Cheap flights from Chicago to Maine from $55
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Maine departing on 7/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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How to get the cheapest flight ticket from Chicago to Maine
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Maine?
The cheapest month to fly to Maine from Chicago is in February. Flight prices, which tend to average around $285, 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 February, then flying in March is also cheap. Prices for this month can be found on momondo for an average of $303.
What is the cheapest day to depart on your flight to Maine?
The cheapest day to depart from Chicago to Maine is on a Tuesday. Travelers who choose to depart for Maine on a Tuesday will often find tickets for as low as $274. Flights from Chicago to Maine on a Friday will generally be more expensive and average around $391. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.
What is the cheapest time of day to depart on your flight to Maine?
The cheapest time of day to fly to Maine is in the afternoon when flights can be purchased for as low as $292. Flights in the morning are often more expensive with an average ticket price of $370.
What is the cheapest Chicago to Maine flight route?
Fly from Chicago O'Hare Intl to Portland for the best Chicago - Maine flight prices
How far in advance should I book a flight to Maine?
You are more likely to see cheaper flights to Maine from Chicago when booking 13 weeks ahead of your departure date. In general, you can expect to find flights to Maine for around $383 when searching 13 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 $275 on momondo.
What cabin class options are available on Chicago to Maine flights?
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.
What is the cheapest airline that flies from Chicago to Maine?
Spirit Airlines, JetBlue, and United Airlines are the most popular carriers operating from Chicago to Maine
What airlines fly to Maine?
United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Maine from Chicago 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 Maine. Keep in mind that there are 5 different airlines that fly to Maine on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to Maine on average per day?
As of June 2025, there are 85 flights per day flying from Chicago to Maine. The most common time of day flights depart is 11:00AM, with 49% of flights taking off at noon.
How many flights depart from Chicago to Maine on average per week?
596 flights are operational weekly from Chicago to Maine as of June 2025. The most popular departure day for this route is Mon, with 16% of flights per week taking off on this day.
Cheap Chicago to Maine flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Maine
When did momondo last update prices for flights from Chicago to Maine?
Prices for flights from Chicago to Maine were last updated today.
How many operators does momondo search for flights from Chicago to Maine?
The number of operators available for flights from Chicago to Maine is 7 as of June 2025.
How old do you have to be to fly from Chicago to Maine?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Maine.
What documentation or ID do you need to fly to Maine?
The travel and health documents required for your trip to Maine can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Maine. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to Maine?
momondo data reveals that the most frequently booked plane model on the route from Chicago to Maine is Embraer 175, representing 24.90% of all bookings. The subsequent popular models are Embraer 175 (Enhanced Winglets) at 18.51%, Boeing 737-800 at 12.49%, and Boeing 737-700 at 10.74%.
Best airlines flying from Chicago to Maine
Compare and see reviews for airlines that fly from Chicago to Maine with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $49 | Free Cancellation | Rating 5.9 3,296 reviews | |||
| PriceFrom $163 | Free Cancellation | Rating 8.0 7,963 reviews | |||
| PriceFrom $175 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $191 | Free Cancellation | Rating 8.0 4,278 reviews | |||
| PriceFrom $213 | Free Cancellation | Rating 7.4 8,801 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Maine?
It is quick and easy to find Chicago to Maine flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Maine that suits you.
Can I find flights from Chicago to Maine with flexible booking policies on momondo?
Yes. All flights to Maine from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from Chicago to Maine?
Once all potential Chicago to Maine flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Chicago to Maine right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Chicago to Maine flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.