$85+ Cheap flights from Maine to Illinois
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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
Jul 21 — Jul 281
Round-trip
1 adult, Economy
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Cheapest flights from Maine to IllinoisExplore the most affordable flight options available from Maine to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 21, 2026.
Explore the most affordable flight options available from Maine to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 21, 2026.
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/155:01 am
BOS
- ORD
1 stop4h 49m
JetBlue
Wed 7/226:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Deal found 6/20![JetBlue logo]()
$177
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 7/85:30 pm
BOS
- MDW
Nonstop2h 55m
Southwest
Mon 7/137:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/18![Southwest logo]()
$178
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 7/83:13 pm
BOS
- ORD
Nonstop2h 52m
United Airlines
Thu 7/97:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 6/18![United Airlines logo]()
$178
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.
Tue 7/145:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Fri 7/177:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/20![Southwest logo]()
$179
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.
Thu 7/97:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Sat 7/116:59 am
ORD
- BOS
Nonstop2h 31m
Delta
Deal found 6/19![Delta logo]()
$179
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 7/145:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 7/217:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 6/16![Southwest logo]()
$180
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.
Tue 7/77:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Wed 7/156:59 am
ORD
- BOS
Nonstop2h 31m
Delta
Deal found 6/17![Delta logo]()
$180
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/45:01 am
BOS
- ORD
1 stop4h 49m
JetBlue
Thu 8/68:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 6/20![JetBlue logo]()
$181
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.
Tue 7/145:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Wed 7/157:40 am
MDW
- BOS
Nonstop2h 15m
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.
Wed 8/264:16 pm
BOS
- ORD
Nonstop3h 04m
Delta
Fri 9/47:30 pm
ORD
- BOS
Nonstop2h 30m
Delta
Deal found 6/19![Delta logo]()
$182
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 7/185:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Sat 7/255:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 6/17![Southwest logo]()
$183
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.
Wed 7/228:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Thu 7/303:19 pm
ORD
- BOS
Nonstop2h 40m
Delta
Deal found 6/19![Delta logo]()
$183
Best flights from Maine to IllinoisDiscover carefully curated flight deals from Maine to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 21, 2026.
Discover carefully curated flight deals from Maine to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 21, 2026.
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.
Mon 7/208:15 am
BOS
- ORD
Nonstop2h 57m
United Airlines
Tue 7/216:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Deal found 6/20![United Airlines logo]()
$180
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.
Mon 8/107:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Wed 8/1210:30 am
ORD
- BOS
Nonstop2h 29m
Delta
Deal found 6/16![Delta logo]()
$188
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 8/169:05 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 8/188:45 am
MDW
- BOS
Nonstop2h 30m
Southwest
Deal found 6/18![Southwest logo]()
$193
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/264:00 pm
BOS
- ORD
1 stop7h 06m
JetBlue
Mon 9/286:30 am
ORD
- BOS
1 stop7h 10m
JetBlue
Deal found 6/19![JetBlue logo]()
$201
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/136:30 pm
BOS
- ORD
Nonstop3h 29m
American Airlines
Wed 7/1511:00 am
ORD
- BOS
Nonstop2h 38m
American Airlines
Deal found 6/16![American Airlines logo]()
$237
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.
Thu 8/205:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Sun 8/239:40 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Deal found 6/18![United Airlines logo]()
$181
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.
Thu 7/308:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Thu 8/137:30 pm
ORD
- BOS
Nonstop2h 30m
Delta
Deal found 6/19![Delta logo]()
$191
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 7/185:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 7/207:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/20![Southwest logo]()
$200
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/44:43 pm
BOS
- ORD
1 stop5h 47m
JetBlue
Thu 7/96:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Deal found 6/19![JetBlue logo]()
$220
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 7/42:05 pm
BOS
- MDW
1 stop4h 25m
Southwest
Tue 7/712:45 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/20![Southwest logo]()
$201
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.
Thu 11/57:30 am
BOS
- ORD
Nonstop3h 03m
Delta
Fri 11/63:00 pm
ORD
- BOS
Nonstop2h 31m
Delta
Deal found 6/20![Delta logo]()
$207
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.
Thu 10/296:00 am
BOS
- ORD
1 stop4h 37m
United Airlines
Sun 11/19:30 pm
ORD
- BOS
Nonstop2h 32m
United Airlines
Deal found 6/18![United Airlines logo]()
$217
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.
Tue 7/215:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Thu 7/237:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/19![Southwest logo]()
$203
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 7/1712:25 pm
BOS
- ORD
Nonstop2h 54m
Delta
Mon 7/203:19 pm
ORD
- BOS
Nonstop2h 40m
Delta
Deal found 6/18![Delta logo]()
$217
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.
Fri 8/285:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Sun 8/306:15 am
ORD
- BOS
Nonstop2h 21m
United Airlines
Deal found 6/16![United Airlines logo]()
$219
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/189:28 am
BOS
- RFD
2 stops9h 27m
Allegiant Air
Thu 1/2111:23 am
RFD
- BOS
1 stop21h 44m
Allegiant Air
Deal found 6/17![Allegiant Air logo]()
$544
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 7/185:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Wed 7/298:10 am
MDW
- BOS
1 stop6h 30m
Southwest
Deal found 6/17![Southwest logo]()
$205
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/105:36 pm
BGR
- ORD
Nonstop3h 25m
American Airlines
Sat 9/126:59 am
ORD
- BGR
1 stop4h 25m
American Airlines
Deal found 6/16![American Airlines logo]()
$285
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.
Mon 7/138:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Wed 7/156:59 am
ORD
- BOS
Nonstop2h 31m
Delta
Deal found 6/16![Delta logo]()
$225
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 8/228:40 am
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 8/243:20 pm
MDW
- BOS
1 stop6h 00m
Southwest
Deal found 6/19![Southwest logo]()
$213
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/276:30 pm
BOS
- BMI
1 stop7h 05m
American Airlines
Sat 8/16:00 pm
BMI
- BOS
1 stop5h 05m
American Airlines
Deal found 6/18![American Airlines logo]()
$319
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 7/25:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 7/67:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/16![Southwest logo]()
$219
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.
Sat 7/42:30 pm
PWM
- ORD
1 stop8h 00m
JetBlue
Sat 7/116:00 am
ORD
- PWM
1 stop6h 45m
JetBlue
Deal found 6/18![JetBlue logo]()
$335
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.
Sat 8/158:40 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 8/186:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 6/16![Southwest logo]()
$232
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/2510:30 am
BOS
- BMI
1 stop8h 00m
American Airlines
Tue 7/286:04 pm
BMI
- BOS
1 stop5h 01m
American Airlines
Deal found 6/20![American Airlines logo]()
$344
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.
Thu 11/129:45 am
PWM
- ORD
Nonstop2h 57m
United Airlines
Sat 11/1410:35 am
ORD
- PWM
Nonstop2h 17m
United Airlines
Deal found 6/18![United Airlines logo]()
$323
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.
Sun 8/237:30 am
BOS
- MDW
Nonstop2h 35m
Southwest
Thu 8/272:35 pm
MDW
- BOS
Nonstop2h 25m
Southwest
Deal found 6/15![Southwest logo]()
$236
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.
Wed 7/295:55 pm
BOS
- BMI
1 stop5h 53m
Delta
Sat 8/14:18 pm
BMI
- BOS
1 stop8h 02m
Delta
Deal found 6/20![Delta logo]()
$319
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/47:24 pm
PWM
- ORD
Nonstop3h 06m
American Airlines
Thu 8/67:13 pm
ORD
- PWM
Nonstop2h 35m
American Airlines
Deal found 6/20![American Airlines logo]()
$370
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 9/165:17 am
BGR
- MDW
2 stops11h 54m
Delta
Sat 9/196:05 am
MDW
- BGR
1 stop6h 29m
Delta
Deal found 6/17![Delta logo]()
$325
Last-minute flights from Maine to IllinoisDiscover last-minute flight deals from Maine to Illinois. Data last updated June 21, 2026 and is based on user searches.
Discover last-minute flight deals from Maine to Illinois. Data last updated June 21, 2026 and is based on user searches.
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/298:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Wed 7/89:40 am
ORD
- BOS
1 stop8h 19m
JetBlue
Deal found 6/15![JetBlue logo]()
$199
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/308:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Tue 7/79:40 am
ORD
- BOS
1 stop8h 19m
JetBlue
Deal found 6/16![JetBlue logo]()
$183
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/308:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Wed 7/89:40 am
ORD
- BOS
1 stop6h 37m
JetBlue
Deal found 6/15![JetBlue logo]()
$190
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 7/48:45 am
BOS
- MDW
2 stops9h 25m
Southwest
Sat 7/115:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 6/20![Southwest logo]()
$185
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 7/85:30 pm
BOS
- MDW
Nonstop2h 55m
Southwest
Mon 7/137:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/18![Southwest logo]()
$178
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.
Thu 7/95:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 7/134:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/20![Southwest logo]()
$187
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 7/95:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Sun 7/125:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 6/19![Southwest logo]()
$192
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.
Sat 7/117:55 am
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 7/137:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/16![Southwest logo]()
$189
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.
Tue 7/145:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Fri 7/177:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/20![Southwest logo]()
$179
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 7/145:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 7/217:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 6/16![Southwest logo]()
$180
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.
Tue 7/145:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Wed 7/157:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 6/19![Southwest logo]()
$182
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 7/185:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Sat 7/255:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 6/17![Southwest logo]()
$183
One-way flights from Maine to IllinoisSearch for one-way flight options from Maine to Illinois. Find affordable one-way fares based on user searches. Data last updated June 21, 2026.
Search for one-way flight options from Maine to Illinois. Find affordable one-way fares based on user searches. Data last updated June 21, 2026.
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/111:17 pm
PWM
- ORD
1 stop5h 03m
JetBlue
Deal found 6/19![JetBlue logo]()
$85
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/202:40 pm
PWM
- ORD
1 stop8h 15m
JetBlue
Deal found 6/20![JetBlue logo]()
$93
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/75:01 am
BOS
- ORD
1 stop4h 47m
JetBlue
Deal found 6/16![JetBlue logo]()
$95
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.
Wed 7/11:25 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 6/17![Southwest logo]()
$96
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 7/17:30 am
BOS
- ORD
Nonstop2h 58m
Delta
Deal found 6/17![Delta logo]()
$96
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.
Sun 7/265:01 am
BOS
- ORD
1 stop4h 49m
JetBlue
Deal found 6/16![JetBlue logo]()
$97
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 8/156:00 pm
BOS
- ORD
1 stop6h 22m
United Airlines
Deal found 6/17![United Airlines logo]()
$98
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/189:12 am
BOS
- STL
1 stop9h 18m
Frontier
Deal found 6/16![Frontier 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.
Wed 9/1610:05 am
BOS
- MDW
Nonstop2h 30m
Southwest
Deal found 6/18![Southwest logo]()
$99
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 9/154:35 pm
BOS
- ORD
Nonstop2h 58m
Delta
Deal found 6/19![Delta logo]()
$99
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1410:19 am
BOS
- RFD
1 stop24h 21m
Allegiant Air
Deal found 6/17![Allegiant Air logo]()
$100
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/254:43 pm
BOS
- ORD
1 stop6h 15m
JetBlue
Deal found 6/20![JetBlue logo]()
$100
Find flight deals from Maine to Illinois
Keep the following information in mind while searching for Maine to Illinois flight deals. Data was last updated June 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $177 (Cheapflightsfares) |
One-way from | $85 (JetBlue) |
Popular in | December |
Cheapest in | September |
Average price | $354 |
Good round-trip deal | $369 or less |
Good one-way deal | $197 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Maine to Illinois 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 21, 2026.
Use the filters below to find and compare flights from Maine to Illinois that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 7/20
8:15 am-10:12 am
Nonstop2h 57m
Chicago O'Hare Intl
Tue 7/21
6:00 am-11:16 am
1 stop4h 16m
$180
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 8/20
5:45 am-9:38 am
1 stop4h 53m
Chicago O'Hare Intl
Sun 8/23
9:40 pm-1:15 am
Nonstop2h 35m
$181
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 8/10
7:30 am-9:26 am
Nonstop2h 56m
Chicago O'Hare Intl
Wed 8/12
10:30 am-1:59 pm
Nonstop2h 29m
$188
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 7/30
8:45 pm-10:39 pm
Nonstop2h 54m
Chicago O'Hare Intl
Thu 8/13
7:30 pm-11:00 pm
Nonstop2h 30m
$191
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sun 8/16
9:05 pm-10:40 pm
Nonstop2h 35m
Chicago Midway
Tue 8/18
8:45 am-12:15 pm
Nonstop2h 30m
$193
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 7/18
5:20 am-6:55 am
Nonstop2h 35m
Chicago Midway
Mon 7/20
7:35 pm-10:55 pm
Nonstop2h 20m
$200
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 9/26
4:00 pm-10:06 pm
1 stop7h 06m
Chicago O'Hare Intl
Mon 9/28
6:30 am-2:40 pm
1 stop7h 10m
$201
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 7/4
2:05 pm-5:30 pm
1 stop4h 25m
Chicago Midway
Tue 7/7
12:45 pm-4:05 pm
Nonstop2h 20m
$201
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 7/21
5:35 am-7:10 am
Nonstop2h 35m
Chicago Midway
Thu 7/23
7:35 pm-10:55 pm
Nonstop2h 20m
$203
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 7/18
5:20 am-6:55 am
Nonstop2h 35m
Chicago Midway
Wed 7/29
8:10 am-3:40 pm
1 stop6h 30m
$205
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Maine to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Maine with our price prediction graph.
BOS-MDW
BOS-ORD
PWM-ORD
PWM-STL
BOS-RFD
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 Maine to Illinois
USME-USIL
BOS-MDW
BOS-ORD
PWM-ORD
PWM-STL
What is the cheapest month to book a flight from Maine to Illinois?
Currently, September is the cheapest month in which you can book a flight from Maine to Illinois (average of $130). Flying from Maine to Illinois 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 ME to IL?
Find hourly flight availability from Maine to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 21, 2026.
One of the essential ways to save on airfare from Maine to Illinois is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 25% on airfare.
Weekly flight availability from Maine to Illinois
Explore weekly flight availability from Maine to Illinois. 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 21, 2026.
The most flights from USME to USIL are scheduled on a Friday (8 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 Maine to Illinois?
How far ahead should I book a flight from Maine to Illinois?
The best time to book flights from Maine to Illinois is 83 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated June 21, 2026.
See what other customers who have flown with Southwest,Delta, andUnited Airlines from Maine to Illinois have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Overall
7.9
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
7.9
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
7.9
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
7.9
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
7.9
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Maine to Illinois. 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
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Alternative routes for Maine to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Illinois by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Maine to Illinois by cabin class
Find flights from Maine to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Maine and Illinois flights
Browse other Maine and Illinois flight options. Last updated on June 21, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Illinois
Find the right flight back to Maine after your stay in Illinois
Maine to Illinois flights
Consider these flights traveling from Maine to Illinois.
Top 4 airlines flying from Maine to Illinois
Discover the top 4 airlines that operate flights from Maine to Illinois. 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 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$209 | Average$348 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$229 | Average$440 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$234 | Average$346 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$267 | Average$397 | FlexibilityNo cancel fee | On-time63% |