MBJ - CHI

$181 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 5/7. 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 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
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$281
Typical prices: $391-$525
American Airlines
Wed 6/10Sun 8/30
MBJ - ORD • Non-stop
Cheapest one-way
$181
Typical prices: $286-$327
Spirit Airlines
Thu 5/7
MBJ - ORD • 1 stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
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
Cheapest • from $281 (round-trip)
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines, United Airlines and Southwest. Average duration is 4h 29m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 33% average savings
Most popular
Insights
Insights
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Insights
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!
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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

Wed, Jun 10 - Sun, Aug 30
American Airlines Logo
2:30 pm - 7:15 pm
MBJ
-
ORD
4h 45mnonstop
American Airlines Logo
8:30 am - 12:31 pm
ORD
-
MBJ
4h 01mnonstop
$281American Airlines
Sat, Jun 6 - Sat, Jun 27
Southwest Logo
2:30 pm - 6:35 pm
MBJ
-
MDW
4h 05mnonstop
Southwest Logo
10:10 am - 2:00 pm
MDW
-
MBJ
3h 50mnonstop
$281Southwest
Wed, May 13 - Sun, May 17
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
American Airlines Logo
9:45 am - 3:37 pm
ORD
-
MBJ
5h 52m
1 stop
$286American Airlines
Tue, May 12 - Sat, May 30
United Airlines Logo
2:40 pm - 12:45 am
MBJ
-
ORD
10h 05m
1 stop
United Airlines Logo
5:00 pm - 3:10 pm
ORD
-
MBJ
22h 10m
1 stop
$291United Airlines
Wed, May 13 - Mon, May 18
United Airlines Logo
2:40 pm - 1:27 am
MBJ
-
ORD
10h 47m
1 stop
United Airlines Logo
9:56 pm - 1:30 pm
ORD
-
MBJ
15h 34m
1 stop
$292United Airlines
Tue, Jun 2 - Tue, Sep 8
American Airlines Logo
2:08 pm - 9:29 pm
MBJ
-
ORD
7h 21m
1 stop
American Airlines Logo
6:34 am - 1:58 pm
ORD
-
MBJ
7h 24m
1 stop
$296American Airlines
Tue, Jun 2 - Wed, Sep 2
American Airlines Logo
2:55 pm - 12:38 am
MBJ
-
ORD
9h 43m
1 stop
American Airlines Logo
8:30 am - 12:31 pm
ORD
-
MBJ
4h 01mnonstop
$297American Airlines
Sat, Jun 6 - Sat, Jun 27
United Airlines Logo
4:12 pm - 11:26 pm
MBJ
-
ORD
7h 14m
1 stop
United Airlines Logo
8:40 am - 12:50 pm
ORD
-
MBJ
4h 10mnonstop
$322United Airlines
Tue, May 12 - Sat, May 30
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
Frontier Logo
11:59 am - 12:11 pm
MDW
-
MBJ
24h 12m
1 stop
$382Frontier
Wed, May 13 - Wed, May 27
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
$384Frontier
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 $241 on the route between Montego Bay (MBJ) and Chicago O'Hare Intl Airport (ORD). Over the past month, this route was, on average, 33% 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.

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.

No, with an average price for the route of $405, prices are generally cheapest when you fly direct.

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

Low seasonNovember
Cheapest flight$181
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly and prices are also 12% 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

  • 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 $181 for a one-way ticket and $281 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?

    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 $226 or less one-way and $300 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

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Direct returns

Chicago to Montego Bay Sangster Intl

Monday

American Airlines,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

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 11472 reviews
6.4Food
7.9Crew
6.9Entertainment
7.2Comfort
7.5Boarding
Airline reviews

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

2.0 MediocreBrendan, Mar 2026
LGA - ORD
Read more American Airlines reviews

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

I understand that there is a catering issue - water should be the minimum stock. During the flight, not once that the attendants came through with water. The conversations in the kitchen were very loud and they were swearing. I do not expect any white glove service, at the minimum, we should be cordial. It was almost an inconveniece that we were on the flight. And it made us feel if you even dare question us, we'll make you deplane.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

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

Information on your arrival and departure airports