Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to Montego Bay from $108

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Montego Bay departing on 5/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago Midway Airport to Montego Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
10:05 am - 1:55 pm
MDW
-
MBJ
3h 50mnonstop
Southwest Logo
1:50 pm - 5:50 pm
MBJ
-
MDW
4h 00mnonstop
$318Southwest
Fri, Jul 3 - Tue, Jul 7
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
Frontier Logo
1:16 pm - 11:12 am
MBJ
-
MDW
21h 56m
1 stop
$324Frontier
Wed, May 6 - Mon, May 11
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
Frontier Logo
1:16 pm - 11:09 am
MBJ
-
MDW
21h 53m
1 stop
$325Frontier
Tue, May 12 - Sun, May 17
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
$328Frontier
Sat, May 9 - Tue, May 12
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
Frontier Logo
1:16 pm - 11:12 am
MBJ
-
MDW
21h 56m
1 stop
$344Frontier
Fri, May 8 - Mon, May 11
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
Frontier Logo
1:16 pm - 11:09 am
MBJ
-
MDW
21h 53m
1 stop
$346Frontier
Tue, May 12 - Sun, May 17
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
$352Frontier
Tue, May 19 - Sat, May 23
Frontier Logo
2:56 pm - 2:23 pm
MDW
-
MBJ
23h 27m
1 stop
Frontier Logo
1:17 pm - 10:14 pm
MBJ
-
MDW
8h 57m
1 stop
$356Frontier
Sat, Apr 11 - Sat, Apr 18
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
$358Frontier
Mon, May 25 - Thu, May 28
Southwest Logo
5:15 am - 2:20 pm
MDW
-
MBJ
9h 05m
1 stop
Southwest Logo
12:15 pm - 8:15 pm
MBJ
-
MDW
8h 00m
2 stops
$367Southwest
Sun, May 3 - Thu, May 7

Frontier flights from Chicago Midway Airport to Montego Bay

Our best Frontier deals on Chicago Midway Airport to Montego Bay flight tickets
Frontier
May 6
MDW6:00 amChicago Midway
6h 11m
1 stop
MBJ12:11 pmMontego Bay Sangster Intl
May 11
MBJ1:16 pmMontego Bay Sangster Intl
21h 56m
1 stop
MDW11:12 amChicago Midway
$324
Frontier
May 12
MDW6:00 amChicago Midway
6h 11m
1 stop
MBJ12:11 pmMontego Bay Sangster Intl
May 17
MBJ1:16 pmMontego Bay Sangster Intl
21h 53m
1 stop
MDW11:09 amChicago Midway
$325
Frontier
May 9
MDW6:00 amChicago Midway
6h 11m
1 stop
MBJ12:11 pmMontego Bay Sangster Intl
May 12
MBJ1:16 pmMontego Bay Sangster Intl
8h 46m
1 stop
MDW10:02 pmChicago Midway
$328

Delta flights from Chicago Midway Airport to Montego Bay

Our best Delta deals on Chicago Midway Airport to Montego Bay flight tickets
Delta
Apr 26
MDW6:00 amChicago Midway
9h 17m
1 stop
MBJ3:17 pmMontego Bay Sangster Intl
Apr 29
MBJ2:10 pmMontego Bay Sangster Intl
8h 18m
1 stop
MDW10:28 pmChicago Midway
$452
Delta
Apr 12
MDW6:00 amChicago Midway
9h 28m
1 stop
MBJ3:28 pmMontego Bay Sangster Intl
Apr 15
MBJ12:44 pmMontego Bay Sangster Intl
9h 44m
1 stop
MDW10:28 pmChicago Midway
$577
Delta
Apr 12
MDW6:00 amChicago Midway
9h 28m
1 stop
MBJ3:28 pmMontego Bay Sangster Intl
Apr 15
MBJ4:32 pmMontego Bay Sangster Intl
16h 15m
2 stops
MDW8:47 amChicago Midway
$582

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Montego Bay that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated April 1, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Montego Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 7/3

10:05 am-1:55 pm

Nonstop3h 50m

Montego Bay Sangster Intl

Tue 7/7

1:50 pm-5:50 pm

Nonstop4h 00m

$318

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 5/6

6:00 am-12:11 pm

1 stop6h 11m

Montego Bay Sangster Intl

Mon 5/11

1:16 pm-11:12 am

1 stop21h 56m

$324

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 5/12

6:00 am-12:11 pm

1 stop6h 11m

Montego Bay Sangster Intl

Sun 5/17

1:16 pm-11:09 am

1 stop21h 53m

$325

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 5/9

6:00 am-12:11 pm

1 stop6h 11m

Montego Bay Sangster Intl

Tue 5/12

1:16 pm-10:02 pm

1 stop8h 46m

$328

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 5/8

6:00 am-12:11 pm

1 stop6h 11m

Montego Bay Sangster Intl

Mon 5/11

1:16 pm-11:12 am

1 stop21h 56m

$344

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 5/12

6:00 am-12:11 pm

1 stop6h 11m

Montego Bay Sangster Intl

Sun 5/17

1:16 pm-11:09 am

1 stop21h 53m

$346

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 5/19

6:00 am-12:11 pm

1 stop6h 11m

Montego Bay Sangster Intl

Sat 5/23

1:16 pm-10:02 pm

1 stop8h 46m

$352

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 4/11

2:56 pm-2:23 pm

1 stop23h 27m

Montego Bay Sangster Intl

Sat 4/18

1:17 pm-10:14 pm

1 stop8h 57m

$356

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 5/25

6:00 am-12:11 pm

1 stop6h 11m

Montego Bay Sangster Intl

Thu 5/28

1:16 pm-10:02 pm

1 stop8h 46m

$358

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 5/3

5:15 am-2:20 pm

1 stop9h 05m

Montego Bay Sangster Intl

Thu 5/7

12:15 pm-8:15 pm

2 stops8h 00m

$367

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Montego Bay from

How to get the cheapest flight ticket from Chicago Midway Airport to Montego Bay

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Chicago Midway Airport and Montego Bay?

What is the cheapest month to fly to Montego Bay?

If you aren’t able to travel to Montego Bay during the month of October, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $568.

What is the cheapest day to depart on your flight to Montego Bay?

On average, the least expensive day to fly to Montego Bay from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $509. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Thursday as prices are generally higher than usual. According to our data, the average ticket price to Montego Bay on Thursday is $655.

What is the cheapest Chicago Midway to Montego Bay Sangster Intl flight route?

Fly from Chicago Midway to Montego Bay Sangster Intl for the best Chicago Midway - Montego Bay Sangster Intl flight prices

What cabin class options are available on Chicago Midway to Montego Bay Sangster Intl flights?

There is only 1 cabin class available to choose from on Chicago Midway to Montego Bay Sangster Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago Midway Airport to Montego Bay flights?

You could potentially save up to 23% on your flight if you consider stops on a Chicago Midway Airport to Montego Bay flight.

When to book flights from Chicago Midway Airport to Montego Bay

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Montego Bay according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Montego Bay (MDW to MBJ) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Montego Bay

Best Price Found

$292

Fastest flight time

3h 50m

Direct flights

Every day

Airports in Montego Bay

1 airport
The best one-way flight to Montego Bay from Chicago Midway Airport in the past 72 hours is $292. The best round-trip flight deal from Chicago Midway Airport to Montego Bay found on momondo in the last 72 hours is $307.
The fastest flight from Chicago Midway Airport to Montego Bay takes 3h 50m
Direct flights go from Chicago Midway Airport to Montego Bay every day.
There is 1 airport in Montego Bay. From Chicago Midway Airport there are direct flights to Montego Bay Sangster Intl (MBJ).
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Montego Bay

  • How far is Chicago Midway to Montego Bay Sangster Intl by plane?

    Chicago Midway and Montego Bay Sangster Intl are 1710.6 mi apart from one another. A reasonable flight in good conditions will take 3h 50m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Montego Bay Sangster Intl Airport?

    Prices for flights from Chicago Midway Airport to Montego Bay Sangster Intl Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to Montego Bay Sangster Intl Airport?

  • How old do you have to be to fly from Chicago Midway Airport to Montego Bay Sangster Intl Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Montego Bay Sangster Intl Airport.

  • What documentation or ID do you need to fly to Montego Bay Sangster Intl Airport?

    The required travel and health documents for your Montego Bay Sangster Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Montego Bay Sangster Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to Montego Bay?

  • What is the most popular airline from Chicago Midway Airport to Montego Bay?

Best airlines flying from Chicago Midway Airport to Montego Bay

Compare and see reviews for airlines that fly from Chicago Midway Airport to Montego Bay with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $341Free CancellationRating
5.7
3,004 reviews
Search Frontier flights
DeltaPriceFrom $395Free CancellationRating
7.9
8,366 reviews
Search Delta flights
SouthwestPriceFrom $518Free CancellationRating
8.0
4,337 reviews
Search Southwest flights

Traveling to a place near Montego Bay?

Book flights to Montego Bay if you plan to visit one of these locations
Lucea
Falmouth
Treasure Beach
Whitehouse

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Montego Bay?

It is quick and easy to find Chicago to Montego Bay flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Montego Bay that suits you.

Can I find flights from Chicago to Montego Bay with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Montego Bay from Chicago with this policy.

How can momondo help me find flights from Chicago to Montego Bay?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Montego Bay.

I’m not ready to book a flight from Chicago to Montego Bay right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Montego Bay flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Montego Bay trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 5/1
Fri 5/8
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Jamaica