Our data shows that February tends to be the cheapest month to fly to Wisconsin from Portland, Maine. Users have commonly found prices around $430 for the month, but tickets can be as low as $267. Due to multiple factors, prepare for potentially higher prices in October.
When flying from Portland, Maine to Wisconsin, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$98 - $244
Route
Depart
Return
Price
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Tue 7/30
Nonstop2h 43m
Chicago O'Hare Intl
Tue 8/6
Nonstop2h 19m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Tue 6/25
Nonstop2h 43m
Chicago O'Hare Intl
Thu 6/27
Nonstop2h 20m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Sun 6/23
Nonstop2h 43m
Chicago O'Hare Intl
Tue 6/25
Nonstop2h 20m
PortlandMinneapolis St Paul
PWM - MSP
PWMMSP
Portland
Thu 6/20
Nonstop3h 11m
Minneapolis St Paul
Sun 6/23
Nonstop2h 45m
PortlandMinneapolis St Paul
PWM - MSP
PWMMSP
Portland
Mon 7/22
Nonstop3h 11m
Minneapolis St Paul
Tue 7/23
1 stop6h 16m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Tue 9/3
Nonstop2h 49m
Chicago O'Hare Intl
Sun 9/8
1 stop5h 33m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Wed 9/18
1 stop6h 34m
Chicago O'Hare Intl
Mon 9/23
1 stop5h 06m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Wed 10/9
Nonstop2h 46m
Chicago O'Hare Intl
Sat 10/12
Nonstop2h 31m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Fri 8/16
1 stop8h 48m
Chicago O'Hare Intl
Sat 8/17
1 stop7h 59m
No data available for this route at this time. Please check back soon.
Overall
Boarding
Crew
Comfort
Food
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Overall
Boarding
Crew
Comfort
Food
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Overall
Boarding
Crew
Comfort
Food
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Overall
Boarding
Crew
Comfort
Food
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Overall
Boarding
Crew
Comfort
Food
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Overall
Boarding
Crew
Comfort
Food
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
When you search for this flight from Portland to Wisconsin, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.
Cheapflights helps you find that perfect flight to Wisconsin from Portland by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!
Users can book flights with no change fees policies with our dedicated filters. Book flights from Portland to Wisconsin flexibly with Cheapflights today.
Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!