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Book $136 Cheap Alaska Airlines flights from Portland (PDX) to Chicago (CHI)

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Flight deals from Portland to Chicago

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Prices shown below were available within the past 3 days for the period specified and should not be considered the final price offered. Please note that availability and prices are subject to change.

Alaska Airlines flight deals from Portland to Chicago

Portland Chicago
BEST
DEAL
Fri, 16 May PDX - ORD
$144 $136
Prime price per passenger
Portland Chicago
BEST
DEAL
Sun, 02 Mar PDX - ORD
Mon, 03 Mar ORD - PDX
$277 $268
Prime price per passenger
Portland Chicago
BEST
DEAL
Fri, 28 Feb PDX - ORD
Fri, 28 Feb ORD - PDX
$561 $543
Prime price per passenger

Best flight offers from other airlines

Portland Chicago
BEST
DEAL
Wed, 26 Feb PDX - ORD
Mon, 03 Mar ORD - PDX
$181 $172
Prime price per passenger
Portland Chicago
BEST
DEAL
Sat, 01 Mar PDX - ORD
Mon, 03 Mar ORD - PDX
-27 %
$188 $137
Prime price per passenger
Portland Chicago
BEST
DEAL
Fri, 28 Feb PDX - ORD
Mon, 03 Mar ORD - PDX
$140 $132
Prime price per passenger
Portland Chicago
BEST
DEAL
Sat, 01 Mar PDX - ORD
Sun, 02 Mar ORD - PDX
$161 $153
Prime price per passenger
Portland Chicago
BEST
DEAL
Fri, 28 Feb PDX - ORD
Sun, 02 Mar ORD - PDX
$162 $154
Prime price per passenger
Portland Chicago
BEST
DEAL
Wed, 26 Feb PDX - ORD
Mon, 03 Mar ORD - PDX
$175 $166
Prime price per passenger

Get your flight with Alaska Airlines to Chicago from Portland starting at $136

The Best Portland to Chicago Flight Deals with Alaska Airlines

With eDreams, finding the best Alaska Airlines deals for your trip from Portland to Chicago couldn’t be easier. Imagine this: exclusive discounts, intuitive booking tools, and plenty of helpful perks—all at your fingertips! Say goodbye to the hassle of planning and hello to the excitement of your upcoming adventure in Chicago.

Whether you’re looking for unbeatable prices, a custom-fit itinerary, or some extra perks, eDreams is your all-in-one travel partner for every part of the Portland (PDX) to Chicago (CHI) journey. Stick around to find out why booking with eDreams is the best way to kick off your trip.

Flying from Portland to Chicago with Alaska Airlines

Flying from Portland (PDX) to Chicago (CHI) with Alaska Airlines (AS) is all about comfort and convenience. From check-in to touchdown, Alaska Airlines ensures a smooth experience, so you can just sit back and relax. You’ll find fast check-ins, extra legroom, and attentive service designed for a stress-free trip.

Once onboard, the friendly crew will make sure you have everything you need. Many routes offer in-flight Wi-Fi, so you can stay connected, binge-watch shows, or catch up on work if you need to. Feeling hungry? Alaska Airlines has a great selection of snacks and meals to keep you satisfied mid-flight. And if you want a bit more luxury, you can treat yourself to upgrades and priority boarding, adding a personal touch to your journey. With great service and a focus on a smooth, enjoyable flight, Alaska Airlines makes your trip from Portland to Chicago easy and fun.

Book Your Flight with eDreams and Enjoy the Perks

Booking affordable flights from Portland (PDX) to Chicago (CHI) with eDreams isn’t just about getting a great deal—it’s about making travel planning effortless. With eDreams, you get awesome perks that make your journey easier and more enjoyable:

Your Journey from Portland to Chicago with Alaska Airlines

The journey from Portland (PDX) to Chicago (CHI) is all about getting you to your destination comfortably and quickly, so your adventure can start as soon as you land. This direct route offers plenty of options, whether you prefer a quick non-stop flight or more flexibility with layovers. Whatever your style, there’s a schedule that fits.

Departing from Portland and Arriving at Chicago: What to Expect

When departing from Portland, enjoy easy airport access, clear signage, and quick check-ins for a stress-free start. You’ll breeze through security, leaving plenty of time to relax before takeoff.

When you land in Chicago, you’ll be greeted by a modern terminal with plenty of transportation options like taxis, buses, and shuttles to get you on your way. Whether heading to your hotel or diving into sightseeing, everything you need is right there.

Best Time to Book Your Portland — Chicago Trip with Alaska Airlines

For the best Alaska Airlines flight deals from Portland to Chicago, timing is everything! Booking in advance often means lower fares, especially during off-peak seasons when Chicago is quieter and flights are more budget-friendly. Check the climate to plan for the ideal weather to suit your trip—whether for mild outdoor adventures or cultural explorations. With a bit of planning, you’re set for an unforgettable getaway!

Alaska Airlines Portland-Chicago flights FAQ's

Which airports does Alaska Airlines fly between Portland and Chicago?
For flights between Portland and Chicago, Alaska Airlines operates the following airport routes: For flights between Portland and Chicago, Alaska Airlines operates from the following airport routes: Portland International Airport (PDX) to O hare International Airport (ORD)
What do Alaska Airlines flights from Portland to Chicago cost?
One of Alaska Airlines cheapest prices for a Portland to Chicago flight we have right now is $136. On average though, flights with Alaska Airlines cost $327.30 for the route Portland to Chicago, but it mostly depends on the season and how far in advance you book your tickets.
Cheapest Ticket Price $136 The most affordable rate found in the last 72 hours for flights operated by Alaska Airlines leaving from Portland and going to Chicago, according to our customers' bookings.
Flight Time 4 h and 5 m The Alaska Airlines flight duration between Portland and Chicago is around 4 h and 5 m, however it could be affected by other circumstances.
Departure Airport Portland International Airport Your departure will be from Portland International Airport, when flying with Alaska Airlines from Portland to Chicago.
Arrival Airport O'hare International Airport When flying with Alaska Airlines from Portland to Chicago, your arrival airport will be Portland International Airport.

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