$108+ Cheap flights from Chicago (CHI) to Falmouth, MA, MA
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Oct 4 — Oct 111
Round-trip
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 February, booked 54 days in advance, depart on a Saturday or Thursday and return on a Friday
Cheap flight deals from Chicago to Falmouth
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Best
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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 September 4, 2026.
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 4, 2026.
This CheapOair deal was found by Cheapflights users on 9/2. 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.
Fri 10/23:50 pm -
1 stop17h 51m
Mon 10/55:00 pm -
Nonstop3h 03m
Deal found 9/2![Multiple Airlines logo]()
$212
This CheapOair deal was found by Cheapflights users on 9/2. 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.
Thu 10/226:58 pm -
1 stop15h 04m
Thu 11/267:55 am -
Nonstop3h 04m
Deal found 9/2![Multiple Airlines logo]()
$213
This KAYAK deal was found by Cheapflights users on 9/3. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/261:00 pm -
Nonstop2h 48m
Thu 10/299:59 am -
Nonstop3h 00m
Deal found 9/3![JetBlue logo]()
$214
This Cheapflightsfares deal was found by Cheapflights users on 9/2. 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.
Thu 10/228:04 pm -
Nonstop2h 55m
Thu 11/267:55 am -
Nonstop3h 04m
Deal found 9/2![JetBlue logo]()
$215
This KAYAK deal was found by Cheapflights users on 9/3. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/271:00 pm -
Nonstop2h 48m
Mon 11/25:15 pm -
Nonstop3h 14m
Deal found 9/3![JetBlue logo]()
$216
This Delta deal was found by Cheapflights users on 9/2. 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 10/227:25 am -
Nonstop2h 35m
Thu 10/227:40 pm -
Nonstop2h 51m
Deal found 9/2![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 9/3. 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.
Wed 10/217:50 am -
Nonstop2h 20m
Tue 10/275:55 pm -
Nonstop2h 35m
Deal found 9/3![Southwest logo]()
$217
This JetBlue deal was found by Cheapflights users on 9/1. 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 10/18:24 pm -
Nonstop2h 45m
Mon 10/55:00 pm -
Nonstop3h 03m
Deal found 9/1![JetBlue logo]()
$218
This CheapOair deal was found by Cheapflights users on 9/3. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/268:24 pm -
Nonstop2h 45m
Tue 9/2912:52 pm -
1 stop6h 31m
Deal found 9/3![Multiple Airlines logo]()
$219
This Expedia deal was found by Cheapflights users on 9/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:38 am -
Nonstop2h 28m
Sat 9/2612:54 pm -
1 stop6h 29m
Deal found 9/2![Multiple Airlines logo]()
$220
This KAYAK deal was found by Cheapflights users on 9/3. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/308:24 pm -
Nonstop2h 44m
Tue 11/35:15 pm -
Nonstop3h 14m
Deal found 9/3![JetBlue logo]()
$221
This Frontier deal was found by Cheapflights users on 9/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:07 pm -
1 stop13h 55m
Mon 12/1411:57 am -
1 stop8h 05m
Deal found 9/2![Frontier logo]()
$221
Best flights from Chicago to FalmouthDiscover carefully curated flight deals from Chicago to Falmouth that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 4, 2026.
Discover carefully curated flight deals from Chicago to Falmouth that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 4, 2026.
This Delta deal was found by Cheapflights users on 9/1. 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 10/157:25 am -
Nonstop2h 35m
Tue 10/204:25 pm -
Nonstop2h 55m
Deal found 9/1![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 9/2. 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 10/166:45 pm -
Nonstop2h 20m
Mon 10/1910:00 pm -
Nonstop2h 40m
Deal found 9/2![Southwest logo]()
$226
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Thu 11/51:59 pm -
Nonstop2h 25m
Sun 11/86:00 am -
Nonstop3h 00m
Deal found 9/3![United Airlines logo]()
$233
This Delta deal was found by Cheapflights users on 9/1. 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 10/110:30 am -
Nonstop2h 35m
Mon 10/58:50 pm -
Nonstop2h 42m
Deal found 9/1![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 9/3. 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.
Thu 10/225:30 am -
Nonstop2h 25m
Tue 10/276:45 am -
1 stop5h 35m
Deal found 9/3![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 9/3. 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.
Thu 10/225:30 am -
Nonstop2h 25m
Sun 10/2510:50 pm -
Nonstop2h 40m
Deal found 9/3![Southwest logo]()
$246
This United Airlines deal was found by Cheapflights users on 8/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/149:40 pm -
Nonstop2h 30m
Thu 9/1710:38 am -
Nonstop2h 51m
Deal found 8/30![United Airlines logo]()
$275
This Southwest deal was found by Cheapflights users on 8/31. 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 9/145:45 am -
Nonstop2h 15m
Thu 9/1712:40 pm -
Nonstop2h 30m
Deal found 8/31![Southwest logo]()
$275
This Delta deal was found by Cheapflights users on 8/31. 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 9/225:40 pm -
1 stop4h 37m
Tue 9/299:10 am -
1 stop4h 49m
Deal found 8/31![Delta logo]()
$315
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Thu 9/1012:52 pm -
Nonstop2h 35m
Sun 9/136:00 am -
Nonstop2h 59m
Deal found 9/3![United Airlines logo]()
$323
This Southwest deal was found by Cheapflights users on 9/2. 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 10/85:30 am -
Nonstop2h 25m
Sun 10/1110:50 pm -
Nonstop2h 40m
Deal found 9/2![Southwest logo]()
$276
This Delta deal was found by Cheapflights users on 8/31. 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 11/255:50 pm -
1 stop4h 27m
Wed 12/21:04 pm -
1 stop6h 22m
Deal found 8/31![Delta logo]()
$315
This Southwest deal was found by Cheapflights users on 8/31. 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 11/244:05 pm -
Nonstop2h 15m
Wed 12/25:00 am -
1 stop8h 15m
Deal found 8/31![Southwest logo]()
$285
This Delta deal was found by Cheapflights users on 9/2. 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 10/208:29 am -
1 stop6h 46m
Thu 10/227:00 am -
1 stop7h 08m
Deal found 9/2![Delta logo]()
$327
This Southwest deal was found by Cheapflights users on 9/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:30 am -
Nonstop2h 25m
Mon 10/262:45 pm -
1 stop7h 10m
Deal found 9/4![Southwest logo]()
$285
This Delta deal was found by Cheapflights users on 9/1. 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.
Mon 9/282:29 pm -
1 stop6h 57m
Sat 10/36:05 am -
1 stop7h 20m
Deal found 9/1![Delta logo]()
$327
This Southwest deal was found by Cheapflights users on 9/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:05 am -
2 stops8h 25m
Sun 11/154:20 pm -
Nonstop2h 45m
Deal found 9/4![Southwest logo]()
$290
This KAYAK deal was found by Cheapflights users on 9/3. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/135:30 am -
1 stop7h 19m
Thu 9/177:30 am -
Nonstop2h 54m
Deal found 9/3![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 9/2. 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 10/73:15 pm -
Nonstop2h 20m
Sun 10/1110:50 pm -
Nonstop2h 40m
Deal found 9/2![Southwest logo]()
$296
This KAYAK deal was found by Cheapflights users on 9/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/285:40 pm -
1 stop4h 37m
Thu 10/16:05 am -
1 stop7h 20m
Deal found 9/2![Delta logo]()
$332
Last-minute flights from Chicago to FalmouthDiscover last-minute flight deals from Chicago to Falmouth. Data last updated September 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Falmouth. Data last updated September 4, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 9/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:38 am -
Nonstop2h 28m
Sat 9/2612:54 pm -
1 stop6h 29m
Deal found 9/2![Multiple Airlines logo]()
$220
This CheapOair deal was found by Cheapflights users on 9/1. 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.
Fri 9/253:50 pm -
1 stop18h 01m
Tue 9/2912:52 pm -
1 stop6h 31m
Deal found 9/1![Frontier logo]()
$222
This CheapOair deal was found by Cheapflights users on 9/3. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/268:24 pm -
Nonstop2h 45m
Tue 9/2912:52 pm -
1 stop6h 31m
Deal found 9/3![Multiple Airlines logo]()
$219
This JetBlue deal was found by Cheapflights users on 9/1. 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 10/18:24 pm -
Nonstop2h 45m
Mon 10/55:00 pm -
Nonstop3h 03m
Deal found 9/1![JetBlue logo]()
$218
This CheapOair deal was found by Cheapflights users on 9/2. 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.
Fri 10/23:50 pm -
1 stop17h 51m
Mon 10/55:00 pm -
Nonstop3h 03m
Deal found 9/2![Multiple Airlines logo]()
$212
This Southwest deal was found by Cheapflights users on 9/3. 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.
Wed 10/217:50 am -
Nonstop2h 20m
Tue 10/275:55 pm -
Nonstop2h 35m
Deal found 9/3![Southwest logo]()
$217
This CheapOair deal was found by Cheapflights users on 9/2. 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.
Thu 10/226:58 pm -
1 stop15h 04m
Thu 11/267:55 am -
Nonstop3h 04m
Deal found 9/2![Multiple Airlines logo]()
$213
This Cheapflightsfares deal was found by Cheapflights users on 9/2. 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.
Thu 10/228:04 pm -
Nonstop2h 55m
Thu 11/267:55 am -
Nonstop3h 04m
Deal found 9/2![JetBlue logo]()
$215
This JetBlue deal was found by Cheapflights users on 9/4. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:38 pm -
1 stop7h 11m
Sat 10/246:55 am -
1 stop5h 29m
Deal found 9/4![JetBlue logo]()
$217
This KAYAK deal was found by Cheapflights users on 9/3. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/261:00 pm -
Nonstop2h 48m
Thu 10/299:59 am -
Nonstop3h 00m
Deal found 9/3![JetBlue logo]()
$214
This KAYAK deal was found by Cheapflights users on 9/3. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/271:00 pm -
Nonstop2h 48m
Mon 11/25:15 pm -
Nonstop3h 14m
Deal found 9/3![JetBlue logo]()
$216
This KAYAK deal was found by Cheapflights users on 9/3. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/308:24 pm -
Nonstop2h 44m
Tue 11/35:15 pm -
Nonstop3h 14m
Deal found 9/3![JetBlue logo]()
$221
One-way flights from Chicago to FalmouthSearch for one-way flight options from Chicago to Falmouth. Find affordable one-way fares based on user searches. Data last updated September 4, 2026.
Search for one-way flight options from Chicago to Falmouth. Find affordable one-way fares based on user searches. Data last updated September 4, 2026.
This American Airlines deal was found by Cheapflights users on 9/1. 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.
Tue 9/298:19 pm -
Nonstop2h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![American Airlines logo]()
$108
This JetBlue deal was found by Cheapflights users on 9/2. 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 9/288:24 pm -
Nonstop2h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![JetBlue logo]()
$109
This Southwest deal was found by Cheapflights users on 9/1. 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 9/286:30 pm -
Nonstop2h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Southwest logo]()
$109
This Jetabroad deal was found by Cheapflights users on 9/2. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1412:38 pm -
1 stop7h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![JetBlue logo]()
$112
This Jetabroad deal was found by Cheapflights users on 9/2. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/227:05 am -
1 stop6h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![JetBlue logo]()
$113
This Super.com deal was found by Cheapflights users on 9/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/258:24 pm -
Nonstop2h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![JetBlue logo]()
$114
This KAYAK deal was found by Cheapflights users on 9/3. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:24 pm -
Nonstop2h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![JetBlue logo]()
$115
This Cheapflightsfares deal was found by Cheapflights users on 9/2. 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.
Fri 10/98:00 pm -
Nonstop2h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![JetBlue logo]()
$116
This Delta deal was found by Cheapflights users on 9/2. 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.
Fri 10/27:30 pm -
Nonstop2h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Delta logo]()
$118
This Southwest deal was found by Cheapflights users on 9/2. 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 10/85:30 am -
Nonstop2h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Southwest logo]()
$118
This Trip.com deal was found by Cheapflights users on 8/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/233:50 pm -
1 stop17h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/30![Frontier logo]()
$119
This Southwest deal was found by Cheapflights users on 9/2. 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 9/292:40 pm -
1 stop6h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Southwest logo]()
$119
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 September 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $212 (CheapOair) |
One-way from | $108 (American Airlines) |
Popular in | August |
Cheapest in | January |
Average price | $258 |
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 7,457,451 searches. Data last updated September 4, 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
Cheapest round-trip
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Mon 9/28
3:05 pm-6:52 pm
Nonstop2h 47m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$109
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Wed 10/21
1:10 pm-4:30 pm
Nonstop2h 20m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$109
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 10/1
7:30 pm-11:09 pm
Nonstop2h 39m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$109
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Mon 10/5
3:30 pm-6:50 pm
Nonstop2h 20m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$109
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Wed 10/7
3:15 pm-6:35 pm
Nonstop2h 20m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$109
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Tue 10/6
8:10 am-4:05 pm
1 stop6h 55m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$119
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Tue 9/29
2:40 pm-10:15 pm
1 stop6h 35m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$119
Quickest round-trip
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Sun 9/20
6:00 am-9:15 am
Nonstop2h 15m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$125
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Fri 9/25
9:24 pm-12:54 am
Nonstop2h 30m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$138
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Sat 9/19
3:10 pm-6:35 pm
Nonstop2h 25m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$138
Showing 1-10 of 41 resultsSorted by cheapest first
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.
ORD-BOS
MDW-BOS
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
CHI-FM5
ORD-BOS
MDW-BOS
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 4, 2026.
It’s optimal to fly from Chicago to Falmouth in the evening. By choosing this option you can save up to 28% on the cost of your flight, compared to a flight in the morning.
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 4, 2026.
The most flights from CHI to FM5 are scheduled on a Thursday (76 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 on average).
How much does it cost to fly round-trip from Chicago to Falmouth?
Airfare is typical for this route at the moment.
Chicago to Falmouth flights typically cost between $204 and $322 in October.The cheapest round-trip price found within the last 5 days was $212 on Multiple Airlines (Oct 2-Oct 5).
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 August 29, 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.
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 4, 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.
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
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
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Complete your trip
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Search flights from Chicago to Falmouth by cabin class
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Chicago and Falmouth flights
Browse other Chicago and Falmouth flight options. Last updated on September 4, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on September 4, 2026.
Popular flight searches
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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 7,457,451 searches. Data last updated September 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$78 | Average$350 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$92 | Average$336 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$133 | Average$377 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$399 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$137 | Average$379 | FlexibilityNo cancel fee | On-time71% |