Cheap Flights from Portland (PWM) to Chicago (CHI)

Portland (PWM) to Chicago (CHI)

Are you flying to Chicago for a much-needed vacation or is it about time for you to have a family reunion? Or maybe you're traveling for work? Hey, anything that gets you away from that desk is a win in our books. You're on the right page to get a killer rate on your upcoming flight from Portland. Whether you fancy yourself an expert at navigating the friendly skies or only have a few trips under your wing, read below to score the best deal on your next flight.

How do you get the best deal on a flight from Portland to Chicago?

Hotwire has been in the game a long time, so we know a few ways to get the best price on your flight to Chicago. You can pocket that extra cash for more than just getting from point A to point B with a little know-how.

What is the cheapest day to fly?

With the right attitude and flexibility, you can fly for less. Below are the cheapest days to fly:

• Tuesday and Wednesday—You know how most stores are not crowded midweek? Same thing here. Most people opt to depart at the beginning or end of the week.
• Thursday and Saturday—Get a head start on that Friday crowd. This also works on your return flight. Shorten your holiday by a day and increase your savings.
• Monday through Thursday—If you're flying internationally, deals are often available when departing these days.

Why are flights cheaper if you stay over the weekend?

Spending the weekend at your destination, like Chicago, usually means a less-expensive ticket since most people fly during this time. Of course, we don't want to twist your rubber arm or anything.

What are shoulder seasons?

It's all about going to a place when its weather is at its best. For example, Europe, Hawaii, and Alaska are big hits in the summer. Popular Spring Break destinations are New Orleans, California, and Florida. Feeling the bitter cold? Well, the Caribbean Islands and Mexico can warm you up. Unless you're a ski bum -- then places like Colorado will be your winter wonderland. During autumn, Northern California, the Pacific Northwest, and New England draw visitors. Flying during less popular periods can mean extra money in your wallet -- yes, please!

If the price is right, pick it!

You're not the only person waiting an amazing price on a ticket from Portland to Chicago. You might miss your chance to dial in the time and the flight you wanted.

Are there any other ways to save on my flight to Chicago?

We think the Hotwire Hot Rate is one of the best deals out there, although we may be slightly biased. You'll get a fantastic price on a flight from Portland (PWM) to Chicago (CHI). You won't find out the time and airline until after you book, but with a little risk you can get huge savings.

Book your Portland to Chicago flight today

Try these tips before you reserve your upcoming flight from Portland to Chicago. You may have enough coin back in your wallet to add something that makes this vacay extra exciting ... or you can roll that money over and put it toward your next trip out of Portland.

^Savings based on all package bookings with Flight + Hotel made on Hotwire.com from January 1, 2018 to December 31, 2018 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.