$83+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Jun 6 — Jun 131
Round-trip
1 adult, Economy
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Find cheap flights from Illinois to Maine with Cheapflights
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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 7, 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 7, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Wed 6/36:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/4![JetBlue logo]()
$162
This Super.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/58:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Wed 8/128:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 5/2![JetBlue logo]()
$164
This Super.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Tue 7/288:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 5/3![JetBlue logo]()
$165
This flygcity.se deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/231:56 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Sun 5/246:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/2![JetBlue logo]()
$166
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Sat 5/305:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Deal found 5/6![Delta logo]()
$167
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:05 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 7/11:25 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 5/3![Southwest logo]()
$167
This American Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/306:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Sat 6/67:46 pm
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 5/2![American Airlines logo]()
$168
This Priceline deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/209:49 am
ORD
- BOS
Nonstop2h 31m
Multiple Airlines
Tue 5/269:12 am
BOS
- ORD
1 stop11h 29m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$169
This Super.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Sun 5/316:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/2![JetBlue logo]()
$170
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/304:30 pm
ORD
- BOS
Nonstop2h 36m
Delta
Sun 5/317:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Deal found 5/5![Delta logo]()
$172
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/107:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 6/155:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/4![Southwest logo]()
$172
This Super.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Sun 5/316:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/2![JetBlue logo]()
$174
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 7, 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 7, 2026.
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/107:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 6/165:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/4![Southwest logo]()
$167
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Sun 5/317:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Deal found 5/4![Delta logo]()
$174
This United Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/57:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Sun 6/75:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 5/3![United Airlines logo]()
$209
This KAYAK deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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.
Tue 5/268:45 pm
ORD
- BOS
Nonstop2h 30m
American Airlines
Thu 5/288:00 am
BOS
- ORD
1 stop5h 18m
American Airlines
Deal found 5/7![American Airlines logo]()
$268
This JetBlue deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:00 am
ORD
- PWM
1 stop5h 21m
JetBlue
Wed 8/192:40 pm
PWM
- ORD
1 stop8h 15m
JetBlue
Deal found 5/2![JetBlue logo]()
$323
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/306:10 am
MDW
- BOS
1 stop4h 50m
Southwest
Sat 6/65:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/2![Southwest logo]()
$192
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Sun 8/167:10 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 5/5![United Airlines logo]()
$215
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/205:20 pm
MDW
- BOS
1 stop5h 45m
Southwest
Thu 7/308:00 pm
BOS
- MDW
1 stop5h 05m
Southwest
Deal found 5/5![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:00 pm
ORD
- BOS
Nonstop2h 37m
Delta
Wed 9/97:30 am
BOS
- ORD
Nonstop2h 58m
Delta
Deal found 5/2![Delta logo]()
$221
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/302:15 pm
MDW
- BOS
2 stops8h 25m
Southwest
Sun 5/315:40 am
BOS
- MDW
1 stop7h 30m
Southwest
Deal found 5/3![Southwest logo]()
$197
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/169:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Sun 7/195:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 5/4![United Airlines logo]()
$224
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:22 pm
ORD
- BOS
1 stop5h 32m
Delta
Tue 7/78:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 5/2![Delta logo]()
$241
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:05 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Sun 5/248:10 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 5/2![Southwest logo]()
$207
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/131:13 pm
STL
- BGR
1 stop7h 34m
United Airlines
Tue 6/167:06 pm
BGR
- STL
1 stop5h 30m
United Airlines
Deal found 5/4![United Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/181:45 pm
ORD
- BOS
1 stop5h 19m
Delta
Wed 5/208:40 pm
BOS
- ORD
Nonstop2h 55m
Delta
Deal found 5/6![Delta logo]()
$261
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/159:20 am
MDW
- BOS
Nonstop2h 20m
Southwest
Sat 6/205:10 am
BOS
- MDW
2 stops9h 00m
Southwest
Deal found 5/6![Southwest logo]()
$222
This JetBlue deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:00 am
ORD
- PWM
1 stop5h 21m
JetBlue
Wed 8/192:40 pm
PWM
- ORD
1 stop8h 15m
JetBlue
Deal found 5/3![JetBlue logo]()
$348
This United Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/296:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Sun 7/56:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 5/6![United Airlines logo]()
$264
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/194:22 pm
PIA
- BOS
1 stop7h 15m
American Airlines
Mon 7/276:55 pm
BOS
- PIA
1 stop6h 03m
American Airlines
Deal found 5/6![American Airlines logo]()
$354
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:05 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Sun 7/1910:05 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 5/2![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Tue 6/164:22 pm
BGR
- ORD
1 stop6h 26m
Delta
Deal found 5/6![Delta logo]()
$296
This United Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/39:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Fri 8/147:10 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 5/2![United Airlines logo]()
$271
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/47:45 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 6/103:45 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 5/3![Southwest logo]()
$227
This American Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:33 am
STL
- BGR
1 stop6h 03m
American Airlines
Thu 10/155:53 am
BGR
- STL
1 stop8h 02m
American Airlines
Deal found 5/2![American Airlines logo]()
$393
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:30 am
STL
- PWM
1 stop4h 25m
Delta
Tue 6/236:57 pm
PWM
- STL
1 stop5h 59m
Delta
Deal found 5/2![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/54:40 pm
MDW
- BOS
1 stop4h 35m
Southwest
Mon 8/107:30 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/2![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/271:59 pm
STL
- BGR
2 stops8h 34m
Delta
Wed 6/35:05 am
BGR
- STL
2 stops8h 15m
Delta
Deal found 5/4![Delta logo]()
$308
This United Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/98:40 am
ORD
- PWM
1 stop4h 54m
United Airlines
Tue 6/166:00 am
PWM
- ORD
Nonstop3h 00m
United Airlines
Deal found 5/6![United Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:30 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Tue 8/188:15 am
BOS
- MDW
2 stops5h 50m
Southwest
Deal found 5/5![Southwest logo]()
$241
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/181:48 pm
ORD
- PWM
1 stop8h 32m
Delta
Wed 8/196:05 am
PWM
- ORD
1 stop7h 31m
Delta
Deal found 5/2![Delta logo]()
$317
Last-minute flights from Illinois to MaineDiscover last-minute flight deals from Illinois to Maine. Data last updated May 7, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Maine. Data last updated May 7, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/209:49 am
ORD
- BOS
Nonstop2h 31m
Multiple Airlines
Tue 5/269:12 am
BOS
- ORD
1 stop11h 29m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$169
This Super.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/209:49 am
ORD
- BOS
Nonstop2h 31m
JetBlue
Tue 5/265:25 pm
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 5/2![JetBlue logo]()
$175
This flygcity.se deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/231:56 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Sun 5/246:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/2![JetBlue logo]()
$166
This Cheapflightsfares deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Wed 6/36:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/4![JetBlue logo]()
$162
This Super.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Tue 6/26:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/3![JetBlue logo]()
$164
This Super.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Sun 5/316:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/2![JetBlue logo]()
$170
This Super.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Sun 5/316:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/2![JetBlue logo]()
$174
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Sat 5/305:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Deal found 5/6![Delta logo]()
$167
This American Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/306:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Sat 6/67:46 pm
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 5/2![American Airlines logo]()
$168
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/304:30 pm
ORD
- BOS
Nonstop2h 36m
Delta
Sun 5/317:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Deal found 5/5![Delta logo]()
$172
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/912:45 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Tue 6/163:45 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 5/5![Southwest logo]()
$167
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/107:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 6/155:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/4![Southwest logo]()
$172
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 7, 2026.
Search for one-way flight options from Illinois to Maine. Find affordable one-way fares based on user searches. Data last updated May 7, 2026.
This Super.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/3![JetBlue logo]()
$83
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 5/5![United Airlines logo]()
$84
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/236:05 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/5![Southwest logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:55 am
ORD
- BOS
1 stop17h 32m
Frontier
Deal found 5/5![Frontier logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.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 5/5![Frontier logo]()
$85
This Flysmarter deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/131:55 pm
ORD
- BOS
Nonstop2h 38m
JetBlue
Deal found 5/4![JetBlue logo]()
$86
This Super.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/298:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/5![JetBlue logo]()
$87
This Cheapflightsfares deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/6![JetBlue logo]()
$88
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/316:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 5/5![United Airlines logo]()
$89
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 5/6![Southwest logo]()
$89
This Super.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/209:49 am
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 5/5![JetBlue logo]()
$92
This Cheapflightsfares deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/199:49 am
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 5/5![JetBlue logo]()
$93
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 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $162 (Cheapflightsfares) |
One-way from | $83 (Super.com) |
Popular in | December |
Cheapest in | May |
Average price | $304 |
Good round-trip deal | $269 or less |
Good one-way deal | $173 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 7, 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
Quickest round-trip
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Wed 6/10
7:40 am-10:55 am
Nonstop2h 15m
Boston Logan Intl
Tue 6/16
5:35 am-7:10 am
Nonstop2h 35m
$167
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 5/30
7:00 am-10:35 am
Nonstop2h 35m
Boston Logan Intl
Sun 5/31
7:35 am-9:27 am
Nonstop2h 52m
$174
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 5/30
6:10 am-12:00 pm
1 stop4h 50m
Boston Logan Intl
Sat 6/6
5:20 am-6:55 am
Nonstop2h 35m
$192
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Mon 7/20
5:20 pm-12:05 am
1 stop5h 45m
Boston Logan Intl
Thu 7/30
8:00 pm-12:05 am
1 stop5h 05m
$197
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 5/30
2:15 pm-11:40 pm
2 stops8h 25m
Boston Logan Intl
Sun 5/31
5:40 am-12:10 pm
1 stop7h 30m
$197
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 5/23
6:05 pm-9:25 pm
Nonstop2h 20m
Boston Logan Intl
Sun 5/24
8:10 am-9:55 am
Nonstop2h 45m
$207
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 6/5
7:45 pm-11:21 pm
Nonstop2h 36m
Boston Logan Intl
Sun 6/7
5:45 am-9:36 am
1 stop4h 51m
$209
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 8/8
6:00 am-11:16 am
1 stop4h 16m
Boston Logan Intl
Sun 8/16
7:10 am-9:09 am
Nonstop2h 59m
$215
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 9/5
4:00 pm-7:37 pm
Nonstop2h 37m
Boston Logan Intl
Wed 9/9
7:30 am-9:28 am
Nonstop2h 58m
$221
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Mon 6/15
9:20 am-12:40 pm
Nonstop2h 20m
Boston Logan Intl
Sat 6/20
5:10 am-1:10 pm
2 stops9h 00m
$222
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
STL-PWM
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
STL-PWM
How far ahead should I book a flight from Illinois to Maine?
Booking 90 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 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 7, 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 evening.
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 2, 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.
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 7, 2026.
The most flights from USIL to USME are scheduled on a Wednesday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).
How much does it cost to fly round-trip from Illinois to Maine?
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 7, 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
Crew
8.6
Overall
7.9
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Overall
7.9
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Overall
7.9
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Overall
7.9
Food
7.0
Entertainment
7.5
Comfort
8.0
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.
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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 7, 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 3 airlines flying from Illinois to Maine
Discover the top 3 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 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$229 | Average$412 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$229 | Average$442 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$259 | Average$434 | FlexibilityNo cancel fee | On-time63% |