Cheap flights from Illinois to Portland from $85

The cheapest month to fly to Portland, Maine from Illinois is in September. Flight prices, which tend to average around $125, 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 October is also cheap. Prices for this month can be found on momondo for an average of $133.

On average, the least expensive day to fly to Portland, Maine from Illinois is on a Wednesday. momondo users have found tickets for Wednesday departures for as low as $337. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Sunday is the most expensive day to depart from Illinois because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $420.

In the evening is the cheapest time of day to fly from Illinois to Portland, Maine when you can find flight prices for as low as $299. 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 $378. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Chicago Midway to Portland for the best Illinois - Portland flight prices

You are more likely to see cheaper flights to Portland, Maine from Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Portland, Maine for around $369 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Portland, Maine from Illinois for as low as $282 on momondo.

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

JetBlue, Southwest, and United Airlines are the most popular carriers operating from Illinois to Portland

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Portland, Maine from Illinois according to our data. United Airlines is the first choice among our users, with 41% of people opting to fly with this airline when traveling to Portland, Maine. Keep in mind that there are 5 different airlines that fly to Portland, Maine on a routine basis, so you have a few additional options to choose from.

As of June 2026, there are 8 flights per day flying from Illinois to Portland, Maine. The most common time of day flights depart is 6:00PM, with 53% of flights taking off in the evening.

As of June 2026, 59 flights take off from Illinois and land in Portland, Maine each week. The most common flight departure day for this route is Thu, with 19% of weekly flights taking off on this day.