Cheap flights from Chicago to Portland from $90
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 Portland departing on 8/31. 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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Southwest flights from Chicago to Portland, Maine
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Sun Country Air flights from Chicago to Portland, Maine
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How to get the cheapest flight ticket from Chicago to Portland, 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 typical price of a round-trip flight between Chicago and Portland, Maine?
What is the cheapest month to fly to Portland, Maine?
The cheapest month to fly to Portland, 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 Portland, 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 Portland, Maine?
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 $274. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Friday 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 $390.
What is the cheapest time of day to depart on your flight to Portland, Maine?
At noon is the cheapest time of day to fly from Chicago to Portland, Maine when you can find flight prices for as low as $282. Flying to Portland, Maine at noon is an ideal time because this is during off-peak travel hours. Try not to purchase tickets in the morning because they tend to be around $371. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Chicago to Portland flight route?
Fly from Chicago O'Hare Intl to Portland for the best Chicago - Portland flight prices
How far in advance should I book a flight to Portland, Maine?
You are more likely to see cheaper flights to Portland, Maine from Chicago when booking 25 weeks ahead of your departure date. In general, you can expect to find flights to Portland, Maine for around $383 when searching 25 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 $270 on momondo.
What cabin class options are available on Chicago to Portland flights?
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.
What is the cheapest airline that flies from Chicago to Portland?
United Airlines, Southwest, and JetBlue are the most popular carriers operating from Chicago to Portland
What airlines fly to Portland, Maine?
American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Portland, Maine from Chicago according to our data. American Airlines is the first choice among our users, with 37% of people opting to fly with this airline when traveling to Portland, Maine. Keep in mind that there are 7 different airlines that fly to Portland, Maine on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to Portland, Maine on average per day?
The number of flights available between Chicago and Portland, Maine is 7 per day as of June 2025. The most frequent departure time is 6:00PM, with 51% of daily flights leaving in the evening.
How many flights depart from Chicago to Portland, Maine on average per week?
As of June 2025, there are 54 flights per week flying from Chicago to Portland, Maine. The most common day of the week flights depart is Mon, with 17% of flights taking off on this day.
When to book flights from Chicago to Portland, Maine
Cheap Chicago to Portland, Maine (CHI to PWM) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Portland, Maine
Best Price Found | $90 |
|---|---|
Fastest flight time | 2h 10m |
Direct flights | Every day |
Airports in Portland, Maine | 1 airport |
How far is Chicago to Portland by plane?
Chicago and Portland are 887.4 mi apart from one another. By plane, this route typically takes 2h 10m.
When did momondo last update prices for flights from Chicago to Portland Airport?
Prices for flights from Chicago to Portland Airport refresh daily.
How many operators does momondo search for flights from Chicago to Portland Airport?
As of June 2025, there are 5 operators available to choose from for flights from Chicago to Portland Airport.
How old do you have to be to fly from Chicago to Portland Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Portland Airport.
What documentation or ID do you need to fly to Portland Airport?
The travel and health documents required for your trip to Portland Airport 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 Portland Airport. 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 Portland, Maine?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to Portland, Maine is Embraer 175 (23.67% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (17.04%), Boeing 737-800 (14.73%), and Boeing 737-700 (13.08%).
What is the most popular airline from Chicago to Portland, Maine?
momondo data reveals that the most frequently booked airline on the route from Chicago to Portland, Maine is United Airlines, representing 52% of all bookings. The subsequent popular airlines are American Airlines at 29%, Frontier at 11%, and Southwest at 6%.
Best airlines flying from Chicago to Portland, Maine
Compare and see reviews for airlines that fly from Chicago to Portland, Maine with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $57 | Free Cancellation | Rating 5.9 3,295 reviews | |||
| PriceFrom $163 | Free Cancellation | Rating 8.0 7,946 reviews | |||
| PriceFrom $176 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $191 | Free Cancellation | Rating 8.0 4,287 reviews | |||
| PriceFrom $213 | Free Cancellation | Rating 7.4 8,790 reviews |
Southwest Flights From Chicago to Portland, Maine
Across 5 Southwest flights from Chicago to Portland, Maine this week, the average price was $401, with the best Southwest deals starting from $191 round-trip. 4,287 users have rated Southwest on momondo, with an average score of 8.0/10.
United Airlines Flights From Chicago to Portland, Maine
United Airlines is also a popular choice for this route. United Airlines flight deals for Chicago to Portland, Maine start from as low as $213 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around $385. United Airlines operates 12 flights to Portland, Maine from Chicago in an average week. Users have rated it 7.4/10 across 8,790 reviews.
Traveling to a place near Portland?
Book flights to Portland if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Chicago to Portland?
It is quick and easy to find Chicago to Portland 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 Portland that suits you.
Can I find flights from Chicago to Portland with flexible booking policies on momondo?
Yes. All flights to Portland 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 Portland?
momondo helps you find the best flight between Chicago and Portland by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
I’m not ready to book a flight from Chicago to Portland right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Chicago to Portland 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.