare booking sites
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5-star hotel
Hyatt Ziva Rose Hall - All Inclusive
📍 Rose Hall, Montego Bay 00000
Compare booking sites
Search Deals →
Hotel Deals in Fairfield Bay (AR)
Fairfield Bay Getaway < 10 Mi to Boating & Hiking
6.2/10
★★★★☆
$72/night
View Deal
Charming Home w/ Porch: Walk to Greers Ferry Lake!
9.6/10
★★★★☆
✓ Free WiFi
$89/night
View Deal
Beautiful Studio Cabin Near Greers Ferry Lake!
9.1/10
★★★☆☆
$112/night
View Deal
Cozy Studio Cabin ~ 1 Mi to Greers Ferry Lake!
10.0/10
★★★☆☆
$112/night
View Deal
Hike & Fish: Studio w/ Pool Access in Shirley!
6.1/10
★★★★☆
$112/night
View Deal
No chain
Sportsman's Lodge
9.0/10
★★☆☆☆
Motel
✓ Free WiFi
📍 7650 Edgemont Road, Fairfield Bay (AR)
Check-in 03:00 PM · Check-out 11:00 AM
$120/night
View Deal
Southern Comfort Inn & Resort
9.2/10
★★★★★
✓ Free WiFi
$129/night
View Deal
Ruby’s Landing Cottage w/ Deck & White River Views
9.8/10
★★★★☆
✓ Free WiFi
$142/night
View Deal
Pet-Friendly Cabin with Designated Boat Slip!
10.0/10
★★★★☆
✓ Free WiFi
$142/night
View Deal
Also search on:
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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