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Falmouth

$88+ 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 6/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Jun 17 — Jun 241
Wed 6/17
Wed 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Falmouth are usually found in January or September, booked 49 days in advance, depart on a Wednesday or Thursday and return on a Friday

Cheap 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 18, 2026.

This SmartFares deal was found by Cheapflights users on 5/14. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:30 pm
ORD
-
BOS
Nonstop2h 29m
JetBlue
Sun 5/316:00 am
BOS
-
ORD
Nonstop3h 00m
JetBlue
Deal found 5/14$172
This SmartFares deal was found by Cheapflights users on 5/17. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/48:50 am
ORD
-
BOS
Nonstop2h 30m
JetBlue
Sun 6/76:00 am
BOS
-
ORD
Nonstop2h 59m
JetBlue
Deal found 5/17$176
This Southwest deal was found by Cheapflights users on 5/17. 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.
Sat 6/65:25 am
MDW
-
BOS
Nonstop2h 15m
Southwest
Tue 6/95:30 pm
BOS
-
MDW
Nonstop2h 50m
Southwest
Deal found 5/17$176
This Southwest deal was found by Cheapflights users on 5/17. 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.
Sat 6/65:45 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Mon 6/84:45 pm
BOS
-
MDW
Nonstop2h 50m
Southwest
Deal found 5/17$181
This Cheapflightsfares deal was found by Cheapflights users on 5/13. 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 6/98:30 pm
ORD
-
BOS
Nonstop2h 29m
JetBlue
Wed 6/106:00 am
BOS
-
ORD
Nonstop2h 59m
JetBlue
Deal found 5/13$182
This flygcity.se deal was found by Cheapflights users on 5/17. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/61:55 pm
ORD
-
BOS
Nonstop2h 29m
JetBlue
Mon 6/86:00 am
BOS
-
ORD
Nonstop2h 59m
JetBlue
Deal found 5/17$183
This Southwest deal was found by Cheapflights users on 5/16. 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.
Thu 5/281:55 pm
MDW
-
BOS
Nonstop2h 15m
Southwest
Sat 6/65:20 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Deal found 5/16$185
This American Airlines deal was found by Cheapflights users on 5/17. 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.
Wed 6/33:10 pm
ORD
-
BOS
Nonstop2h 36m
American Airlines
Tue 6/95:00 am
BOS
-
ORD
Nonstop2h 58m
American Airlines
Deal found 5/17$186
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 6/96:00 am
MDW
-
BOS
1 stop18h 27m
Frontier
Wed 6/106:00 am
BOS
-
MDW
1 stop17h 11m
Frontier
Deal found 5/13$186
This Delta deal was found by Cheapflights users on 5/13. 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 6/37:00 am
ORD
-
BOS
Nonstop2h 35m
Delta
Wed 6/104:15 pm
BOS
-
ORD
Nonstop3h 05m
Delta
Deal found 5/13$187
This Southwest deal was found by Cheapflights users on 5/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Wed 6/37:20 am
BOS
-
MDW
Nonstop2h 45m
Southwest
Deal found 5/14$187
This Priceline deal was found by Cheapflights users on 5/13. 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.
Tue 6/98:30 pm
ORD
-
BOS
Nonstop2h 29m
Multiple Airlines
Wed 6/1012:01 pm
BOS
-
ORD
1 stop8h 49m
Multiple Airlines
Deal found 5/13$189

Find 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 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$172
(SmartFares)

One-way from

$88
(Kiwi.com)

Popular in

April

Cheapest in

January

Average price

$237
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Boston Logan Intl flights.
Search Deals
From Chicago (CHI) to Falmouth
Search Deals
One-way flight from Chicago (CHI) to Falmouth
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

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 18, 2026.
Use the filters below to find and compare flights from Chicago to Falmouth that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 6/2

6:00 pm-9:20 pm

Nonstop2h 20m

Boston Logan Intl

Thu 6/4

5:25 am-7:00 am

Nonstop2h 35m

$192

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 6/16

9:41 pm-1:14 am

Nonstop2h 33m

Boston Logan Intl

Wed 6/17

7:19 am-9:17 am

Nonstop2h 58m

$197

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 6/1

6:05 am-9:29 am

Nonstop2h 24m

Boston Logan Intl

Mon 6/1

6:40 pm-8:40 pm

Nonstop3h 00m

$197

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 8/11

6:00 pm-9:20 pm

Nonstop2h 20m

Boston Logan Intl

Sun 8/16

7:30 am-9:05 am

Nonstop2h 35m

$201

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 5/29

9:25 am-12:40 pm

Nonstop2h 15m

Boston Logan Intl

Sun 5/31

6:10 am-7:55 am

Nonstop2h 45m

$201
Quickest round-trip

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 6/12

7:35 pm-10:50 pm

Nonstop2h 15m

Boston Logan Intl

Sat 6/13

5:20 am-6:55 am

Nonstop2h 35m

$201

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 6/3

6:05 am-9:29 am

Nonstop2h 24m

Boston Logan Intl

Sun 6/7

5:45 am-9:36 am

1 stop4h 51m

$202

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 5/27

7:10 am-1:12 pm

1 stop5h 02m

Boston Logan Intl

Sat 5/30

7:19 am-9:17 am

Nonstop2h 58m

$202

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 6/19

7:25 pm-11:02 pm

Nonstop2h 37m

Boston Logan Intl

Mon 6/22

8:45 pm-10:42 pm

Nonstop2h 57m

$205

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 7/22

10:56 am-2:23 pm

Nonstop2h 27m

Boston Logan Intl

Tue 7/28

5:20 pm-7:25 pm

Nonstop3h 05m

$205

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/13

Showing 1-10 of 46 resultsSorted by cheapest first
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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

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 May 18, 2026.

It’s optimal to fly from Chicago to Falmouth in the evening. By choosing this option you can save up to 50% on the cost of your flight, compared to a flight in the morning.

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 May 16, 2026.

Travelers seeking maximum savings on their Chicago to Falmouth flight should consider departing on Thursday afternoons 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 May 18, 2026.

The most flights from CHI to FM5 are scheduled on a Sunday (74 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (15 on average).

How much does it cost to fly round-trip from Chicago to Falmouth?

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 18, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited 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
7.9
Good
4,287 reviews

Comfort

8.0

Overall

7.9

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,287 reviews
Southwest
7.9
Good
4,287 reviews

Comfort

8.0

Overall

7.9

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,448 reviews
Southwest
7.9
Good
4,287 reviews

Comfort

8.0

Overall

7.9

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,737 reviews
Southwest
7.9
Good
4,287 reviews

Comfort

8.0

Overall

7.9

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
JetBlue
7.2
Good
2,979 reviews
Southwest
7.9
Good
4,287 reviews

Comfort

8.0

Overall

7.9

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,648 reviews
Southwest
7.9
Good
4,287 reviews

Comfort

8.0

Overall

7.9

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 $192, 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 cheapest airlines to fly from Chicago to Falmouth one-way?

    The cheapest airline one-way is JetBlue, with whom users have recently found tickets for as low as $64. However, be on the lookout for offers from United Airlines and American Airlines, as they are both options that can get you from Chicago to Falmouth for a low price.

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

    The top 3 most reliable airlines when flying from Chicago to Falmouth are Avianca (96%), Icelandair (88%) and TAP AIR PORTUGAL (87%).

  • What are the cheapest flights from Chicago to Falmouth?

    On average you can expect to pay $439 for a flight from Chicago to Falmouth. The cheapest flight overall is $83 while the most popular route, (Chicago O'Hare Intl - Boston Logan Intl) is currently priced at $186.

  • 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.

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 May 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$68Average$415FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$79Average$166FlexibilityNo cancel feeOn-time65%
DeltaCheapest$85Average$329FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$124Average$260FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$126Average$250FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$136Average$302FlexibilityNo cancel feeOn-time71%

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