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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 6/6. 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
Thu 6/27
Thu 7/4

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 42,816,550 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 - 10:53 pmORD-PDX
4h 27mnonstop
11:53 pm - 6:00 amPDX-ORD
4h 07mnonstop
$83Spirit Airlines
Find Deal
Mon, Jun 10 - Wed, Jun 12
8:26 pm - 10:53 pmORD-PDX
4h 27mnonstop
11:53 pm - 6:00 amPDX-ORD
4h 07mnonstop
$84Spirit Airlines
Find Deal
Sat, Jun 8 - Wed, Jun 12
8:26 pm - 10:56 pmORD-PDX
4h 30mnonstop
12:48 am - 1:03 amPDX-ORD
22h 15m1 stop
Wed, Aug 28 - Tue, Sep 3
8:23 pm - 3:55 pmORD-PDX
21h 32m1 stop
11:53 pm - 6:00 amPDX-ORD
4h 07mnonstop
Mon, Jun 10 - Wed, Jun 12
2:25 pm - 4:45 pmORD-PDX
4h 20mnonstop
11:11 pm - 5:15 amPDX-ORD
4h 04mnonstop
$179Alaska Airlines
Find Deal
Thu, Jul 4 - Wed, Jul 10
6:00 am - 11:40 pmMDW-PDX
19h 40m1 stop
12:48 am - 11:52 amPDX-MDW
9h 04m1 stop
$179Frontier
Find Deal
Sat, Sep 14 - Fri, Sep 20
6:00 am - 11:40 pmMDW-PDX
19h 40m1 stop
9:26 pm - 10:42 amPDX-MDW
11h 16m1 stop
$180Frontier
Find Deal
Wed, Aug 14 - Mon, Aug 19
1:58 pm - 4:29 pmORD-PDX
4h 31mnonstop
11:29 pm - 5:28 amPDX-ORD
3h 59mnonstop
$218Alaska Airlines
Find Deal
Tue, Nov 5 - Mon, Nov 18
6:00 am - 1:34 pmMDW-PDX
9h 34m1 stop
12:50 am - 8:41 amPDX-MDW
5h 51m1 stop
$237Delta
Find Deal
Thu, Oct 31 - Mon, Nov 18
6:00 am - 1:34 pmMDW-PDX
9h 34m1 stop
12:50 am - 10:22 amPDX-MDW
7h 32m1 stop
$321Delta
Find Deal
Sat, Nov 2 - Fri, Nov 15
8:26 pm - 10:53 pmORD-PDX
4h 27mnonstop
$49Spirit Airlines
Find Deal
Thu, Jun 6
8:26 pm - 10:53 pmORD-PDX
4h 27mnonstop
$50Spirit Airlines
Find Deal
Mon, Jun 10
8:00 am - 10:20 amORD-PDX
4h 20mnonstop
$90Alaska Airlines
Find Deal
Tue, Jun 18
11:26 am - 6:58 pmMDW-PDX
9h 32m1 stop
$90Frontier
Find Deal
Wed, Jun 12
6:35 am - 4:26 pmMDW-PDX
11h 51m1 stop
$96Frontier
Find Deal
Thu, Jun 6
6:20 pm - 11:41 pmORD-PDX
7h 21m1 stop
$99Alaska Airlines
Find Deal
Thu, Jul 4
8:30 pm - 11:02 pmORD-PDX
4h 32mnonstop
$104American Airlines
Find Deal
Tue, Oct 15
7:10 am - 9:38 amORD-PDX
4h 28mnonstop
$115United Airlines
Find Deal
Thu, Jul 25
8:00 pm - 10:26 pmORD-PDX
4h 26mnonstop
$127United Airlines
Find Deal
Tue, Jun 11
8:30 pm - 10:58 pmORD-PDX
4h 28mnonstop
$204American Airlines
Find Deal
Sun, Jun 16
8:00 pm - 10:30 pmORD-PDX
4h 30mnonstop
11:53 pm - 6:00 amPDX-ORD
4h 07mnonstop
$114Spirit Airlines
Find Deal
Sun, Jun 2 - Fri, Jun 7
8:00 pm - 10:30 pmORD-PDX
4h 30mnonstop
11:53 pm - 6:00 amPDX-ORD
4h 07mnonstop
$119Spirit Airlines
Find Deal
Sun, Jun 2 - Sun, Jun 9
8:00 pm - 10:30 pmORD-PDX
4h 30mnonstop
11:53 pm - 6:00 amPDX-ORD
4h 07mnonstop
$120Spirit Airlines
Find Deal
Sun, Jun 2 - Sat, Jun 8
5:56 pm - 9:11 amORD-PDX
17h 15m1 stop
12:49 am - 12:40 amPDX-ORD
21h 51m1 stop
$179Frontier
Find Deal
Sat, Jun 1 - Mon, Jun 10
10:01 pm - 9:11 amMDW-PDX
13h 10m1 stop
12:48 am - 11:09 amPDX-MDW
8h 21m1 stop
$180Frontier
Find Deal
Sat, Jun 1 - Sun, Jun 2
7:10 am - 9:38 amORD-PDX
4h 28mnonstop
12:15 am - 6:13 amPDX-ORD
3h 58mnonstop
$333United Airlines
Find Deal
Fri, May 31 - Mon, Jun 3
6:30 pm - 8:56 pmORD-PDX
4h 26mnonstop
12:20 am - 6:18 amPDX-ORD
3h 58mnonstop
$346United Airlines
Find Deal
Sat, Jun 1 - Fri, Aug 16
8:00 am - 10:20 amORD-PDX
4h 20mnonstop
7:43 am - 1:54 pmPDX-ORD
4h 11mnonstop
$358Alaska Airlines
Find Deal
Wed, May 29 - Fri, May 31
8:25 pm - 10:53 pmORD-PDX
4h 28mnonstop
9:55 pm - 8:56 amPDX-ORD
9h 01m1 stop
$367American Airlines
Find Deal
Wed, May 29 - Fri, May 31
6:00 am - 1:38 pmORD-PDX
9h 38m2 stops
1:25 pm - 11:49 pmPDX-ORD
8h 24m1 stop
$645Alaska Airlines
Find Deal
Wed, May 29 - Fri, May 31
8:26 pm - 10:53 pmORD-PDX
4h 27mnonstop
11:53 pm - 6:00 amPDX-ORD
4h 07mnonstop
$83Spirit Airlines
Find Deal
Mon, Jun 10 - Wed, Jun 12
8:26 pm - 10:53 pmORD-PDX
4h 27mnonstop
11:53 pm - 6:00 amPDX-ORD
4h 07mnonstop
$84Spirit Airlines
Find Deal
Sat, Jun 8 - Wed, Jun 12
8:26 pm - 10:53 pmORD-PDX
4h 27mnonstop
11:11 pm - 5:15 amPDX-ORD
4h 04mnonstop
Mon, Jul 1 - Tue, Jul 9
8:00 am - 10:20 amORD-PDX
4h 20mnonstop
11:51 pm - 5:41 amPDX-ORD
3h 50mnonstop
Wed, Aug 14 - Sat, Aug 24
2:25 pm - 4:45 pmORD-PDX
4h 20mnonstop
11:11 pm - 5:15 amPDX-ORD
4h 04mnonstop
$179Alaska Airlines
Find Deal
Thu, Jul 4 - Wed, Jul 10
8:29 pm - 11:01 pmORD-PDX
4h 32mnonstop
11:58 pm - 6:00 amPDX-ORD
4h 02mnonstop
$189American Airlines
Find Deal
Fri, Aug 16 - Tue, Aug 20
8:05 pm - 10:30 pmORD-PDX
4h 25mnonstop
12:45 am - 6:49 amPDX-ORD
4h 04mnonstop
$199United Airlines
Find Deal
Fri, Aug 16 - Thu, Aug 22
8:00 am - 10:20 amORD-PDX
4h 20mnonstop
11:11 pm - 5:15 amPDX-ORD
4h 04mnonstop
$204Alaska Airlines
Find Deal
Tue, Jun 18 - Thu, Jun 27
7:10 am - 9:38 amORD-PDX
4h 28mnonstop
12:25 am - 6:29 amPDX-ORD
4h 04mnonstop
$214United Airlines
Find Deal
Thu, Jul 25 - Wed, Aug 21
8:24 pm - 10:49 pmORD-PDX
4h 25mnonstop
11:41 pm - 5:36 amPDX-ORD
3h 55mnonstop
$253American Airlines
Find Deal
Thu, Jul 25 - Sun, Jul 28
3:05 pm - 11:17 amChicago Union-
Portland Union Station
46h 12mnonstop
4:45 pm - 4:45 pmPortland Union Station-
Chicago Union
46h 00mnonstop
$339Amtrak
Find Deal
Sat, Jun 8 - Fri, Jun 14
3:05 pm - 10:35 amChicago Union-
Vancouver
45h 30mnonstop
5:09 pm - 4:45 pmVancouver-
Chicago Union
45h 36mnonstop
$339Amtrak
Find Deal
Sun, Jun 9 - Fri, Jun 14
3:05 pm - 10:35 amChicago Union-
Vancouver
45h 30mnonstop
5:09 pm - 4:45 pmVancouver-
Chicago Union
45h 36mnonstop
$339Amtrak
Find Deal
Sun, Jun 9 - Fri, Jun 14
3:05 pm - 10:35 amChicago Union-
Vancouver
45h 30mnonstop
5:09 pm - 4:45 pmVancouver-
Chicago Union
45h 36mnonstop
$339Amtrak
Find Deal
Sat, Jun 8 - Fri, Jun 14
3:05 pm - 11:17 amChicago Union-
Portland Union Station
46h 12mnonstop
4:45 pm - 4:45 pmPortland Union Station-
Chicago Union
46h 00mnonstop
$339Amtrak
Find Deal
Sun, Jun 9 - Fri, Jun 14
3:05 pm - 11:17 amChicago Union-
Portland Union Station
46h 12mnonstop
4:45 pm - 4:45 pmPortland Union Station-
Chicago Union
46h 00mnonstop
$339Amtrak
Find Deal
Sun, Jun 9 - Fri, Jun 14
3:05 pm - 10:35 amChicago Union-
Vancouver
45h 30mnonstop
5:09 pm - 4:45 pmVancouver-
Chicago Union
45h 36mnonstop
$378Amtrak
Find Deal
Fri, Jun 14 - Sun, Jun 16
3:05 pm - 10:35 amChicago Union-
Vancouver
45h 30mnonstop
5:09 pm - 4:45 pmVancouver-
Chicago Union
45h 36mnonstop
$378Amtrak
Find Deal
Tue, Jun 11 - Sun, Jun 16
3:05 pm - 10:35 amChicago Union-
Vancouver
45h 30mnonstop
5:09 pm - 4:45 pmVancouver-
Chicago Union
45h 36mnonstop
$378Amtrak
Find Deal
Thu, Jun 13 - Sun, Jun 16
3:05 pm - 10:35 amChicago Union-
Vancouver
45h 30mnonstop
5:09 pm - 4:45 pmVancouver-
Chicago Union
45h 36mnonstop
$378Amtrak
Find Deal
Fri, Jun 14 - Sun, Jun 16

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 $418 and $409 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 Alaska Airlines ($179). Spirit Airlines proposed the cheapest one-way flight at $49.

Which airlines fly most frequently between Chicago and Portland?

United Airlines connects Chicago to Portland with up to 5 flights per day. Alaska Airlines also offers 2 flights per day, while American Airlines follows with 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 11 and 16 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 92 flights. The most frequent day of departure is Thursday, when 17% 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 $314 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 9192 reviews
7.3Entertainment
7.3Food
8.2Boarding
8.6Crew
7.9Comfort
Airline reviews

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

10.0 ExcellentAnonymous, May 2024GEG - PDX
Read more about Alaska Airlines reviews

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… 👎🏻

Alaska continues to provide one of the best domestic US airline experiences.

I liked the fast internet and twice serving of snacks and drinks. Paid food options could have included more.

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.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

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.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

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…

The flight was on time and nice as always for me with spirit but the cabin crew were not good. They left the lights on on a red eye for the entire flight.

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

I got a one-way, last-minute nonstop flight from PDX to BWI for only $125. Yes, I got nicked $79 more for a checked suitcase and $89 more for the BIG SEAT option, but it was worth it, even with $4.50 for coffee and $10 for a snack (the latter no different than any other airline). The grand total was still less flying on any other airline.

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

This recognisable no-frills airline gets me from point-A to point-B. I was able to get to Chicago without stress. The checked baggage collection and reclaim could be improved.

The crew was the best and very accommodating I know you don't offer any complimentary items but water and coffee will not break the bank !!

My flight was cancelled!!! I had to spend 200.00 on another flight!!

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.

My experience with frontier staff at the Denver airport was absolutely horrible. The manager on duty was even worst if was the worst experience I have ever had, I have never been treated so poorly as a customer in my life! The staff was extremely rude, eye rolls and attitude and then refusal to help me at all. I wish I could never fly frontier again that’s how horrible it was!

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Plane could have been more on time. More leg room .

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

Check in online was easy. Seats aren’t very comfortable

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.
6/6Thu
nonstopSpirit Airlines
4h 27mORD-PDX
$49
6/10Mon
nonstopSpirit Airlines
4h 27mORD-PDX
$50
6/18Tue
nonstopAlaska Airlines
4h 20mORD-PDX
$90
6/12Wed
1 stopFrontier
9h 32mMDW-PDX
$90
6/6Thu
1 stopFrontier
11h 51mMDW-PDX
$96
7/4Thu
1 stopAlaska Airlines
7h 21mORD-PDX
$99
10/15Tue
nonstopAmerican Airlines
4h 32mORD-PDX
$104
7/25Thu
nonstopUnited Airlines
4h 28mORD-PDX
$115
6/11Tue
nonstopUnited Airlines
4h 26mORD-PDX
$127
6/16Sun
nonstopAmerican Airlines
4h 28mORD-PDX
$204

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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.
6/2Sun
nonstopSpirit Airlines
4h 30mORD-PDX
6/7Fri
nonstopSpirit Airlines
4h 07mPDX-ORD
$114
6/2Sun
nonstopSpirit Airlines
4h 30mORD-PDX
6/9Sun
nonstopSpirit Airlines
4h 07mPDX-ORD
$119
6/2Sun
nonstopSpirit Airlines
4h 30mORD-PDX
6/8Sat
nonstopSpirit Airlines
4h 07mPDX-ORD
$120
6/1Sat
multi-stopFrontier
17h 15mORD-PDX
6/10Mon
multi-stopFrontier
21h 51mPDX-ORD
$179
6/1Sat
multi-stopFrontier
13h 10mMDW-PDX
6/2Sun
multi-stopFrontier
8h 21mPDX-MDW
$180
5/31Fri
nonstopUnited Airlines
4h 28mORD-PDX
6/3Mon
nonstopUnited Airlines
3h 58mPDX-ORD
$333
6/1Sat
nonstopUnited Airlines
4h 26mORD-PDX
8/16Fri
nonstopUnited Airlines
3h 58mPDX-ORD
$346
5/29Wed
nonstopAlaska Airlines
4h 20mORD-PDX
5/31Fri
nonstopAlaska Airlines
4h 11mPDX-ORD
$358
5/29Wed
nonstopAmerican Airlines
4h 28mORD-PDX
5/31Fri
multi-stopAmerican Airlines
9h 01mPDX-ORD
$367
5/29Wed
multi-stopAlaska Airlines
9h 38mORD-PDX
5/31Fri
multi-stopAlaska Airlines
8h 24mPDX-ORD
$645

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Flights to Portland

Destination:

Portland (PDX)United States

Return flight deals:

Portland - Chicago

Cabin classes:

$549
$1,332
$610
$108

Compare transportation modes for Chicago to Portland

Average priceAverage duration
Flights$4644h 20m
Trains$37846h 12m