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Cheap flights from Chicago to Montego Bay

Chicago
CHI
Montego Bay
MBJ

Flight deals from Chicago to Montego Bay

Below you can see the best deals on flights Chicago — Montego Bay for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 7 September, from $149.

Top 10 cheap flights from Chicago to Montego Bay

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DL
DL
$ 184

Chicago — Montego Bay

06:35—13:06
28 Jul 2026
6 h 31 m
1 stop
DL
DL
$ 184

Chicago — Montego Bay

06:00—13:06
28 Jul 2026
7 h 6 m
1 stop
DL
DL
$ 184

Chicago — Montego Bay

05:30—13:06
28 Jul 2026
7 h 36 m
1 stop
AA
AA
$ 228

Chicago — Montego Bay

06:59—13:09
26 Jul 2026
6 h 10 m
1 stop
AA
AA
$ 228

Chicago — Montego Bay

05:07—11:25
26 Jul 2026
6 h 18 m
1 stop
AA
AA
$ 228

Chicago — Montego Bay

05:07—11:25
27 Jul 2026
6 h 18 m
1 stop
AA
AA
$ 228

Chicago — Montego Bay

06:10—13:09
27 Jul 2026
6 h 59 m
1 stop
AA
AA
$ 228

Chicago — Montego Bay

06:10—13:09
26 Jul 2026
6 h 59 m
1 stop
AA
AA
$ 228

Chicago — Montego Bay

06:30—13:31
27 Jul 2026
7 h 1 m
1 stop
AA
AA
$ 228

Chicago — Montego Bay

06:30—13:31
28 Jul 2026
7 h 1 m
1 stop
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Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the Chicago — Montego Bay flight

On this page, you can find and book flights from Chicago to Montego Bay. The distance between the cities is 2,754 km, and there are approximately 7 flights per week on this route.

Regular flights are provided by UA and AA. Ticket prices are constantly changing, so we recommend using the low-fare calendar and price dynamics chart to choose the optimal date. If you need to plan your route to the terminal, check the information on how to get to the airport of departure or getting from the airport upon arrival.

Flight ticket prices by day: Chicago — Montego Bay

Below is a calendar of the lowest flight ticket prices for Chicago — Montego Bay by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $149 in F, and the most expensive are around $280 in r. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
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Prices by month

Chicago → Montego Bay, average one-way price

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$310highMay$253mediumSep$230low
Feb$310highJun$276mediumOct$236low
Mar$299highJul$299highNov$247medium
Apr$264mediumAug$264mediumDec$322high

Some values are estimated based on seasonality.

When to fly

The weather in Montego Bay remains consistently hot throughout the year. The warmest month is July, with temperatures reaching 31°C, while the rainiest period is typically August and September, when rainfall is at its peak.

According to statistics, the most affordable time to purchase tickets is in September, with prices starting $149. The highest prices are usually seen in April, when a flight can cost $242.

As a compromise between weather and price, March is a great option: the air temperature is comfortable, although ticket prices starting $235 are slightly above average. We recommend avoiding travel in September due to frequent tropical downpours.

Temperature · Montego Bay

Dry and wet days · Montego Bay

Wind speed and direction · Montego Bay

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Destination

How to get the best deal on a Chicago — Montego Bay ticket

  • Book in advance: The optimal time to search for tickets to Jamaica is 1.5–2 months before your trip, which allows you to find fares $149.
  • Watch the day of the week: Mid-week departures (Tuesday or Wednesday) are typically cheaper than flights over the weekend.
  • Check baggage allowances: Rules for UA and AA may vary; choosing a fare that includes carry-on luggage can help you save at the airport.
  • Use the tools on this page: The low-fare calendar clearly shows price differences for nearby dates, helping you pick the most budget-friendly day for your trip.

Airlines

Airlines operating on the Chicago to Montego Bay route include United Airlines and American Airlines. There are approximately 7 flights per week, including both direct options and flights with short layovers. To view the detailed schedule for specific days of the week and find the best option for you, please refer to the interactive list below.

  • American AirlinesAA
    5x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight ORD → MBJ5x/week
      Duration
      4h 9m
      Days
      MTWTFSS
    70.0%Open →
  • United AirlinesUA
    2x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight ORD → MBJ2x/week
      Duration
      4h 8m
      Days
      MTWTFSS
    30.0%Open →

Cities and airports on the Chicago — Montego Bay route

Flights Chicago — Montego Bay depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport and arrive at Sangster International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Arrival

Montego Bay

MBJ
Jamaica
About the cityHow to get thereWeatherAll about the country Jamaica
Departure airports
Arrival airports

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Frequently asked questions about the Chicago — Montego Bay flight

How long is the flight from Chicago to Montego Bay?

The average travel time for a direct flight is approximately 3 hours and 15 minutes, covering a distance of 2,754 km.

Which airlines operate flights?

Regular flights from Chicago are operated by United Airlines (UA) and American Airlines (AA).

Are there direct flights on this route?

Yes, there are direct flights on this route, with a total frequency of about 7 departures per week.

Which airport do flights arrive at?

Flights arrive at Sangster International Airport (MBJ), which is located directly in the city of Montego Bay.

When is the best time to buy flight tickets?

Prices are dynamic and depend on the season. To secure the best deal, we recommend monitoring the price chart and booking as soon as you see a suitable fare in the calendar.

Where else you can fly from Chicago

See all
New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverNashvilleLondonIndianapolisSan DiegoMontrealMilwaukeeSt. LouisCharlottePhiladelphiaColumbusKansas CityMiamiPhoenixLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochester

Where else you can fly from Montego Bay

See all
New York CityAtlantaFort LauderdaleTorontoMiamiOrlandoHoustonPhiladelphiaCharlotteDallasPanama CityMontrealLondonMinneapolisCalgaryBostonDetroitLimaWashington, D.C.HalifaxRaleighEdmontonOttawaFrankfurt am MainGeorge TownWinnipegDenverHartfordNassau

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