When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 26 days in advance, which can save you up to 134% on flights from Portland, Maine to Indiana compared to booking the week you need them. Waiting 26 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $550. For sooner than that we have options available in the next 3 days from $676.
Flights from Portland, Maine to Indiana lean towards being more expensive in February. Prices are generally better when you fly from Portland, Maine to Indiana in July, with the cheapest ticket starting at $305.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Portland, Maine to Indiana as you normally would.
Fly from
Fly to
Budget
$68 - $259
Route
Depart
Return
Price
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Thu 7/18
Nonstop2h 43m
Chicago O'Hare Intl
Tue 7/23
Nonstop2h 19m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Tue 7/16
Nonstop2h 43m
Chicago O'Hare Intl
Thu 7/25
Nonstop2h 19m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Thu 6/6
Nonstop2h 43m
Chicago O'Hare Intl
Sun 6/9
Nonstop2h 20m
PortlandCincinnati Cinci./N. Kentucky
PWM - CVG
PWMCVG
Portland
Thu 8/29
Nonstop2h 34m
Cincinnati Cinci./N. Kentucky
Tue 9/3
Nonstop2h 18m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Fri 7/5
1 stop7h 06m
Chicago O'Hare Intl
Tue 7/9
Nonstop2h 21m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Tue 7/30
1 stop5h 06m
Chicago O'Hare Intl
Tue 8/6
1 stop4h 11m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Thu 6/13
1 stop8h 58m
Chicago O'Hare Intl
Tue 6/18
1 stop7h 24m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Thu 7/4
Nonstop2h 53m
Chicago O'Hare Intl
Mon 7/8
Nonstop2h 29m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Sun 6/2
Nonstop2h 49m
Chicago O'Hare Intl
Wed 6/5
Nonstop2h 30m
No data available for this route at this time. Please check back soon.
Boarding
Entertainment
Food
Overall
Crew
Comfort
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.
Boarding
Entertainment
Food
Overall
Crew
Comfort
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.
Boarding
Entertainment
Food
Overall
Crew
Comfort
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.
Boarding
Entertainment
Food
Overall
Crew
Comfort
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.
Boarding
Entertainment
Food
Overall
Crew
Comfort
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.
Boarding
Entertainment
Food
Overall
Crew
Comfort
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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