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
Cheap one-way flights
Cheap last-minute flights
Cheap direct flights
Cheap bus & train deals from Chicago to Portland
All return flight deals from Chicago to Portland
See travel insights to Portland from
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 to Portland, Maine?
The cheapest month to fly to Portland, Maine from Chicago is in June. Flight prices, which tend to average around R5 439, are often lower during this time because this is during the off-season. If you don’t want to visit Portland, Maine in June, then you should wait until August to fly from Chicago, when ticket prices are also cheap, with an average price of R5 644.
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 13 weeks ahead of your departure date. In general, you can expect to find flights to Portland, Maine for around R7 485 when searching 13 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 R3 769 on momondo.
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
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?
Based on momondo bookings for flights between Chicago and Portland, Maine, the leading plane model is Embraer 175 (Enhanced Winglets), making up 39,46% of the total bookings. Other popular models include Boeing 737-700 with 16,22%, Embraer 175 with 15,14%, and Embraer 170 with 13,78%.
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.