MBJ - CHI

$161 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 5/29. 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

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

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

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

Flights Deals
Expert advice
Useful Info
Flights Deals

Cheap Flight Deals 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.

Recent round-trip flight deals from Montego Bay to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Montego Bay to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Spirit Airlines Logo
12:07 pm - 12:05 amMBJ-ORD
11h 58m1 stop
Spirit Airlines Logo
7:35 pm - 11:02 amORD-MBJ
15h 27m1 stop
$300Spirit Airlines
Find Deal
Sat, May 24 - Thu, May 29
Spirit Airlines Logo
12:07 pm - 11:04 pmMBJ-ORD
10h 57m1 stop
Spirit Airlines Logo
5:05 am - 11:02 amORD-MBJ
5h 57m1 stop
$302Spirit Airlines
Find Deal
Tue, Jun 3 - Tue, Jun 10
Frontier Logo
9:08 am - 10:44 pmMBJ-MDW
13h 36m1 stop
Frontier Logo
5:36 pm - 12:37 pmMDW-MBJ
19h 01m1 stop
$412Frontier
Find Deal
Tue, Jun 3 - Tue, Jun 10
American Airlines Logo
1:40 pm - 11:57 pmMBJ-ORD
10h 17m1 stop
American Airlines Logo
4:49 pm - 9:30 amORD-MBJ
16h 41m1 stop
$427American Airlines
Find Deal
Wed, Jul 2 - Sat, Jul 5
United Airlines Logo
1:51 pm - 6:20 pmMBJ-ORD
4h 29mnonstop
United Airlines Logo
2:24 pm - 3:10 pmORD-MBJ
24h 46m1 stop
$431United Airlines
Find Deal
Sat, May 24 - Thu, May 29
 Logo
2:08 pm - 11:11 pmMBJ-ORD
9h 03m1 stop
 Logo
5:05 am - 11:02 amORD-MBJ
5h 57m1 stop
Mon, May 19 - Tue, May 20
 Logo
9:08 am - 10:44 pmMBJ-MDW
13h 36m1 stop
 Logo
5:36 pm - 11:02 amMDW-MBJ
17h 26m2 stops
Tue, Jun 3 - Tue, Jun 10
Frontier Logo
3:53 pm - 11:59 pmMBJ-ORD
8h 06m1 stop
Frontier Logo
6:16 pm - 2:43 pmORD-MBJ
20h 27m1 stop
$502Frontier
Find Deal
Mon, Jun 9 - Thu, Jun 12
United Airlines Logo
1:51 pm - 6:20 pmMBJ-ORD
4h 29mnonstop
United Airlines Logo
8:42 am - 12:49 pmORD-MBJ
4h 07mnonstop
$523United Airlines
Find Deal
Sat, May 31 - Sun, Jun 8
American Airlines Logo
3:40 pm - 10:48 pmMBJ-ORD
7h 08m1 stop
American Airlines Logo
8:44 am - 12:42 pmORD-MBJ
3h 58mnonstop
$539American Airlines
Find Deal
Tue, Jun 3 - Tue, Jun 10
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.

United Airlines

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


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

Airports
MBJ

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

ORD

Take the CTA Blue Line from ORD to downtown Chicago for a 45-minute, traffic-free commute.

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
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
Useful Info

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Montego Bay to Chicago.

Our data shows that the cheapest route for a return flight from Montego Bay to Chicago cost $423 and was between Montego Bay (MBJ) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $423.

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 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 May, where tickets cost $371 (return) on average. On the other hand, the most expensive months are January and June, where the average cost of round-trip tickets is $608 and $567 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 2 stops layover the cheapest option at $510 on average.

Good to know

Low seasonFebruary
High seasonDecember
Cheapest flight$161
Best time to beat the crowds but there is an average 2% 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

  • 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 $161 for a one-way ticket and $300 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, JetBlue, 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, and Star Alliance are the airline alliances operating flights between Montego Bay and Chicago, with oneworld 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.

  • Which is the best airline for flights from Montego Bay to Chicago, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Montego Bay to Chicago are United Airlines and American Airlines. With an average price for the route of $441 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $567 and an overall rating of 7.2.

  • 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 $287 or less one-way and $532 or less round-trip.

Prefer to fly direct from Montego Bay 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, Southwest

American Airlines, United Airlines, +1 more

Tuesday

American Airlines, Southwest

American Airlines, Southwest

Wednesday

American Airlines, Southwest

American Airlines, Southwest

Thursday

American Airlines, Southwest

American Airlines, Southwest

Friday

American Airlines, United Airlines, Southwest

American Airlines, United Airlines, +1 more

Saturday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Sunday

American Airlines, United Airlines, Southwest

American Airlines, United Airlines, +1 more

See more direct flights

Direct returns

Chicago to Montego Bay Sangster Intl

Monday

American Airlines, United Airlines, Southwest

American Airlines, United Airlines, +1 more

Tuesday

American Airlines, Southwest

American Airlines, Southwest

Wednesday

American Airlines, Southwest

American Airlines, Southwest

Thursday

American Airlines, Southwest

American Airlines, Southwest

Friday

American Airlines, United Airlines, Southwest

American Airlines, United Airlines, +1 more

Saturday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Sunday

American Airlines, United Airlines, Southwest

American Airlines, United Airlines, +1 more

See more direct flights
See more direct flights

Top 3 airlines serving 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 8696 reviews
6.6Food
7.7Boarding
8.1Crew
7.1Entertainment
7.3Comfort
Airline reviews

So far so good but food and entertainment are not available for this flight

8.0 ExcellentAnonymous, Apr 2025YUL - ORD
Read more United Airlines reviews

So far so good but food and entertainment are not available for this flight

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

Terrible-extreme delay with very little communication, plane was overfull, luggage was returned on baggage claim in filthy condition.

Lower cost is the reason to fly Spirit. Should give free baggage with credit card.

Very difficult. Flew out on Dec 24th and it was a mess. They know it is going to be the busiest time of the year and they had no organization. Finally they called for people going on certiam flights so they could get them thru thw line then we had to rush to our gate to get in li e to board.We missed our flight do to being stuck at the border of Mexico. They would not work with us to make an affordable price so we had to wait a day with no where to go and pay 280 more for our flights. I would think that a complimentary drink would be nice. But we had to pay 4.49 for a coke. Not an overall good experience

I very late and supose be in home at 12 pm from yesterday but I stiill in detroi airport

My experience with Spirit airlines was terrible. We had a 5 hour delay going to Jamaica and about a 3.5 hour delay returning home with no explanation keep in mind there was already a 4 hour layover in addition to the delay on the return home . We should have arrived in Montego Bay at 1:30pm on 12/22/24 instead we did not get there until about 5 or 6pm our final destination was Negril which is about a 2 hour drive from the airport so we did not reach our hotel until after 8pm so we literally spun the entire day traveling. On 12/27/24 we headed back home. We had arrived in Fort Lauderdale around 4-4:30pm for our layover expecting to be fly from there a little after 9pm and get back to Philadelphia by 12:05am Saturday morning 12/28/24. Once at the airport we kept receiving emails every 15-30 minutes or so apologizing for a delay with the time pushed further and further back. We did not depart from Fort Lauderdale until 12:33am. I forgot to mention that I was traveling with my 5 year old son so if you have small children you already know how that went. The only compensation they gave was two 12 dollar meal vouchers one for my son and one for for myself that we were not able to use because by the time they sent them the places in the airport were mostly closed and we were finally boarding the plane. The staff were very unprofessional and were being rude when we asked them questions about why the time kept getting pushed back. This was my first and absolute last time traveling by way of Spirit airlines. I most absolutely will not ever travel Spirit again. By far the most terrible travel experience thus far.

I’ve now flown Spirit a few times and while the general perception of Spirit I feel is poor, I’ve had a great experience each time. They do charge extra for everything but you should know that going in

Horrible. Take off was delayed by an hour. They were letting people board d the plane right before takeoff. I was delayed an hour when I arrived and late for my meeting. Spirit is NEVER on time.

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.