To save up to 202% on this flight, we recommend booking at least 59 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Portland, Maine to Wisconsin from $491 1-2 weeks out and tickets from $566 for flights departing within the next 72 hours.
Our data shows that February tends to be the cheapest month to fly to Wisconsin from Portland, Maine. Users have commonly found prices around $437 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
$65 - $208
Route
Depart
Return
Price
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Tue 6/11
Nonstop2h 43m
Chicago O'Hare Intl
Tue 6/18
Nonstop2h 20m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Tue 6/11
Nonstop2h 43m
Chicago O'Hare Intl
Tue 6/18
Nonstop2h 20m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Thu 6/13
Nonstop2h 43m
Chicago O'Hare Intl
Tue 6/18
Nonstop2h 20m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Thu 6/6
Nonstop2h 43m
Chicago O'Hare Intl
Sun 6/9
Nonstop2h 20m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Tue 6/4
Nonstop2h 46m
Chicago O'Hare Intl
Thu 6/6
Nonstop2h 20m
PortlandMinneapolis St Paul
PWM - MSP
PWMMSP
Portland
Thu 6/27
Nonstop3h 11m
Minneapolis St Paul
Sun 6/30
Nonstop2h 37m
PortlandMinneapolis St Paul
PWM - MSP
PWMMSP
Portland
Sat 6/8
1 stop8h 51m
Minneapolis St Paul
Sun 6/16
Nonstop2h 37m
PortlandMinneapolis St Paul
PWM - MSP
PWMMSP
Portland
Fri 6/21
Nonstop3h 08m
Minneapolis St Paul
Sun 6/23
Nonstop2h 50m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Fri 8/23
Nonstop2h 46m
Chicago O'Hare Intl
Tue 8/27
Nonstop2h 23m
No data available for this route at this time. Please check back soon.
Crew
Comfort
Entertainment
Overall
Food
Boarding
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.
Crew
Comfort
Entertainment
Overall
Food
Boarding
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.
Crew
Comfort
Entertainment
Overall
Food
Boarding
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.
Crew
Comfort
Entertainment
Overall
Food
Boarding
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.
Crew
Comfort
Entertainment
Overall
Food
Boarding
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.
Crew
Comfort
Entertainment
Overall
Food
Boarding
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.
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