Cheap flights from Chicago to Maine from $145

The cheapest month to fly to Maine from Chicago is in April. Flight prices, which tend to average around $334, are often lower during this time because this is during the off-season. If you aren’t able to travel to Maine during the month of April, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $337.

The cheapest day to depart from Chicago to Maine is on a Wednesday. Travelers who choose to depart for Maine on a Wednesday will often find tickets for as low as $345. Flights from Chicago to Maine on a Sunday will generally be more expensive and average around $478. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

The cheapest time of day to fly to Maine is in the evening when flights can be purchased for as low as $312. Flights in the afternoon are often more expensive with an average ticket price of $410.

Fly from Chicago O'Hare Intl to Portland for the best Chicago - Maine flight prices

You are more likely to see cheaper flights to Maine from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Maine for around $387 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Maine from Chicago for as low as $343 on momondo.

There are 4 cabin classes available to choose from on Chicago to Maine flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

As of November 2026, there are 5 flights per day flying from Chicago to Maine. The most common time of day flights depart is 6:00PM, with 54% of flights taking off in the evening.

37 flights are operational weekly from Chicago to Maine as of November 2026. The most popular departure day for this route is Mon, with 19% of flights per week taking off on this day.