$67+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Mar 8 — Mar 151
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
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 February 6, 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 February 6, 2026.
This Super.com deal was found by Cheapflights users on 2/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/97:40 am
ORD
- BOS
Nonstop2h 25m
JetBlue
Wed 2/187:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/3![JetBlue logo]()
$133
This Cheapflightsfares deal was found by Cheapflights users on 2/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/1510:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Wed 2/187:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/4![JetBlue logo]()
$134
This United Airlines deal was found by Cheapflights users on 2/5. 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 2/119:13 am
ORD
- BOS
Nonstop2h 33m
United Airlines
Wed 2/187:45 am
BOS
- ORD
Nonstop3h 05m
United Airlines
Deal found 2/5![United Airlines logo]()
$135
This Southwest deal was found by Cheapflights users on 2/3. 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.
Tue 2/179:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 2/235:20 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/3![Southwest logo]()
$135
This Cheapflightsfares deal was found by Cheapflights users on 2/6. 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 4/47:45 am
ORD
- BOS
1 stop5h 30m
JetBlue
Tue 4/77:10 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 2/6![JetBlue logo]()
$136
This American Airlines deal was found by Cheapflights users on 2/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/97:05 am
ORD
- BOS
Nonstop2h 34m
American Airlines
Mon 4/137:40 pm
BOS
- ORD
Nonstop3h 10m
American Airlines
Deal found 2/4![American Airlines logo]()
$137
This Southwest deal was found by Cheapflights users on 2/4. 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.
Wed 3/42:00 pm
MDW
- BOS
Nonstop2h 10m
Southwest
Wed 3/116:00 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/4![Southwest logo]()
$137
This CheapOair deal was found by Cheapflights users on 2/4. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1211:00 am
ORD
- BOS
Nonstop2h 24m
Multiple Airlines
Wed 3/185:45 am
BOS
- ORD
1 stop12h 30m
Multiple Airlines
Deal found 2/4![Multiple Airlines logo]()
$138
This Priceline deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/274:42 pm
ORD
- BOS
1 stop7h 31m
Multiple Airlines
Thu 3/57:00 am
BOS
- ORD
Nonstop3h 10m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$139
This Priceline deal was found by Cheapflights users on 2/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/38:55 am
ORD
- BOS
Nonstop2h 32m
Multiple Airlines
Tue 4/712:42 pm
BOS
- ORD
1 stop10h 57m
Multiple Airlines
Deal found 2/4![Multiple Airlines logo]()
$140
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/66:04 am
ORD
- BOS
1 stop7h 31m
JetBlue
Sun 3/87:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/3![JetBlue logo]()
$141
This United Airlines deal was found by Cheapflights users on 2/5. 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 3/27:30 am
ORD
- BOS
Nonstop2h 19m
United Airlines
Thu 3/56:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 2/5![United Airlines logo]()
$142
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 February 6, 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 February 6, 2026.
This JetBlue deal was found by Cheapflights users on 2/5. 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 5/68:31 am
ORD
- BOS
1 stop4h 45m
JetBlue
Sat 5/97:35 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Deal found 2/5![JetBlue logo]()
$137
This Southwest deal was found by Cheapflights users on 2/4. 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.
Tue 2/245:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Thu 2/265:00 am
BOS
- MDW
Nonstop2h 55m
Southwest
Deal found 2/4![Southwest logo]()
$137
This Delta deal was found by Cheapflights users on 2/5. 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 5/46:50 am
ORD
- BOS
Nonstop2h 21m
Delta
Wed 5/64:54 pm
BOS
- ORD
Nonstop3h 04m
Delta
Deal found 2/5![Delta logo]()
$142
This United Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/219:15 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Sun 4/265:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Deal found 2/6![United Airlines logo]()
$147
This Delta deal was found by Cheapflights users on 2/2. 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.
Wed 4/1510:20 am
ORD
- BOS
Nonstop2h 20m
Delta
Sat 4/188:59 pm
BOS
- ORD
Nonstop2h 51m
Delta
Deal found 2/2![Delta logo]()
$142
This Southwest deal was found by Cheapflights users on 2/3. 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.
Sat 4/44:35 pm
MDW
- BOS
1 stop6h 20m
Southwest
Sat 4/113:30 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 2/3![Southwest logo]()
$142
This United Airlines deal was found by Cheapflights users on 2/5. 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 7/139:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Mon 7/206:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 2/5![United Airlines logo]()
$150
This Delta deal was found by Cheapflights users on 2/5. 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 5/77:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Sun 5/107:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Deal found 2/5![Delta logo]()
$142
This Southwest deal was found by Cheapflights users on 2/2. 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 2/256:50 am
MDW
- BOS
1 stop4h 35m
Southwest
Sun 3/15:00 am
BOS
- MDW
Nonstop2h 55m
Southwest
Deal found 2/2![Southwest logo]()
$147
This United Airlines deal was found by Cheapflights users on 2/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/107:40 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Sun 7/126:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 2/2![United Airlines logo]()
$151
This Delta deal was found by Cheapflights users on 2/2. 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.
Wed 3/117:00 am
ORD
- BOS
Nonstop2h 25m
Delta
Sun 3/157:25 am
BOS
- ORD
Nonstop3h 10m
Delta
Deal found 2/2![Delta logo]()
$147
This Southwest deal was found by Cheapflights users on 2/4. 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 2/266:05 am
MDW
- BOS
Nonstop2h 20m
Southwest
Mon 3/25:20 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/4![Southwest logo]()
$147
This United Airlines deal was found by Cheapflights users on 2/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/179:15 am
ORD
- BOS
1 stop5h 01m
United Airlines
Sat 3/217:16 am
BOS
- ORD
Nonstop3h 06m
United Airlines
Deal found 2/2![United Airlines logo]()
$152
This Delta deal was found by Cheapflights users on 2/5. 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 2/277:05 am
ORD
- BOS
Nonstop2h 32m
Delta
Sun 3/17:15 am
BOS
- ORD
Nonstop3h 13m
Delta
Deal found 2/5![Delta logo]()
$147
This United Airlines deal was found by Cheapflights users on 2/3. 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.
Fri 2/277:30 am
ORD
- BOS
Nonstop2h 19m
United Airlines
Wed 3/412:05 pm
BOS
- ORD
1 stop4h 58m
United Airlines
Deal found 2/3![United Airlines logo]()
$152
This Southwest deal was found by Cheapflights users on 2/4. 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 2/166:05 am
MDW
- BOS
Nonstop2h 20m
Southwest
Tue 2/175:20 pm
BOS
- MDW
1 stop6h 10m
Southwest
Deal found 2/4![Southwest logo]()
$156
This Southwest deal was found by Cheapflights users on 2/4. 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.
Wed 2/186:00 am
MDW
- BOS
1 stop6h 40m
Southwest
Sat 2/215:45 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/4![Southwest logo]()
$156
This United Airlines deal was found by Cheapflights users on 2/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/182:30 pm
ORD
- BOS
1 stop6h 21m
United Airlines
Sat 2/214:25 pm
BOS
- ORD
Nonstop3h 05m
United Airlines
Deal found 2/4![United Airlines logo]()
$161
This Southwest deal was found by Cheapflights users on 2/5. 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 3/75:40 pm
MDW
- BOS
1 stop4h 25m
Southwest
Sun 3/87:05 am
BOS
- MDW
Nonstop2h 55m
Southwest
Deal found 2/5![Southwest logo]()
$167
This Southwest deal was found by Cheapflights users on 2/3. 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.
Mon 3/22:40 pm
MDW
- BOS
1 stop6h 30m
Southwest
Fri 3/63:10 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 2/3![Southwest logo]()
$167
This Southwest deal was found by Cheapflights users on 2/5. 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 4/47:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 4/810:45 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 2/5![Southwest logo]()
$167
This Southwest deal was found by Cheapflights users on 2/4. 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.
Fri 3/207:00 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 3/2411:25 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/4![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 2/4. 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.
Wed 3/256:10 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Sun 3/297:05 am
BOS
- MDW
Nonstop2h 55m
Southwest
Deal found 2/4![Southwest logo]()
$177
Last-minute flights from Chicago to FalmouthDiscover last-minute flight deals from Chicago to Falmouth. Data last updated February 6, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Falmouth. Data last updated February 6, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 2/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/97:40 am
ORD
- BOS
Nonstop2h 25m
JetBlue
Wed 2/187:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/3![JetBlue logo]()
$133
This JetBlue deal was found by Cheapflights users on 2/5. 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 2/117:40 am
ORD
- BOS
Nonstop2h 25m
JetBlue
Thu 2/197:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/5![JetBlue logo]()
$135
This American Airlines deal was found by Cheapflights users on 2/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/127:18 am
ORD
- BOS
Nonstop2h 28m
American Airlines
Sat 2/285:54 pm
BOS
- ORD
Nonstop3h 06m
American Airlines
Deal found 2/3![American Airlines logo]()
$137
This Cheapflightsfares deal was found by Cheapflights users on 2/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/1510:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Wed 2/187:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/4![JetBlue logo]()
$134
This Southwest deal was found by Cheapflights users on 2/5. 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 2/176:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Thu 2/195:20 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/5![Southwest logo]()
$135
This Expedia deal was found by Cheapflights users on 2/6. 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.
Fri 2/274:42 pm
ORD
- BOS
1 stop7h 31m
Multiple Airlines
Wed 3/47:00 am
BOS
- ORD
Nonstop3h 10m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$139
This United Airlines deal was found by Cheapflights users on 2/5. 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 3/27:30 am
ORD
- BOS
Nonstop2h 19m
United Airlines
Thu 3/56:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 2/5![United Airlines logo]()
$142
This Southwest deal was found by Cheapflights users on 2/4. 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.
Wed 3/42:00 pm
MDW
- BOS
Nonstop2h 10m
Southwest
Wed 3/116:00 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/4![Southwest logo]()
$137
This Cheapflightsfares deal was found by Cheapflights users on 2/5. 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.
Wed 3/410:44 am
ORD
- BOS
1 stop10h 17m
Spirit Airlines
Wed 3/115:27 am
BOS
- ORD
1 stop14h 44m
Spirit Airlines
Deal found 2/5![Spirit Airlines logo]()
$140
This JetBlue deal was found by Cheapflights users on 2/4. 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 3/512:41 pm
ORD
- BOS
1 stop6h 17m
JetBlue
Mon 3/97:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/4![JetBlue logo]()
$143
This Cheapflightsfares deal was found by Cheapflights users on 2/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/66:04 am
ORD
- BOS
1 stop7h 05m
JetBlue
Sun 3/87:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/4![JetBlue logo]()
$141
This CheapOair deal was found by Cheapflights users on 2/5. 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 3/1211:00 am
ORD
- BOS
Nonstop2h 24m
Multiple Airlines
Wed 3/185:45 am
BOS
- ORD
1 stop12h 30m
Multiple Airlines
Deal found 2/5![Multiple Airlines logo]()
$138
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 February 6, 2026.
Search for one-way flight options from Chicago to Falmouth. Find affordable one-way fares based on user searches. Data last updated February 6, 2026.
This Super.com deal was found by Cheapflights users on 2/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/116:00 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 2/3![JetBlue logo]()
$67
This United Airlines deal was found by Cheapflights users on 2/6. 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 2/167:30 am
ORD
- BOS
Nonstop2h 19m
United Airlines
Deal found 2/6![United Airlines logo]()
$68
This Southwest deal was found by Cheapflights users on 2/3. 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.
Sat 2/1410:15 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/3![Southwest logo]()
$68
This Delta deal was found by Cheapflights users on 2/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/197:05 am
ORD
- BOS
Nonstop2h 32m
Delta
Deal found 2/3![Delta logo]()
$69
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1112:44 pm
ORD
- BOS
1 stop8h 17m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$70
This Southwest deal was found by Cheapflights users on 2/4. 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.
Sat 4/46:45 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/4![Southwest logo]()
$70
This United Airlines deal was found by Cheapflights users on 2/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Deal found 2/4![United Airlines logo]()
$71
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:30 am
MDW
- BOS
1 stop30h 25m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$71
This Trip.com deal was found by Cheapflights users on 2/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/266:20 pm
ORD
- BOS
Nonstop2h 33m
JetBlue
Deal found 2/3![JetBlue logo]()
$72
This United Airlines deal was found by Cheapflights users on 2/3. 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.
Fri 5/19:30 pm
ORD
- BOS
Nonstop2h 29m
United Airlines
Deal found 2/3![United Airlines logo]()
$73
This Expedia deal was found by Cheapflights users on 2/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/24:42 pm
ORD
- BOS
1 stop7h 31m
Frontier
Deal found 2/3![Frontier logo]()
$74
This Frontier deal was found by Cheapflights users on 2/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:16 pm
MDW
- BOS
1 stop6h 57m
Frontier
Deal found 2/3![Frontier logo]()
$74
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 February 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $133 (Super.com) |
One-way from | $67 (Super.com) |
Popular in | April |
Cheapest in | January |
Average price | $237 |
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 February 6, 2026.
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
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 5/6
8:31 am-2:16 pm
1 stop4h 45m
Boston Logan Intl
Sat 5/9
7:35 pm-9:36 pm
Nonstop3h 01m
$137
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Tue 2/24
5:35 pm-8:50 pm
Nonstop2h 15m
Boston Logan Intl
Thu 2/26
5:00 am-6:55 am
Nonstop2h 55m
$137
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 5/4
6:50 am-10:11 am
Nonstop2h 21m
Boston Logan Intl
Wed 5/6
4:54 pm-6:58 pm
Nonstop3h 04m
$142
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 4/15
10:20 am-1:40 pm
Nonstop2h 20m
Boston Logan Intl
Sat 4/18
8:59 pm-10:50 pm
Nonstop2h 51m
$142
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 4/4
4:35 pm-11:55 pm
1 stop6h 20m
Boston Logan Intl
Sat 4/11
3:30 pm-5:15 pm
Nonstop2h 45m
$142
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 5/7
7:00 am-10:35 am
Nonstop2h 35m
Boston Logan Intl
Sun 5/10
7:35 am-9:27 am
Nonstop2h 52m
$142
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 4/21
9:15 am-12:46 pm
Nonstop2h 31m
Boston Logan Intl
Sun 4/26
5:45 am-9:38 am
1 stop4h 53m
$147
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Wed 2/25
6:50 am-12:25 pm
1 stop4h 35m
Boston Logan Intl
Sun 3/1
5:00 am-6:55 am
Nonstop2h 55m
$147
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 3/11
7:00 am-10:25 am
Nonstop2h 25m
Boston Logan Intl
Sun 3/15
7:25 am-9:35 am
Nonstop3h 10m
$147
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Thu 2/26
6:05 am-9:25 am
Nonstop2h 20m
Boston Logan Intl
Mon 3/2
5:20 am-7:10 am
Nonstop2h 50m
$147
Showing 1-10 of 41 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.
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
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 January 30, 2026.
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, September is the cheapest month in which you can book a flight from Chicago to Falmouth (average of $91). Flying from Chicago to Falmouth in July is currently the most expensive (average of $117). 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 February 6, 2026.
It’s optimal to fly from Chicago to Falmouth in the evening. By choosing this option you can save up to 19% 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 January 31, 2026.
Travelers seeking maximum savings on their Chicago to Falmouth flight should consider departing on Saturday afternoons 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 February 6, 2026.
The most flights from CHI to FM5 are scheduled on a Friday (57 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (25 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 February 6, 2026.
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.
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Boarding
8.1
Comfort
8.0
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.
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.
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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.
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 February 6, 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 February 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 February 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$61 | Average$158 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$79 | Average$158 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$91 | Average$216 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$343 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$117 | Average$404 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$136 | Average$293 | FlexibilityNo cancel fee | On-time63% |