MBJ - CHI

$149 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 2/14. 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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Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$230
Typical prices: $455-$497
Spirit Airlines
Wed 2/25Wed 3/4
MBJ - ORD • 1 stop
Cheapest non-stop
$320
American Airlines
Tue 3/24Tue 4/14
MBJ - ORD • Non-stop
Our travelers' advice
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
Spirit Airlines
Cheapest • from $230 (round-trip)
American Airlines
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
MBJ
-
ORD
Cheapest • 23% average savings
MBJ
-
ORD
Most popular
Insights
Insights
Insights
Insights
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Expert advice
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, Feb 25 - Wed, Mar 4
Spirit Airlines Logo
1:00 pm - 9:13 pm
MBJ
-
ORD
9h 13m
1 stop
Spirit Airlines Logo
5:15 am - 12:02 pm
ORD
-
MBJ
5h 47m
1 stop
$230Spirit Airlines
Tue, Mar 24 - Tue, Apr 14
Spirit Airlines Logo
12:00 pm - 7:46 pm
MBJ
-
ORD
7h 46m
1 stop
Spirit Airlines Logo
8:41 pm - 11:02 am
ORD
-
MBJ
14h 21m
1 stop
$269Spirit Airlines
Tue, Mar 24 - Tue, Apr 14
American Airlines Logo
1:14 pm - 5:55 pm
MBJ
-
ORD
4h 41mnonstop
American Airlines Logo
8:10 am - 12:15 pm
ORD
-
MBJ
4h 05mnonstop
$320American Airlines
Tue, Mar 24 - Tue, Apr 14
United Airlines Logo
1:48 pm - 6:13 pm
MBJ
-
ORD
4h 25mnonstop
United Airlines Logo
8:45 am - 3:10 pm
ORD
-
MBJ
6h 25m
1 stop
$325United Airlines
Wed, Feb 25 - Wed, Mar 4
Spirit Airlines Logo
1:00 pm - 7:54 am
MBJ
-
ORD
19h 54m
2 stops
Spirit Airlines Logo
5:15 am - 12:02 pm
ORD
-
MBJ
5h 47m
1 stop
$329Spirit Airlines
Thu, May 14 - Mon, May 18
American Airlines Logo
3:20 pm - 11:53 pm
MBJ
-
ORD
8h 33m
1 stop
American Airlines Logo
6:58 pm - 11:51 am
ORD
-
MBJ
16h 53m
1 stop
$335American Airlines
Thu, May 14 - Sun, May 17
Delta Logo
4:55 pm - 7:26 am
MBJ
-
ORD
14h 31m
2 stops
Delta Logo
9:30 am - 3:29 pm
ORD
-
MBJ
5h 59m
1 stop
$351Delta
Thu, May 14 - Mon, May 18
Delta Logo
2:40 pm - 9:45 pm
MBJ
-
MDW
7h 05m
1 stop
Delta Logo
6:00 am - 1:16 pm
MDW
-
MBJ
7h 16m
1 stop
$351Delta
Sat, Mar 14 - Sat, Mar 21
Southwest Logo
2:20 pm - 6:35 pm
MBJ
-
MDW
4h 15mnonstop
Southwest Logo
8:45 am - 12:35 pm
MDW
-
MBJ
3h 50mnonstop
$531Southwest
Sat, Mar 14 - Sat, Mar 21
Southwest Logo
12:00 pm - 8:10 pm
MBJ
-
MDW
8h 10m
1 stop
Southwest Logo
8:45 am - 12:35 pm
MDW
-
MBJ
3h 50mnonstop
$728Southwest
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 $295 on the route between Montego Bay (MBJ) and Chicago O'Hare Intl Airport (ORD). Over the past month, this route was, on average, 23% 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, Friday 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 $437, prices are generally cheapest when you fly direct.

Find deals
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.

Read more
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.

Read more
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.

Read more
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.

Read more

Good to know

Low seasonNovember
Cheapest flight$149
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly and prices are also 7% 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 $149 for a one-way ticket and $230 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 737-800 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 $282 or less one-way and $365 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, 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, 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, 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.
7.2
American AirlinesOverall score based on 11201 reviews
8.0Crew
7.2Comfort
6.9Entertainment
6.4Food
7.5Boarding
Airline reviews

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

10.0 Excellentaras, Jan 2026
PIT - ORD
Read more American Airlines reviews

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Flight, food and crew were all good, friendly and very satisfactory.

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

Information on your arrival and departure airports

Montego Bay (MBJ)