MBJ - CHI

$156 Find Cheap Flights from Montego Bay to Chicago

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 10/11. 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 Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Montego Bay to Chicago, 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 Montego Bay to Chicago, as well as popular online travel agencies
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Booking Insights
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

Tue, Oct 7 - Sat, Oct 11
Spirit Airlines Logo
12:09 pm - 11:45 pmMBJ-ORD
11h 36m1 stop
Spirit Airlines Logo
7:43 pm - 11:00 amORD-MBJ
15h 17m1 stop
$239Spirit Airlines
Find Deal
Thu, Oct 2 - Sun, Oct 5
Spirit Airlines Logo
12:10 pm - 10:48 pmMBJ-ORD
10h 38m1 stop
Spirit Airlines Logo
5:05 am - 11:00 amORD-MBJ
5h 55m1 stop
$249Spirit Airlines
Find Deal
Thu, Oct 2 - Sun, Oct 5
Spirit Airlines Logo
12:10 pm - 10:48 pmMBJ-ORD
10h 38m1 stop
Spirit Airlines Logo
6:58 pm - 11:00 amORD-MBJ
16h 02m2 stops
$272Spirit Airlines
Find Deal
Tue, Oct 7 - Sat, Oct 11
American Airlines Logo
1:50 pm - 6:23 pmMBJ-ORD
4h 33mnonstop
American Airlines Logo
9:45 pm - 2:15 pmORD-MBJ
16h 30m1 stop
$338American Airlines
Find Deal
Thu, Oct 2 - Sun, Oct 5
Spirit Airlines Logo
12:10 pm - 4:12 pmMBJ-ORD
28h 02m3 stops
Spirit Airlines Logo
5:05 am - 11:00 amORD-MBJ
5h 55m1 stop
$358Spirit Airlines
Find Deal
Fri, Dec 12 - Fri, Jan 2
United Airlines Logo
2:48 pm - 6:13 pmMBJ-ORD
4h 25mnonstop
United Airlines Logo
8:42 am - 1:46 pmORD-MBJ
4h 04mnonstop
$372United Airlines
Find Deal
Fri, Dec 12 - Fri, Jan 2
American Airlines Logo
2:30 pm - 6:17 pmMBJ-ORD
4h 47mnonstop
American Airlines Logo
8:03 am - 4:14 pmORD-MBJ
7h 11m1 stop
$376American Airlines
Find Deal
Fri, Dec 12 - Fri, Jan 2
Delta Logo
5:59 pm - 12:01 amMBJ-ORD
7h 02m1 stop
Delta Logo
5:40 am - 8:36 pmORD-MBJ
13h 56m1 stop
$377Delta
Find Deal
Sun, Sep 28 - Sun, Oct 5
Logo
12:14 pm - 10:52 amMBJ-ORD
46h 38m2 stops
Logo
7:43 pm - 11:00 amORD-MBJ
15h 17m1 stop
$414
Find Deal
Mon, Sep 29 - Mon, Oct 6
Logo
10:52 am - 6:43 pmMBJ-MDW
7h 51m1 stop
Logo
9:47 pm - 11:00 amMDW-MBJ
13h 13m2 stops
$683
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
Upgrade to Economy Plus on United for extra legroom.
Arrive two hours early at MBJ for smooth security.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Spirit Airlines
Cheapest • from $239 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
MBJ-ORD
Cheapest • 64% average savings
MBJ-ORD
Most popular
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 20% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$239
Overall average: $523
Spirit Airlines
Tue 10/7Sat 10/11
MBJ - ORD • 1 stop
Cheapest non-stop
$372
Typical prices: $479-600
United Airlines
Fri 12/12Fri 1/2
MBJ - ORD • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Expert advice

Expert advice for your flight from Montego Bay to Chicago

 
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

Main Cabin Extra offers early boarding and free drinks, ideal for longer flights.


Consider Basic Economy for budget travel, but check total costs against Main Cabin fares.

Read more about American Airlinesby Harriet Baskas
Southwest

Southwest offers free snacks and soft drinks; download the app for onboard entertainment.


Book flights with points and cash for flexibility if points are insufficient.

Read more about Southwestby Blane Bachelor
United Airlines

Upgrade to Economy Plus for extra legroom, especially on longer flights.


Use Priority Boarding to ensure overhead bin space for carry-ons.

Read more about United Airlinesby Stefanie Waldek
Airports
MBJ

Arrive two hours before your flight at MBJ for a smooth security process, even during busy seasons.

Read more about MBJby Bill Fink
ORD

Take the CTA Blue Line from ORD to downtown Chicago for a reliable 45-minute journey, avoiding traffic delays.

Read more about ORDby Stefanie Waldek
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
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor

Blane Bachelor

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.

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 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 $158 on the route between Montego Bay (MBJ) and Chicago O'Hare Intl Airport (ORD). Over the past month, this route was, on average, 64% 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 Saturday, 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 Sunday 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 September, where tickets cost $373 (return) on average. On the other hand, the most expensive months are January and February, where the average cost of round-trip tickets is $608 and $572 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 $406 on average.

Find deals

Good to know

Low seasonFebruary
Cheapest flight$156
Best time to beat the crowds but there is an average 22% increase in price.
Most popular time to fly and prices are also 5% lower on average.
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

  • How many flights are there between Montego Bay and Chicago per day?

    There is a maximum of 1 nonstop flight a day that takes off from Montego Bay and lands in Chicago, with an average flight time of 4h 33m. The most common departure time is 1:00 pm and most flights take off in the afternoon. Each week, there are 7 flights.

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

    In the last 3 days, the lowest price for a flight from Montego Bay to Chicago was $156 for a one-way ticket and $239 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?

    American Airlines, Delta, and Air Canada 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?

    oneworld is the only airline alliance operating flights between Montego Bay and Chicago.

  • 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 $292 or less one-way and $496 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, 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, Southwest

American Airlines, United Airlines, +1 more

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Direct returns

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, Southwest

American Airlines, United Airlines, +1 more

Sunday

American Airlines, United Airlines

American Airlines, United 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.
7.4
United AirlinesOverall score based on 8929 reviews
8.1Crew
7.1Entertainment
7.7Boarding
7.3Comfort
6.6Food
Airline reviews

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

8.0 ExcellentAnonymous, Aug 2025YOW - ORD
Read more United Airlines reviews

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Inoperable monitor left no entert for 9 hours. Crew was not helpful Food was awful.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

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

Information on your arrival and departure airports

Montego Bay (MBJ)

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