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$129+ 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 5/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
Apr 9 — Apr 161
Wed 4/9
Wed 4/16
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 April 4, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$458
(Booking.com)

One-way from

$129
(CheapOair)

Popular in

December

Cheapest in

February

Average price

$533
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 ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 4, 2025.

This Booking.com deal was found by Cheapflights users on 4/4. 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 5/158:30 amMDW - MBJ
1 stop28h 11mFrontier
Sun 5/182:07 pmMBJ - MDW
1 stop23h 27mFrontier
Deal found 4/4$458
This Cheapflightsfares deal was found by Cheapflights users on 4/3. 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.
Tue 4/155:36 amORD - MBJ
1 stop5h 19mSpirit Airlines
Mon 4/2112:00 pmMBJ - ORD
1 stop12h 58mSpirit Airlines
Deal found 4/3$460
This Mytrip deal was found by Cheapflights users on 4/3. 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 5/17:33 pmORD - MBJ
1 stop15h 22mMultiple Airlines
Mon 5/53:05 pmMBJ - ORD
3 stops26h 55mMultiple Airlines
Deal found 4/3$461
This American Airlines deal was found by Cheapflights users on 4/4. 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.
Thu 8/288:35 pmORD - MBJ
1 stop14h 32mAmerican Airlines
Thu 9/43:15 pmMBJ - ORD
1 stop16h 15mAmerican Airlines
Deal found 4/4$464
This Delta deal was found by Cheapflights users on 4/4. 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.
Tue 4/296:04 amMDW - MBJ
1 stop9h 27mDelta
Sat 5/311:28 amMBJ - MDW
1 stop6h 52mDelta
Deal found 4/4$470
This Delta deal was found by Cheapflights users on 4/4. 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.
Tue 4/296:45 amORD - MBJ
2 stops8h 46mDelta
Sat 5/311:31 amMBJ - ORD
1 stop7h 29mDelta
Deal found 4/4$474
This Booking.com deal was found by Cheapflights users on 4/4. 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 6/65:10 amORD - MBJ
1 stop26h 48mFrontier
Tue 6/109:08 amMBJ - ORD
1 stop25h 29mFrontier
Deal found 4/4$478
This JetBlue Airways deal was found by Cheapflights users on 4/3. 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 JetBlue Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/176:00 amORD - MBJ
1 stop9h 06mJetBlue
Tue 6/2410:45 amMBJ - ORD
1 stop12h 40mJetBlue
Deal found 4/3$519
This Southwest deal was found by Cheapflights users on 4/3. 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.
Mon 4/77:15 amMDW - MBJ
1 stop7h 20mSouthwest
Wed 4/912:00 pmMBJ - MDW
1 stop9h 50mSouthwest
Deal found 4/3$521
This United Airlines deal was found by Cheapflights users on 4/3. 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.
Fri 4/118:45 amORD - MBJ
Nonstop4h 04mUnited Airlines
Sat 4/191:51 pmMBJ - ORD
Nonstop4h 29mUnited Airlines
Deal found 4/3$566
This Air Canada deal was found by Cheapflights users on 4/3. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/176:15 pmORD - MBJ
2 stops17h 00mAir Canada
Tue 6/2412:10 pmMBJ - ORD
2 stops19h 49mAir Canada
Deal found 4/3$588
This Kiwi.com deal was found by Cheapflights users on 4/3. 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.
Tue 7/16:00 amMDW - MBJ
1 stop25h 58mMultiple Airlines
Tue 7/1510:19 amMBJ - MDW
2 stops12h 22mMultiple Airlines
Deal found 4/3$610

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 April 4, 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

Thu 5/15

8:30 am-12:41 pm

1 stop28h 11m

Montego Bay Sangster Intl

Sun 5/18

2:07 pm-1:34 pm

1 stop23h 27m

$458

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 4/15

5:36 am-10:55 am

1 stop5h 19m

Montego Bay Sangster Intl

Mon 4/21

12:00 pm-12:58 am

1 stop12h 58m

$460

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 5/1

7:33 pm-10:55 am

1 stop15h 22m

Montego Bay Sangster Intl

Mon 5/5

3:05 pm-6:00 pm

3 stops26h 55m

$461

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 8/28

8:35 pm-11:07 am

1 stop14h 32m

Montego Bay Sangster Intl

Thu 9/4

3:15 pm-7:30 am

1 stop16h 15m

$464

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 4/29

6:04 am-3:31 pm

1 stop9h 27m

Montego Bay Sangster Intl

Sat 5/3

11:28 am-6:20 pm

1 stop6h 52m

$470

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 4/29

6:45 am-3:31 pm

2 stops8h 46m

Montego Bay Sangster Intl

Sat 5/3

11:31 am-7:00 pm

1 stop7h 29m

$474

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 6/6

5:10 am-7:58 am

1 stop26h 48m

Montego Bay Sangster Intl

Tue 6/10

9:08 am-10:37 am

1 stop25h 29m

$478

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 6/17

6:00 am-3:06 pm

1 stop9h 06m

Montego Bay Sangster Intl

Tue 6/24

10:45 am-11:25 pm

1 stop12h 40m

$519

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 5/3

9:40 am-1:40 pm

Nonstop4h 00m

Montego Bay Sangster Intl

Wed 5/7

12:35 pm-8:15 pm

1 stop7h 40m

$527

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 4/19

8:45 am-12:49 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Fri 4/25

1:51 pm-6:20 pm

Nonstop4h 29m

$546

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/3

Showing 1-10 of 27 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 March 28, 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 April 4, 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 April 4, 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 April 4, 2025.
See what other customers who have flown with Southwest, Delta and United 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
4,276 reviews

Crew

8.6

Overall

8.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,276 reviews
Southwest
8.0
Very good
4,276 reviews

Crew

8.6

Overall

8.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,901 reviews
Southwest
8.0
Very good
4,276 reviews

Crew

8.6

Overall

8.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,621 reviews
Southwest
8.0
Very good
4,276 reviews

Crew

8.6

Overall

8.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
JetBlue
7.3
Good
2,919 reviews
Southwest
8.0
Very good
4,276 reviews

Crew

8.6

Overall

8.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,276 reviews

Crew

8.6

Overall

8.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $129. 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 $434, our data shows the cheapest flight currently is $196. When looking at the most popular route, (Chicago O'Hare Intl - Montego Bay Sangster Intl), you can expect to pay $286 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 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 April 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$205Average$265FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$273Average$440FlexibilityNo cancel feeOn-time65%
DeltaCheapest$295Average$679FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$393Average$696FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$393Average$610FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$579Average$735FlexibilityNo cancel feeOn-time63%

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