Cheap flights from Maine to Chicago from $68

The month of September is, on average, the cheapest month to fly to Chicago from Maine, with most prices found around $187. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Maine to Chicago during January average around $200.

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $308. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Maine to Chicago for around $401.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Maine to Chicago during this time can be as low as $272. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $366.

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

You are more likely to see cheaper flights to Chicago from Maine when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $248 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Maine for as low as $219 on momondo.

There are 4 cabin classes available to choose from on Maine to Chicago 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 Maine to Chicago

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Maine according to our data. United Airlines is the first choice among our users, with 53% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

As of February 2026, 50 flights take off from Maine and land in Chicago each day. The most common flight departure time for this route is 4:00PM, with 100% of daily flights taking off in the afternoon.

As of February 2026, there are 351 flights per week flying from Maine to Chicago. The most common day of the week flights depart is Mon, with 20% of flights taking off on this day.