$94+ Cheap flights from Chicago (CHI) to Maine
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 7/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PWM
Jul 25 — Aug 11
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Maine with Cheapflights
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Cheapest flights from Chicago to MaineExplore the most affordable flight options available from Chicago to Maine. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 25, 2026.
Explore the most affordable flight options available from Chicago to Maine. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 25, 2026.
This Jetabroad deal was found by Cheapflights users on 6/20. 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 7/219:40 am
ORD
- BOS
1 stop6h 37m
JetBlue
Tue 7/285:01 am
BOS
- ORD
1 stop4h 49m
JetBlue
Deal found 6/20![JetBlue logo]()
$176
This Cheapflightsfares deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Fri 8/214:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Deal found 6/24![JetBlue logo]()
$177
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:30 am
ORD
- BOS
Nonstop2h 29m
Delta
Fri 9/117:30 am
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 6/23![Delta logo]()
$178
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/255:45 pm
MDW
- BOS
Nonstop2h 25m
Southwest
Fri 7/315:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/24![Southwest logo]()
$178
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/107:25 pm
ORD
- BOS
Nonstop2h 35m
Delta
Wed 7/158:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 6/23![Delta logo]()
$179
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/207:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Wed 7/225:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/22![Southwest logo]()
$179
This JetBlue deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Wed 8/268:15 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 6/22![JetBlue logo]()
$180
This Southwest deal was found by Cheapflights users on 6/20. 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 7/47:10 am
MDW
- BOS
1 stop5h 15m
Southwest
Sat 7/115:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/20![Southwest logo]()
$180
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/67:55 am
ORD
- BOS
Nonstop2h 29m
Delta
Sat 9/126:00 pm
BOS
- ORD
Nonstop2h 59m
Delta
Deal found 6/23![Delta logo]()
$181
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2910:30 am
ORD
- BOS
Nonstop2h 29m
Delta
Thu 9/37:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 6/24![Delta logo]()
$182
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:40 am
MDW
- BOS
Nonstop2h 20m
Southwest
Sat 8/298:40 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/22![Southwest logo]()
$182
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:59 am
ORD
- BOS
Nonstop2h 31m
Delta
Fri 7/247:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 6/23![Delta logo]()
$183
Best flights from Chicago to MaineDiscover carefully curated flight deals from Chicago to Maine that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 25, 2026.
Discover carefully curated flight deals from Chicago to Maine that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 25, 2026.
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:15 am
ORD
- BOS
Nonstop2h 21m
United Airlines
Sun 8/235:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Deal found 6/23![United Airlines logo]()
$182
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/177:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Tue 7/215:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/24![Southwest logo]()
$182
This Delta deal was found by Cheapflights users on 6/20. 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 7/316:59 am
ORD
- BOS
Nonstop2h 31m
Delta
Mon 8/38:50 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 6/20![Delta logo]()
$191
This JetBlue deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/61:00 pm
ORD
- BOS
1 stop5h 51m
JetBlue
Mon 11/97:05 am
BOS
- ORD
1 stop5h 51m
JetBlue
Deal found 6/22![JetBlue logo]()
$201
This United Airlines deal was found by Cheapflights users on 6/20. 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 7/107:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Mon 7/135:00 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 6/20![United Airlines logo]()
$187
This Delta deal was found by Cheapflights users on 6/20. 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 7/317:25 pm
ORD
- BOS
Nonstop2h 35m
Delta
Sat 8/17:59 pm
BOS
- ORD
Nonstop3h 00m
Delta
Deal found 6/20![Delta logo]()
$191
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/79:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Thu 7/95:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/22![Southwest logo]()
$200
This United Airlines deal was found by Cheapflights users on 6/20. 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 7/126:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Wed 7/156:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 6/20![United Airlines logo]()
$189
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/177:25 pm
ORD
- BOS
Nonstop2h 35m
Delta
Sun 7/267:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 6/23![Delta logo]()
$191
This United deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/79:40 pm
ORD
- AUG
1 stop19h 48m
Multiple Airlines
Fri 9/113:07 pm
AUG
- ORD
1 stop20h 52m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$433
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/145:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Fri 9/188:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 6/24![Southwest logo]()
$207
This United Airlines deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Wed 7/297:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 6/24![United Airlines logo]()
$198
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/97:25 pm
ORD
- BOS
Nonstop2h 35m
Delta
Sat 7/117:59 pm
BOS
- ORD
Nonstop3h 00m
Delta
Deal found 6/22![Delta logo]()
$200
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Sun 7/126:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 6/22![United Airlines logo]()
$200
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/155:20 pm
MDW
- BOS
1 stop5h 15m
Southwest
Tue 7/215:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/24![Southwest logo]()
$223
This United Airlines deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:20 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Sat 7/117:27 pm
BOS
- ORD
1 stop5h 04m
United Airlines
Deal found 6/24![United Airlines logo]()
$201
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/147:50 am
MDW
- BOS
2 stops6h 50m
Southwest
Fri 7/175:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/22![Southwest logo]()
$226
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/39:24 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Mon 10/59:23 am
BOS
- ORD
Nonstop2h 52m
United Airlines
Deal found 6/22![United Airlines logo]()
$202
This Southwest deal was found by Cheapflights users on 6/20. 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 7/107:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Sun 7/1210:05 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 6/20![Southwest logo]()
$226
This JetBlue deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:00 am
ORD
- PWM
1 stop5h 30m
JetBlue
Fri 7/313:18 pm
PWM
- ORD
1 stop7h 40m
JetBlue
Deal found 6/22![JetBlue logo]()
$372
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/912:45 pm
MDW
- BOS
1 stop4h 50m
Southwest
Mon 9/146:40 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 6/24![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 6/20. 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 8/251:50 pm
ORD
- BGR
2 stops8h 50m
Delta
Sat 8/292:33 pm
BGR
- ORD
1 stop7h 22m
Delta
Deal found 6/20![Delta logo]()
$286
This Southwest deal was found by Cheapflights users on 6/21. 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 7/115:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 7/133:55 pm
BOS
- MDW
1 stop5h 10m
Southwest
Deal found 6/21![Southwest logo]()
$234
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:05 am
MDW
- BGR
2 stops8h 37m
Delta
Sat 8/292:33 pm
BGR
- MDW
1 stop9h 03m
Delta
Deal found 6/24![Delta logo]()
$286
This Southwest deal was found by Cheapflights users on 6/21. 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 8/218:45 am
MDW
- BOS
2 stops8h 05m
Southwest
Sat 8/227:05 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/21![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/255:30 am
ORD
- BGR
2 stops9h 12m
Delta
Tue 9/15:20 am
BGR
- ORD
2 stops12h 31m
Delta
Deal found 6/22![Delta logo]()
$291
This United deal was found by Cheapflights users on 6/21. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:00 am
ORD
- BHB
1 stop5h 25m
Multiple Airlines
Sun 11/82:20 pm
BHB
- ORD
1 stop22h 03m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$474
This Delta deal was found by Cheapflights users on 6/20. 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 8/2512:46 pm
MDW
- BGR
2 stops9h 54m
Delta
Tue 9/15:20 am
BGR
- MDW
2 stops11h 24m
Delta
Deal found 6/20![Delta logo]()
$291
This Southwest deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/125:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Wed 7/1511:35 am
BOS
- MDW
2 stops6h 25m
Southwest
Deal found 6/20![Southwest logo]()
$248
This Expedia deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:00 am
ORD
- AUG
2 stops13h 40m
Multiple Airlines
Thu 8/137:14 am
AUG
- ORD
2 stops15h 44m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$490
Last-minute flights from Chicago to MaineDiscover last-minute flight deals from Chicago to Maine. Data last updated June 25, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maine. Data last updated June 25, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/20. 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 7/47:10 am
MDW
- BOS
1 stop5h 15m
Southwest
Sat 7/115:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/20![Southwest logo]()
$180
This Cheapflightsfares deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/76:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Tue 7/145:01 am
BOS
- ORD
1 stop4h 49m
JetBlue
Deal found 6/21![JetBlue logo]()
$182
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/87:25 pm
ORD
- BOS
Nonstop2h 35m
Delta
Thu 7/167:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 6/23![Delta logo]()
$178
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/107:25 pm
ORD
- BOS
Nonstop2h 35m
Delta
Wed 7/158:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 6/23![Delta logo]()
$179
This Cheapflightsfares deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/108:10 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Wed 7/154:31 pm
BOS
- ORD
1 stop6h 27m
JetBlue
Deal found 6/24![JetBlue logo]()
$181
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/177:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Tue 7/215:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/24![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/207:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Sat 7/255:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/22![Southwest logo]()
$179
This Jetabroad deal was found by Cheapflights users on 6/20. 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 7/219:40 am
ORD
- BOS
1 stop6h 37m
JetBlue
Tue 7/285:01 am
BOS
- ORD
1 stop4h 49m
JetBlue
Deal found 6/20![JetBlue logo]()
$176
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:59 am
ORD
- BOS
Nonstop2h 31m
Delta
Fri 7/247:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 6/23![Delta logo]()
$183
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/255:45 pm
MDW
- BOS
Nonstop2h 25m
Southwest
Fri 7/315:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/24![Southwest logo]()
$178
This Cheapflightsfares deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/315:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Mon 8/35:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 6/24![JetBlue logo]()
$177
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/319:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Wed 8/55:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 6/22![United Airlines logo]()
$180
One-way flights from Chicago to MaineSearch for one-way flight options from Chicago to Maine. Find affordable one-way fares based on user searches. Data last updated June 25, 2026.
Search for one-way flight options from Chicago to Maine. Find affordable one-way fares based on user searches. Data last updated June 25, 2026.
This Super.com deal was found by Cheapflights users on 6/20. 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 7/88:21 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 6/20![JetBlue logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 6/20. 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.
Fri 8/149:25 pm
MDW
- BOS
1 stop11h 44m
Allegiant Air
Deal found 6/20![Allegiant Air logo]()
$94
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/116:20 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 6/22![United Airlines logo]()
$96
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/712:45 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/22![Southwest logo]()
$96
This Cheapflightsfares deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Deal found 6/24![JetBlue logo]()
$97
This Cheapflightsfares deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/262:15 pm
ORD
- BOS
Nonstop2h 37m
JetBlue
Deal found 6/25![JetBlue logo]()
$98
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/155:05 am
MDW
- BOS
1 stop6h 40m
Southwest
Deal found 6/25![Southwest logo]()
$98
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:30 am
ORD
- BOS
Nonstop2h 31m
Delta
Deal found 6/23![Delta logo]()
$99
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:10 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/23![Southwest logo]()
$99
This JetBlue deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue 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 02m
JetBlue
Deal found 6/22![JetBlue logo]()
$101
This Super.com deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/98:10 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 6/24![JetBlue logo]()
$102
This Cheapflightsfares deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/288:24 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Deal found 6/24![JetBlue logo]()
$103
Find flight deals from Chicago to Maine
Keep the following information in mind while searching for Chicago to Maine flight deals. Data was last updated June 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $176 (Jetabroad) |
One-way from | $94 (Super.com) |
Popular in | July |
Cheapest in | May |
Average price | $407 |
Good round-trip deal | $327 or less |
Good one-way deal | $153 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Maine 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 June 25, 2026.
Use the filters below to find and compare flights from Chicago to Maine that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 8/20
6:15 am-9:36 am
Nonstop2h 21m
Boston Logan Intl
Sun 8/23
5:45 am-9:38 am
1 stop4h 53m
$182
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 7/17
7:35 pm-10:55 pm
Nonstop2h 20m
Boston Logan Intl
Tue 7/21
5:35 am-7:10 am
Nonstop2h 35m
$182
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 7/10
7:45 pm-11:21 pm
Nonstop2h 36m
Boston Logan Intl
Mon 7/13
5:00 pm-7:00 pm
Nonstop3h 00m
$187
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sun 7/12
6:05 am-9:29 am
Nonstop2h 24m
Boston Logan Intl
Wed 7/15
6:00 am-7:58 am
Nonstop2h 58m
$189
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 7/31
6:59 am-10:30 am
Nonstop2h 31m
Boston Logan Intl
Mon 8/3
8:50 pm-10:44 pm
Nonstop2h 54m
$191
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 7/31
7:25 pm-11:00 pm
Nonstop2h 35m
Boston Logan Intl
Sat 8/1
7:59 pm-9:59 pm
Nonstop3h 00m
$191
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 7/17
7:25 pm-11:00 pm
Nonstop2h 35m
Boston Logan Intl
Sun 7/26
7:30 am-9:26 am
Nonstop2h 56m
$191
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 7/22
6:00 am-11:16 am
1 stop4h 16m
Boston Logan Intl
Wed 7/29
7:19 am-9:17 am
Nonstop2h 58m
$198
Quickest round-trip
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Tue 7/7
9:00 am-12:15 pm
Nonstop2h 15m
Boston Logan Intl
Thu 7/9
5:25 am-7:00 am
Nonstop2h 35m
$200
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 7/9
7:25 pm-11:00 pm
Nonstop2h 35m
Boston Logan Intl
Sat 7/11
7:59 pm-9:59 pm
Nonstop3h 00m
$200
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Maine
Have a flexible travel schedule? Discover the best time to fly to Maine from Chicago with our price prediction graph.
ORD-BOS
MDW-BOS
ORD-AUG
ORD-PWM
ORD-BGR
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 Maine
CHI-USME
ORD-BOS
MDW-BOS
ORD-AUG
ORD-PWM
What is the cheapest month to book a flight from Chicago to Maine?
Currently, September is the cheapest month in which you can book a flight from Chicago to Maine (average of $125). Flying from Chicago to Maine in July is currently the most expensive (average of $212). 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 ME?
Find hourly flight availability from Chicago to Maine. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 25, 2026.
When flying from Chicago to Maine, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 11% versus a flight in the morning.
Weekly flight availability from Chicago to Maine
Explore weekly flight availability from Chicago to Maine. 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 June 25, 2026.
The most flights from CHI to USME are scheduled on a Thursday (9 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Chicago to Maine?
How far ahead should I book a flight from Chicago to Maine?
The price you pay for your flight from Chicago to Maine may vary depending on when you book. For the best chance of a lower fare, look to book 87 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest day to fly from Chicago to Maine?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Maine. Price data was last updated on June 20, 2026.
Travelers seeking maximum savings on their Chicago to Maine flight should consider departing on Sunday afternoons when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Maine
Get insights into the airlines that provide service to Maine. 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 Maine. Reviews last updated June 25, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Chicago to Maine by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago to Maine. 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 Maine
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Maine by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Maine by cabin class
Find flights from Chicago to Maine, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Maine flights
Browse other Chicago and Maine flight options. Last updated on June 25, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Maine flights
Consider these flights traveling from Chicago to Maine.
Top 2 airlines flying from Chicago to Maine
Discover the top 2 airlines that operate flights from Chicago to Maine. 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 June 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$229 | Average$395 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$229 | Average$376 | FlexibilityNo cancel fee | On-time71% |