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Selected fares from Portland to Chicago

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Route Information for Flights from Portland to Chicago

Origin Airport IATA Code PDX
Destination Airport IATA Code ORD
Flight Price $90
Distance 2,774 km

Portland (PDX) to Chicago (CHI)

What?! A trip to Chicago! You'll be needing a flight from Portland. Well, unless you'd rather walk. And although we agree walking is great exercise, you probably want to get there before the year ends. Luckily, you found us. We can get you a fabulous deal on your flight from PDX to CHI.

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

Hotwire has been doing this for years, so we know a couple ways to snag 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.

Which days of the week are cheapest to fly?

Just like a yogi, it pays to be flexible. Those middle children of the work week, Tuesday and Wednesday, typically have the best rates. Next in line are Thursday and, surprisingly, Saturday. Most people like to come back on Sunday so you can save by leaving a day earlier.

What's the Saturday night stay rule?

Staying the weekend at your destination, like Chicago, usually means lower airfare since most people fly during this time. We are all for that!

Can you save while traveling during the off-peak season?

There's good reason that many people travel during certain times of the year -- they want to enjoy incredible weather. Summertime is when Europe, Hawaii, and Alaska are at their most popular. Popular Spring Break destinations are New Orleans, California, and Florida. Winter is prime for Mexico and the Caribbean because of its warm weather, as well as ski and snowboard destinations like the Colorado Rockies. Who doesn't love that harvest of autumn colors? The Pacific Northwest, Northern California, and New England are popular this time of the year. If you can plan your trip around these peak seasons, you'll not only save money, but you'll typically avoid the crowds. Win-win in our books.

If the price is right, pick it!

Unsurprisingly, you're not the only one longing for a terrific rate on a ticket from Portland to Chicago. You may miss out on your chance to get the carrier and the time you like.

What is the Hotwire Hot Rate?

We think the Hotwire Hot Rate is one of the best deals out there, although we may be slightly biased. You'll get a great deal on a flight from Portland (PDX) to Chicago (CHI). After your purchase, you'll get the time and name of the airline, but it is a risk where you can reap the rewards.

Book today

We are all about you saving as much as you can on your ticket from Portland to Chicago. These tips can help you score that unreal deal. For those risk-takers that don't like to be too risky, go for the Hotwire Hot Rate. You'll get your flight and have more coin in your pockets to do Chicago up right. So say "So long" to Portland and "Hello" to Chicago.

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^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.