$89+ 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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Jun 22 — Jun 291
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 May 23, 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 May 23, 2026.
This SmartFares deal was found by Cheapflights users on 5/20. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/48:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Sun 6/76:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 5/20![JetBlue logo]()
$176
This Cheapflightsfares deal was found by Cheapflights users on 5/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Wed 6/106:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 5/22![JetBlue logo]()
$182
This Super.com deal was found by Cheapflights users on 5/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Tue 6/95:26 pm
BOS
- ORD
Nonstop3h 08m
JetBlue
Deal found 5/21![JetBlue logo]()
$183
This Super.com deal was found by Cheapflights users on 5/20. 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.
Mon 6/88:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Wed 6/106:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 5/20![JetBlue logo]()
$185
This United Airlines deal was found by Cheapflights users on 5/18. 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 6/37:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Wed 6/108:20 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 5/18![United Airlines logo]()
$187
This Southwest deal was found by Cheapflights users on 5/20. 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.
Tue 6/99:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 6/107:30 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 5/20![Southwest logo]()
$187
This Flysmarter deal was found by Cheapflights users on 5/22. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Sun 6/76:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 5/22![JetBlue logo]()
$189
This Super.com deal was found by Cheapflights users on 5/20. 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 6/38:50 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 6/76:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 5/20![JetBlue logo]()
$190
This Frontier deal was found by Cheapflights users on 5/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1812:27 pm
MDW
- BOS
1 stop12h 00m
Frontier
Wed 8/266:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Deal found 5/18![Frontier logo]()
$190
This Cheapflightsfares deal was found by Cheapflights users on 5/21. 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.
Thu 6/48:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Wed 6/106:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 5/21![JetBlue logo]()
$191
This JetBlue deal was found by Cheapflights users on 5/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Wed 6/106:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 5/19![JetBlue logo]()
$192
This Southwest deal was found by Cheapflights users on 5/18. 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 6/75:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Wed 6/103:45 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 5/18![Southwest logo]()
$192
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 May 23, 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 May 23, 2026.
This JetBlue deal was found by Cheapflights users on 5/22. 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 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Wed 6/106:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 5/22![JetBlue logo]()
$187
This Southwest deal was found by Cheapflights users on 5/18. 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.
Fri 6/57:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 6/87:30 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 5/18![Southwest logo]()
$197
This United Airlines deal was found by Cheapflights users on 5/20. 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.
Mon 8/179:00 pm
ORD
- BOS
Nonstop2h 34m
United Airlines
Sat 8/226:50 pm
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 5/20![United Airlines logo]()
$201
This Delta deal was found by Cheapflights users on 5/20. 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 7/243:19 pm
ORD
- BOS
Nonstop2h 40m
Delta
Wed 7/297:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 5/20![Delta logo]()
$201
This Southwest deal was found by Cheapflights users on 5/20. 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.
Tue 6/910:10 am
MDW
- BOS
2 stops6h 35m
Southwest
Wed 6/107:30 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 5/20![Southwest logo]()
$202
This United Airlines deal was found by Cheapflights users on 5/18. 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.
Mon 7/209:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Thu 7/238:15 am
BOS
- ORD
Nonstop2h 57m
United Airlines
Deal found 5/18![United Airlines logo]()
$205
This JetBlue deal was found by Cheapflights users on 5/18. 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.
Thu 8/208:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Sat 8/2911:05 am
BOS
- ORD
Nonstop2h 54m
JetBlue
Deal found 5/18![JetBlue logo]()
$205
This JetBlue deal was found by Cheapflights users on 5/18. 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.
Mon 8/178:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Thu 8/278:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 5/18![JetBlue logo]()
$205
This Southwest deal was found by Cheapflights users on 5/22. 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 6/97:50 am
MDW
- BOS
1 stop6h 10m
Southwest
Tue 6/163:45 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 5/22![Southwest logo]()
$206
This United Airlines deal was found by Cheapflights users on 5/19. 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 6/249:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Wed 7/85:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 5/19![United Airlines logo]()
$207
This American Airlines deal was found by Cheapflights users on 5/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/2611:11 am
MLI
- BOS
1 stop8h 46m
American Airlines
Sat 6/275:00 am
BOS
- MLI
1 stop14h 22m
American Airlines
Deal found 5/18![American Airlines logo]()
$495
This United Airlines deal was found by Cheapflights users on 5/18. 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.
Thu 7/96:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Mon 7/136:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 5/18![United Airlines logo]()
$215
This United Airlines deal was found by Cheapflights users on 5/22. 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.
Sun 8/99:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Thu 8/135:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Deal found 5/22![United Airlines logo]()
$215
This Southwest deal was found by Cheapflights users on 5/22. 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 6/227:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Sun 6/2810:05 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 5/22![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 5/22. 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.
Wed 9/21:15 pm
ORD
- BGR
2 stops9h 13m
Delta
Sat 9/512:59 pm
BGR
- ORD
2 stops11h 58m
Delta
Deal found 5/22![Delta logo]()
$291
This Delta deal was found by Cheapflights users on 5/19. 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.
Wed 7/85:00 pm
STL
- BGR
1 stop5h 11m
Delta
Wed 9/26:00 am
BGR
- STL
2 stops13h 02m
Delta
Deal found 5/19![Delta logo]()
$292
This United Airlines deal was found by Cheapflights users on 5/20. 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.
Tue 6/26:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Wed 6/310:35 am
BOS
- ORD
Nonstop2h 53m
United Airlines
Deal found 5/20![United Airlines logo]()
$222
This Southwest deal was found by Cheapflights users on 5/19. 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 5/298:00 am
MDW
- BOS
2 stops9h 15m
Southwest
Mon 6/16:55 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 5/19![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 5/20. 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.
Tue 6/24:40 pm
MDW
- BOS
1 stop4h 40m
Southwest
Wed 6/38:10 am
BOS
- MDW
2 stops8h 35m
Southwest
Deal found 5/20![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 5/19. 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 8/2111:19 am
ORD
- BGR
2 stops11h 21m
Delta
Sat 8/296:00 am
BGR
- ORD
2 stops11h 54m
Delta
Deal found 5/19![Delta logo]()
$305
This United Airlines deal was found by Cheapflights users on 5/22. 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.
Thu 6/49:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Tue 6/95:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 5/22![United Airlines logo]()
$232
This Southwest deal was found by Cheapflights users on 5/18. 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 6/172:35 pm
MDW
- BOS
1 stop7h 05m
Southwest
Mon 6/225:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/18![Southwest logo]()
$251
This United Airlines deal was found by Cheapflights users on 5/21. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Mon 7/66:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 5/21![United Airlines logo]()
$234
This Delta deal was found by Cheapflights users on 5/18. 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.
Tue 6/91:46 pm
ORD
- BGR
2 stops8h 49m
Delta
Sat 6/134:52 pm
BGR
- ORD
1 stop4h 39m
Delta
Deal found 5/18![Delta logo]()
$314
This Southwest deal was found by Cheapflights users on 5/21. 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.
Tue 7/217:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Sat 7/256:45 pm
BOS
- MDW
1 stop4h 45m
Southwest
Deal found 5/21![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 5/22. 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.
Sat 10/105:00 pm
MLI
- BOS
1 stop6h 58m
Delta
Sat 10/249:05 am
BOS
- MLI
1 stop8h 17m
Delta
Deal found 5/22![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 5/22. 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 5/307:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 6/13:45 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 5/22![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 5/19. 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 7/31:26 pm
MDW
- BGR
2 stops9h 09m
Delta
Fri 7/105:20 am
BGR
- MDW
2 stops11h 55m
Delta
Deal found 5/19![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 5/22. 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 6/15:40 pm
MDW
- BOS
1 stop4h 30m
Southwest
Thu 6/45:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/22![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 5/18. 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.
Thu 8/201:48 pm
ORD
- BGR
2 stops8h 52m
Delta
Sat 8/292:33 pm
BGR
- ORD
1 stop7h 13m
Delta
Deal found 5/18![Delta logo]()
$325
Last-minute flights from Illinois to MaineDiscover last-minute flight deals from Illinois to Maine. Data last updated May 23, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Maine. Data last updated May 23, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 5/18. 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 6/37:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Wed 6/108:20 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 5/18![United Airlines logo]()
$187
This Super.com deal was found by Cheapflights users on 5/20. 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 6/38:50 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 6/76:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 5/20![JetBlue logo]()
$190
This SmartFares deal was found by Cheapflights users on 5/20. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/48:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Sun 6/76:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 5/20![JetBlue logo]()
$176
This Cheapflightsfares deal was found by Cheapflights users on 5/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/48:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Tue 6/95:26 pm
BOS
- ORD
Nonstop3h 08m
JetBlue
Deal found 5/20![JetBlue logo]()
$191
This Super.com deal was found by Cheapflights users on 5/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Tue 6/95:26 pm
BOS
- ORD
Nonstop3h 08m
JetBlue
Deal found 5/21![JetBlue logo]()
$183
This Flysmarter deal was found by Cheapflights users on 5/22. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Sun 6/76:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 5/22![JetBlue logo]()
$189
This JetBlue deal was found by Cheapflights users on 5/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Wed 6/106:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 5/19![JetBlue logo]()
$192
This Southwest deal was found by Cheapflights users on 5/18. 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 6/75:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Wed 6/103:45 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 5/18![Southwest logo]()
$192
This Super.com deal was found by Cheapflights users on 5/20. 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.
Mon 6/88:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Wed 6/106:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 5/20![JetBlue logo]()
$185
This Cheapflightsfares deal was found by Cheapflights users on 5/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Wed 6/106:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 5/22![JetBlue logo]()
$182
This Southwest deal was found by Cheapflights users on 5/20. 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.
Tue 6/99:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 6/107:30 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 5/20![Southwest logo]()
$187
This Expedia deal was found by Cheapflights users on 5/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1712:04 pm
MDW
- BOS
1 stop12h 23m
Frontier
Wed 6/246:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Deal found 5/18![Frontier logo]()
$190
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 May 23, 2026.
Search for one-way flight options from Illinois to Maine. Find affordable one-way fares based on user searches. Data last updated May 23, 2026.
This Super.com deal was found by Cheapflights users on 5/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/21![JetBlue logo]()
$89
This SmartFares deal was found by Cheapflights users on 5/22. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/178:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 5/22![JetBlue logo]()
$90
This Super.com deal was found by Cheapflights users on 5/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/88:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/18![JetBlue logo]()
$93
This United Airlines deal was found by Cheapflights users on 5/18. 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 6/36:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 5/18![United Airlines logo]()
$94
This Southwest deal was found by Cheapflights users on 5/18. 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 6/97:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/18![Southwest logo]()
$94
This Super.com deal was found by Cheapflights users on 5/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/21![JetBlue logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:55 am
ORD
- BOS
1 stop17h 32m
Frontier
Deal found 5/19![Frontier logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1012:04 pm
MDW
- BOS
1 stop12h 23m
Frontier
Deal found 5/19![Frontier logo]()
$97
This Super.com deal was found by Cheapflights users on 5/22. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/298:50 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 5/22![JetBlue logo]()
$98
This Delta deal was found by Cheapflights users on 5/20. 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.
Sat 6/64:30 pm
ORD
- BOS
Nonstop2h 36m
Delta
Deal found 5/20![Delta logo]()
$99
This Southwest deal was found by Cheapflights users on 5/18. 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.
Fri 6/54:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 5/18![Southwest logo]()
$99
This Super.com deal was found by Cheapflights users on 5/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/912:27 pm
MDW
- BOS
1 stop12h 00m
Frontier
Deal found 5/18![Frontier logo]()
$100
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 May 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $176 (SmartFares) |
One-way from | $89 (Super.com) |
Popular in | December |
Cheapest in | May |
Average price | $299 |
Good round-trip deal | $304 or less |
Good one-way deal | $174 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 May 23, 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 6/9
8:30 pm-11:59 pm
Nonstop2h 29m
Boston Logan Intl
Wed 6/10
6:00 am-7:59 am
Nonstop2h 59m
$187
Quickest round-trip
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 6/5
7:35 pm-10:50 pm
Nonstop2h 15m
Boston Logan Intl
Mon 6/8
7:30 am-9:10 am
Nonstop2h 40m
$197
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 8/17
9:00 pm-12:34 am
Nonstop2h 34m
Boston Logan Intl
Sat 8/22
6:50 pm-8:48 pm
Nonstop2h 58m
$201
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 7/24
3:19 pm-6:59 pm
Nonstop2h 40m
Boston Logan Intl
Wed 7/29
7:30 am-9:26 am
Nonstop2h 56m
$201
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Tue 6/9
10:10 am-5:45 pm
2 stops6h 35m
Boston Logan Intl
Wed 6/10
7:30 am-9:10 am
Nonstop2h 40m
$202
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 7/20
9:41 pm-1:14 am
Nonstop2h 33m
Boston Logan Intl
Thu 7/23
8:15 am-10:12 am
Nonstop2h 57m
$205
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 8/20
8:20 pm-11:51 pm
Nonstop2h 31m
Boston Logan Intl
Sat 8/29
11:05 am-12:59 pm
Nonstop2h 54m
$205
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 8/17
8:20 pm-11:51 pm
Nonstop2h 31m
Boston Logan Intl
Thu 8/27
8:10 am-10:06 am
Nonstop2h 56m
$205
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Tue 6/9
7:50 am-3:00 pm
1 stop6h 10m
Boston Logan Intl
Tue 6/16
3:45 pm-5:30 pm
Nonstop2h 45m
$206
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 6/24
9:41 pm-1:14 am
Nonstop2h 33m
Boston Logan Intl
Wed 7/8
5:45 am-9:36 am
1 stop4h 51m
$207
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-PWM
ORD-PWM
MDW-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 Illinois to Maine
USIL-USME
ORD-BOS
MDW-BOS
STL-PWM
ORD-PWM
What is the cheapest month to book a flight from Illinois to Maine?
Currently, July is the cheapest month in which you can book a flight from Illinois to Maine (average of $101). Flying from Illinois to Maine in January is currently the most expensive (average of $209). 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 May 23, 2026.
It’s optimal to fly from Illinois to Maine in the afternoon. By choosing this option you can save up to 12% 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 May 23, 2026.
The most flights from USIL to USME are scheduled on a Thursday (13 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (7 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 May 16, 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. Thursday 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 May 23, 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.
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 May 23, 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 May 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$229 | Average$403 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$230 | Average$418 | FlexibilityNo cancel fee | On-time69% |