MBJ - CHI

$209 Find Cheap Flights from Montego Bay to Chicago - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Montego Bay to Chicago departing on 11/2. 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

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Everything you should know

Cheapest round-trip
$396
Typical prices: $348-$370
American Airlines
Fri 9/4Fri 9/11
MBJ - ORD • Non-stop
Cheapest non-stop
$432
United Airlines
Mon 11/23Sun 11/29
MBJ - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
American Basic Economy can save money; compare total cost with Main Cabin fares.
United Economy Plus adds legroom, while American Main Cabin Extra adds perks.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $396 (round-trip)
Best reviews • 7.1 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines and United Airlines. Average duration is 4h 33m
Direct flights
Direct flights
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Direct flights
Direct flights
+1
Top routes
Cheapest • 20% average savings
Most popular
Insights
Insights
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Top layover airports
Cheapest • Avg $293 (round-trip)
Shortest trip • 6h 30m (one-way)
Insights
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Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Montego Bay to Chicago 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 Montego Bay to Chicago

Fri, Sep 4 - Fri, Sep 11
American Airlines Logo
2:12 pm - 6:55 pm
MBJ
-
ORD
4h 43mnonstop
American Airlines Logo
5:48 pm - 11:17 am
ORD
-
MBJ
17h 29m
1 stop
$396American Airlines
Sat, Sep 5 - Sat, Sep 12
Delta Logo
4:59 pm - 11:57 pm
MBJ
-
ORD
6h 58m
1 stop
Delta Logo
6:40 am - 1:01 pm
ORD
-
MBJ
6h 21m
1 stop
$397Delta
Thu, Oct 29 - Tue, Dec 29
Delta Logo
2:26 pm - 10:33 pm
MBJ
-
MDW
8h 07m
1 stop
Delta Logo
9:30 am - 8:41 pm
MDW
-
MBJ
10h 11m
2 stops
$397Delta
Sat, Dec 19 - Sat, Jan 2
United Airlines Logo
3:45 pm - 10:07 am
MBJ
-
ORD
19h 22m
1 stop
United Airlines Logo
8:17 pm - 2:39 pm
ORD
-
MBJ
17h 22m
1 stop
$403United Airlines
Mon, Nov 23 - Sun, Nov 29
Air Canada Logo
6:20 pm - 9:23 am
MBJ
-
ORD
16h 03m
1 stop
Air Canada Logo
4:30 pm - 5:20 pm
ORD
-
MBJ
23h 50m
1 stop
$425Air Canada
Mon, Nov 23 - Sun, Nov 29
Air Canada Logo
6:20 pm - 9:23 am
MBJ
-
ORD
16h 03m
1 stop
Air Canada Logo
3:45 pm - 12:50 pm
ORD
-
MBJ
20h 05m
2 stops
$429Air Canada
Mon, Nov 23 - Sun, Nov 29
United Airlines Logo
2:54 pm - 6:20 pm
MBJ
-
ORD
4h 26mnonstop
United Airlines Logo
8:40 am - 1:48 pm
ORD
-
MBJ
4h 08mnonstop
$432United Airlines
Fri, Sep 4 - Fri, Sep 11
Southwest Logo
2:15 pm - 10:45 pm
MBJ
-
MDW
8h 30m
1 stop
Southwest Logo
7:50 pm - 12:25 pm
MDW
-
MBJ
16h 35m
2 stops
$449Southwest
Thu, Aug 13 - Sun, Aug 16
Frontier Logo
1:32 pm - 10:03 pm
MBJ
-
MDW
8h 31m
1 stop
Frontier Logo
6:05 am - 12:24 pm
MDW
-
MBJ
6h 19m
1 stop
$508Frontier
Fri, Sep 4 - Fri, Sep 11
Southwest Logo
2:15 pm - 10:45 pm
MBJ
-
MDW
8h 30m
1 stop
Southwest Logo
5:00 am - 1:15 pm
MDW
-
MBJ
8h 15m
1 stop
$514Southwest
Booking Insights

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

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

What is the cheapest Montego Bay to Chicago flight route?

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

The cheapest return flight from Montego Bay to Chicago costs $359 on the route between Montego Bay (MBJ) and Chicago O'Hare Intl Airport (ORD). Over the past month, this route was, on average, 20% cheaper than other Montego Bay-Chicago routes. It is also the most popular route.

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

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

If your flying dates are flexible, you should consider flying to Chicago on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Montego Bay to Chicago. For your return ticket, we recommend flying on a Tuesday and avoiding Thursdays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Montego Bay to Chicago, 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 Montego Bay to Chicago is January, where tickets cost $0 (return) on average. On the other hand, the most expensive months are August and October, where the average cost of round-trip tickets is $563 and $539 respectively.

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

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $651 on average.

Expert advice

Expert advice for your flight from Montego Bay to Chicago

 
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
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.

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.

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.

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

Cheapest flight

$209
Flight from Montego Bay to Chicago O'Hare Airport

When to book flights from Montego Bay to Chicago

Are your dates flexible? Find out the best times to travel from Montego Bay to Chicago 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 Montego Bay to Chicago

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

    In the last 5 days, the lowest price for a flight from Montego Bay to Chicago was $209 for a one-way ticket and $396 for a round-trip.

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

    A passport is required to fly from Montego Bay to Chicago.

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

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

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

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

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

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Montego Bay to Chicago flight route.

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

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

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

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

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

    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 Montego Bay to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Montego Bay 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 Montego Bay to Chicago?

    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 Chicago with an airline and back to Montego Bay with another airline.

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

    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 Chicago from Montego Bay 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 Montego Bay to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $245 or less one-way and $385 or less round-trip.

Prefer to fly direct from Montego Bay to Chicago?

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

Direct departures

Montego Bay Sangster Intl to Chicago

Monday

American Airlines

American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

American Airlines

American Airlines

Friday

American Airlines

American Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines

American Airlines

See more direct flights

Direct returns

Chicago to Montego Bay Sangster Intl

Monday

American Airlines

American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

American Airlines

American Airlines

Friday

American Airlines

American Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines

American Airlines

See more direct flights

Reviews of the top airline flying from Montego Bay to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Montego Bay to Chicago. 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 Montego Bay to Chicago? 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.
7.1
American AirlinesOverall score based on 11837 reviews
6.8Entertainment
7.9Crew
7.2Comfort
7.5Boarding
6.4Food
Airline reviews

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

10.0 ExcellentAnonymous, Jul 2026
LAX - ORD
Read more American Airlines reviews

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

Take this flight regularly. Every single week same thing. Departure delayed. Make up some time in the air. Land at ORD and then wait for gate in "L" concourse Terminal 3 for 30-40 min-which yields a very delayed final arrival. Plus I get to taxi around and see every runway and drive over the bridge (IFKYK) over the expressway 2-4 times in most cases. Change the sched of incoming plane/work with FAA to improve traffic flow at ORD/change the timing of these flights. Whatever it takes. But do better.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Boarding and Delays The boarding process for my American Airlines flight from Copenhagen to Philadelphia was a bit tricky. We experienced a gate change that required a long walk to a new area of the airport. Additionally, boarding was not via a jet bridge; we had to take a shuttle bus to the plane and then carry our luggage up the stairs ourselves. Furthermore, the bag drop didn't open until about 12:20 PM, which was only three hours before our scheduled departure. This meant I couldn't drop my bag off early and had to wait outside of security in order to drop off my bag and use the kiosk. The bag drop self-service kiosks also didn't open until about 12:00 PM when an American Airlines employee unlocked them so that we could print out our boarding passes and bag tags, which further created a backlog. The flight was delayed by over an hour because we had to wait for one of the tires on the plane to be changed. Flight Attendant Professionalism On a positive note, the flight attendant was very professional when handling a passenger who was sitting in the wrong seat. Even though the passenger was persistent and reluctant to move, the flight attendant calmly ensured the assigned passenger could take their seat. Kudos to the flight attendant for keeping his calm and composure, not allowing the issue to escalate, and handling it well under pressure while a line of passengers waited in the aisle to board. In-Flight Service The in-flight service was also fast, prompt, and efficient, although service had to be suspended for the last two hours of the flight due to weather and turbulence, which was outside of the crew's control. Limited Flight Options Please note that American Airlines only operates one flight per day in and out of Copenhagen. This means there are limited options available if your flight is delayed or canceled, which is something to take into consideration when booking.

This may have been the hottest cabin temperatures I have experienced on any flight prior to take off lasting for approximately 30 minutes. I am not typically one to complain but I was genuinely worried about the health of several passengers on the flight due to the extreme temperatures including a small toddler.

I will never but. through kayak again. and American Airlines. I will never fly again on. They're both thieves.

Nothing, I wont be flying American Airlines again and will not be recommending anyone to fly American Airlines. It was the worst experience flying I've ever had.

My luggage was not sent with us. Not sure if this is Envoy Air responsibility but that was a very BAD experience

The gates should be ready when we land. Waiting on the runway for a hour is ridiculous.

They don't make it easy or promote their food options. Dirty plane. Delayed.

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

Information on your arrival and departure airports