$64+ 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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Jan 25 — Feb 11
1 adult, Economy
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Find cheap flights from Chicago to Falmouth with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to Falmouth are usually found in January or September, booked 89 days in advance, depart on a Wednesday or Thursday and return on a Wednesday
Cheap flight deals from Chicago to Falmouth
Cheapest flights from Chicago to FalmouthExplore 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 December 26, 2025.
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 December 26, 2025.
This United Airlines deal was found by Cheapflights users on 12/24. 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 12/316:11 pmORD - BOS
Nonstop2h 33mUnited Airlines
Thu 1/16:29 pmBOS - ORD
Nonstop3h 06mUnited Airlines
Deal found 12/24![United Airlines logo]()
$127
This United Airlines deal was found by Cheapflights users on 12/22. 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 12/259:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Thu 1/17:45 amBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 12/22![United Airlines logo]()
$137
This Priceline deal was found by Cheapflights users on 12/24. 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.
Wed 12/317:41 pmORD - BOS
Nonstop2h 29mJetBlue
Thu 1/14:31 pmBOS - ORD
Nonstop3h 15mJetBlue
Deal found 12/24![JetBlue logo]()
$142
This United Airlines deal was found by Cheapflights users on 12/24. 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 12/289:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Tue 12/306:23 pmBOS - ORD
Nonstop3h 02mUnited Airlines
Deal found 12/24![United Airlines logo]()
$157
This United Airlines deal was found by Cheapflights users on 12/22. 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 12/259:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Fri 1/27:45 amBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 12/22![United Airlines logo]()
$159
This United Airlines deal was found by Cheapflights users on 12/24. 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 12/316:11 pmORD - BOS
Nonstop2h 33mUnited Airlines
Fri 1/27:45 amBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 12/24![United Airlines logo]()
$163
This American Airlines deal was found by Cheapflights users on 12/25. 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.
Sun 12/288:20 pmORD - BOS
Nonstop2h 31mAmerican Airlines
Thu 1/16:36 amBOS - ORD
Nonstop3h 11mAmerican Airlines
Deal found 12/25![American Airlines logo]()
$172
This Southwest deal was found by Cheapflights users on 12/22. 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 12/2511:25 amMDW - BOS
1 stop4h 55mSouthwest
Thu 1/110:20 amBOS - MDW
1 stop5h 35mSouthwest
Deal found 12/22![Southwest logo]()
$172
This Southwest deal was found by Cheapflights users on 12/22. 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 12/2511:25 amMDW - BOS
1 stop4h 55mSouthwest
Fri 1/25:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 12/22![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 12/24. 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 12/289:40 pmMDW - BOS
1 stop9h 30mSouthwest
Thu 1/15:30 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 12/24![Southwest logo]()
$188
This Southwest deal was found by Cheapflights users on 12/25. 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 12/316:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Thu 1/15:30 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 12/25![Southwest logo]()
$206
This Southwest deal was found by Cheapflights users on 12/23. 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 12/265:30 amMDW - BOS
Nonstop2h 15mSouthwest
Wed 12/315:35 pmBOS - MDW
1 stop4h 30mSouthwest
Deal found 12/23![Southwest logo]()
$233
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 December 26, 2025.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $127 (United Airlines) |
One-way from | $64 (Cheapflightsfares) |
Popular in | April |
Cheapest in | January |
Average price | $267 |
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 December 26, 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
Sat 1/17
10:15 am-1:30 pm
Nonstop2h 15m
Boston Logan Intl
Sun 1/18
5:30 am-7:20 am
Nonstop2h 50m
$127
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Thu 1/15
9:40 am-12:55 pm
Nonstop2h 15m
Boston Logan Intl
Sun 1/18
2:40 pm-4:30 pm
Nonstop2h 50m
$132
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 3/13
6:22 pm-9:55 pm
Nonstop2h 33m
Boston Logan Intl
Fri 3/20
3:20 pm-5:24 pm
Nonstop3h 04m
$137
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 4/29
7:00 am-10:30 am
Nonstop2h 30m
Boston Logan Intl
Sat 5/2
5:10 pm-7:17 pm
Nonstop3h 07m
$137
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 2/24
10:00 am-1:20 pm
Nonstop2h 20m
Boston Logan Intl
Sun 3/1
7:00 am-9:10 am
Nonstop3h 10m
$137
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 2/25
6:40 pm-10:09 pm
Nonstop2h 29m
Boston Logan Intl
Sat 2/28
5:15 pm-7:23 pm
Nonstop3h 08m
$137
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 1/9
7:45 am-11:10 am
Nonstop2h 25m
Boston Logan Intl
Tue 1/13
3:35 pm-5:43 pm
Nonstop3h 08m
$137
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 1/21
6:59 pm-10:31 pm
Nonstop2h 32m
Boston Logan Intl
Wed 1/28
8:25 pm-10:29 pm
Nonstop3h 04m
$137
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Mon 2/16
6:05 am-9:25 am
Nonstop2h 20m
Boston Logan Intl
Fri 2/20
7:05 pm-8:55 pm
Nonstop2h 50m
$137
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 1/31
7:45 am-11:10 am
Nonstop2h 25m
Boston Logan Intl
Tue 2/3
3:35 pm-5:43 pm
Nonstop3h 08m
$137
Showing 1-10 of 40 results
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 December 19, 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 $88). Flying from Chicago to Falmouth in February is currently the most expensive (average of $137). 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 December 26, 2025.
It’s optimal to fly from Chicago to Falmouth in the evening. By choosing this option you can save up to 42% 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 December 20, 2025.
Travelers seeking maximum savings on their Chicago to Falmouth flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday afternoons 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 December 26, 2025.
The most flights from CHI to FM5 are scheduled on a Thursday (35 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (17 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 December 26, 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.
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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.
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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.
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 December 26, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$78 | Average$175 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$83 | Average$166 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$103 | Average$225 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$104 | Average$115 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$117 | Average$406 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$117 | Average$349 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$135 | Average$288 | FlexibilityNo cancel fee | On-time63% |