Cheap flights from Portland, Maine to Chicago 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 Portland, Maine to Chicago departing on 10/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Portland, Maine to Chicago
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
Delta flights from Portland, Maine to Chicago
Our best Delta deals on Portland, Maine to Chicago flight tickets
American Airlines flights from Portland, Maine to Chicago
Our best American Airlines deals on Portland, Maine to Chicago flight tickets
See travel insights to Chicago from
How to get the cheapest flight ticket from Portland, Maine to Chicago
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 Portland, Maine and Chicago?
What is the cheapest month to fly to Chicago?
The month of September is, on average, the cheapest month to fly to Chicago from Portland, Maine, with most prices found around $282. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Portland, Maine to Chicago during August average around $287.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $437. 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 Portland, Maine to Chicago for around $633.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Portland, Maine to Chicago during this time can be as low as $250. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $499.
What is the cheapest Portland to Chicago flight route?
Fly from Portland to Chicago Midway for the best Portland - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Portland, Maine when booking 20 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $375 when searching 20 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Portland, Maine for as low as $155 on momondo.
What cabin class options are available on Portland to Chicago flights?
There are 4 cabin classes available to choose from on Portland to Chicago 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 Portland to Chicago?
American Airlines, Southwest, and United Airlines are the most popular carriers operating from Portland to Chicago
What airlines fly to Chicago?
American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Chicago from Portland, Maine according to our data. American Airlines is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Portland, Maine to Chicago on average per day?
8 flights are operational daily from Portland, Maine to Chicago as of June 2025. The most popular departure time for this route is 6:00AM, with 70% of flights per day taking off at noon.
How many flights depart from Portland, Maine to Chicago on average per week?
As of June 2025, 59 flights take off from Portland, Maine and land in Chicago each week. The most common flight departure day for this route is Tue, with 15% of weekly flights taking off on this day.
When to book flights from Portland, Maine to Chicago
Cheap Portland, Maine to Chicago (PWM to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Portland, Maine to Chicago
How far is Portland to Chicago by plane?
There are 887.4 mi between Portland and Chicago. Flights usually cover this in 2h 30m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Portland Airport to Chicago?
Prices for flights from Portland Airport to Chicago are updated daily.
How many operators does momondo search for flights from Portland Airport to Chicago?
As of June 2025, there are 5 operators available to choose from for flights from Portland Airport to Chicago.
How old do you have to be to fly from Portland Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago 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 Chicago. 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 Portland, Maine to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Portland, Maine to Chicago is Embraer 175 (21.65% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (17.02%), Airbus A319 (14.21%), and Boeing 737-900 (12.14%).
What is the most popular airline from Portland, Maine to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Portland, Maine to Chicago is United Airlines (63% of total bookings). The next most popular airlines are American Airlines (26%), Frontier (5%), and Southwest (4%).
Best airlines flying from Portland, Maine to Chicago
Compare and see reviews for airlines that fly from Portland, Maine to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $32 | Free Cancellation | Rating 5.9 3,296 reviews | |||
| PriceFrom $124 | Free Cancellation | Rating 8.0 7,963 reviews | |||
| PriceFrom $158 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $209 | Free Cancellation | Rating 7.4 8,801 reviews | |||
| PriceFrom $264 | Free Cancellation | Rating 8.0 4,278 reviews |
Southwest Flights From Portland, Maine to Chicago
Southwest is one of the most popular airlines flying from Portland, Maine to Chicago, operating 9 flights/week on average for this route. A good Southwest flight deal for Portland, Maine to Chicago starts from $264 round-trip, up to an average price of $371. Our users have rated Southwest at 8.0/10.
United Airlines Flights From Portland, Maine to Chicago
United Airlines (7.4/10 from 8,801 reviews) operates around 14 flights from Portland, Maine to Chicago in any given week. The average United Airlines airfare for this route is around $375, with deals from around $209 rare but found on momondo. Referenced prices are for round-trip Portland, Maine to Chicago flight searches in the last 72 hours.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Portland to Chicago?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Portland to Chicago. momondo saves you time and could save you money on your trip.
Can I find flights from Portland to Chicago with flexible booking policies on momondo?
Yes. All flights to Chicago from Portland on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from Portland to Chicago?
Once you have performed a search for Portland to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.
I’m not ready to book a flight from Portland to Chicago right now. Can momondo alert me if prices change?
Of course. momondo tracks the price of Portland to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.