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Falmouth

$69+ Cheap flights from Chicago (CHI) to Falmouth, MA, MA

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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Falmouth are usually found in September or January, booked 89 days in advance, depart on a Thursday or Wednesday and return on a Friday

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 September 16, 2025.

Round-trip from

$127
(JetBlue)

One-way from

$69
(United Airlines)

Popular in

April

Cheapest in

September

Average price

$207
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. 6% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 16, 2025.

This JetBlue deal was found by Cheapflights users on 9/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/297:50 pmORD - BOS
Nonstop2h 35mJetBlue
Sat 10/47:00 amBOS - ORD
Nonstop2h 56mJetBlue
Deal found 9/15$127
This Southwest deal was found by Cheapflights users on 9/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/216:05 amMDW - BOS
Nonstop2h 15mSouthwest
Tue 10/215:05 pmBOS - MDW
1 stop8h 00mSouthwest
Deal found 9/15$127
This JetBlue deal was found by Cheapflights users on 9/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/19:51 amORD - BOS
Nonstop2h 29mJetBlue
Wed 10/14:40 pmBOS - ORD
Nonstop3h 15mJetBlue
Deal found 9/15$130
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/267:50 pmORD - BOS
Nonstop2h 35mJetBlue
Wed 10/17:00 amBOS - ORD
Nonstop2h 56mJetBlue
Deal found 9/14$132
This Southwest deal was found by Cheapflights users on 9/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/79:30 amMDW - BOS
2 stops7h 45mSouthwest
Sun 11/95:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 9/16$132
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/11:30 pmORD - BOS
Nonstop2h 32mUnited Airlines
Sun 10/56:00 amBOS - ORD
Nonstop2h 57mUnited Airlines
Deal found 9/14$133
This Southwest deal was found by Cheapflights users on 9/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/79:05 pmMDW - BOS
1 stop10h 00mSouthwest
Mon 11/105:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 9/16$133
This JetBlue deal was found by Cheapflights users on 9/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/611:20 amORD - BOS
Nonstop2h 24mJetBlue
Wed 11/123:55 pmBOS - ORD
Nonstop3h 00mJetBlue
Deal found 9/15$135
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/86:00 amORD - BOS
1 stop6h 20mSpirit Airlines
Wed 10/156:16 amBOS - ORD
1 stop18h 29mSpirit Airlines
Deal found 9/15$136
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2311:05 amORD - BOS
Nonstop2h 35mUnited Airlines
Wed 9/244:27 pmBOS - ORD
Nonstop2h 54mUnited Airlines
Deal found 9/16$137
This Southwest deal was found by Cheapflights users on 9/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/264:05 pmMDW - BOS
Nonstop2h 15mSouthwest
Fri 11/285:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 9/15$137
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/309:25 pmORD - BOS
Nonstop2h 20mUnited Airlines
Sat 11/16:26 pmBOS - ORD
Nonstop2h 59mUnited Airlines
Deal found 9/16$138

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 September 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

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 10/20

9:20 pm-12:40 am

Nonstop2h 20m

Boston Logan Intl

Wed 10/22

1:35 pm-6:10 pm

1 stop5h 35m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 10/18

6:30 am-9:45 am

Nonstop2h 15m

Boston Logan Intl

Sat 10/25

6:30 am-4:25 pm

2 stops10h 55m

$132

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 11/15

1:15 pm-7:35 pm

1 stop5h 20m

Boston Logan Intl

Wed 11/19

5:35 pm-9:05 pm

1 stop4h 30m

$132

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 1/7

7:00 am-10:33 am

Nonstop2h 33m

Boston Logan Intl

Sun 1/11

7:00 am-9:10 am

Nonstop3h 10m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 12/13

11:25 am-2:49 pm

Nonstop2h 24m

Boston Logan Intl

Wed 12/17

8:30 am-10:35 am

Nonstop3h 05m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 11/26

1:06 pm-4:34 pm

Nonstop2h 28m

Boston Logan Intl

Sat 11/29

5:35 pm-7:50 pm

Nonstop3h 15m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 11/26

4:05 pm-7:20 pm

Nonstop2h 15m

Boston Logan Intl

Fri 11/28

5:15 am-7:00 am

Nonstop2h 45m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 9/29

6:45 pm-10:05 pm

Nonstop2h 20m

Boston Logan Intl

Tue 9/30

3:15 pm-4:50 pm

Nonstop2h 35m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 11/14

9:30 am-6:15 pm

2 stops7h 45m

Boston Logan Intl

Tue 11/18

5:35 pm-9:05 pm

1 stop4h 30m

$138

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 12/13

9:50 am-1:10 pm

Nonstop2h 20m

Boston Logan Intl

Wed 12/17

5:35 pm-9:05 pm

1 stop4h 30m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 43 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 September 12, 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 89 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 $218). Flying from Chicago to Falmouth in July is currently the most expensive (average of $311). 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 FM5?

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 September 16, 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 September 14, 2025.

Travelers seeking maximum savings on their Chicago to Falmouth flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday at noon 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 September 16, 2025.

The most flights from CHI to FM5 are scheduled on a Monday (78 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (33 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 September 16, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Chicago to Falmouth to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

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
7,957 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

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
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

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
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

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
JetBlue
7.2
Good
2,914 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

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 $127, Southwest can have you in Falmouth from Chicago in 2h 20m. Airlines will cover a distance of 857 mi. All flights are typically nonstop.

  • What are the most reliable airlines from Chicago to Falmouth?

    The top 3 most reliable airlines when flying from Chicago to Falmouth are Envoy Air (96%), Air France (78%) and Scandinavian Airlines (76%).

  • What are the cheapest flights from Chicago to Falmouth?

    On average you can expect to pay $430 for a flight from Chicago to Falmouth. The cheapest flight overall is $64 while the most popular route, (Chicago O'Hare Intl - Boston Logan Intl) is currently priced at $112.

  • 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 $218). Flying from Chicago to Falmouth in July is currently the most expensive (average of $311). 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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Alternative routes for Chicago to Falmouth

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Chicago to Falmouth

Discover the top 7 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$37Average$152FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$78Average$184FlexibilityNo cancel feeOn-time62%
DeltaCheapest$95Average$250FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$100Average$115FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$118Average$403FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$132Average$337FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$141Average$300FlexibilityNo cancel feeOn-time63%

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