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 7/2. 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 Portland, Maine to Chicago Midway Airport
Our best Southwest deals on Portland, Maine to Chicago Midway Airport flight tickets
Alaska Airlines flights from Portland, Maine to Chicago Midway Airport
Our best Alaska Airlines deals on Portland, Maine to Chicago Midway Airport flight tickets
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How to get the cheapest flight ticket from Portland, Maine to Chicago Midway Airport
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 day to depart on your flight to Chicago Midway Airport?
According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Portland, Maine. The lowest ticket price found for a Thursday departure recently was $413. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Saturday is the most expensive day to depart from Portland, Maine because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $572.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Portland, Maine in the evening is the least expensive time of day to depart. momondo users have found prices as low as $438 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $480. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Portland to Chicago Midway flight route?
Fly from Portland to Chicago Midway for the best Portland - Chicago Midway flight prices
What cabin class options are available on Portland to Chicago Midway flights?
There are 1 cabin classes available to choose from on Portland to Chicago Midway 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 Midway?
Southwest, Delta, and Frontier are the most popular carriers operating from Portland to Chicago Midway
What airlines fly to Chicago Midway Airport?
Southwest, Delta and Frontier are the top three most popular airlines that fly to Chicago Midway Airport from Portland, Maine according to our data. Southwest is the first choice among our users, with 88% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 6 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Portland, Maine to Chicago Midway Airport on average per day?
The number of flights available between Portland, Maine and Chicago Midway Airport is 1 per day as of June 2025. The most frequent departure time is 7:00PM, with 100% of daily flights leaving in the evening.
How many flights depart from Portland, Maine to Chicago Midway Airport on average per week?
As of June 2025, there are 7 flights per week flying from Portland, Maine to Chicago Midway Airport. The most common day of the week flights depart is Tue, with 29% of flights taking off on this day.
When to book flights from Portland, Maine to Chicago Midway Airport
Cheap Portland, Maine to Chicago Midway Airport (PWM to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Portland, Maine to Chicago Midway Airport
How far is Portland to Chicago Midway by plane?
The straight-line distance from Portland to Chicago Midway is 894.8 mi. Typically, this will take 2h 30m by plane in normal conditions.
When did momondo last update prices for flights from Portland Airport to Chicago Midway Airport?
Prices for flights from Portland Airport to Chicago Midway Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Portland Airport to Chicago Midway Airport?
The number of operators available for flights from Portland Airport to Chicago Midway Airport is 2 as of June 2025.
How old do you have to be to fly from Portland Airport to Chicago Midway Airport?
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 Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway 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 Chicago Midway 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 Portland, Maine to Chicago Midway Airport?
Based on momondo bookings for flights between Portland, Maine and Chicago Midway Airport, the leading plane model is Boeing 737-800, making up 17.78% of the total bookings. Other popular models include Airbus A319 with 15.56%, Embraer 175 with 13.33%, and Boeing 737-700 Passenger/BBJ1 (winglets) with 11.11%.
What is the most popular airline from Portland, Maine to Chicago Midway Airport?
Based on momondo bookings for flights between Portland, Maine and Chicago Midway Airport, the leading airline is Southwest, making up 65% of the total bookings. Other popular airlines include Delta with 35%.
Best airlines flying from Portland, Maine to Chicago Midway Airport
Compare and see reviews for airlines that fly from Portland, Maine to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $201 | Free Cancellation | Rating 8.0 7,950 reviews | |||
| PriceFrom $264 | Free Cancellation | Rating 8.0 4,287 reviews |
Southwest Flights From Portland, Maine to Chicago Midway Airport
Southwest flies from Portland, Maine to Chicago Midway Airport around 7 times per week, with 4,287 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Portland, Maine to Chicago Midway Airport in the last 72 hours was $264 (round-trip), much lower than the average airfare cost of $371 for Southwest flights on this route.
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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?
Flights from Portland to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Portland to Chicago?
Once all potential Portland to Chicago 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 Portland to Chicago right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Portland to Chicago 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.