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CHI - PDX

$49 Find cheap flights from Chicago to Portland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Portland departing on 8/6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Tue 7/2
Tue 7/9

Search hundreds of travel sites at once for deals on flights to Portland

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Portland.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Portland.
In the last 7 days travelers have searched 41,909,192 times on KAYAK, and here is why:

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Cheap flight deals from Chicago to Portland (CHI-PDX)

 
These are the cheapest deals for flights from Chicago to Portland currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Chicago to Portland

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to Portland.

Recent one-way flight deals from Chicago to Portland

Only flying one-way? Below are some of the best one-way flight deals from Chicago to Portland found on KAYAK recently.

Recent last minute flight deals from Chicago to Portland

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Chicago to Portland.

Recent direct flight deals from Chicago to Portland

The latest deals for direct flights from Chicago to Portland so you can sit back and relax without the need for a layover.

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.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
8:26 pm - 10:56 pmORD-PDX
4h 30mnonstop
11:51 pm - 5:41 amPDX-ORD
3h 50mnonstop
$83Spirit Airlines
Find Deal
Sat, Sep 7 - Wed, Sep 11
9:04 pm - 11:28 pmORD-PDX
4h 24mnonstop
12:30 am - 6:31 amPDX-ORD
4h 01mnonstop
$84Spirit Airlines
Find Deal
Mon, Aug 19 - Tue, Aug 27
8:26 pm - 10:56 pmORD-PDX
4h 30mnonstop
11:51 pm - 5:41 amPDX-ORD
3h 50mnonstop
$85Spirit Airlines
Find Deal
Sat, Sep 7 - Wed, Sep 11
8:26 pm - 10:53 pmORD-PDX
4h 27mnonstop
11:53 pm - 6:00 amPDX-ORD
4h 07mnonstop
$93Spirit Airlines
Find Deal
Fri, Jun 14 - Mon, Jun 17
4:09 pm - 2:50 pmMDW-PDX
24h 41m1 stop
9:26 pm - 10:42 amPDX-MDW
11h 16m1 stop
$177Frontier
Find Deal
Fri, Aug 23 - Mon, Sep 2
4:09 pm - 2:50 pmMDW-PDX
24h 41m1 stop
9:26 pm - 10:42 amPDX-MDW
11h 16m1 stop
$178Frontier
Find Deal
Mon, Aug 19 - Wed, Aug 28
8:00 am - 10:20 amORD-PDX
4h 20mnonstop
11:11 pm - 5:15 amPDX-ORD
4h 04mnonstop
$188Alaska Airlines
Find Deal
Wed, Aug 14 - Mon, Aug 19
8:00 am - 10:20 amORD-PDX
4h 20mnonstop
11:11 pm - 5:15 amPDX-ORD
4h 04mnonstop
$199Alaska Airlines
Find Deal
Thu, Aug 15 - Mon, Aug 19
7:10 am - 9:38 amORD-PDX
4h 28mnonstop
12:20 am - 6:18 amPDX-ORD
3h 58mnonstop
$233United Airlines
Find Deal
Wed, Jul 17 - Fri, Jul 19
6:50 pm - 11:54 pmORD-PDX
7h 04m1 stop
12:30 am - 8:42 amPDX-ORD
6h 12m1 stop
$252Delta
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Wed, Jun 26 - Sat, Jun 29
8:34 pm - 10:56 pmORD-PDX
4h 22mnonstop
$49Spirit Airlines
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Tue, Aug 6
8:26 pm - 10:53 pmORD-PDX
4h 27mnonstop
$53Spirit Airlines
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Thu, Jun 27
11:32 am - 8:36 pmMDW-PDX
11h 04m1 stop
$96Frontier
Find Deal
Mon, Sep 9
10:11 pm - 8:45 amORD-PDX
12h 34m1 stop
$96Frontier
Find Deal
Sat, Jun 15
6:20 pm - 11:41 pmORD-PDX
7h 21m1 stop
$118Alaska Airlines
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Fri, Jul 26
2:25 pm - 4:45 pmORD-PDX
4h 20mnonstop
$127Alaska Airlines
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Tue, Jun 18
7:10 am - 9:38 amORD-PDX
4h 28mnonstop
$130United Airlines
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Tue, Jul 2
8:30 pm - 11:02 pmORD-PDX
4h 32mnonstop
$139American Airlines
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Tue, Oct 15
7:10 am - 9:38 amORD-PDX
4h 28mnonstop
$161United Airlines
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Sun, Jul 21
2:46 pm - 10:48 pmORD-PDX
10h 02m1 stop
$176American Airlines
Find Deal
Fri, Aug 30
8:26 pm - 10:53 pmORD-PDX
4h 27mnonstop
11:53 pm - 6:00 amPDX-ORD
4h 07mnonstop
$99Spirit Airlines
Find Deal
Fri, Jun 7 - Wed, Jun 12
8:26 pm - 10:53 pmORD-PDX
4h 27mnonstop
11:53 pm - 6:00 amPDX-ORD
4h 07mnonstop
$119Spirit Airlines
Find Deal
Fri, Jun 7 - Thu, Jun 13
7:05 am - 5:48 pmMDW-PDX
12h 43m1 stop
8:39 am - 9:30 pmPDX-MDW
10h 51m1 stop
$180Frontier
Find Deal
Tue, Jun 4 - Sat, Jun 8
6:35 am - 4:26 pmMDW-PDX
11h 51m1 stop
12:49 am - 9:30 pmPDX-MDW
18h 41m1 stop
$185Frontier
Find Deal
Thu, Jun 6 - Fri, Jun 7
8:00 am - 10:20 amORD-PDX
4h 20mnonstop
11:11 pm - 5:15 amPDX-ORD
4h 04mnonstop
$256Alaska Airlines
Find Deal
Tue, Jun 4 - Wed, Jul 10
8:00 am - 10:20 amORD-PDX
4h 20mnonstop
7:43 am - 1:54 pmPDX-ORD
4h 11mnonstop
$308Alaska Airlines
Find Deal
Thu, Jun 6 - Sat, Jun 8
10:09 am - 12:39 pmORD-PDX
4h 30mnonstop
12:59 am - 11:02 amPDX-ORD
8h 03m1 stop
$343American Airlines
Find Deal
Thu, Jun 6 - Fri, Jun 7
4:10 pm - 6:35 pmORD-PDX
4h 25mnonstop
12:15 am - 6:13 amPDX-ORD
3h 58mnonstop
$358United Airlines
Find Deal
Wed, Jun 5 - Thu, Jun 6
8:00 pm - 10:26 pmORD-PDX
4h 26mnonstop
12:20 am - 6:18 amPDX-ORD
3h 58mnonstop
$360United Airlines
Find Deal
Tue, Jun 4 - Tue, Jul 9
10:09 am - 12:39 pmORD-PDX
4h 30mnonstop
12:59 am - 9:55 amPDX-ORD
6h 56m1 stop
$410American Airlines
Find Deal
Fri, Jun 7 - Sun, Jun 9
8:26 pm - 10:56 pmORD-PDX
4h 30mnonstop
11:51 pm - 5:41 amPDX-ORD
3h 50mnonstop
$83Spirit Airlines
Find Deal
Sat, Sep 7 - Wed, Sep 11
9:04 pm - 11:28 pmORD-PDX
4h 24mnonstop
12:30 am - 6:31 amPDX-ORD
4h 01mnonstop
$84Spirit Airlines
Find Deal
Mon, Aug 19 - Tue, Aug 27
8:26 pm - 10:56 pmORD-PDX
4h 30mnonstop
11:29 pm - 5:30 amPDX-ORD
4h 01mnonstop
Thu, Oct 3 - Mon, Oct 14
9:05 pm - 11:29 pmORD-PDX
4h 24mnonstop
11:25 pm - 5:27 amPDX-ORD
4h 02mnonstop
$177United Airlines
Find Deal
Wed, Aug 21 - Sat, Aug 24
8:00 am - 10:20 amORD-PDX
4h 20mnonstop
11:11 pm - 5:15 amPDX-ORD
4h 04mnonstop
$188Alaska Airlines
Find Deal
Wed, Aug 14 - Mon, Aug 19
8:34 pm - 10:56 pmORD-PDX
4h 22mnonstop
11:11 pm - 5:15 amPDX-ORD
4h 04mnonstop
Mon, Aug 12 - Thu, Aug 15
8:00 am - 10:20 amORD-PDX
4h 20mnonstop
11:11 pm - 5:15 amPDX-ORD
4h 04mnonstop
$199Alaska Airlines
Find Deal
Thu, Aug 15 - Mon, Aug 19
7:10 am - 9:38 amORD-PDX
4h 28mnonstop
12:15 am - 6:12 amPDX-ORD
3h 57mnonstop
$214United Airlines
Find Deal
Thu, Jul 25 - Sun, Aug 4
8:24 pm - 10:49 pmORD-PDX
4h 25mnonstop
11:58 pm - 6:00 amPDX-ORD
4h 02mnonstop
$257American Airlines
Find Deal
Sun, Aug 4 - Wed, Aug 14
10:12 am - 12:43 pmORD-PDX
4h 31mnonstop
11:27 am - 5:29 pmPDX-ORD
4h 02mnonstop
$260American Airlines
Find Deal
Fri, Aug 16 - Tue, Aug 20
3:05 pm - 11:17 amChicago Union-
Portland Union Station
46h 12mnonstop
4:45 pm - 4:45 pmPortland Union Station-
Chicago Union
46h 00mnonstop
$354Amtrak
Find Deal
Mon, Jul 1 - Mon, Jul 8
3:05 pm - 10:35 amChicago Union-
Vancouver
45h 30mnonstop
5:09 pm - 4:45 pmVancouver-
Chicago Union
45h 36mnonstop
$354Amtrak
Find Deal
Mon, Jul 1 - Mon, Jul 8
3:05 pm - 10:35 amChicago Union-
Vancouver
45h 30mnonstop
5:09 pm - 4:45 pmVancouver-
Chicago Union
45h 36mnonstop
$354Amtrak
Find Deal
Mon, Jul 1 - Mon, Jul 8
3:05 pm - 11:17 amChicago Union-
Portland Union Station
46h 12mnonstop
4:45 pm - 4:45 pmPortland Union Station-
Chicago Union
46h 00mnonstop
$354Amtrak
Find Deal
Mon, Jul 1 - Mon, Jul 8

Flights from Chicago to Portland - Travel Insights & Trends

Get data-powered insights and trends into flights from Chicago to Portland to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to Portland flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Chicago to Portland.
Our data shows that the cheapest route for a one-way flight from Chicago to Portland cost $50 and was between Chicago O'Hare Intl Airport and Portland. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $104.

What’s the cheapest day of the week to fly from Chicago to Portland?

The average price of all flights from Chicago to Portland clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to Portland on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Chicago to Portland. For your return ticket, we recommend flying on a Saturday and avoiding Mondays for the best deals.

What is the cheapest month to fly from Chicago to Portland?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago to Portland, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago to Portland is January, where tickets cost $313 on average. On the other hand, the most expensive months are July and June, where the average cost of tickets is $417 and $405 respectively.

How far in advance should I book a flight from Chicago to Portland?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago to Portland, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago to Portland, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 86 days before departure.

Which airlines provide the cheapest flights from Chicago to Portland?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the best return deals on flights connecting Chicago to Portland were found on Spirit Airlines ($83) and Frontier ($177). Spirit Airlines proposed the cheapest one-way flight at $49.

Which airlines fly most frequently between Chicago and Portland?

The airlines most regularly connecting Chicago to Portland are United Airlines (6 flights per day), Southwest (3 flights per day), and Alaska Airlines (2 flights per day).

Which airlines fly non-stop between Chicago and Portland?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Chicago to Portland.
There are 5 airlines that fly nonstop from Chicago to Portland. They are: Alaska Airlines, American Airlines, Southwest, Spirit Airlines and United Airlines. The cheapest price of all airlines flying this route was found with Spirit Airlines at $68 for a one-way flight. On average, the best prices for this route can be found at Spirit Airlines.

How many flights are there between Chicago and Portland per day?

Each day, there are between 13 and 17 nonstop flights that take off from Chicago and land in Portland, with an average flight time of 4h 23m. The most common departure time is 8:00 pm and most flights take off in the morning. Each week, there are 106 flights. The most frequent day of departure is Monday, when 16% of all weekly flights depart. The fewest flights depart on a Sunday.

Which cabin class options are there for flights between Chicago and Portland?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Chicago to Portland take?

The average nonstop flight takes 4h 20m, covering a distance of 1,749 miles.

What’s the earliest departure time from Chicago to Portland?

Early birds can take the earliest flight from Chicago at 7:10 am and will be landing in Portland at 9:38 am.

What’s the latest departure time from Chicago to Portland?

If you prefer to fly at night, the latest flight from Chicago to Portland jets off at 10:50 pm and lands at 1:10 am.

Good to know

Low season

February

High season

June

Cheapest flight

$49
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Chicago O'Hare Airport to Portland

When to book flights from Chicago to Portland

Are your dates flexible? Find out the best times to travel from Chicago to Portland based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Portland

  • Can I fly out of Chicago with pets?

    Traveling with your pet out of Chicago is a breeze as both O’Hare International Airport and Midway International Airport are pet friendly. The pet relief stations in O’Hare International Airport are located at Terminals 1, 2, 3, 5, and the Multi-Modal Facility. Midway International Airport also has pet relief stations located both outside and inside the terminal. The pet relief station located inside the terminal is just past the Concourse A security checkpoint and features artificial turf and an automatic flushing system for easy cleanup.

  • Which airport is best for people with disability needs?

    If you may require accessibility services, you should consider flying out of Midway International Airport. The airport is less crowded than O’Hare International Airport, meaning that most areas and facilities will be available for use. The airport also provides a multitude of accessibility features, such as wheelchair-accessible restrooms and elevators with raised numerals and Braille. The airport also provides parking spots for people with disabilities, which are wide enough for ramp and lift access.

  • How do I get from Portland International Airport to downtown Portland?

    The easiest and most convenient way to get from Portland International Airport to downtown Portland is by using the Max Light rail Red Line, which will take you less than 40min. The last train leaves the airport at 11:50 pm. You can also decide to use private means, such as taxicabs, ridesharing services, or car rental from any of the several car rental companies that operate from within the airport.

  • How do I get from downtown Chicago to O’Hare International Airport?

    Getting to O’Hare International Airport from downtown Chicago is made easy by the city’s intricate public transportation system. You can conveniently use the CTA L Trains to get from the city to the airport, as well as the airport shuttle services that transport passengers to the airport. Additionally, the airport has multiple parking options that allow you to drive to the airport and leave your vehicle for either a short or a long time.

  • What is the cheapest flight from Chicago to Portland?

    In the last 3 days, the lowest price for a flight from Chicago to Portland was $49 for a one-way ticket and $83 for a round-trip.

  • Do I need a passport to fly between Chicago and Portland?

    No, a passport isn't needed to fly from Chicago to Portland. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Chicago to Portland?

    There are 2 airports in Chicago (Chicago Midway and Chicago O'Hare Intl.) and only 1 airport in Portland (Portland). The cheapest flights are generally found on the Chicago O'Hare Airport to Portland flight route.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Portland?

    American Airlines, Alaska Airlines, and Delta offer inflight Wi-Fi service on the Chicago to Portland flight route.

  • Which aircraft models fly most regularly from Chicago to Portland?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago to Portland flight route.

  • Which airline alliances offer flights from Chicago to Portland?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago and Portland, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Portland?

    There are nonstop flights from Chicago to Portland on a daily basis.

  • Which is the best airline for flights from Chicago to Portland, Alaska Airlines or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to Portland are Alaska Airlines and Delta. With an average price for the route of $338 and an overall rating of 8.0, Alaska Airlines is the most popular choice. Delta is also a great choice for the route, with an average price of $326 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from Chicago to Portland?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Portland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Portland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Portland from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Portland?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Portland with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Portland?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Portland from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding a cheap flight from Chicago to Portland

  • Looking for a cheap flight? 25% of our users found flights on this route for $103 or less one-way and $187 or less round-trip.
  • When traveling out of Chicago, you have the option of departing from any of the two major international airports serving the city: O’Hare International Airport (ORD) or Midway International Airport (MDW).
  • If you have an early flight from Chicago to Portland, consider departing from O’Hare International Airport as the airport has a hotel on its premises where you can book a stay for the night to allow you to be on time for your early morning flight.
  • If you need to get some work done or relax after your flight into Portland International Airport (PDX), make use of the several lounges available at the airport. These lounges are located inside security at Concourse C, D, and E, while there is one lounge located outside security at the Main Terminal.
  • Midway International Airport as the airport provides lactation pods where mothers can breastfeed or pump in a private and safe space. You can find the lactation pod at Concourse A, next to Gate A5.
  • If you misplace any of your items when traveling out of O’Hare International Airport, make sure to contact the organization closest to where you last saw the items. You can contact any of the following agencies: Parking Facilities, food service, TSA Checkpoints, On the Airport Transit Systems, or the Customs Area.
See more tips

Prefer to fly non-stop from Chicago to Portland?

Find which airlines fly direct from Chicago to Portland, which days they fly and book direct flights.

Nonstop departures

Chicago to Portland

Monday

Air Canada, Alaska Airlines, American Airlines, +10 more

Air Canada, Alaska Airlines, +11 more

Tuesday

Air Canada, Alaska Airlines, American Airlines, +11 more

Air Canada, Alaska Airlines, +12 more

Wednesday

Air Canada, Alaska Airlines, American Airlines, +11 more

Air Canada, Alaska Airlines, +12 more

Thursday

Air Canada, Alaska Airlines, American Airlines, +10 more

Air Canada, Alaska Airlines, +11 more

Friday

Air Canada, Alaska Airlines, American Airlines, +11 more

Air Canada, Alaska Airlines, +12 more

Saturday

Air Canada, Alaska Airlines, American Airlines, +11 more

Air Canada, Alaska Airlines, +12 more

Sunday

Air Canada, Alaska Airlines, American Airlines, +11 more

Air Canada, Alaska Airlines, +12 more

See more direct flights

Nonstop returns

Portland to Chicago

Monday

Air Canada, Alaska Airlines, American Airlines, +11 more

Air Canada, Alaska Airlines, +12 more

Tuesday

Air Canada, Alaska Airlines, American Airlines, +12 more

Air Canada, Alaska Airlines, +13 more

Wednesday

Air Canada, Alaska Airlines, American Airlines, +12 more

Air Canada, Alaska Airlines, +13 more

Thursday

Air Canada, Alaska Airlines, American Airlines, +11 more

Air Canada, Alaska Airlines, +12 more

Friday

Air Canada, Alaska Airlines, American Airlines, +12 more

Air Canada, Alaska Airlines, +13 more

Saturday

Air Canada, Alaska Airlines, American Airlines, +12 more

Air Canada, Alaska Airlines, +13 more

Sunday

Air Canada, Alaska Airlines, American Airlines, +12 more

Air Canada, Alaska Airlines, +13 more

See more direct flights
See more direct flights

Top 5 airlines serving from Chicago to Portland

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Portland. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Portland? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Alaska AirlinesOverall score based on 9198 reviews
7.3Food
7.9Comfort
7.3Entertainment
8.2Boarding
8.6Crew
Airline reviews

Loved the airport. The announcements for boarding were too loud & echoing in the large waiting area, so hard to follow. Other than that, we had a great experience.

10.0 ExcellentNancy, Jun 2024STS - PDX
Read more about Alaska Airlines reviews

Loved the airport. The announcements for boarding were too loud & echoing in the large waiting area, so hard to follow. Other than that, we had a great experience.

Staff was very friendly. Flight was on time and arrived early. Flight was comfortable.

Easy and quick boarding. A bit of a hard landing at PDX

I think u could offer more than apple juice or water.

Pleasant crew and on time travel. It was all good.

It was ok. Alaska was adequate. Efficient and what I paid for it was fair. The boarding area at the gate was a joke. By the time they get past the C boarding group people all line up impatiently and then it’s chaos. We were boarding early then we sat on the tarmac for 30 minutes. I would of rather sat in the airport.

The entire flight was terrible. I recently had neurocervical surgery, and I needed a wheelchair to get to the gate. They were wonderful, truly. The flight staff was lovely, as well. Despite the need for assistance, I was put in the middle seat in the last row in front of the toilets. It was "policy" that I couldn't be moved. The pain I felt after the flight was astromnomical. The flight was so WARM, I was sweating, and the "air" did nothing to the stuffy feeling. The seats were uncomfortable, the plane itself was in bad/worn condition (although very clean - thanks to the staff) - and the flight was definitely rocky (not the pilot's fault, of course). All in all - one of the worst flights I've ever taken. The humans were wonderful!! You have a really great team. But your flight policies and your plane are absymal. For what you charge, you need to upgrade your plane and your policies.

First flights on Alaska Air, and I will go out of my way to fly them whenever I can in the future. An incredible experience, above and beyond any other airline.

The seats were incredibly small and the attendants were grumpy the whole time.

It was a tiny plane … even though I paid for upgrade, no internet… no plug ins, no entertainment… 👎🏻

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

they made me check my carryon. There was space in the overhead bins.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

We were re routed due to a flight cancellation. We did not fly out of Miami. We originally booked first class and were moved to coach without being compensated.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

2 gate changes, several announced delays, not enough room and seats at the gate. Many had to stand while waiting. The actual flight was fine.

The non stop flight and able to go into Atlantic City airport. They could lower the prices. It starts out low but then if you want to bring luggage and pick your seat the price goes up quite a bit.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

We can’t predict circumstances like this ahead of time, but I give your staff a hats off for immediately giving us updated informations.

It was nice! There was a very unhappy child in front of us and the flight attendant did a great job calming the child. I was impressed.

The plane was not on time for boarding or departure or arrivals.

EVERYTHING WAS WONDERFUL HOSPITALITY THE HELP.THE SEATING FRIENDLY ALWAYS HAVE A GOOD RIDE NOT ONE BAD EXPERIENCE WITH THEM

This was the smoothest flight I have had in awhile. I was also offered an exit row seat for a great upgrade cost and was able to sleep almost thr whole flight due to comfort and a smooth flight. We left on time and arrived on time.

No food not even water offered unless you buy it and no usb in the seat but other than that everything was good

Because our flight from marsh Harbor to Fort Lauderdale was over three hours delayed it caused us to miss our flight in Fort Lauderdale. Because we missed that flight, it cost us nearly $100 apiece for four different travelers which totaled nearly $400. We are seeking a reimbursement for the flight that we missed in Fort Lauderdale Florida.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

Book cheap flights from Chicago to Portland

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Portland found on KAYAK in the last 72 hours.
8/6Tue
nonstopSpirit Airlines
4h 22mORD-PDX
$49
6/27Thu
nonstopSpirit Airlines
4h 27mORD-PDX
$53
9/9Mon
1 stopFrontier
11h 04mMDW-PDX
$96
6/15Sat
1 stopFrontier
12h 34mORD-PDX
$96
7/26Fri
1 stopAlaska Airlines
7h 21mORD-PDX
$118
6/18Tue
nonstopAlaska Airlines
4h 20mORD-PDX
$127
7/2Tue
nonstopUnited Airlines
4h 28mORD-PDX
$130
10/15Tue
nonstopAmerican Airlines
4h 32mORD-PDX
$139
7/21Sun
nonstopUnited Airlines
4h 28mORD-PDX
$161
8/30Fri
1 stopAmerican Airlines
10h 02mORD-PDX
$176

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Last minute flights from Chicago to Portland

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Portland that are departing in the next 10 days.
6/7Fri
nonstopSpirit Airlines
4h 27mORD-PDX
6/12Wed
nonstopSpirit Airlines
4h 07mPDX-ORD
$99
6/7Fri
nonstopSpirit Airlines
4h 27mORD-PDX
6/13Thu
nonstopSpirit Airlines
4h 07mPDX-ORD
$119
6/4Tue
multi-stopFrontier
12h 43mMDW-PDX
6/8Sat
multi-stopFrontier
10h 51mPDX-MDW
$180
6/6Thu
multi-stopFrontier
11h 51mMDW-PDX
6/7Fri
multi-stopFrontier
18h 41mPDX-MDW
$185
6/4Tue
nonstopAlaska Airlines
4h 20mORD-PDX
7/10Wed
nonstopAlaska Airlines
4h 04mPDX-ORD
$256
6/6Thu
nonstopAlaska Airlines
4h 20mORD-PDX
6/8Sat
nonstopAlaska Airlines
4h 11mPDX-ORD
$308
6/6Thu
nonstopAmerican Airlines
4h 30mORD-PDX
6/7Fri
multi-stopAmerican Airlines
8h 03mPDX-ORD
$343
6/5Wed
nonstopUnited Airlines
4h 25mORD-PDX
6/6Thu
nonstopUnited Airlines
3h 58mPDX-ORD
$358
6/4Tue
nonstopUnited Airlines
4h 26mORD-PDX
7/9Tue
nonstopUnited Airlines
3h 58mPDX-ORD
$360
6/7Fri
nonstopAmerican Airlines
4h 30mORD-PDX
6/9Sun
multi-stopAmerican Airlines
6h 56mPDX-ORD
$410

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Flights to Portland

Destination:

Portland (PDX)United States

Return flight deals:

Portland - Chicago

Cabin classes:

$640
$932
$598
$104

Compare transportation modes for Chicago to Portland

Average priceAverage duration
Flights$4644h 20m
Trains$35446h 12m