When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 44 days in advance, which can save you up to 101% on flights from Maine to Chicago compared to booking the week you need them. Waiting 44 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 $329. 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 $408 for the month, but tickets can be as low as $158. 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
$55 - $137
Route
Depart
Return
Price
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/11
Nonstop2h 54m
Chicago O'Hare Intl
Tue 6/18
Nonstop2h 28m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/11
1 stop12h 38m
Chicago O'Hare Intl
Tue 6/18
Nonstop2h 28m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/11
Nonstop2h 54m
Chicago O'Hare Intl
Wed 6/12
Nonstop2h 29m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/11
Nonstop2h 54m
Chicago O'Hare Intl
Tue 6/18
Nonstop2h 28m
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
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Sun 5/26
1 stop12h 30m
Chicago O'Hare Intl
Sat 6/1
1 stop6h 08m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Wed 6/5
Nonstop2h 55m
Chicago O'Hare Intl
Wed 6/12
Nonstop2h 28m
No data available for this route at this time. Please check back soon.
Boarding
Entertainment
Food
Comfort
Overall
Crew
Reviews
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
Boarding
Entertainment
Food
Comfort
Overall
Crew
Reviews
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
Boarding
Entertainment
Food
Comfort
Overall
Crew
Reviews
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
Boarding
Entertainment
Food
Comfort
Overall
Crew
Reviews
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
Boarding
Entertainment
Food
Comfort
Overall
Crew
Reviews
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
Boarding
Entertainment
Food
Comfort
Overall
Crew
Reviews
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
1%of flight departures | Early morningMidnight to 6 am |
---|---|
57%of flight departures | Morning6 am to noon |
42%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.
Certainly. Search results for flights to Chicago from Maine shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.
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!