CHI - MBJ

$98 Find Cheap Flights from Chicago to Montego Bay

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Montego Bay departing on 9/20. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Montego Bay

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Montego Bay, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Montego Bay, as well as popular online travel agencies
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Cheap Flights from Chicago to Montego Bay (CHI-MBJ)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Montego Bay that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Montego Bay

czw., paź 16 - pon., paź 20
Spirit Airlines Logo
11:52 am - 11:00 amORD-MBJ
23h 08m1 stop
Spirit Airlines Logo
12:09 pm - 11:45 pmMBJ-ORD
11h 36m1 stop
$398Spirit Airlines
Find Deal
pt., lis 14 - czw., lis 20
Frontier Logo
6:20 am - 3:15 pmMDW-MBJ
7h 55m1 stop
Frontier Logo
4:53 pm - 11:06 pmMBJ-MDW
7h 13m1 stop
$398Frontier
Find Deal
pon., wrz 29 - sob., paź 4
 Logo
8:15 am - 11:05 amMDW-MBJ
26h 50m2 stops
 Logo
2:05 pm - 11:41 pmMBJ-MDW
9h 36m1 stop
czw., lis 6 - pon., lis 10
 Logo
10:49 am - 1:54 pmORD-MBJ
26h 05m2 stops
 Logo
4:30 pm - 11:14 amMBJ-ORD
19h 44m1 stop
sob., wrz 6 - sob., wrz 13
American Airlines Logo
8:29 pm - 12:05 pmORD-MBJ
15h 36m2 stops
American Airlines Logo
3:54 pm - 11:12 pmMBJ-ORD
7h 18m1 stop
$414American Airlines
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ndz., lis 2 - czw., lis 6
American Airlines Logo
5:18 am - 2:59 pmORD-MBJ
8h 41m1 stop
American Airlines Logo
3:14 pm - 6:55 pmMBJ-ORD
4h 41mnonstop
$415American Airlines
Find Deal
pon., paź 20 - pt., paź 24
Southwest Logo
7:05 am - 1:55 pmMDW-MBJ
6h 50m1 stop
Southwest Logo
12:50 pm - 8:40 pmMBJ-MDW
7h 50m2 stops
$420Southwest
Find Deal
pon., paź 20 - pt., paź 24
Southwest Logo
8:45 pm - 2:00 pmMDW-MBJ
17h 15m2 stops
Southwest Logo
12:50 pm - 8:40 pmMBJ-MDW
7h 50m2 stops
$424Southwest
Find Deal
pon., lis 17 - wt., lis 25
Delta Logo
7:10 am - 4:33 pmORD-MBJ
8h 23m1 stop
Delta Logo
5:58 pm - 8:34 amMBJ-ORD
15h 36m1 stop
$425Delta
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ndz., lis 16 - śr., lis 26
Delta Logo
6:00 am - 4:33 pmMDW-MBJ
9h 33m1 stop
Delta Logo
5:58 pm - 9:51 amMBJ-MDW
16h 53m1 stop
$425Delta
Find Deal
Expert advice

Expert advice for your flight from Chicago to Montego Bay

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
American Airlines

Consider Main Cabin Extra for early boarding and complimentary drinks, enhancing comfort on longer flights.


Use American Airlines’ app for inflight entertainment; seatback screens are being removed on many aircraft.

United Airlines

Opt for Economy Plus for up to six inches more legroom, enhancing comfort on medium-haul flights.


Download the United app for entertainment access; some aircraft lack seatback screens.

Airports
ORD

For a quicker commute to downtown Chicago, take the CTA Blue Line from ORD, which runs 24 hours and avoids traffic delays.

Read more about ORDby Stefanie Waldek
MBJ

At MBJ, pre-arrange your ride to avoid touts. Many resorts offer free shuttles, or use official taxis for a hassle-free transfer.

Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Bill Fink

Bill Fink

Expert on MBJ

Bill Fink

Bill Fink

Bill is an award-winning travel writer with extensive credits covering airlines and the aviation industry for publications including AARP, AFAR, The Points Guy and Yahoo. Based in Portland, Oregon, Bill has traveled to more than 75 countries - and been late for his flight in most of them. He once achieved top-level frequent flier status for all of American, Delta and United Airlines during a single year.

Read more
Booking Insights

KAYAK's insights & trends for Chicago to Montego Bay flights

Get data-powered insights and trends into flights from Chicago to Montego Bay to help you find the cheapest flights, the best time to fly and much more.

What is the most popular layover airport when flying from Chicago to Montego Bay?

Percentage of 1-stop round-trip flights from Chicago to Montego Bay chosen by KAYAK users via each layover airport in the last 12 months (only includes trips with the same layover airport on both legs).

Fort Lauderdale (FLL) is the top choice – 42% of KAYAK users who clicked on 1-stop flights from Chicago to Montego Bay picked an itinerary connecting there.

What is the cheapest layover airport when flying from Chicago to Montego Bay?

Average round-trip price for 1-stop flights from Chicago to Montego Bay clicked by KAYAK users in the last 12 months (only includes trips with the same layover airport on both legs).

Flights via Detroit (DTW) offer the most affordable fares, with an average round-trip price of $379.

Which layover airport offers the shortest total travel time from Chicago to Montego Bay?

Shortest average total travel time for 1-stop one-way flights from Chicago to Montego Bay via different layover airports, based on KAYAK user data from the last 12 months.

Consider flying via St. Louis (STL) for the shortest journey. The average one-way travel time for flights connecting there is 6h 00m.

Which layover airport has the quickest connection when flying from Chicago to Montego Bay?

Average layover duration at different layover airports for 1-stop one-way flights from Chicago to Montego Bay, based on KAYAK user data from the last 12 months.

If you prefer a quick connection, Chicago (ORD) often has the shortest layovers from Chicago to Montego Bay, with an average of 0h 58m.

Good to know

Low seasonAugust
Cheapest flight$98
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 23% increase in price.
Flight from Chicago O'Hare Airport to Montego Bay

When to book flights from Chicago to Montego Bay

Are your dates flexible? Find out the best times to travel from Chicago to Montego Bay based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.
  • What other cities can I visit during my trip to Montego Bay from Chicago?

    You can explore a number of cities in Jamaica when you land at Sangster International Airport in Montego Bay. Some of the cities to consider visiting include Anchovy, Sandy Bay, and Cambridge. Buses provide affordable and convenient means of connecting to these cities from Montego Bay.

  • What is the best way to connect from Sangster International Airport to Montego Bay city center?

    Taxis offer the fastest and most reliable means of transport for travelers from Sangster International Airport to Montego Bay city center. The taxis are available at the airport's parking lot, located immediately after the baggage claim area. In light traffic, a taxi ride to the city center from the airport will take about 10 minutes.

  • Which airline should I use when flying from Chicago to Montego Bay with kids?

    Consider using either American Airlines or Delta Airlines any time you fly from Chicago to Montego Bay. Using American Airlines reduce the time you spend with your kids in the air before arriving at Montego Bay. You will get to your destination in good time before your kids get tired and develop discomfort. If you use Delta Airlines, you and your kids will enjoy traveling comfortably in spacious seats with extra legroom.

  • Are there car rentals at Sangster International Airport?

    Yes. There is an on-site car rental facility at Sangster International airport. This enhances the convenience of those who want to rent a car and enjoy self-drive from the airport to their preferred destination in Montego Bay. The car rental facility features Hertz, Enterprise, Avis, Budget, and other car rentals and is located inside the Arrivals Hall.

KAYAK’s top tips for finding a cheap flight from Chicago to Montego Bay

  • Looking for a cheap flight? 25% of our users found flights on this route for $194 or less one-way and $513 or less round-trip.
  • Most flights from Chicago to Montego Bay have Chicago O'Hare International airport (ORD) as the departure station. It is easier for travelers to access this airport from any point in Chicago compared to other airports in the city. Having the highest number of daily flights to Montego Bay, travelers will certainly get a flight that is suitable to their schedule.
  • Sangster International Airport (MBJ) serves as the arrival airport for quite a number of flights from Chicago to Montego Bay. The airport offers several transport options, including buses, taxis, airport shuttles, and car rentals, for travelers arriving at the airport. Compared to other airports in Montego Bay, it is easier to connect from MBJ to various destinations in the city.
  • Are you worried about your flight from Chicago arriving in Montego Bay late at night? Worry no more. Once you deplane, head straight to The Blue Orchid, one of the hotels closest to the airport, where you can spend the rest of the night. You can safely connect to the hotel using its free airport shuttles, which operate on a 24h basis.
  • The best way to connect from Chicago downtown to Chicago O'Hare International Airport is the use of Rapid Transit Trains. This saves you from the traffic in Chicago, which can be quite terrible during the morning rush hour. The L trains provide nonstop train rides from downtown Chicago to ORD, taking about 20 minutes to arrive at the airport.
  • If you want to catch up with the earliest flight from Chicago to Montego Bay, consider spending your night in one of the hotels near the ORD Airport. For instance, if you spend the night at Hilton Chicago O'Hare Airport, which is about 0.3 miles from the airport, you will have greater convenience accessing the airport in the morning.

Prefer to fly direct from Chicago to Montego Bay?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Montego Bay Sangster Intl.
Find which airlines fly direct from Chicago to Montego Bay Sangster Intl Airport, which days they fly and book direct flights.

Direct departures

Chicago to Montego Bay Sangster Intl

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Direct returns

Montego Bay Sangster Intl to Chicago

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Reviews of the top 5 airlines serving from Chicago to Montego Bay

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Montego Bay. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Montego Bay? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4245 reviews
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
8.1Boarding
Airline reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

6.0 GoodDavid, Aug 2025MCO - DEN
Read more Southwest reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

I was uncomfortably cold on the plane. Other than that it was uneventful and therefore as enjoyable as a plane ride can be.

There was supposed to be a meal served, but there wasn’t and the major toilet was out of order

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

Flight was late, after my first leg was cancelled altogether causing me to spend $$$ with another carrier. Seating is ridiculously tight, I can't recommend spirit if I cant depend on them to get me there and back on time.

Wow truly top notch airline Efficient nice snacks courteous staff Fast boarding !

The staff was very very rude in Las Vegas when boarding the flight. When presenting the boarding ticket. Las Vegas flight, it was hot and stuffy, it smelled really bad.

Dear All, I have harassment and accident with the flight attendant . This is my phone to talk 8168073567, please, leave phone message . Regards Emily,

The incoming plane ✈️ was delayed 5 hours en route to Raleigh. My flight was delayed for 5 hours 😢. Finally boarded and then de boarded due to an AC problem. A very tough and long night.

Flight was on time but the amount of noise from several children and the kicking of my seat the entire flight was overwhelming.

I liked the check in procedure. The luggage charges and overweight cost can be better.

The flight was delayed be over 3 hours. I tried to get a refund for Vivian Kirby and my session kept being stopped. I was NEVER able to finish the prosses...after 2 hours of attempting.

Again, when I use Kayak I expect to pay the total amount and that´s it. Someone added an additional charge few days later after purchasing the tickets.

My experience with Spirit was good, but the experience with Kayak was not. Based on the Spirit agent Kayak added an additional charge after purchasing the tickets. When I buy the tickets I paid the total amount and I only pay once. This time they added an additional charge because based on Spirit they partially charge the tickets and I still needed to pay a second time. This is not good at all and Unprofessional

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