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Cheap flight tickets from Chicago to Montego Bay

Compare Chicago to Montego Bay flight deals

Find the cheapest month or even day of the year to fly to Montego Bay

Book the best Montego Bay fare with no extra fees

Flight deals from Chicago to Montego Bay Airport

Looking for a cheap last-minute deal or the best return flight from Chicago to Montego Bay Airport? If you want to travel next month, return fares start from RM1,229. Find the lowest prices on one-way and return tickets right here.
Montego Bay.RM1,229 per passenger.Departing Tue, 14 Apr, returning Thu, 16 Apr.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Tue, 14 Apr, arriving in Montego Bay.Inbound indirect flight with Spirit Airlines, departs from Montego Bay on Thu, 16 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM1,229, select.
Montego Bay.RM1,235 per passenger.Departing Sat, 2 May, returning Sat, 9 May.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 2 May, arriving in Montego Bay.Inbound direct flight with United departs from Montego Bay on Sat, 9 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM1,235, select.
Montego Bay.RM1,235 per passenger.Departing Tue, 19 Jan, returning Fri, 22 Jan.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Tue, 19 Jan, arriving in Montego Bay.Inbound indirect flight with United, departs from Montego Bay on Fri, 22 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM1,235, select.
Montego Bay.RM1,235 per passenger.Departing Sun, 25 Oct, returning Sat, 7 Nov.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sun, 25 Oct, arriving in Montego Bay.Inbound direct flight with United departs from Montego Bay on Sat, 7 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM1,235, select.
Montego Bay.RM1,236 per passenger.Departing Sun, 8 Nov, returning Fri, 13 Nov.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sun, 8 Nov, arriving in Montego Bay.Inbound direct flight with United departs from Montego Bay on Fri, 13 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM1,236, select.
Montego Bay.RM1,242 per passenger.Departing Sat, 11 Apr, returning Thu, 16 Apr.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 11 Apr, arriving in Montego Bay.Inbound direct flight with United departs from Montego Bay on Thu, 16 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM1,242, select.
Montego Bay.RM1,259 per passenger.Departing Tue, 7 Jul, returning Sat, 11 Jul.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Tue, 7 Jul, arriving in Montego Bay.Inbound indirect flight with United, departs from Montego Bay on Sat, 11 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM1,259, select.
Montego Bay.RM1,267 per passenger.Departing Tue, 24 Mar, returning Wed, 25 Mar.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Tue, 24 Mar, arriving in Montego Bay.Inbound indirect flight with United, departs from Montego Bay on Wed, 25 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM1,267, select.
Montego Bay.RM1,267 per passenger.Departing Sat, 25 Apr, returning Sat, 2 May.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Sat, 25 Apr, arriving in Montego Bay.Inbound indirect flight with United, departs from Montego Bay on Sat, 2 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM1,267, select.
Montego Bay.RM1,274 per passenger.Departing Thu, 31 Dec, returning Sat, 9 Jan.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Thu, 31 Dec, arriving in Montego Bay.Inbound indirect flight with United, departs from Montego Bay on Sat, 9 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM1,274, select.
Montego Bay.RM1,276 per passenger.Departing Sat, 6 Jun, returning Fri, 12 Jun.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Sat, 6 Jun, arriving in Montego Bay.Inbound indirect flight with United, departs from Montego Bay on Fri, 12 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM1,276, select.
Montego Bay.RM1,299 per passenger.Departing Mon, 5 Oct, returning Sat, 10 Oct.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Mon, 5 Oct, arriving in Montego Bay.Inbound indirect flight with United, departs from Montego Bay on Sat, 10 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM1,299, select.
Montego Bay.RM1,299 per passenger.Departing Sun, 28 Jun, returning Wed, 1 Jul.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Sun, 28 Jun, arriving in Montego Bay.Inbound indirect flight with United, departs from Montego Bay on Wed, 1 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM1,299, select.
Montego Bay.RM1,362 per passenger.Departing Fri, 29 May, returning Mon, 1 Jun.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Fri, 29 May, arriving in Montego Bay.Inbound indirect flight with United, departs from Montego Bay on Mon, 1 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM1,362, select.
Montego Bay.RM1,486 per passenger.Departing Sat, 1 Aug, returning Wed, 5 Aug.Return flight with Copa.Outbound indirect flight with Copa, departs from Chicago O'Hare International on Sat, 1 Aug, arriving in Montego Bay.Inbound indirect flight with Copa, departs from Montego Bay on Wed, 5 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM1,486, select.
Montego Bay.RM1,527 per passenger.Departing Tue, 31 Mar, returning Thu, 16 Apr.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Tue, 31 Mar, arriving in Montego Bay.Inbound indirect flight with Spirit Airlines, departs from Montego Bay on Thu, 16 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM1,527, select.

Find the cheapest month to fly from Chicago to Montego Bay

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Montego Bay flights are currently cheapest in April.
Mar
from RM1,267
Apr
from RM1,229
May
from RM1,235
Jun
from RM1,276
Jul
from RM1,259
Aug
from RM1,486
Sep
from RM1,541
Oct
from RM1,299
Nov
from RM1,236
Dec
from RM1,622
Jan
from RM1,235
Feb
Find prices

Direct flights from Chicago to Montego Bay

Chicago to Montego Bay: Alternative routes

Compare routes from Chicago to Montego Bay below. You may find an airport to fly into that's cheaper, faster, or easier than Montego Bay.

Montego Bay

3km from central Montego Bay
ClosestCheapest
from RM1,229
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Chicago to Montego Bay: Flight information

The things to know before you go.
Cheapest flight foundRM1,229
Cheapest month to flyApril
Average flight time3 hrs, 60 mins
Most popular airlineAmerican Airlines
Average flights per week22

Finding cheap flights from Chicago to Montego Bay: Frequently asked questions

The best price we found for a return flight from Chicago to Montego Bay is RM1,229. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
3 hours and 59 minutes is the average flight time from Chicago to Montego Bay.
American Airlines, United and Southwest Airlines fly direct from Chicago to Montego Bay.
As of March 2026, there are 44 flights per week flying from Chicago to Montego Bay.
The cheapest month to fly from Chicago to Montego Bay is usually April.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Montego Bay Airport on Tuesday, 14 April 2026.
Yes – the average flight time is 3 hours and 59 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Montego Bay but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Montego Bay is around 40 days in advance, so don’t leave your flight to the last minute.

Travelling from Chicago to Sangster International Airport (MBJ): What you need to know

  • Start your holiday planning by considering where you'll board your flight from Chicago to Sangster International Airport (MBJ). Chicago O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are the main airports in Chicago.

  • Hop on a direct Chicago to Sangster International Airport flight and you'll be travelling for an average of 4 hours 5 minutes.

  • Montego Bay is one hour ahead of Chicago. Sangster International Airport is located in Montego Bay, which follows the UTC-5 timezone.

  • Chicago O'Hare International Airport (ORD) to Sangster International Airport (MBJ) is the most popular route, with 10 direct services every week. You can travel from ORD to MBJ on American Airlines's 7am departure.

  • For a stress-free journey, turn up at the airport two hours ahead of international flights and one hour before domestic departures. This will give you plenty of time to board your flight from Chicago to MBJ.

  • With more travellers during busy months like July, get to the terminal earlier than usual. Two hours for domestic flights and as much as four for international journeys will allow for additional wait times. Remember things also get busy during major holidays like Christmas.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Enjoy an uninterrupted journey from Chicago O'Hare International Airport (ORD). Direct flights from Chicago to Sangster International Airport (MBJ) can be booked from here.

  • You can travel on a direct flight from Chicago to Sangster International Airport with American Airlines. This top carrier offers services from ORD.

  • Most passengers choose to book seats with American Airlines between ORD and MBJ.

  • The carrier with the most consistent on-time arrivals rate on this route is American Airlines.

  • A stopover is the ideal opportunity to take a travel break and perhaps even tour another city. When searching for cheap flights from Chicago to MBJ departing from Chicago O'Hare International Airport (ORD), uncheck the 'Direct flights only' box to discover where you can stop along the way. Some popular options include:

    • Atlanta Hartsfield-Jackson International Airport (ATL)

    • Charlotte Douglas International Airport (CLT)

    • Fort Lauderdale-Hollywood International Airport (FLL)

  • ORD is around 27 kilometres from central Chicago. If you're ride-sharing, driving or catching a taxi from the centre, it'll take you 30 minutes or so to get there, depending on traffic conditions. If you're using public transport, expect the trip time to be around 45 minutes.

  • Searching for a convenient hotel close to Chicago O'Hare International Airport? If you're catching an early flight from Chicago to Sangster International Airport, these stays will have you sleeping moments from your departure lounge:

  • When it comes to the on-time performance of Chicago O'Hare International Airport, 70% of flights arrive within the scheduled time frame.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Catching a flight out of Chicago Midway International Airport (MDW)? Direct Chicago to Sangster International Airport (MBJ) plane tickets can be booked from this popular hub.

  • Southwest Airlines operates direct flights from Chicago to MBJ departing from MDW. Book your favourite window seat and reach your destination in a single stretch.

  • On the MDW to MBJ route, Southwest Airlines is the go-to airline for most travellers on this route.

  • The carrier with the best on-time performance is Southwest Airlines. Its Chicago Midway International Airport to Sangster International Airport flights land without delay 66.67% of the time.

  • Check a new destination off your list or just take a moment to recharge with a stopover. If you'd like to split up your flight from Chicago to Sangster International Airport, check out these options when departing from Chicago Midway International Airport:

    • Atlanta Hartsfield-Jackson International Airport (ATL)

    • Charlotte Douglas International Airport (CLT)

    • Orlando International Airport (MCO)

  • On public transport, you can travel from central Chicago to MDW in around 30 minutes. The airport is roughly 16 kilometres away, and making the journey by car takes approximately 25 minutes.

  • Get your holiday started early with an additional night away from home. Before catching your Chicago to MBJ flight, kick back in one of these hotels near Chicago Midway International Airport:

  • Chicago Midway International Airport has an on-time performance rate of 76%. This figure highlights how often flights departing from this airport land on schedule.

  • MDW is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • From the centre of Chicago, RFD is around 145 kilometres away. It'll take you roughly 1 hour 40 minutes to get there by car and 2 hours or so if you use public transport.

  • Take the uncertainty out of departure day — stay near Chicago Rockford International Airport and know you'll get to the terminal with time to spare. Check in to one of these hotels the day before if you've booked an early Chicago to Sangster International Airport flight:

  • Airports have an on-time performance rating that measures how often flights touch down when they should. At RFD, that rate is 71%.

  • You'll find Chicago Rockford International Airport at 2 Airport Cir.

About Sangster International Airport (MBJ)

Getting from Sangster International Airport (MBJ) to central Montego Bay

  • The centre of Montego Bay is around 3 kilometres from Sangster International Airport. Journey times by car hire or taxi will vary based on time of day, so do some research before you go.

  • It'll take around 25 minutes if you're using public transport.

How to find the cheapest flights from Chicago to Sangster International Airport (MBJ)

  • Currently, RM413 is the best price we've found for a one-way ticket from Chicago to Sangster International Airport. The cheapest price for a return flight is RM1,229. Remember fares may change due to demand at the time of booking.

  • Booking ahead of time is often the key to finding a cheap flight from Chicago to MBJ. Fares tend to rise as demand increases, so the closer your departure date, the more it could cost you.

  • Affordable Chicago to Sangster International Airport tickets are easier to find when you have flexibility in your schedule. Use the 'Whole month' search function to compare fares across each month and then pick the cheapest day.

  • There's no need to check every day to find out if fares have dropped when you create a Price Alert. We'll let you know when there's a better deal on plane tickets from Chicago to MBJ.

  • Find the best deal on a flight from Chicago to Sangster International Airport with the help of the filters. Pick your preferred departure and arrival times, airlines and number of stops. You can also sort your results by 'Cheapest,' 'Best' or 'Fastest.'

The best time to fly from Chicago to Sangster International Airport (MBJ)

  • October is the quietest month for flights from Chicago to Sangster International Airport (MBJ), while July is the busiest. Work out the ideal time to go to Montego Bay based on whether you like a laid-back vibe or a lively atmosphere.

  • The warmest month in Montego Bay is August, with temperatures ranging between 25ºC (77ºF) and 31ºC (88ºF). Book your Chicago to MBJ plane ticket then if that's your ideal forecast.

  • Look for cheap tickets from Chicago to Sangster International Airport in February if you like travelling in cooler conditions. Temperatures are at their lowest then, ranging between 22ºC (72ºF) and 28ºC (82ºF).

More about Montego Bay

  • Once you've booked your flight from Chicago to Sangster International Airport, find a hotel that keeps you close to what you want to see. Make one of these accommodation options your base for exploring Montego Bay:

  • You'll find loads of things to do in Montego Bay when you're ready to get out and sightsee. Start exploring at Coral Gardens Neighbourhood Beach followed by Harmony Beach Park and Aqua Sol Theme Park.

Explore more of Jamaica

  • You've seen Montego Bay, now it's time to explore more of Jamaica. Travel around 129 kilometres southeast to Kingston to check off its top sights. From Bob Marley museum to Bob Marley Statue and Blue Mountains, your itinerary will be busy.

  • Spanish Town is another must-experience destination in Jamaica and is around 121 kilometres southeast of Montego Bay. No journey is complete without experiencing First Iron Bridge In The Caribbean, St. Jago De La Vega Cathedral and People's Museum of Craft & Technology.

Plan the rest of your trip from Chicago to Montego Bay

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.