Cheap flights from Chicago to Portland from $107

The cheapest month to fly to Portland, Maine from Chicago is in September. Flight prices, which tend to average around $307, are often lower during this time because this is during the off-season. If you aren’t able to travel to Portland, Maine during the month of September, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $319.

On average, the least expensive day to fly to Portland, Maine from Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $301. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Thursday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $376.

In the evening is the cheapest time of day to fly from Chicago to Portland, Maine when you can find flight prices for as low as $301. Flying to Portland, Maine in the evening is an ideal time because this is during off-peak travel hours. Try not to purchase tickets in the afternoon because they tend to be around $375. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

You are more likely to see cheaper flights to Portland, Maine from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Portland, Maine for around $366 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Portland, Maine from Chicago for as low as $281 on momondo.

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

United Airlines, Southwest, and Delta are the most popular carriers operating from Chicago to Portland

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Portland, Maine from Chicago according to our data. United Airlines is the first choice among our users, with 38% of people opting to fly with this airline when traveling to Portland, Maine. Keep in mind that there are 6 different airlines that fly to Portland, Maine on a routine basis, so you have a few additional options to choose from.

Historically, on average around 16% of flights between Chicago and Portland have experienced a delay on any given week. The average delay length over the past 12 months has been 132 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights at night have, in the past, seen delays more frequently in comparison.

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 8% of their flights experiencing any sort of delay.

New York (JFK) was the most common stop: 67% of momondo users choosing 1-stop flights on this route connected there.

Flights via New York (JFK) offer the lowest average round-trip price of $204.

Flights connecting via Baltimore (BWI) have the shortest average one-way travel time: 5h 05m.

Baltimore (BWI) has the shortest average layover time for this route: 1h 25m.

The number of flights available between Chicago and Portland, Maine is 6 per day as of March 2026. The most frequent departure time is 11:00AM, with 37% of daily flights leaving at noon.

As of March 2026, there are 46 flights per week flying from Chicago to Portland, Maine. The most common day of the week flights depart is Thu, with 17% of flights taking off on this day.