Find Cheap Flights from Chicago to Montego Bay (CHI - MBJ)

Flights overview

Useful information for finding cheap flights from Chicago to Montego Bay and booking your next trip

Cheapest round-trip flights	$318	American Nonstop 5 hr Thu, Apr 16 — Wed, Apr 22	The cheapest round-trip flight from Chicago to Montego Bay is currently $318
Cheapest one-way flight	$138	Southwest Nonstop 4 hr Wed, Jul 8	The cheapest one-way flight from Chicago to Montego Bay is currently $138
Last-minute weekend getaway	$318	United Nonstop 5 hr Fri, Apr 17 — Sun, Apr 19	The cheapest last-minute weekend getaway from Chicago to Montego Bay is currently $318
Cheapest business class flights	$680	Frontier 1 stop 7 hr Mon, Jun 15 — Tue, Jun 23	The cheapest business class round-trip flight from Chicago to Montego Bay is currently $680

Fastest flight	3 hr 50 min	The fastest nonstop flight from Chicago to Montego Bay takes 3 hr 50 min
Nonstop flights	Every day	There are direct flights on this route every day.

When is the cheapest time to fly?

The cheapest month to fly from Chicago to Montego Bay is typically April. The most expensive month to fly is typically July.

April Cheapest	Typical prices: $295–475
July Most expensive	Typical prices: $370–465

Popular airlines from Chicago to Montego Bay

Southwest

from $318

Typical price: $465–790

1088 weekly connecting flights

MDW, ORD - MBJ Every day
American

Nonstop

from $318

Typical price: $380–610

7 weekly nonstop flights

ORD - MBJ Every day

398 weekly connecting flights

ORD - MBJ Every day
Delta

from $452

Typical price: $435–980

382 weekly connecting flights

MDW, ORD - MBJ Every day
United

Nonstop

from $318

Typical price: $405–800

5 weekly nonstop flights

ORD - MBJ Every Mon, Thu, Fri, Sat, Sun

72 weekly connecting flights

ORD - MBJ Every day
JetBlue

from $1,449

Typical price: $650–1,300

21 weekly connecting flights

ORD - MBJ Every day
COPA

from $480

Typical price: $500–1,300

14 weekly connecting flights

ORD - MBJ Every day

Popular airports near Chicago

Chicago O'Hare International Airport (ORD)

Chicago United States 25 min 16 mi
Chicago Midway International Airport (MDW)

Chicago United States 24 min 9 mi
Milwaukee Mitchell International Airport (MKE)

Milwaukee United States 1 hr 23 min 75 mi
Indianapolis International Airport (IND)

Indianapolis United States 2 hr 58 min 165 mi

Popular airports near Montego Bay

Sangster International Airport (MBJ)

Montego Bay Jamaica 14 min 2 mi
Norman Manley International Airport (KIN)

Kingston Jamaica 2 hr 53 min 83 mi
Ian Fleming International Airport (OCJ)

Ocho Rios Jamaica 1 hr 58 min 62 mi

Frequently asked questions about flying from Chicago to Montego Bay

The cheapest flights from Chicago to Montego Bay are usually in April. Typical ticket prices in April range from $295 to $475.

The cheapest round-trip flight from Chicago to Montego Bay recently found on Google Flights was with American from $318. The cheapest one-way flight was with Southwest from $138.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest Southwest flight from Chicago to Montego Bay is $318, flying from Jul 10 to Jul 16.
The cheapest American flight from Chicago to Montego Bay is $318, flying from Apr 16 to Apr 22.
The cheapest Delta flight from Chicago to Montego Bay is $452, flying from May 1 to May 7.
The cheapest United flight from Chicago to Montego Bay is $318, flying from Apr 17 to Apr 23.
The cheapest JetBlue flight from Chicago to Montego Bay is $1,449, flying from Apr 25 to May 2.
The cheapest COPA flight from Chicago to Montego Bay is $480, flying from Apr 19 to Apr 28.

The cheapest round-trip flight from Chicago to Montego Bay starts at $318 from Thu, Apr 16 to Wed, Apr 22. The cheapest one-way flight starts at $138 and departs on Wed, Jul 8.

3 hr 50 min is the shortest flight time from Chicago to Montego Bay.

Mid-Dec–May is peak travel season, particularly during U.S. college students’ Spring Break (Mar–Apr). Key annual events include Jamaica Jazz & Blues Festival (Jan), a concert series at Rose Hall Great House; Bob Marley’s Birthday Bash (Feb); Carnival (Apr); and the Reggae Sumfest, a music festival held each Jul. During rainy/hurricane season (Jun–Nov), some attractions might be closed. The weather is warm year-round.

It's easy to use Google Flights to find the cheapest days to fly from Chicago to Montego Bay.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.

What counts as the best airline for your flights from Chicago to Montego Bay really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Chicago to Montego Bay.

In terms of nonstop flights, American is the most popular. American offers 7 nonstop flights and 398 connecting flights per week. American flies from Chicago O'Hare International Airport (ORD) to Sangster International Airport (MBJ) .

In terms of flights, Southwest is the most popular. Southwest offers 1,088 connecting flights per week. Southwest flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Sangster International Airport (MBJ) .

Other popular airlines flying from Chicago to Montego Bay are:

Delta offers 382 connecting flights per week. Delta flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Sangster International Airport (MBJ) .
United offers 5 nonstop flights and 72 connecting flights per week. United flies from Chicago O'Hare International Airport (ORD) to Sangster International Airport (MBJ) .
JetBlue offers 21 connecting flights per week. JetBlue flies from Chicago O'Hare International Airport (ORD) to Sangster International Airport (MBJ) .
COPA offers 14 connecting flights per week. COPA flies from Chicago O'Hare International Airport (ORD) to Sangster International Airport (MBJ) .

The number of connecting flights refers to distinct flights with at least one stop between Chicago and Montego Bay.

The cheapest round-trip flight from Chicago to Montego Bay recently found on Google Flights was with American from $318. The cheapest one-way flight was with Southwest from $138.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest Southwest flight from Chicago to Montego Bay is $318, flying from Jul 10 to Jul 16.
The cheapest American flight from Chicago to Montego Bay is $318, flying from Apr 16 to Apr 22.
The cheapest Delta flight from Chicago to Montego Bay is $452, flying from May 1 to May 7.
The cheapest United flight from Chicago to Montego Bay is $318, flying from Apr 17 to Apr 23.
The cheapest JetBlue flight from Chicago to Montego Bay is $1,449, flying from Apr 25 to May 2.
The cheapest COPA flight from Chicago to Montego Bay is $480, flying from Apr 19 to Apr 28.

American and United fly direct from Chicago to Montego Bay.

There are 7 American direct flights from Chicago to Montego Bay per week. Flights are available every day.
There are 5 United direct flights from Chicago to Montego Bay per week. Flights are available on Monday, Thursday, Friday, Saturday and Sunday.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

The cheapest last-minute deal between Chicago and Montego Bay at price $318 is offered by United from Fri, Apr 17 to Sun, Apr 19.

American and United fly direct from Chicago to Montego Bay.

There are 7 American direct flights from Chicago to Montego Bay per week. Flights are available every day.
There are 5 United direct flights from Chicago to Montego Bay per week. Flights are available on Monday, Thursday, Friday, Saturday and Sunday.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

There are direct flights from Chicago to Montego Bay on a daily basis.

The cheapest direct (nonstop) round-trip flights between Chicago and Montego Bay start at $318 from Thu, Apr 16 to Wed, Apr 22 with American.

It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Chicago to Montego Bay, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.

The cheapest business class round-trip flights between Chicago and Montego Bay start at $680 from Mon, Jun 15 to Tue, Jun 23 with Frontier.

The cheapest economy class round-trip flights between Chicago and Montego Bay start at $318 from Thu, Apr 16 to Wed, Apr 22.

To book business class trips from Chicago to Montego Bay, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.

The best last-minute getaway deal for the next weekend between Chicago and Montego Bay starts at $318 from Fri, Apr 17 to Sun, Apr 19 with United.

The cheapest last-minute deal between Chicago and Montego Bay at price $318 is offered by United from Fri, Apr 17 to Sun, Apr 19.

To find last-minute flight deals from Chicago to Montego Bay, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.