
Keep the following information in mind while searching for Illinois to Maine flight deals. Data was last updated November 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $289 (United Airlines) |
One-way from | $145 (American Airlines) |
Popular in | December |
Cheapest in | May |
Average price | $449 |
Good round-trip deal | $389 or less |
Good one-way deal | $209 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Wed 12/9
8:50 am-4:39 pm
1 stop6h 49m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Fri 12/11
5:50 pm-9:29 pm
Nonstop2h 39m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
ChicagoPortland
MDW Chicago Midway - PWM Portland
MDWPWM
Chicago Midway
Thu 11/26
6:00 am-1:06 pm
1 stop6h 06m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
ChicagoPortland
MDW Chicago Midway - PWM Portland
MDWPWM
Chicago Midway
Tue 12/1
12:33 pm-11:48 am
3 stops22h 15m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
ChicagoBangor
ORD Chicago O'Hare Intl - BGR Bangor
ORDBGR
Chicago O'Hare Intl
Thu 12/24
7:00 am-3:59 pm
1 stop7h 59m
Bangor
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
ChicagoBangor
ORD Chicago O'Hare Intl - BGR Bangor
ORDBGR
Chicago O'Hare Intl
Fri 12/25
9:42 am-3:59 pm
1 stop5h 17m
Bangor
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
ChicagoPortland
MDW Chicago Midway - PWM Portland
MDWPWM
Chicago Midway
Mon 11/23
5:05 am-10:30 am
1 stop4h 25m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Fri 12/18
11:59 am-3:31 pm
Nonstop2h 32m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
ChicagoPortland
MDW Chicago Midway - PWM Portland
MDWPWM
Chicago Midway
Sat 11/21
9:30 am-4:10 pm
1 stop5h 40m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Fri 11/20
6:18 pm-9:52 pm
Nonstop2h 34m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
Everything you need to know about your flight from Illinois to Maine
Entertainment
Crew
Food
Boarding
Comfort
Overall
Reviews
Patricia,Oct 2026
DAL - TPA
Entertainment
Crew
Food
Boarding
Comfort
Overall
Reviews
Patricia,Oct 2026
DAL - TPA
Entertainment
Crew
Food
Boarding
Comfort
Overall
Reviews
Patricia,Oct 2026
DAL - TPA
Entertainment
Crew
Food
Boarding
Comfort
Overall
Reviews
Patricia,Oct 2026
DAL - TPA
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.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$229 | Average$512 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$234 | Average$410 | FlexibilityNo cancel fee | On-time69% |