$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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Aug 17 — Aug 241
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 58 days in advance, depart on a Saturday or Thursday and return on a Friday
Cheap flight deals from Chicago to Falmouth
Cheapest
Best
Last-minute
One-way
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 July 18, 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 July 18, 2026.
This SmartFares deal was found by Cheapflights users on 7/13. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/285:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Fri 9/44:55 pm
BOS
- ORD
1 stop6h 03m
JetBlue
Deal found 7/13![JetBlue logo]()
$176
This Traveloka deal was found by Cheapflights users on 7/13. 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 Traveloka is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Tue 8/1812:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Deal found 7/13![JetBlue logo]()
$181
This Super.com deal was found by Cheapflights users on 7/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:30 am
ORD
- BOS
1 stop7h 10m
JetBlue
Fri 9/254:00 pm
BOS
- ORD
1 stop7h 06m
JetBlue
Deal found 7/13![JetBlue logo]()
$182
This Super.com deal was found by Cheapflights users on 7/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/111:00 pm
ORD
- BOS
1 stop6h 49m
JetBlue
Mon 9/146:55 am
BOS
- ORD
1 stop5h 52m
JetBlue
Deal found 7/15![JetBlue logo]()
$183
This Cheapflightsfares deal was found by Cheapflights users on 7/13. 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.
Sat 9/269:38 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Sat 9/265:00 pm
BOS
- ORD
Nonstop3h 22m
JetBlue
Deal found 7/13![JetBlue logo]()
$190
This Super.com deal was found by Cheapflights users on 7/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/149:42 am
ORD
- BOS
1 stop6h 49m
JetBlue
Tue 8/182:45 pm
BOS
- ORD
1 stop8h 13m
JetBlue
Deal found 7/15![JetBlue logo]()
$193
This Super.com deal was found by Cheapflights users on 7/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/161:00 pm
ORD
- BOS
1 stop6h 49m
JetBlue
Sun 9/203:13 pm
BOS
- ORD
1 stop7h 53m
JetBlue
Deal found 7/16![JetBlue logo]()
$194
This Cheapflightsfares deal was found by Cheapflights users on 7/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/268:24 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Wed 9/306:55 am
BOS
- ORD
Nonstop2h 51m
JetBlue
Deal found 7/14![JetBlue logo]()
$195
This Southwest deal was found by Cheapflights users on 7/15. 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 9/96:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Tue 9/1510:05 am
BOS
- MDW
Nonstop2h 30m
Southwest
Deal found 7/15![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 7/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/179:55 am
MDW
- BOS
Nonstop2h 20m
Southwest
Mon 10/195:50 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/13![Southwest logo]()
$206
This Southwest deal was found by Cheapflights users on 7/16. 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.
Tue 9/226:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Sat 9/267:05 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/16![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 7/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2311:55 am
MDW
- BOS
2 stops5h 40m
Southwest
Sat 9/267:05 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/13![Southwest logo]()
$212
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 July 18, 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 July 18, 2026.
This JetBlue deal was found by Cheapflights users on 7/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/149:42 am
ORD
- BOS
1 stop6h 49m
JetBlue
Sat 8/224:43 pm
BOS
- ORD
1 stop6h 15m
JetBlue
Deal found 7/13![JetBlue logo]()
$201
This Southwest deal was found by Cheapflights users on 7/14. 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.
Sat 8/15:45 pm
MDW
- BOS
Nonstop2h 25m
Southwest
Mon 8/35:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/14![Southwest logo]()
$215
This United Airlines deal was found by Cheapflights users on 7/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:10 am
ORD
- BOS
Nonstop2h 23m
United Airlines
Tue 10/205:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Deal found 7/13![United Airlines logo]()
$216
This Delta deal was found by Cheapflights users on 7/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/73:05 pm
ORD
- BOS
Nonstop2h 39m
Delta
Sun 10/117:30 am
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 7/14![Delta logo]()
$245
This JetBlue deal was found by Cheapflights users on 7/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/11:00 pm
ORD
- BOS
1 stop6h 49m
JetBlue
Sat 10/34:00 pm
BOS
- ORD
1 stop7h 06m
JetBlue
Deal found 7/17![JetBlue logo]()
$211
This Southwest deal was found by Cheapflights users on 7/18. 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 10/209:10 am
MDW
- BOS
Nonstop2h 20m
Southwest
Thu 10/2210:00 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/18![Southwest logo]()
$216
This United Airlines deal was found by Cheapflights users on 7/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:00 am
ORD
- BOS
1 stop4h 17m
United Airlines
Wed 8/195:01 pm
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 7/15![United Airlines logo]()
$225
This JetBlue deal was found by Cheapflights users on 7/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:00 pm
ORD
- BOS
1 stop6h 49m
JetBlue
Thu 10/226:55 am
BOS
- ORD
1 stop5h 52m
JetBlue
Deal found 7/17![JetBlue logo]()
$211
This Southwest deal was found by Cheapflights users on 7/17. 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.
Fri 9/42:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Mon 9/78:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 7/17![Southwest logo]()
$225
This United Airlines deal was found by Cheapflights users on 7/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:00 am
ORD
- BOS
Nonstop2h 23m
United Airlines
Wed 10/286:00 am
BOS
- ORD
1 stop4h 45m
United Airlines
Deal found 7/17![United Airlines logo]()
$226
This Delta deal was found by Cheapflights users on 7/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/256:00 am
ORD
- BOS
1 stop6h 47m
Delta
Sat 10/311:35 pm
BOS
- ORD
Nonstop2h 52m
Delta
Deal found 7/17![Delta logo]()
$262
This JetBlue deal was found by Cheapflights users on 7/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/91:00 pm
ORD
- BOS
1 stop6h 49m
JetBlue
Fri 9/116:55 am
BOS
- ORD
Nonstop2h 51m
JetBlue
Deal found 7/16![JetBlue logo]()
$218
This Southwest deal was found by Cheapflights users on 7/16. 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.
Wed 9/96:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Fri 9/111:10 pm
BOS
- MDW
1 stop7h 10m
Southwest
Deal found 7/16![Southwest logo]()
$226
This United Airlines deal was found by Cheapflights users on 7/16. 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 9/107:55 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Sun 9/138:30 pm
BOS
- ORD
1 stop4h 58m
United Airlines
Deal found 7/16![United Airlines logo]()
$235
This Southwest deal was found by Cheapflights users on 7/15. 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 8/1912:45 pm
MDW
- BOS
2 stops7h 40m
Southwest
Tue 8/257:15 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/15![Southwest logo]()
$230
This Southwest deal was found by Cheapflights users on 7/18. 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 11/119:55 am
MDW
- BOS
2 stops8h 05m
Southwest
Mon 11/167:05 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 7/18![Southwest logo]()
$231
This United Airlines deal was found by Cheapflights users on 7/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Sun 8/97:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 7/13![United Airlines logo]()
$261
This JetBlue deal was found by Cheapflights users on 7/15. 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.
Fri 10/169:38 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Sun 10/2511:15 am
BOS
- ORD
Nonstop3h 05m
JetBlue
Deal found 7/15![JetBlue logo]()
$261
This Southwest deal was found by Cheapflights users on 7/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:55 pm
MDW
- BOS
1 stop11h 05m
Southwest
Tue 9/87:30 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/13![Southwest logo]()
$231
This Southwest deal was found by Cheapflights users on 7/16. 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.
Sat 8/2911:25 am
MDW
- BOS
Nonstop2h 20m
Southwest
Mon 8/315:25 am
BOS
- MDW
1 stop6h 35m
Southwest
Deal found 7/16![Southwest logo]()
$235
This Southwest deal was found by Cheapflights users on 7/16. 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.
Wed 8/1912:45 pm
MDW
- BOS
2 stops7h 40m
Southwest
Sat 8/227:05 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/16![Southwest logo]()
$240
This Southwest deal was found by Cheapflights users on 7/17. 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.
Thu 8/205:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Sun 8/235:55 am
BOS
- MDW
1 stop5h 10m
Southwest
Deal found 7/17![Southwest logo]()
$255
This Southwest deal was found by Cheapflights users on 7/17. 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.
Wed 9/306:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Sun 10/47:40 am
BOS
- MDW
2 stops7h 15m
Southwest
Deal found 7/17![Southwest logo]()
$262
Last-minute flights from Chicago to FalmouthDiscover last-minute flight deals from Chicago to Falmouth. Data last updated July 18, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Falmouth. Data last updated July 18, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 7/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/318:10 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Tue 8/42:45 pm
BOS
- ORD
1 stop8h 13m
JetBlue
Deal found 7/14![JetBlue logo]()
$195
This Southwest deal was found by Cheapflights users on 7/16. 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 7/317:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Sat 8/15:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/16![Southwest logo]()
$231
This Super.com deal was found by Cheapflights users on 7/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/129:35 am
ORD
- BOS
1 stop6h 42m
JetBlue
Wed 8/194:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Deal found 7/13![JetBlue logo]()
$183
This Traveloka deal was found by Cheapflights users on 7/13. 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 Traveloka is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Tue 8/1812:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Deal found 7/13![JetBlue logo]()
$181
This Southwest deal was found by Cheapflights users on 7/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/139:20 am
MDW
- BOS
1 stop6h 45m
Southwest
Tue 8/185:25 am
BOS
- MDW
1 stop4h 35m
Southwest
Deal found 7/13![Southwest logo]()
$235
This Super.com deal was found by Cheapflights users on 7/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/149:42 am
ORD
- BOS
1 stop6h 49m
JetBlue
Tue 8/182:45 pm
BOS
- ORD
1 stop8h 13m
JetBlue
Deal found 7/15![JetBlue logo]()
$193
This Cheapflightsfares deal was found by Cheapflights users on 7/13. 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.
Thu 8/206:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Sat 8/224:43 pm
BOS
- ORD
1 stop6h 15m
JetBlue
Deal found 7/13![JetBlue logo]()
$199
This Southwest deal was found by Cheapflights users on 7/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Sat 8/227:05 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/13![Southwest logo]()
$215
This Southwest deal was found by Cheapflights users on 7/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 8/255:25 am
BOS
- MDW
1 stop4h 35m
Southwest
Deal found 7/13![Southwest logo]()
$225
This SmartFares deal was found by Cheapflights users on 7/13. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/285:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Fri 9/44:55 pm
BOS
- ORD
1 stop6h 03m
JetBlue
Deal found 7/13![JetBlue logo]()
$176
This Cheapflightsfares deal was found by Cheapflights users on 7/13. 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.
Sat 8/296:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Sat 9/125:00 pm
BOS
- ORD
Nonstop3h 22m
JetBlue
Deal found 7/13![JetBlue logo]()
$197
This Southwest deal was found by Cheapflights users on 7/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:40 am
MDW
- BOS
Nonstop2h 20m
Southwest
Tue 9/18:15 am
BOS
- MDW
2 stops5h 50m
Southwest
Deal found 7/13![Southwest logo]()
$230
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 July 18, 2026.
Search for one-way flight options from Chicago to Falmouth. Find affordable one-way fares based on user searches. Data last updated July 18, 2026.
This SmartFares deal was found by Cheapflights users on 7/13. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:00 pm
ORD
- BOS
1 stop6h 49m
JetBlue
Deal found 7/13![JetBlue logo]()
$88
This Super.com deal was found by Cheapflights users on 7/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Deal found 7/13![JetBlue logo]()
$90
This Super.com deal was found by Cheapflights users on 7/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Deal found 7/13![JetBlue logo]()
$92
This Traveloka deal was found by Cheapflights users on 7/14. 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 Traveloka is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:00 pm
ORD
- BOS
1 stop6h 49m
JetBlue
Deal found 7/14![JetBlue logo]()
$93
This Super.com deal was found by Cheapflights users on 7/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/189:35 am
ORD
- BOS
1 stop6h 42m
JetBlue
Deal found 7/15![JetBlue logo]()
$94
This Super.com deal was found by Cheapflights users on 7/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/75:27 pm
ORD
- BOS
1 stop5h 37m
JetBlue
Deal found 7/17![JetBlue logo]()
$96
This Cheapflightsfares deal was found by Cheapflights users on 7/13. 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.
Sat 9/269:38 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Deal found 7/13![JetBlue logo]()
$97
This SmartFares deal was found by Cheapflights users on 7/15. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/318:10 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 7/15![JetBlue logo]()
$98
This Southwest deal was found by Cheapflights users on 7/14. 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.
Wed 10/73:15 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/14![Southwest logo]()
$99
This JetBlue deal was found by Cheapflights users on 7/15. 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 9/26:00 am
ORD
- BOS
1 stop7h 49m
JetBlue
Deal found 7/15![JetBlue logo]()
$100
This Southwest deal was found by Cheapflights users on 7/15. 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.
Sat 10/179:55 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/15![Southwest logo]()
$104
This Southwest deal was found by Cheapflights users on 7/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/317:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/13![Southwest logo]()
$108
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 July 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $176 (SmartFares) |
One-way from | $88 (SmartFares) |
Popular in | April |
Cheapest in | January |
Average price | $245 |
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 July 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
Cheapest round-trip
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 8/14
9:42 am-5:31 pm
1 stop6h 49m
Boston Logan Intl
Sat 8/22
4:43 pm-9:58 pm
1 stop6h 15m
$201
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 10/1
1:00 pm-8:49 pm
1 stop6h 49m
Boston Logan Intl
Sat 10/3
4:00 pm-10:06 pm
1 stop7h 06m
$211
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 10/15
1:00 pm-8:49 pm
1 stop6h 49m
Boston Logan Intl
Thu 10/22
6:55 am-11:47 am
1 stop5h 52m
$211
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 8/1
5:45 pm-9:10 pm
Nonstop2h 25m
Boston Logan Intl
Mon 8/3
5:25 am-7:00 am
Nonstop2h 35m
$215
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 10/15
6:10 am-9:33 am
Nonstop2h 23m
Boston Logan Intl
Tue 10/20
5:45 am-9:38 am
1 stop4h 53m
$216
Quickest round-trip
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Tue 10/20
9:10 am-12:30 pm
Nonstop2h 20m
Boston Logan Intl
Thu 10/22
10:00 pm-11:35 pm
Nonstop2h 35m
$216
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 9/9
1:00 pm-8:49 pm
1 stop6h 49m
Boston Logan Intl
Fri 9/11
6:55 am-8:46 am
Nonstop2h 51m
$218
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 8/12
6:00 am-11:17 am
1 stop4h 17m
Boston Logan Intl
Wed 8/19
5:01 pm-7:00 pm
Nonstop2h 59m
$225
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 9/4
2:35 pm-5:55 pm
Nonstop2h 20m
Boston Logan Intl
Mon 9/7
8:20 pm-10:00 pm
Nonstop2h 40m
$225
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sun 10/25
7:00 am-10:23 am
Nonstop2h 23m
Boston Logan Intl
Wed 10/28
6:00 am-9:45 am
1 stop4h 45m
$226
Showing 1-10 of 43 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 July 18, 2026.
It’s optimal to fly from Chicago to Falmouth in the evening. By choosing this option you can save up to 41% 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 July 18, 2026.
The most flights from CHI to FM5 are scheduled on a Wednesday (87 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (26 on average).
How much does it cost to fly round-trip from Chicago to Falmouth?
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 July 18, 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 July 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.
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Chicago
Popular flights
Alternative routes for Chicago to Falmouth
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Falmouth by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Falmouth by cabin class
Find flights from Chicago to Falmouth, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Falmouth flights
Browse other Chicago and Falmouth flight options. Last updated on July 18, 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 July 18, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 2,558,603 searches. Data last updated July 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$69 | Average$346 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$87 | Average$309 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$126 | Average$282 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$127 | Average$276 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$369 | FlexibilityNo cancel fee | On-time71% |