$94+ Cheap flights from Illinois 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 7/7. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Jul 20 — Jul 271
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Illinois to Maine 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.Cheap flight deals from Illinois to Maine
Cheapest
Best
Last-minute
One-way
Cheapest flights from Illinois to MaineExplore the most affordable flight options available from Illinois to Maine. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 20, 2026.
Explore the most affordable flight options available from Illinois to Maine. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 20, 2026.
This Jetabroad deal was found by Cheapflights users on 6/16. 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 Jetabroad 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 6/16![JetBlue logo]()
$176
This JetBlue deal was found by Cheapflights users on 6/18. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/176:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Tue 8/45:01 am
BOS
- ORD
1 stop4h 49m
JetBlue
Deal found 6/18![JetBlue logo]()
$177
This United Airlines deal was found by Cheapflights users on 6/17. 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.
Tue 7/71:55 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Fri 7/106:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 6/17![United Airlines logo]()
$178
This Southwest deal was found by Cheapflights users on 6/18. 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.
Sun 7/195:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Sat 7/255:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/18![Southwest logo]()
$178
This Delta deal was found by Cheapflights users on 6/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/34:00 pm
ORD
- BOS
Nonstop2h 43m
Delta
Sat 7/117:59 pm
BOS
- ORD
Nonstop3h 00m
Delta
Deal found 6/18![Delta logo]()
$179
This Southwest deal was found by Cheapflights users on 6/17. 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 7/107:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Wed 7/155:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/17![Southwest logo]()
$179
This United Airlines deal was found by Cheapflights users on 6/19. 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 8/66:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Thu 8/205:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Deal found 6/19![United Airlines logo]()
$180
This Southwest deal was found by Cheapflights users on 6/18. 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 7/215:30 pm
MDW
- BOS
1 stop4h 55m
Southwest
Wed 7/227:30 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 6/18![Southwest logo]()
$180
This United Airlines deal was found by Cheapflights users on 6/19. 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 7/106:12 pm
ORD
- BOS
1 stop4h 47m
United Airlines
Mon 7/133:13 pm
BOS
- ORD
Nonstop2h 52m
United Airlines
Deal found 6/19![United Airlines logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 6/16. 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 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 stop4h 21m
JetBlue
Wed 8/124:30 pm
BOS
- ORD
1 stop6h 25m
JetBlue
Deal found 6/16![JetBlue logo]()
$182
This Southwest deal was found by Cheapflights users on 6/19. 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 7/185:45 pm
MDW
- BOS
Nonstop2h 25m
Southwest
Wed 7/227:30 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 6/19![Southwest logo]()
$182
This Delta deal was found by Cheapflights users on 6/19. 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 7/217:25 pm
ORD
- BOS
Nonstop2h 35m
Delta
Sat 7/257:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 6/19![Delta logo]()
$183
Best flights from Illinois to MaineDiscover carefully curated flight deals from Illinois to Maine that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 20, 2026.
Discover carefully curated flight deals from Illinois to Maine that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 20, 2026.
This Delta deal was found by Cheapflights users on 6/19. 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 7/77:25 pm
ORD
- BOS
Nonstop2h 35m
Delta
Sun 7/127:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 6/19![Delta logo]()
$178
This Southwest deal was found by Cheapflights users on 6/16. 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.
Mon 8/32:40 pm
ORD
- BOS
1 stop8h 30m
Southwest
Sat 8/85:40 am
BOS
- ORD
1 stop10h 35m
Southwest
Deal found 6/16![Southwest logo]()
$182
This United Airlines deal was found by Cheapflights users on 6/19. 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 9/97:30 am
ORD
- BOS
Nonstop2h 34m
United Airlines
Sun 9/136:00 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 6/19![United Airlines logo]()
$202
This JetBlue deal was found by Cheapflights users on 6/17. 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.
Wed 7/156:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Mon 7/205:09 pm
BOS
- ORD
1 stop5h 49m
JetBlue
Deal found 6/17![JetBlue logo]()
$213
This Southwest deal was found by Cheapflights users on 6/19. 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 7/185:45 pm
MDW
- BOS
Nonstop2h 25m
Southwest
Thu 7/235:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/19![Southwest logo]()
$190
This Delta deal was found by Cheapflights users on 6/19. 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 7/247:25 pm
ORD
- BOS
Nonstop2h 35m
Delta
Sun 7/267:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 6/19![Delta logo]()
$191
This American Airlines deal was found by Cheapflights users on 6/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/105:55 pm
ORD
- BGR
1 stop5h 04m
American Airlines
Mon 7/136:00 am
BGR
- ORD
1 stop7h 53m
American Airlines
Deal found 6/14![American Airlines logo]()
$389
This United Airlines deal was found by Cheapflights users on 6/15. 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.
Sun 7/269:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Wed 7/296:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 6/15![United Airlines logo]()
$203
This Delta deal was found by Cheapflights users on 6/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:55 am
ORD
- BOS
Nonstop2h 29m
Delta
Sat 8/227:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 6/15![Delta logo]()
$192
This JetBlue deal was found by Cheapflights users on 6/16. 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.
Tue 6/306:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Fri 7/38:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 6/16![JetBlue logo]()
$220
This United Airlines deal was found by Cheapflights users on 6/17. 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.
Sat 7/111:30 pm
ORD
- BOS
1 stop4h 44m
United Airlines
Sun 7/198:15 am
BOS
- ORD
Nonstop2h 57m
United Airlines
Deal found 6/17![United Airlines logo]()
$206
This Southwest deal was found by Cheapflights users on 6/19. 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 9/115:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Fri 9/188:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 6/19![Southwest logo]()
$207
This United Airlines deal was found by Cheapflights users on 6/19. 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 9/177:55 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Sun 9/205:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Deal found 6/19![United Airlines logo]()
$217
This Southwest deal was found by Cheapflights users on 6/17. 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.
Tue 8/188:45 am
MDW
- BOS
Nonstop2h 30m
Southwest
Sun 8/237:30 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/17![Southwest logo]()
$224
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/304:00 pm
ORD
- BOS
Nonstop2h 43m
Delta
Sat 7/45:05 pm
BOS
- ORD
Nonstop3h 12m
Delta
Deal found 6/16![Delta logo]()
$233
This United Airlines deal was found by Cheapflights users on 6/16. 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.
Sat 7/48:43 am
ORD
- BOS
1 stop4h 57m
United Airlines
Sun 7/57:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 6/16![United Airlines logo]()
$223
This Southwest deal was found by Cheapflights users on 6/19. 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 7/106:00 pm
MDW
- BOS
1 stop4h 30m
Southwest
Mon 7/135:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/19![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 6/15. 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 7/85:20 pm
MDW
- BOS
1 stop5h 15m
Southwest
Fri 7/105:45 am
BOS
- MDW
1 stop5h 50m
Southwest
Deal found 6/15![Southwest logo]()
$232
This Southwest deal was found by Cheapflights users on 6/15. 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 7/155:30 pm
MDW
- BOS
1 stop4h 55m
Southwest
Sat 7/185:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/15![Southwest logo]()
$235
This Delta deal was found by Cheapflights users on 6/17. 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.
Wed 8/191:59 pm
ORD
- BGR
2 stops8h 41m
Delta
Wed 9/24:22 pm
BGR
- ORD
1 stop6h 30m
Delta
Deal found 6/17![Delta logo]()
$286
This Southwest deal was found by Cheapflights users on 6/16. 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 6/232:40 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Tue 6/305:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/16![Southwest logo]()
$239
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/111:59 pm
ORD
- BGR
2 stops8h 41m
Delta
Tue 8/185:20 am
BGR
- ORD
2 stops12h 31m
Delta
Deal found 6/16![Delta logo]()
$291
This United Airlines deal was found by Cheapflights users on 6/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1911:00 am
ORD
- PWM
Nonstop2h 34m
United Airlines
Wed 8/266:03 am
PWM
- ORD
Nonstop2h 57m
United Airlines
Deal found 6/18![United Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 6/16. 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.
Thu 8/135:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Sat 8/158:40 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/16![Southwest logo]()
$240
This Delta deal was found by Cheapflights users on 6/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2510:54 am
MDW
- BGR
2 stops11h 46m
Delta
Tue 9/112:05 pm
BGR
- MDW
2 stops11h 31m
Delta
Deal found 6/15![Delta logo]()
$291
This Delta deal was found by Cheapflights users on 6/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:46 pm
MDW
- BGR
2 stops9h 54m
Delta
Tue 8/255:20 am
BGR
- MDW
2 stops8h 50m
Delta
Deal found 6/18![Delta logo]()
$291
This United Airlines deal was found by Cheapflights users on 6/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:13 am
MLI
- BOS
2 stops7h 35m
United Airlines
Sat 9/266:00 am
BOS
- MLI
1 stop5h 12m
United Airlines
Deal found 6/18![United Airlines logo]()
$324
This Southwest deal was found by Cheapflights users on 6/17. 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.
Sat 8/226:35 am
MDW
- BOS
1 stop6h 10m
Southwest
Sat 8/298:40 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/17![Southwest logo]()
$244
This United Airlines deal was found by Cheapflights users on 6/17. 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.
Tue 8/115:50 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Thu 8/135:15 am
PWM
- ORD
1 stop5h 23m
United Airlines
Deal found 6/17![United Airlines logo]()
$328
This Southwest deal was found by Cheapflights users on 6/19. 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 9/175:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Sun 9/207:30 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/19![Southwest logo]()
$247
Last-minute flights from Illinois to MaineDiscover last-minute flight deals from Illinois to Maine. Data last updated June 20, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Maine. Data last updated June 20, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/34:00 pm
ORD
- BOS
Nonstop2h 43m
Delta
Sat 7/117:59 pm
BOS
- ORD
Nonstop3h 00m
Delta
Deal found 6/18![Delta logo]()
$179
This United Airlines deal was found by Cheapflights users on 6/17. 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.
Sat 7/48:43 am
ORD
- BOS
1 stop4h 57m
United Airlines
Sat 7/117:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 6/17![United Airlines logo]()
$180
This United Airlines deal was found by Cheapflights users on 6/17. 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.
Tue 7/71:55 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Fri 7/106:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 6/17![United Airlines logo]()
$178
This Southwest deal was found by Cheapflights users on 6/17. 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 7/107:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Wed 7/155:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/17![Southwest logo]()
$179
This United Airlines deal was found by Cheapflights users on 6/19. 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 7/106:12 pm
ORD
- BOS
1 stop4h 47m
United Airlines
Mon 7/133:13 pm
BOS
- ORD
Nonstop2h 52m
United Airlines
Deal found 6/19![United Airlines logo]()
$181
This Super.com deal was found by Cheapflights users on 6/17. 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 7/108:10 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Sat 7/184:43 pm
BOS
- ORD
1 stop6h 15m
JetBlue
Deal found 6/17![JetBlue logo]()
$182
This JetBlue deal was found by Cheapflights users on 6/18. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/176:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Tue 8/45:01 am
BOS
- ORD
1 stop4h 49m
JetBlue
Deal found 6/18![JetBlue logo]()
$177
This Southwest deal was found by Cheapflights users on 6/19. 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 7/185:45 pm
MDW
- BOS
Nonstop2h 25m
Southwest
Wed 7/227:30 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 6/19![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 6/18. 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.
Sun 7/195:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Sat 7/255:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/18![Southwest logo]()
$178
This Southwest deal was found by Cheapflights users on 6/18. 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 7/215:30 pm
MDW
- BOS
1 stop4h 55m
Southwest
Wed 7/227:30 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 6/18![Southwest logo]()
$180
This Delta deal was found by Cheapflights users on 6/19. 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 7/217:25 pm
ORD
- BOS
Nonstop2h 35m
Delta
Sat 7/257:59 pm
BOS
- ORD
Nonstop3h 00m
Delta
Deal found 6/19![Delta logo]()
$183
This Jetabroad deal was found by Cheapflights users on 6/16. 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 Jetabroad 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 6/16![JetBlue logo]()
$176
One-way flights from Illinois to MaineSearch for one-way flight options from Illinois to Maine. Find affordable one-way fares based on user searches. Data last updated June 20, 2026.
Search for one-way flight options from Illinois to Maine. Find affordable one-way fares based on user searches. Data last updated June 20, 2026.
This Super.com deal was found by Cheapflights users on 6/19. 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 7/78:21 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 6/19![JetBlue logo]()
$94
This Cheapflightsfares deal was found by Cheapflights users on 6/19. 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 7/41:55 pm
ORD
- BOS
Nonstop2h 38m
JetBlue
Deal found 6/19![JetBlue logo]()
$95
This Delta deal was found by Cheapflights users on 6/17. 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.
Sat 7/44:00 pm
ORD
- BOS
Nonstop2h 45m
Delta
Deal found 6/17![Delta logo]()
$96
This Southwest deal was found by Cheapflights users on 6/19. 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 7/46:30 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/19![Southwest logo]()
$96
This Cheapflightsfares deal was found by Cheapflights users on 6/19. 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 8/66:00 am
ORD
- BOS
1 stop7h 41m
JetBlue
Deal found 6/19![JetBlue logo]()
$97
This JetBlue deal was found by Cheapflights users on 6/16. 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.
Fri 7/105:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Deal found 6/16![JetBlue logo]()
$98
This Southwest deal was found by Cheapflights users on 6/18. 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 8/58:15 am
MDW
- BOS
1 stop7h 40m
Southwest
Deal found 6/18![Southwest logo]()
$98
This JetBlue deal was found by Cheapflights users on 6/17. 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.
Wed 9/162:15 pm
ORD
- BOS
Nonstop2h 37m
JetBlue
Deal found 6/17![JetBlue logo]()
$99
This Southwest deal was found by Cheapflights users on 6/18. 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 9/156:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/18![Southwest logo]()
$99
This Cheapflightsfares deal was found by Cheapflights users on 6/19. 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 9/101:00 pm
ORD
- BOS
1 stop6h 02m
JetBlue
Deal found 6/19![JetBlue logo]()
$100
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/17:10 am
ORD
- BOS
Nonstop2h 36m
Delta
Deal found 6/16![Delta logo]()
$101
This Southwest deal was found by Cheapflights users on 6/16. 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 7/2112:45 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/16![Southwest logo]()
$101
Find flight deals from Illinois to Maine
Keep the following information in mind while searching for Illinois to Maine flight deals. Data was last updated June 20, 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 | $412 |
Good round-trip deal | $339 or less |
Good one-way deal | $153 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Illinois 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 20, 2026.
Use the filters below to find and compare flights from Illinois 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
Tue 7/7
7:25 pm-11:00 pm
Nonstop2h 35m
Boston Logan Intl
Sun 7/12
7:30 am-9:26 am
Nonstop2h 56m
$178
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 8/3
2:40 pm-12:10 am
1 stop8h 30m
Boston Logan Intl
Sat 8/8
5:40 am-3:15 pm
1 stop10h 35m
$182
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 7/18
5:45 pm-9:10 pm
Nonstop2h 25m
Boston Logan Intl
Thu 7/23
5:25 am-7:00 am
Nonstop2h 35m
$190
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 7/24
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
Mon 8/17
7:55 am-11:24 am
Nonstop2h 29m
Boston Logan Intl
Sat 8/22
7:30 am-9:26 am
Nonstop2h 56m
$192
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 9/9
7:30 am-11:04 am
Nonstop2h 34m
Boston Logan Intl
Sun 9/13
6:00 am-7:59 am
Nonstop2h 59m
$202
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sun 7/26
9:41 pm-1:14 am
Nonstop2h 33m
Boston Logan Intl
Wed 7/29
6:00 am-7:58 am
Nonstop2h 58m
$203
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 7/11
1:30 pm-7:14 pm
1 stop4h 44m
Boston Logan Intl
Sun 7/19
8:15 am-10:12 am
Nonstop2h 57m
$206
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 9/11
5:45 am-9:00 am
Nonstop2h 15m
Boston Logan Intl
Fri 9/18
8:20 pm-10:00 pm
Nonstop2h 40m
$207
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 7/15
6:00 am-2:22 pm
1 stop7h 22m
Boston Logan Intl
Mon 7/20
5:09 pm-9:58 pm
1 stop5h 49m
$213
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Illinois to Maine
Have a flexible travel schedule? Discover the best time to fly to Maine from Illinois with our price prediction graph.
ORD-BOS
MDW-BOS
STL-BGR
MDW-BGR
ORD-PWM
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 Illinois to Maine
USIL-USME
ORD-BOS
MDW-BOS
STL-BGR
MDW-BGR
What is the cheapest month to book a flight from Illinois to Maine?
Currently, September is the cheapest month in which you can book a flight from Illinois to Maine (average of $125). Flying from Illinois 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 IL to ME?
Find hourly flight availability from Illinois 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 20, 2026.
It’s optimal to fly from Illinois to Maine in the afternoon. By choosing this option you can save up to 11% on the cost of your flight, compared to a flight in the morning.
Weekly flight availability from Illinois to Maine
Explore weekly flight availability from Illinois 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 20, 2026.
The most flights from USIL to USME are scheduled on a Monday (9 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (4 on average).
How much does it cost to fly round-trip from Illinois to Maine?
How far ahead should I book a flight from Illinois to Maine?
Booking 87 days in advance of your planned departure date is, on average, the best time to get cheap flights from Illinois to Maine. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Illinois to Maine?
Use this chart to determine the cheapest time to fly round-trip from Illinois to Maine. Price data was last updated on June 13, 2026.
Travelers seeking maximum savings on their Illinois 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 20, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican Airlines from Illinois to Maine. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.9
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Illinois 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.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Return Flight Options
Top destinations
Alternative routes for Illinois 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 Illinois to Maine by cabin class
Find flights from Illinois to Maine, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Illinois and Maine flights
Browse other Illinois and Maine flight options. Last updated on June 20, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Maine
Find the right flight back to Illinois after your stay in Maine
Illinois to Maine flights
Consider these flights traveling from Illinois to Maine.
Top 2 airlines flying from Illinois to Maine
Discover the top 2 airlines that operate flights from Illinois 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 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$229 | Average$404 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$229 | Average$411 | FlexibilityNo cancel fee | On-time69% |