$193 Find Cheap Flights from Chicago to Falmouth - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Falmouth departing on 9/5. 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

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Everything you should know

Cheapest round-trip
$428
Typical prices: $412-$596
American Airlines
Tue 1/26Tue 2/9
ORD - MBJ • Non-stop
Cheapest one-way
$193
Typical prices: $138-$164
American Airlines
Sat 9/5
ORD - MBJ • Non-stop
Arrival airport
You can't fly directly to Falmouth. It is served by Montego Bay (MBJ), located 16.9 miles from Falmouth.
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Chicago to Falmouth (CHI-MBJ)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Falmouth 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 Chicago to Falmouth

Tue, Jan 26 - Tue, Feb 9
American Airlines Logo
8:05 am - 1:19 pm
ORD
-
MBJ
4h 14mnonstop
American Airlines Logo
3:17 pm - 6:56 pm
MBJ
-
ORD
4h 39mnonstop
$428American Airlines
Sat, Oct 24 - Sat, Oct 31
American Airlines Logo
8:05 am - 12:06 pm
ORD
-
MBJ
4h 01mnonstop
American Airlines Logo
2:27 pm - 7:00 pm
MBJ
-
ORD
4h 33mnonstop
$428American Airlines
Wed, Nov 4 - Wed, Nov 11
United Airlines Logo
8:40 am - 1:48 pm
ORD
-
MBJ
4h 08mnonstop
United Airlines Logo
2:54 pm - 6:20 pm
MBJ
-
ORD
4h 26mnonstop
$428United Airlines
Sun, Jan 24 - Thu, Jan 28
United Airlines Logo
8:42 am - 1:46 pm
ORD
-
MBJ
4h 04mnonstop
United Airlines Logo
3:55 pm - 11:42 pm
MBJ
-
ORD
8h 47m
1 stop
$428United Airlines
Sat, Sep 12 - Sat, Sep 19
Southwest Logo
5:55 am - 12:25 pm
MDW
-
MBJ
6h 30m
1 stop
Southwest Logo
11:40 am - 8:35 pm
MBJ
-
MDW
8h 55m
1 stop
$442Southwest
Tue, Sep 22 - Tue, Sep 29
Southwest Logo
6:30 am - 12:55 pm
MDW
-
MBJ
6h 25m
1 stop
Southwest Logo
12:55 pm - 9:25 pm
MBJ
-
MDW
8h 30m
1 stop
$442Southwest
Tue, Nov 10 - Thu, Nov 19
Delta Logo
6:00 am - 4:35 pm
MDW
-
MBJ
9h 35m
1 stop
Delta Logo
2:20 pm - 10:56 pm
MBJ
-
MDW
9h 36m
1 stop
$442Delta
Sun, Dec 6 - Thu, Dec 10
Delta Logo
6:00 am - 4:35 pm
MDW
-
MBJ
9h 35m
1 stop
Delta Logo
3:40 pm - 10:56 pm
MBJ
-
MDW
8h 16m
1 stop
$442Delta
Wed, Oct 28 - Sun, Nov 1
Air Canada Logo
9:05 pm - 11:50 am
ORD
-
MBJ
14h 45m
1 stop
Air Canada Logo
2:20 pm - 2:52 pm
MBJ
-
ORD
25h 32m
1 stop
$450Air Canada
Thu, Dec 10 - Sun, Dec 13
Air Canada Logo
3:45 pm - 1:25 pm
ORD
-
MBJ
20h 40m
1 stop
Air Canada Logo
2:20 pm - 2:52 pm
MBJ
-
ORD
25h 32m
1 stop
$450Air Canada
Useful Info

Good to know

Low season

September

Cheapest flight

$193
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from Chicago O'Hare Airport to Montego Bay

When to book flights from Chicago to Falmouth

Are your dates flexible? Find out the best times to travel from Chicago to Falmouth based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Falmouth

  • Which airports will I be using when flying from Chicago to Falmouth?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Falmouth does not have its own airport so you’ll be flying into nearby Montego Bay Sangster Intl airport, which is 16.9 mi away.

  • How long does a flight from Chicago to Falmouth take?

    Direct flights cover the 1,712 miles separating Chicago and Falmouth in about 4h 10m.

  • How many flights are there between Chicago and Falmouth?

    1 direct flights run between Chicago and Falmouth on a daily basis. On average, there are about 8 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Falmouth?

    Consider leaving on a Saturday and avoid Wednesdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Fridays and the most expensive ones on Sundays.

  • How does KAYAK find such low prices on flights from Chicago to Falmouth?

    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 Chicago to Falmouth.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Falmouth?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Falmouth from Chicago 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 Chicago to Falmouth?

    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 Falmouth with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Falmouth?

    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 Falmouth from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Falmouth?

    In the last 5 days, the cheapest one-way ticket between Chicago and Falmouth found on KAYAK was with Frontier for $108. Frontier offered a round-trip connection from $144 and Delta from $162.

Top tips for finding cheap flights from Chicago to Falmouth

  • There is no airport in Falmouth. Instead, you’ll be flying into Montego Bay Airport when flying between Chicago and Falmouth.
  • The cheapest flight from Chicago to Falmouth was found 51 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be November, December and January. The cheapest month to fly is September.

Reviews of the top 5 airlines serving Chicago to Falmouth

 
Need help choosing which airline to fly with from Chicago to Falmouth? 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.
8.0
SouthwestOverall score based on 4227 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
Airline reviews

Overall good, just screaming kids in the area the whole flight.

8.0 ExcellentAnonymous, Jul 2026
MDW - MHT
Read more Southwest reviews

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

It was very cold because the air conditioner was on high power, and my son got sick.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

We were forced to eat vegetarian food because non veg food ran out. The breakfast was mediocre.

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

The kid in the middle seat kicked me almost the whole flight, almost kicked my hot tea off my tray. The flight was delayed due to the first plane not being able to be de-iced in July! We had to get a new plane. Now I drive 3 hours back to Edmonton because direct flights from PVR were way to expensive

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Agents at gate were not immediately available to solve problems and once they did they didn’t fix all the fight connections

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

During the flight I suddenly felt very sick, and no one from the crew even tried to help me or check on my condition. They seemed completely indifferent and showed no concern for my well-being. I was very disappointed by the lack of care and compassion. I hope the airline improves its customer service and trains its crew to respond better when passengers need assistance.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

Everything you need to know for your flight from Chicago to Falmouth

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