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 7/1. 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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JetBlue flights from Portland, Maine to Chicago O'Hare Intl Airport
Our best JetBlue deals on Portland, Maine to Chicago O'Hare Intl Airport flight tickets
United Airlines flights from Portland, Maine to Chicago O'Hare Intl Airport
Our best United Airlines deals on Portland, Maine to Chicago O'Hare Intl Airport flight tickets
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How to get the cheapest flight ticket from Portland, Maine to Chicago O'Hare Intl 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 month to fly to Chicago O'Hare Intl Airport?
The month of May is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Portland, Maine averaging around $296.
What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?
The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Thursday when prices can be found for as low as $464. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday 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 $619.
What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?
Flying to Chicago O'Hare Intl Airport from Portland, Maine in the evening is the least expensive time of day to depart. momondo users have found prices as low as $107 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $534. 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 O'Hare Intl flight route?
Fly from Portland to Chicago O'Hare Intl for the best Portland - Chicago O'Hare Intl flight prices
How far in advance should I book a flight to Chicago O'Hare Intl Airport?
You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Portland, Maine when booking 20 weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $376 when searching 20 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Portland, Maine for as low as $210 on momondo.
What cabin class options are available on Portland to Chicago O'Hare Intl flights?
There are 4 cabin classes available to choose from on Portland to Chicago O'Hare Intl 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 O'Hare Intl?
American Airlines, Frontier, and United Airlines are the most popular carriers operating from Portland to Chicago O'Hare Intl
What airlines fly to Chicago O'Hare Intl Airport?
American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport. Keep in mind that there are 7 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Portland, Maine to Chicago O'Hare Intl Airport on average per day?
The number of flights available between Portland, Maine and Chicago O'Hare Intl Airport is 4 per day as of May 2025. The most frequent departure time is 4:00PM, with 55% of daily flights leaving at noon.
How many flights depart from Portland, Maine to Chicago O'Hare Intl Airport on average per week?
The number of flights available between Portland, Maine and Chicago O'Hare Intl Airport is 33 per week as of May 2025. The most frequent departure day is Thu, with 21% of weekly flights leaving on this day.
When to book flights from Portland, Maine to Chicago O'Hare Intl Airport
Cheap Portland, Maine to Chicago O'Hare Intl Airport (PWM to ORD) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Portland, Maine to Chicago O'Hare Intl Airport
How far is Portland to Chicago O'Hare Intl by plane?
There are 899.6 mi between Portland and Chicago O'Hare Intl. A reasonable flight in good conditions will take 2h 50m.
When did momondo last update prices for flights from Portland Airport to Chicago O'Hare Intl Airport?
Prices for flights from Portland Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Portland Airport to Chicago O'Hare Intl Airport?
There are 4 operators available for flights from Portland Airport to Chicago O'Hare Intl Airport as of May 2025.
How old do you have to be to fly from Portland Airport to Chicago O'Hare Intl 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 Portland Airport to Chicago O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Portland, Maine to Chicago O'Hare Intl Airport?
momondo data reveals that the most frequently booked plane model on the route from Portland, Maine to Chicago O'Hare Intl Airport is Embraer 175 (Enhanced Winglets), representing 27.65% of all bookings. The subsequent popular models are Embraer 175 at 16.47%, Airbus A319 at 14.29%, and Embraer 170 at 8.99%.
What is the most popular airline from Portland, Maine to Chicago O'Hare Intl Airport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Portland, Maine to Chicago O'Hare Intl Airport is United Airlines (65% of total bookings). The next most popular airlines are American Airlines (23%), Frontier (10%), and Delta (2%).
Best airlines flying from Portland, Maine to Chicago O'Hare Intl Airport
Compare and see reviews for airlines that fly from Portland, Maine to Chicago O'Hare Intl Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $38 | Free Cancellation | Rating 5.9 3,287 reviews | |||
| PriceFrom $124 | Free Cancellation | Rating 8.0 7,934 reviews | |||
| PriceFrom $158 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $205 | Free Cancellation | Rating 7.4 8,696 reviews |
United Airlines Flights From Portland, Maine to Chicago O'Hare Intl Airport
United Airlines flies from Portland, Maine to Chicago O'Hare Intl Airport around 13 times per week, with 8,696 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Portland, Maine to Chicago O'Hare Intl Airport in the last 72 hours was $205 (round-trip), much lower than the average airfare cost of $387 for United Airlines flights on this route.
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Why should I use momondo to find a flight deal from Portland to Chicago?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Portland to Chicago for you.
Can I find flights from Portland to Chicago with flexible booking policies on momondo?
momondo does allow users to show only those flights to Chicago from Portland which offer a flexible booking policy as well as other useful filters and features.
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?
Yes momondo offers price alerts on flights to Chicago from Portland. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.