Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Chicago to Portland, Maine

1 adult
0 bags
'This year, momondo is the #1 place for airfares on the internet.'
Save money when you book flights with momondo
Big names, great deals
Big names, great deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customise 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 Chicago to Portland

Cheap return flights

These are some of the best return flight deals from Chicago to Portland that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Portland.

Cheap last-minute flights

Planning a quick getaway from Chicago to Portland? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Portland, so you can enjoy a seamless trip without stopovers.

Cheap bus & train deals from Chicago to Portland

Find recent round-trip train or bus tickets from Chicago to Portland.

All round-trip flight deals to Portland

The cheapest plane tickets to Portland found on KAYAK recently.
ORD-PWM
2h 30mdirect
PWM-ORD
3h 06mdirect
Emirates
Find Deal
ORD-PWM
2h 23mdirect
PWM-ORD
3h 05mdirect
Air New Zealand
Find Deal
ORD-PWM
2h 23mdirect
PWM-ORD
2h 57mdirect
United Airlines
Find Deal
ORD-PWM
2h 30mdirect
Emirates
Find Deal
ORD-PWM
2h 23mdirect
Air New Zealand
Find Deal
ORD-PWM
2h 23mdirect
United Airlines
Find Deal

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 cheapest month to fly from Chicago to Portland, Maine?

January. The cheapest time of year to fly to Portland, Maine from Chicago is January. The most expensive is December.

How far in advance should you book Chicago to Portland, Maine flights?

59 days before. The cheapest time to buy a flight from Chicago to Portland, Maine is approximately 59 days to departure

How have Chicago to Portland, Maine flight prices changed over time?

As of November 2024, prices for Chicago to Portland, Maine flights are approximately 27% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Portland, Maine

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Portland, Maine according to our flight data. Find out which month and days have the cheapest flights.
Estimated return price

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

Direct flights

None
There are no direct flights from Chicago to Portland, Maine. There are no popular flight routes from Chicago to Portland, Maine.

  • How far is Chicago to Portland by plane?

    A flight from Chicago to Portland will travel around 1428,2 km.

  • When did momondo last update prices for flights from Chicago to Portland Airport?

    Prices for flights from Chicago to Portland Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Chicago to Portland Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Portland Airport.

  • What documentation or ID do you need to fly to Portland Airport?

    The required travel and health documents for your Portland Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's licence and a passport valid for six months after your intended arrival at Portland Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Chicago to Portland, Maine?


Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Portland?

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 Chicago to Portland for you.

Can I find flights from Chicago to Portland with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to Portland flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Portland?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Portland from Chicago.

I’m not ready to book a flight from Chicago to Portland right now. Can momondo alert me if prices change?

Price alerts on flights to Portland from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.


An easier way to manage your Portland, Maine trip

We make it super easy to schedule, organise and travel with friends or family. Trips is free – and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Sun 24/11
Sun 1/12
Email me momondo's favourite deals

Find better results for your trip to the United States

Fly your favourite airline to Portland

Airlines are sorted and displayed according to clicks in the past 7 days on momondo