CHI - MBJ

$104 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 4/13. 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, 0 bags

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.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Montego Bay.
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Everything you should know

Cheapest round-trip
$295
Typical prices: $638-$426
Spirit Airlines, Frontier
Tue 4/28Tue 5/5
ORD - MBJ • 1 stop
Cheapest non-stop
$318
Typical prices: $674-$422
American Airlines
Tue 4/14Wed 4/22
ORD - MBJ • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Choose Economy Plus on United for extra legroom.
Pre-arrange rides at Montego Bay for hassle-free transfers.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $299 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines, Southwest and United Airlines. Average duration is 4h 02m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 2% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $427 (round-trip)
Shortest trip • 6h 05m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 9% price drop
Most popular
Good to know
Good to know
+1
+1
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Good to know
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We hope you love your trip to Montego Bay!
Flight Deals
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Expert advice
Flight Deals

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

Tue, Apr 28 - Tue, May 5
Multiple Airlines Logo
5:05 am - 12:16 pm
ORD
-
MBJ
7h 11m
1 stop
Multiple Airlines Logo
1:16 pm - 7:55 am
MBJ
-
ORD
18h 39m
1 stop
$295Multiple Airlines
Sat, Apr 25 - Sat, May 9
Frontier Logo
5:50 am - 12:12 pm
ORD
-
MBJ
6h 22m
1 stop
Frontier Logo
1:16 pm - 7:55 am
MBJ
-
ORD
18h 39m
1 stop
$299Frontier
Tue, May 5 - Wed, May 13
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
$308Frontier
Tue, Apr 21 - Tue, Apr 28
Spirit Airlines Logo
5:05 am - 12:16 pm
ORD
-
MBJ
7h 11m
1 stop
Spirit Airlines Logo
1:21 pm - 12:24 am
MBJ
-
ORD
11h 03m
1 stop
$315Spirit Airlines
Tue, May 5 - Mon, May 11
Frontier Logo
4:05 pm - 12:11 pm
ORD
-
MBJ
20h 06m
2 stops
Frontier Logo
1:16 pm - 7:55 am
MBJ
-
ORD
18h 39m
1 stop
$317Frontier
Tue, Apr 14 - Wed, Apr 22
American Airlines Logo
8:05 am - 12:13 pm
ORD
-
MBJ
4h 08mnonstop
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
$318American Airlines
Thu, May 7 - Tue, May 12
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
$318Frontier
Tue, May 19 - Sat, May 23
Multiple Airlines Logo
5:05 am - 12:31 pm
ORD
-
MBJ
7h 26m
1 stop
Multiple Airlines Logo
1:16 pm - 7:55 am
MBJ
-
ORD
18h 39m
1 stop
$320Multiple Airlines
Sat, May 2 - Thu, May 7
Spirit Airlines Logo
4:50 pm - 12:16 pm
ORD
-
MBJ
19h 26m
2 stops
Spirit Airlines Logo
1:36 pm - 11:15 pm
MBJ
-
ORD
9h 39m
1 stop
$321Spirit Airlines
Tue, Apr 14 - Wed, Apr 22
American Airlines Logo
7:22 am - 1:19 pm
ORD
-
MBJ
5h 57m
1 stop
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
$322American Airlines
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.

How much is a round-trip flight from Chicago to Montego Bay?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Montego Bay departing in April.

What is the cheapest Chicago to Montego Bay flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The absolute cheapest return flight from Chicago to Montego Bay costs $282 on the route between Chicago O'Hare Intl Airport (ORD) and Montego Bay (MBJ). However, over the past month, flights between Chicago Midway Airport (MDW) and Montego Bay (MBJ) were, on average, 2% cheaper than other Chicago-Montego Bay routes. The most popular route is between Chicago O'Hare Intl Airport (ORD) and Montego Bay (MBJ).

What’s the cheapest day of the week to fly from Chicago to Montego Bay?

The average price of all round-trip flights from Chicago to Montego Bay clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Montego Bay on a Tuesday and more expensive on a Thursday. On your return trip to Chicago, you should consider flying back on a Wednesday, and avoid Mondays for better deals.

What is the cheapest month to fly from Chicago to Montego Bay?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Montego Bay, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Montego Bay is January, where tickets cost $516 (return) on average. On the other hand, the most expensive months are June and December, where the average cost of round-trip tickets is $660 and $596 respectively.

Can I save money by flying with a layover from Chicago to Montego Bay?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $522, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from Chicago to Montego Bay?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Montego Bay, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Montego Bay, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to Montego Bay

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

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.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

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.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Bill Fink

Bill Fink

Expert on MBJ

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.

Good to know

Low seasonAugust
Cheapest flight$104
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 5% 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.

FAQs for booking flights from Chicago to Montego Bay

  • What is the cheapest flight from Chicago to Montego Bay?

    In the last 3 days, the lowest price for a flight from Chicago to Montego Bay was $104 for a one-way ticket and $295 for a round-trip.

  • Do I need a passport to fly between Chicago and Montego Bay?

    Yes

  • Which airports will I be using when flying from Chicago to Montego Bay?

    Chicago is served by 2 major airports and there is only 1 main airport in Montego Bay. You will leave Chicago from one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be arriving at Montego Bay Sangster Intl.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Montego Bay?

    American Airlines, JetBlue, Delta, and Alaska Airlines offer inflight Wi-Fi service on the Chicago to Montego Bay flight route.

  • Which aircraft models fly most regularly from Chicago to Montego Bay?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago to Montego Bay flight route.

  • Which airline alliances offer flights from Chicago to Montego Bay?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Montego Bay, with SkyTeam being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Montego Bay?

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

  • Which is the best airline for flights from Chicago to Montego Bay, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to Montego Bay are Southwest and Delta. With an average price for the route of $652 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $515 and an overall rating of 7.9.

  • How does KAYAK find such low prices on flights from Chicago to Montego Bay?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Montego Bay.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Montego Bay?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Montego Bay from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Montego Bay?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Montego Bay with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Montego Bay?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Montego Bay from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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 $215 or less one-way and $316 or less round-trip.

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,Southwest

American Airlines,Southwest

Tuesday

American Airlines,Southwest

American Airlines,Southwest

Wednesday

American Airlines,Southwest

American Airlines,Southwest

Thursday

American Airlines,Southwest

American Airlines,Southwest

Friday

American Airlines,Southwest

American Airlines,Southwest

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest

American Airlines,Southwest

See more direct flights

Direct returns

Montego Bay Sangster Intl to Chicago

Monday

American Airlines,Southwest

American Airlines,Southwest

Tuesday

American Airlines,Southwest

American Airlines,Southwest

Wednesday

American Airlines,Southwest

American Airlines,Southwest

Thursday

American Airlines,Southwest

American Airlines,Southwest

Friday

American Airlines,Southwest

American Airlines,Southwest

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest

American Airlines,Southwest

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 4337 reviews
7.5Entertainment
7.0Food
8.0Comfort
8.1Boarding
8.6Crew
Airline reviews

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

2.0 MediocreCourtenay, Apr 2026
DAL - CLT
Read more Southwest reviews

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Had a great flight. Delayed takeoff, but comfortable. Snacks were good.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

I liked it better when you were truer to your roots Am paying more for less fun

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

Awful. No counter attendants. No dinner offered due to delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Attention to detail. Luggage was lost in flight, after I confirmed it was connecting. Never made it to the destination airport.

The ticket price are reasonable, however, they can do better with the price on the luggage. Overall, I will continue using spirit.

That this is my second time the they cancel flights and they always wait until the last minute to let people know

The flight was supposed to leave at 6:22pm we are just now leaving the gate after deplaning twice at 1:07am.

Spirit is always late. Every single time. Always a different reason

They cancelled our flight. 2 hours before we were supposed to take off and offered us nothing! We got our money back and that was it. No other flight to get to our cruise no working with another airline or with us to get there. Terrible customer service, no apology.

We get stuck in the plane when landed during 45min and no communication from the crew People were listening to their phone and music out loud and nobody told them anything I definitely want stop booking spirit flight it is a disaster

Good: It was cheap and they got us to our destination safely. Not so Good: Gates experience with many, many nauseatingly (almost) threatening announcements about bags size and how much they were going to charge us if our bag was too big, even to the point of having a gate agent roaming around through the passengers eyeballing bags size and making people go check their bags in the sizers.

Terrible. The flight was randomly delayed in Chicago causing us to miss our connection and they offered us a flight the next day at 6 am and it would have taken till 345 to get to Pensacola. They didn’t cover any fees. Our bags also supposedly were on the flight to Pensacola and we tried to get them yesterday after driving 6 hours and nobody was available. Worst company ever and will never use them again. Had to pay for a rental. Spirit is claiming in climate weather for the delay but there wasn’t any weather issuesz it’s a bunch of bullshit and I am not happy

Checking in at desk in Chicago was horrible. Person was not friendly never smiled and said my flight was not paid for so I had to give another credit card. Then it ended up that I was charged twice. Then after arriving at my destination had to wait on the phone a long time to speak to a person to fix the double charge! Thank goodness the flight was perfect.

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Everything you need to know for your flight from Chicago to Montego Bay

Information on your arrival and departure airports