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Falmouth

$106+ Cheap flights from Chicago (CHI) to Falmouth, Jamaica

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
Jan 7 — Jan 141
Wed 1/7
Wed 1/14
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Falmouth are usually found in January or September, booked 28 days in advance, depart on a Tuesday or Sunday and return on a Wednesday

Cheap flight deals from Chicago to Falmouth

Cheapest flights from Chicago to Falmouth
Explore the most affordable flight options available from Chicago to Falmouth. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 8, 2025.

This Frontier deal was found by Cheapflights users on 12/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:11 amORD - MBJ
1 stop8h 40mFrontier
Wed 12/243:49 pmMBJ - ORD
1 stop7h 35mFrontier
Deal found 12/6$353
This Frontier deal was found by Cheapflights users on 12/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:11 amORD - MBJ
1 stop8h 40mFrontier
Sat 12/273:34 pmMBJ - ORD
1 stop8h 12mFrontier
Deal found 12/6$354
This Priceline deal was found by Cheapflights users on 12/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/156:11 amORD - MBJ
1 stop7h 01mFrontier
Sat 12/273:34 pmMBJ - ORD
1 stop8h 12mFrontier
Deal found 12/7$363
This Mytrip deal was found by Cheapflights users on 12/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:11 amORD - MBJ
1 stop8h 40mFrontier
Sat 12/203:34 pmMBJ - ORD
1 stop8h 12mFrontier
Deal found 12/6$365
This Mytrip deal was found by Cheapflights users on 12/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:00 amORD - MBJ
1 stop25h 59mFrontier
Mon 12/2210:14 amMBJ - ORD
1 stop9h 19mFrontier
Deal found 12/7$367
This Mytrip deal was found by Cheapflights users on 12/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:12 amMDW - MBJ
1 stop25h 47mFrontier
Mon 12/223:47 pmMBJ - MDW
1 stop7h 25mFrontier
Deal found 12/7$367
This Gotogate deal was found by Cheapflights users on 12/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:00 amORD - MBJ
1 stop26h 57mFrontier
Wed 12/3110:24 amMBJ - ORD
1 stop13h 00mFrontier
Deal found 12/6$368
This Gotogate deal was found by Cheapflights users on 12/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/198:15 amMDW - MBJ
1 stop24h 42mFrontier
Wed 12/313:49 pmMBJ - MDW
1 stop7h 23mFrontier
Deal found 12/6$368
This Kiwi.com deal was found by Cheapflights users on 12/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:00 amORD - MBJ
1 stop25h 59mMultiple Airlines
Sun 12/211:05 pmMBJ - ORD
1 stop12h 21mMultiple Airlines
Deal found 12/6$369
This American Airlines deal was found by Cheapflights users on 12/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/810:15 amORD - MBJ
Nonstop4h 07mAmerican Airlines
Thu 12/113:12 pmMBJ - ORD
Nonstop4h 47mAmerican Airlines
Deal found 12/7$376
This American Airlines deal was found by Cheapflights users on 12/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/78:20 amORD - MBJ
1 stop6h 33mAmerican Airlines
Tue 12/163:12 pmMBJ - ORD
Nonstop4h 47mAmerican Airlines
Deal found 12/6$377
This Frontier deal was found by Cheapflights users on 12/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:11 amORD - MBJ
1 stop8h 40mFrontier
Thu 12/253:47 pmMBJ - ORD
1 stop7h 37mFrontier
Deal found 12/6$378

Find flight deals from Chicago to Falmouth

Keep the following information in mind while searching for Chicago to Falmouth flight deals. Data was last updated December 8, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$353
(Frontier)

One-way from

$106
(Cheapflightsfares)

Popular in

March

Cheapest in

January

Average price

$617
Provider with most accurate pricing for Chicago (CHI)-Montego Bay Sangster Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Montego Bay Sangster Intl flights.
Search Deals
From Chicago (CHI) to Falmouth
Search Deals
One-way flight from Chicago (CHI) to Falmouth
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Falmouth that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 8, 2025.
Use the filters below to find and compare flights from Chicago to Falmouth that are best for you.

Fly from

Chicago

Fly to

Falmouth

Route

Depart

Return

Price

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 2/17

4:45 pm-12:02 pm

2 stops18h 17m

Montego Bay Sangster Intl

Wed 2/25

1:00 pm-6:52 pm

1 stop6h 52m

$362

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 1/24

10:07 am-12:02 pm

2 stops24h 55m

Montego Bay Sangster Intl

Thu 1/29

12:57 pm-9:03 pm

1 stop9h 06m

$369

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 2/1

6:00 am-3:20 pm

1 stop8h 20m

Montego Bay Sangster Intl

Fri 2/6

4:45 pm-10:22 pm

1 stop6h 37m

$391

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 2/2

5:00 am-1:00 pm

1 stop7h 00m

Montego Bay Sangster Intl

Fri 2/6

1:30 pm-9:25 pm

1 stop8h 55m

$391

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 1/6

5:31 pm-11:13 am

1 stop16h 42m

Montego Bay Sangster Intl

Thu 1/22

4:45 pm-10:22 pm

1 stop6h 37m

$391

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 1/7

5:31 pm-11:13 am

1 stop16h 42m

Montego Bay Sangster Intl

Thu 1/22

12:38 pm-10:22 pm

1 stop10h 44m

$391

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 1/27

6:00 am-3:20 pm

1 stop8h 20m

Montego Bay Sangster Intl

Tue 2/3

4:45 pm-10:22 pm

1 stop6h 37m

$391

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 3/9

5:38 pm-10:10 am

1 stop16h 32m

Montego Bay Sangster Intl

Tue 3/24

4:55 pm-9:55 am

1 stop17h 00m

$391

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 3/29

7:20 pm-1:40 pm

1 stop18h 20m

Montego Bay Sangster Intl

Thu 4/2

4:55 pm-9:55 am

1 stop17h 00m

$391

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 3/10

6:30 am-12:13 pm

1 stop5h 43m

Montego Bay Sangster Intl

Wed 3/25

4:55 pm-9:55 am

1 stop17h 00m

$391

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/7

Showing 1-10 of 41 results
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Best time to book a flight from Chicago to Falmouth

Have a flexible travel schedule? Discover the best time to fly to Falmouth from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

How far ahead should I book a flight from Chicago to Falmouth?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Falmouth. Price data was last updated on December 5, 2025.

The price you pay for your flight from Chicago to Falmouth may vary depending on when you book. For the best chance of a lower fare, look to book 28 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago to Falmouth?

Currently, January is the cheapest month in which you can book a flight from Chicago to Falmouth (average of $193). Flying from Chicago to Falmouth in March is currently the most expensive (average of $408). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to FL9?

Find hourly flight availability from Chicago to Falmouth. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 8, 2025.

It’s typically best to fly out from Chicago to Falmouth in the afternoon. Doing so could potentially save you 65% on the flight price compared to flying in the evening, which is usually more expensive.

What is the cheapest day to fly from Chicago to Falmouth?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Falmouth. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Falmouth flight should consider departing on Sunday at noon when fares are most often at their lowest. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Falmouth

Explore weekly flight availability from Chicago to Falmouth. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated December 8, 2025.

The most flights from CHI to FL9 are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

How much does it cost to fly round-trip from Chicago to Falmouth?

Reviews of airlines servicing Falmouth

Get insights into the airlines that provide service to Falmouth. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Falmouth. Reviews last updated December 8, 2025.
See what other customers who have flown with Southwest, Delta, and United Airlines from Chicago to Falmouth have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,254 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,011 reviews
Southwest
8.0
Very good
4,254 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,089 reviews
Southwest
8.0
Very good
4,254 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,045 reviews
Southwest
8.0
Very good
4,254 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,168 reviews
Southwest
8.0
Very good
4,254 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Chicago to Falmouth. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Falmouth?

    For as low as $391, Spirit Airlines can have you in Falmouth from Chicago in 7h. Airlines will cover a distance of 1709 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago to Falmouth one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $98. However, be on the lookout for offers from American Airlines and United Airlines, as they are both options that can get you from Chicago to Falmouth for a low price.

  • What are the cheapest flights from Chicago to Falmouth?

    While on average a flight from Chicago to Falmouth is generally $769, our data shows the cheapest flight currently is $161. When looking at the most popular route, (Chicago O'Hare Intl - Montego Bay Sangster Intl), you can expect to pay $260 for that flight.

  • Can I find deals for flights from Chicago to Falmouth that include hotel bookings?

    Yes. In addition to deals on Chicago to Falmouth flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Falmouth?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Falmouth.

  • Can I find deals for business class flights from Chicago to Falmouth?

    Yes. Cheapflights offers flight deals from Chicago to Falmouth by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Falmouth?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Falmouth (average of $193). Flying from Chicago to Falmouth in March is currently the most expensive (average of $408). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Top 6 airlines flying from Chicago to Falmouth

Discover the top 6 airlines that operate flights from Chicago to Falmouth. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$174Average$414FlexibilityNo cancel feeOn-time65%
DeltaCheapest$186Average$709FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$356Average$606FlexibilityNo cancel feeOn-time69%
FrontierCheapest$370Average$662FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$433Average$672FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$549Average$724FlexibilityNo cancel feeOn-time63%

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