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Falmouth

$98+ 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 9/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
août 26 — sept. 21
mar. 8/26
mar. 9/2
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Falmouth are usually found in February or January, booked 55 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 août 21, 2025.

Round-trip from

$398
(FlightHub)

One-way from

$98
(FlightHub)

Popular in

March

Cheapest in

February

Average price

$551
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. 2% potential increase in price ($16 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 August 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 août 21, 2025.

This Frontier deal was found by Cheapflights users on 8/18. 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.
ven. 11/146:20 amMDW - MBJ
1 stop7h 55mFrontier
jeu. 11/204:53 pmMBJ - MDW
1 stop7h 13mFrontier
Deal found 8/18$398
This FlightHub deal was found by Cheapflights users on 8/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 10/1611:52 amORD - MBJ
1 stop23h 08mSpirit Airlines
lun. 10/2012:09 pmMBJ - ORD
1 stop11h 36mSpirit Airlines
Deal found 8/21$398
This Priceline deal was found by Cheapflights users on 8/19. 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.
ven. 10/36:20 amMDW - MBJ
1 stop6h 25mFrontier
ven. 10/103:51 pmMBJ - MDW
1 stop7h 34mFrontier
Deal found 8/19$399
This FlightHub deal was found by Cheapflights users on 8/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 9/256:44 pmORD - MBJ
1 stop16h 21mSpirit Airlines
dim. 9/2812:10 pmMBJ - ORD
1 stop22h 42mSpirit Airlines
Deal found 8/21$399
This Mytrip deal was found by Cheapflights users on 8/20. 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. 9/295:05 amORD - MBJ
1 stop6h 00mSpirit Airlines
mar. 9/3012:10 pmMBJ - ORD
3 stops24h 59mSpirit Airlines
Deal found 8/20$400
This FlightHub deal was found by Cheapflights users on 8/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 9/115:17 pmORD - MBJ
2 stops41h 48mSpirit Airlines
jeu. 9/1812:10 pmMBJ - ORD
1 stop10h 38mSpirit Airlines
Deal found 8/21$401
This Frontier deal was found by Cheapflights users on 8/20. 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.
lun. 9/296:20 amMDW - MBJ
1 stop6h 25mFrontier
sam. 10/42:05 pmMBJ - MDW
1 stop9h 12mFrontier
Deal found 8/20$402
This FlightHub deal was found by Cheapflights users on 8/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 10/169:26 pmMDW - MBJ
1 stop17h 10mFrontier
lun. 10/203:51 pmMBJ - MDW
1 stop21h 47mFrontier
Deal found 8/19$403
This FlightHub deal was found by Cheapflights users on 8/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/85:05 amORD - MBJ
1 stop6h 00mSpirit Airlines
ven. 9/1212:10 pmMBJ - ORD
2 stops28h 02mSpirit Airlines
Deal found 8/21$403
This Kiwi.com deal was found by Cheapflights users on 8/20. 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.
lun. 9/298:15 amMDW - MBJ
2 stops26h 50mMultiple Airlines
sam. 10/42:05 pmMBJ - MDW
1 stop9h 36mMultiple Airlines
Deal found 8/20$404
This Frontier deal was found by Cheapflights users on 8/21. 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.
jeu. 12/45:10 amORD - MBJ
1 stop9h 23mFrontier
jeu. 12/114:53 pmMBJ - ORD
1 stop8h 15mFrontier
Deal found 8/21$404
This Mytrip deal was found by Cheapflights users on 8/20. 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.
ven. 9/57:09 pmORD - MBJ
3 stops39h 56mSpirit Airlines
mar. 9/912:10 pmMBJ - ORD
1 stop10h 38mSpirit Airlines
Deal found 8/20$405

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 août 21, 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

MDW - MBJ

MDWMBJ

Chicago Midway

dim. 11/16

6:20 am-3:15 pm

1 stop7h 55m

Montego Bay Sangster Intl

jeu. 11/20

4:53 pm-11:06 pm

1 stop7h 13m

$398

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

mar. 11/4

5:05 am-12:01 pm

1 stop5h 56m

Montego Bay Sangster Intl

dim. 11/9

2:59 pm-6:23 pm

2 stops28h 24m

$398

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

ven. 11/14

6:20 am-3:15 pm

1 stop7h 55m

Montego Bay Sangster Intl

jeu. 11/20

4:53 pm-11:06 pm

1 stop7h 13m

$398

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

jeu. 10/16

11:52 am-11:00 am

1 stop23h 08m

Montego Bay Sangster Intl

lun. 10/20

12:09 pm-11:45 pm

1 stop11h 36m

$398

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

jeu. 10/9

5:05 am-11:00 am

1 stop5h 55m

Montego Bay Sangster Intl

dim. 10/12

12:09 pm-11:45 pm

1 stop11h 36m

$398

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

dim. 10/5

8:49 pm-12:45 pm

2 stops15h 56m

Montego Bay Sangster Intl

sam. 10/25

4:01 pm-11:29 pm

1 stop7h 28m

$398

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

dim. 10/5

8:49 pm-11:00 am

2 stops14h 11m

Montego Bay Sangster Intl

mar. 10/7

12:09 pm-6:36 pm

1 stop6h 27m

$399

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

dim. 10/5

8:49 pm-11:00 am

2 stops14h 11m

Montego Bay Sangster Intl

mer. 10/8

12:09 pm-6:36 pm

1 stop6h 27m

$399

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

jeu. 12/4

6:00 am-3:33 pm

1 stop8h 33m

Montego Bay Sangster Intl

lun. 12/8

4:53 pm-11:05 pm

1 stop7h 12m

$399

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

jeu. 9/25

6:44 pm-11:05 am

1 stop16h 21m

Montego Bay Sangster Intl

dim. 9/28

12:10 pm-10:52 am

1 stop22h 42m

$399

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/21

Showing 1-10 of 35 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 August 8, 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 55 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 $403). Flying from Chicago to Falmouth in July is currently the most expensive (average of $560). 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 août 21, 2025.

When flying from Chicago to Falmouth, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 Tuesday evenings when fares are most often at their lowest. Thursday mornings 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 août 21, 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 août 21, 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
4,245 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

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
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

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
7,981 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

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
8,930 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

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
10,000 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

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
8,035 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

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 $398, Frontier can have you in Falmouth from Chicago in 5h 56m. Airlines will cover a distance of 1724 mi. This flight may include one or multiple stops.

  • What are the cheapest flights from Chicago to Falmouth?

    While on average a flight from Chicago to Falmouth is generally $649, our data shows the cheapest flight currently is $164. When looking at the most popular route, (Chicago O'Hare Intl - Montego Bay Sangster Intl), you can expect to pay $267 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 $403). Flying from Chicago to Falmouth in July is currently the most expensive (average of $560). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 5 airlines flying from Chicago to Falmouth

Discover the top 5 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 août 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$266Average$443FlexibilityNo cancel feeOn-time65%
DeltaCheapest$295Average$773FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$424Average$624FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$436Average$676FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$549Average$724FlexibilityNo cancel feeOn-time63%

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