MBJ - CHI

$153 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 2/7. 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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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
$330
Overall average: $388
Spirit Airlines
Sun 3/1Wed 3/4
MBJ - ORD • 1 stop
Cheapest non-stop
$495
Typical prices: $480-$566
American Airlines
Sun 3/1Wed 3/4
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 $330 (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 • 1% average savings
MBJ-ORD
Most popular
Insights
Insights
Insights
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!
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

Sun, Mar 1 - Wed, Mar 4
Spirit Airlines Logo
1:00 pm - 6:52 pm
MBJ
-
ORD
6h 52m1 stop
Spirit Airlines Logo
5:15 am - 12:02 pm
ORD
-
MBJ
5h 47m1 stop
$330Spirit Airlines
Wed, Jan 14 - Wed, Jan 21
Delta Logo
4:45 pm - 11:59 pm
MBJ
-
ORD
8h 14m1 stop
Delta Logo
5:30 am - 12:54 pm
ORD
-
MBJ
6h 24m1 stop
$346Delta
Wed, Jan 14 - Wed, Jan 21
Delta Logo
2:19 pm - 10:07 pm
MBJ
-
MDW
8h 48m1 stop
Delta Logo
6:00 am - 12:54 pm
MDW
-
MBJ
5h 54m1 stop
$346Delta
Wed, Jan 14 - Wed, Jan 21
American Airlines Logo
1:58 pm - 10:34 pm
MBJ
-
ORD
9h 36m2 stops
American Airlines Logo
6:54 am - 3:16 pm
ORD
-
MBJ
7h 22m1 stop
$359American Airlines
Sun, Mar 1 - Wed, Mar 4
Multiple Airlines Logo
1:00 pm - 6:52 pm
MBJ
-
ORD
6h 52m1 stop
Multiple Airlines Logo
6:04 pm - 12:30 pm
ORD
-
MBJ
41h 26m2 stops
$378Multiple Airlines
Wed, Jan 14 - Wed, Jan 21
American Airlines Logo
1:58 pm - 11:27 pm
MBJ
-
ORD
10h 29m2 stops
American Airlines Logo
9:10 pm - 11:33 am
ORD
-
MBJ
13h 23m2 stops
$381American Airlines
Wed, Jan 14 - Wed, Jan 21
Southwest Logo
2:00 pm - 9:00 pm
MBJ
-
MDW
8h 00m1 stop
Southwest Logo
7:55 pm - 1:00 pm
MDW
-
MBJ
16h 05m2 stops
$409Southwest
Sun, Mar 1 - Wed, Mar 4
Delta Logo
4:44 pm - 10:42 pm
MBJ
-
MDW
6h 58m1 stop
Delta Logo
6:00 am - 3:19 pm
MDW
-
MBJ
8h 19m1 stop
$416Delta
Sun, Mar 1 - Wed, Mar 4
JetBlue Logo
6:17 pm - 11:48 am
MBJ
-
ORD
18h 31m2 stops
JetBlue Logo
12:41 pm - 12:53 pm
ORD
-
MBJ
23h 12m2 stops
$452JetBlue
Wed, Jan 14 - Wed, Jan 21
Southwest Logo
2:00 pm - 10:05 pm
MBJ
-
MDW
9h 05m2 stops
Southwest Logo
7:55 pm - 1:00 pm
MDW
-
MBJ
16h 05m2 stops
$459Southwest
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 absolute cheapest return flight from Montego Bay to Chicago costs $360 on the route between Montego Bay (MBJ) and Chicago O'Hare Intl Airport (ORD). However, over the past month, flights between Montego Bay (MBJ) and Chicago Midway Airport (MDW) were, on average, 1% cheaper than other Montego Bay-Chicago routes. The most popular route is between Montego Bay (MBJ) and Chicago O'Hare Intl Airport (ORD).

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.

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 $418 on average.

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.
Airlines
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
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
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
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
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
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

Good to know

Low seasonNovember
Cheapest flight$153
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly and prices are also 2% 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 $153 for a one-way ticket and $330 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 $237 or less one-way and $414 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, Southwest

American Airlines, Southwest

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, Southwest

American Airlines, Southwest

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.
7.2
American AirlinesOverall score based on 11048 reviews
7.2Comfort
6.5Food
7.5Boarding
6.9Entertainment
8.0Crew
Airline reviews

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

2.0 MediocreJohn, Dec 2025
GSO - ORD
Read more American Airlines reviews

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.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Premium economy seat was decent. As always poor headphones, poor food and beverage, crew is not overly friendly

Excellent - explanations were clear staff was nice and flight was comfortable

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

Information on your arrival and departure airports

Montego Bay (MBJ)