When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 43 days in advance, which can save you up to 92% on flights from Maine to Chicago compared to booking the week you need them. Waiting 43 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 $478. For sooner than that we have options available in the next 3 days from $539.
Our data shows that September tends to be the cheapest month to fly to Chicago from Maine. Users have commonly found prices around $384 for the month, but tickets can be as low as $166. Due to multiple factors, prepare for potentially higher prices in April.
When flying from Maine to Chicago, 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
$138 - $415
Route
Depart
Return
Price
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Tue 5/14
1 stop12h 53m
Chicago O'Hare Intl
Tue 5/21
Nonstop2h 20m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Tue 5/14
1 stop12h 53m
Chicago O'Hare Intl
Tue 5/21
1 stop6h 45m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Tue 8/13
Nonstop2h 46m
Chicago O'Hare Intl
Sat 8/17
1 stop17h 56m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Sat 8/31
1 stop7h 26m
Chicago O'Hare Intl
Mon 9/2
Nonstop2h 28m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Tue 5/14
1 stop12h 53m
Chicago O'Hare Intl
Wed 5/15
1 stop13h 46m
BangorChicago O'Hare Intl
BGR - ORD
BGRORD
Bangor
Thu 9/12
1 stop6h 57m
Chicago O'Hare Intl
Mon 9/16
1 stop7h 33m
BangorChicago O'Hare Intl
BGR - ORD
BGRORD
Bangor
Thu 9/12
1 stop6h 57m
Chicago O'Hare Intl
Mon 9/16
2 stops9h 12m
BangorChicago O'Hare Intl
BGR - ORD
BGRORD
Bangor
Tue 7/16
1 stop5h 47m
Chicago O'Hare Intl
Sun 7/21
Nonstop2h 43m
AugustaChicago O'Hare Intl
AUG - ORD
AUGORD
Augusta
Sat 4/27
1 stop6h 56m
Chicago O'Hare Intl
Wed 5/1
1 stop4h 57m
No data available for this route at this time. Please check back soon.
Overall
Boarding
Entertainment
Comfort
Food
Crew
Reviews
It was a good experience other than a short delay.
Overall
Boarding
Entertainment
Comfort
Food
Crew
Reviews
It was a good experience other than a short delay.
Overall
Boarding
Entertainment
Comfort
Food
Crew
Reviews
It was a good experience other than a short delay.
Overall
Boarding
Entertainment
Comfort
Food
Crew
Reviews
It was a good experience other than a short delay.
Overall
Boarding
Entertainment
Comfort
Food
Crew
Reviews
It was a good experience other than a short delay.
Overall
Boarding
Entertainment
Comfort
Food
Crew
Reviews
It was a good experience other than a short delay.
1%of flight departures | Early morningMidnight to 6 am |
---|---|
38%of flight departures | Morning6 am to noon |
61%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |
900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Chicago from Maine today with Cheapflights!
It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Maine to Chicago.
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Yes, you can often find last-minute deals on Maine to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.
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Cancellation policies vary by airline and fare type. After entering your flight details, you can view the cancellation policies for each deal in the search results. Some deals may offer flexibility in terms of cancellation and changes.