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$107+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Falmouth are usually found in February or October, 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 May 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$447
(FlightHub)

One-way from

$107
(Priceline)

Popular in

March

Cheapest in

February

Average price

$549
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. 1% potential increase in price ($6 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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.
Wed 10/155:05 amORD - MBJ
1 stop6h 36mSpirit Airlines
Mon 10/2012:46 pmMBJ - ORD
1 stop7h 54mSpirit Airlines
Deal found 4/30$445
This American Airlines deal was found by Cheapflights users on 4/30. 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 8/258:30 amORD - MBJ
Nonstop4h 01mAmerican Airlines
Fri 8/292:00 pmMBJ - ORD
Nonstop4h 30mAmerican Airlines
Deal found 4/30$446
This CheapOair deal was found by Cheapflights users on 4/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/274:46 pmMDW - MBJ
1 stop15h 04mFrontier
Sat 5/318:55 amMBJ - MDW
1 stop13h 22mFrontier
Deal found 4/30$447
This Booking.com deal was found by Cheapflights users on 4/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/226:26 pmORD - MBJ
1 stop13h 24mMultiple Airlines
Wed 5/2812:07 pmMBJ - ORD
1 stop10h 57mMultiple Airlines
Deal found 4/30$449
This Delta deal was found by Cheapflights users on 4/30. 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.
Wed 5/76:00 amMDW - MBJ
1 stop9h 30mDelta
Wed 5/141:02 pmMBJ - MDW
1 stop8h 26mDelta
Deal found 4/30$449
This Booking.com deal was found by Cheapflights users on 4/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/95:31 pmORD - MBJ
1 stop20h 22mFrontier
Mon 5/122:08 pmMBJ - ORD
1 stop9h 03mFrontier
Deal found 4/30$458
This Southwest deal was found by Cheapflights users on 4/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/89:00 amMDW - MBJ
Nonstop4h 00mSouthwest
Tue 6/102:20 pmMBJ - MDW
Nonstop4h 10mSouthwest
Deal found 4/30$462
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Mon 6/29:12 pmMDW - MBJ
2 stops13h 50mMultiple Airlines
Sat 6/79:18 amMBJ - MDW
1 stop28h 31mMultiple Airlines
Deal found 4/30$483
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Sun 7/138:42 amORD - MBJ
Nonstop4h 07mUnited Airlines
Sun 7/201:51 pmMBJ - ORD
Nonstop4h 29mUnited Airlines
Deal found 4/29$501
This CheapOair deal was found by Cheapflights users on 4/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/139:14 pmORD - MBJ
1 stop14h 01mAir Canada
Mon 7/2112:10 pmMBJ - ORD
1 stop20h 59mAir Canada
Deal found 4/30$531
This Delta deal was found by Cheapflights users on 4/30. 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.
Thu 5/15:30 amORD - MBJ
1 stop6h 27mDelta
Sun 5/41:22 pmMBJ - ORD
1 stop10h 37mDelta
Deal found 4/30$551

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 May 1, 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

Wed 10/15

5:05 am-11:41 am

1 stop6h 36m

Montego Bay Sangster Intl

Mon 10/20

12:46 pm-8:40 pm

1 stop7h 54m

$445

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 8/25

8:30 am-12:31 pm

Nonstop4h 01m

Montego Bay Sangster Intl

Fri 8/29

2:00 pm-6:30 pm

Nonstop4h 30m

$446

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 5/27

4:46 pm-7:50 am

1 stop15h 04m

Montego Bay Sangster Intl

Sat 5/31

8:55 am-10:17 pm

1 stop13h 22m

$447

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 8/10

5:42 pm-11:41 am

2 stops17h 59m

Montego Bay Sangster Intl

Thu 8/14

9:05 am-10:25 am

1 stop25h 20m

$448

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 8/25

6:00 am-11:49 am

1 stop5h 49m

Montego Bay Sangster Intl

Fri 8/29

1:15 pm-9:47 pm

1 stop8h 32m

$461

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 6/8

9:00 am-1:00 pm

Nonstop4h 00m

Montego Bay Sangster Intl

Tue 6/10

2:20 pm-6:30 pm

Nonstop4h 10m

$462

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 6/2

9:12 pm-11:02 am

2 stops13h 50m

Montego Bay Sangster Intl

Sat 6/7

9:18 am-1:49 pm

1 stop28h 31m

$483

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 6/4

5:03 pm-7:58 am

2 stops14h 55m

Montego Bay Sangster Intl

Wed 6/11

2:02 pm-10:22 am

1 stop20h 20m

$487

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 9/26

2:00 pm-11:10 am

1 stop21h 10m

Montego Bay Sangster Intl

Sun 9/28

12:05 pm-9:51 am

2 stops21h 46m

$500

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 7/13

8:42 am-12:49 pm

Nonstop4h 07m

Montego Bay Sangster Intl

Sun 7/20

1:51 pm-6:20 pm

Nonstop4h 29m

$501

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 26 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 April 25, 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 $569). 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 May 1, 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 May 1, 2025.

The most flights from CHI to FL9 are scheduled on a Monday (2 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

Rainfall in Falmouth by month

Plan your trip to Falmouth by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Falmouth ranges from 1.6 - 7.1 inches per month. October is typically the wettest month, when rainfall can reach 7.1 in. February is typically the driest time to visit Falmouth when rainfall is around 1.6 in.

Temperature in Falmouth by month

Plan your trip to Falmouth by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Falmouth, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 May 1, 2025.
See what other customers who have flown with Southwest, Delta and Copa Airlines from Chicago to Falmouth have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Copa Airlines
7.5
Good
1,414 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,924 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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.

  • 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 $107. However, be on the lookout for offers from Frontier and American 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 $702, our data shows the cheapest flight currently is $252. When looking at the most popular route, (Chicago O'Hare Intl - Montego Bay Sangster Intl), you can expect to pay $299 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 $569). 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 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$273Average$441FlexibilityNo cancel feeOn-time65%
DeltaCheapest$295Average$831FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$393Average$694FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$396Average$620FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$579Average$748FlexibilityNo cancel feeOn-time63%

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