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Falmouth

$105+ 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
nov. 15 — nov. 221
sáb. 11/15
sáb. 11/22
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Falmouth are usually found in September or February, booked 28 days in advance, depart on a Sunday or Monday and return on a Wednesday

Cheap flight deals from Chicago to Falmouth

Keep the following information in mind while searching for Chicago to Falmouth flight deals. Data was last updated octubre 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$356
(United Airlines)

One-way from

$105
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$583
Provider with most accurate pricing for Chicago (CHI)-Montego Bay Sangster Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Montego Bay Sangster Intl flights.
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From Chicago (CHI) to Falmouth
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One-way flight from Chicago (CHI) to Falmouth
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Highest demand for flights based on searches. 3% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 octubre 16, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 10/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/85:10 amORD - MBJ
1 stop5h 52mSpirit Airlines
sáb. 11/151:07 pmMBJ - ORD
1 stop12h 20mSpirit Airlines
Deal found 10/16$354
This American Airlines deal was found by Cheapflights users on 10/15. 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.
mar. 10/288:44 amORD - MBJ
Nonstop4h 01mAmerican Airlines
vie. 10/311:50 pmMBJ - ORD
Nonstop4h 33mAmerican Airlines
Deal found 10/15$356
This Priceline deal was found by Cheapflights users on 10/15. 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.
mar. 12/25:00 amORD - MBJ
1 stop6h 02mMultiple Airlines
lun. 12/85:45 pmMBJ - ORD
1 stop16h 28mMultiple Airlines
Deal found 10/15$357
This Cheapflightsfares deal was found by Cheapflights users on 10/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/85:05 amORD - MBJ
1 stop6h 00mSpirit Airlines
sáb. 12/131:12 pmMBJ - ORD
1 stop8h 48mSpirit Airlines
Deal found 10/15$360
This American Airlines deal was found by Cheapflights users on 10/15. 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.
sáb. 11/16:36 pmORD - MBJ
1 stop15h 32mAmerican Airlines
jue. 11/62:04 pmMBJ - ORD
Nonstop4h 36mAmerican Airlines
Deal found 10/15$361
This Delta deal was found by Cheapflights users on 10/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/36:45 amORD - MBJ
1 stop6h 35mDelta
mié. 11/125:59 pmMBJ - ORD
1 stop15h 42mDelta
Deal found 10/15$362
This Delta deal was found by Cheapflights users on 10/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/36:00 amMDW - MBJ
1 stop7h 20mDelta
mié. 11/123:36 pmMBJ - MDW
2 stops18h 18mDelta
Deal found 10/15$362
This Mytrip deal was found by Cheapflights users on 10/16. 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.
lun. 10/277:51 pmORD - MBJ
2 stops15h 09mSpirit Airlines
vie. 10/3112:09 pmMBJ - ORD
3 stops26h 36mSpirit Airlines
Deal found 10/16$363
This United Airlines deal was found by Cheapflights users on 10/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/118:42 amORD - MBJ
Nonstop4h 04mUnited Airlines
mar. 11/181:25 pmMBJ - ORD
1 stop8h 51mUnited Airlines
Deal found 10/15$367
This American Airlines deal was found by Cheapflights users on 10/16. 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.
sáb. 11/18:35 pmORD - MBJ
1 stop18h 18mAmerican Airlines
mié. 11/53:13 pmMBJ - ORD
Nonstop4h 41mAmerican Airlines
Deal found 10/16$368
This Delta deal was found by Cheapflights users on 10/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/286:00 amMDW - MBJ
1 stop7h 20mDelta
vie. 10/312:45 pmMBJ - MDW
1 stop7h 29mDelta
Deal found 10/14$371
This Mytrip deal was found by Cheapflights users on 10/15. 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.
mar. 11/185:10 amORD - MBJ
1 stop5h 52mMultiple Airlines
mar. 11/182:40 pmMBJ - ORD
1 stop28h 08mMultiple Airlines
Deal found 10/15$374

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 octubre 16, 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

mié. 10/29

8:42 am-12:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

mié. 11/5

2:48 pm-6:13 pm

Nonstop4h 25m

$356

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mar. 2/17

6:00 am-3:15 pm

1 stop8h 15m

Montego Bay Sangster Intl

mié. 2/25

12:35 pm-9:46 pm

1 stop10h 11m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mié. 12/10

5:05 am-12:50 pm

1 stop6h 45m

Montego Bay Sangster Intl

mié. 12/17

1:00 pm-9:05 pm

1 stop9h 05m

$371

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

mié. 11/12

6:02 am-2:29 pm

1 stop7h 27m

Montego Bay Sangster Intl

mar. 11/18

3:36 pm-11:34 pm

1 stop8h 58m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mar. 10/28

6:00 am-1:20 pm

1 stop7h 20m

Montego Bay Sangster Intl

vie. 10/31

1:32 pm-10:14 pm

1 stop8h 42m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mar. 2/10

6:00 am-3:15 pm

1 stop8h 15m

Montego Bay Sangster Intl

jue. 2/19

8:00 am-6:34 pm

2 stops11h 34m

$376

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

lun. 2/9

6:00 am-3:15 pm

1 stop8h 15m

Montego Bay Sangster Intl

jue. 2/19

8:00 am-6:34 pm

2 stops11h 34m

$376

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

dom. 2/8

5:59 pm-12:47 pm

2 stops17h 48m

Montego Bay Sangster Intl

mié. 2/18

8:00 am-8:50 am

2 stops25h 50m

$376

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

vie. 12/5

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

mar. 12/9

2:48 pm-6:13 pm

Nonstop4h 25m

$381

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

mar. 12/2

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

sáb. 12/6

2:48 pm-6:13 pm

Nonstop4h 25m

$381

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/15

Showing 1-10 of 40 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 October 10, 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, February is the cheapest month in which you can book a flight from Chicago to Falmouth (average of $258). Flying from Chicago to Falmouth in March is currently the most expensive (average of $419). 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 octubre 16, 2025.

It’s typically best to fly out from Chicago to Falmouth in the afternoon. Doing so could potentially save you 61% 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 octubre 16, 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).

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 octubre 16, 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
4,241 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,984 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,982 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,043 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,097 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 $356, United Airlines can have you in Falmouth from Chicago in 4h 04m. Airlines will cover a distance of 1724 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 United Airlines, with whom users have recently found tickets for as low as $157. However, be on the lookout for offers from Delta and Southwest, 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 $1,018, our data shows the cheapest flight currently is $157. When looking at the most popular route, (Chicago O'Hare Intl - Montego Bay Sangster Intl), you can expect to pay $257 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, February is the cheapest month in which you can book a flight from Chicago to Falmouth (average of $258). Flying from Chicago to Falmouth in March is currently the most expensive (average of $419). 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

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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 octubre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$258Average$439FlexibilityNo cancel feeOn-time65%
FrontierCheapest$333Average$657FlexibilityNo cancel feeOn-time62%
DeltaCheapest$369Average$709FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$380Average$631FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$441Average$657FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$549Average$723FlexibilityNo cancel feeOn-time63%

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