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$48 Find cheap flights from Portland to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to Chicago departing on 9/7. 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 Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Chicago.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Chicago.
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 Portland to Chicago (PDX-CHI)

 
These are the cheapest deals for flights from Portland to Chicago 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 Portland to Chicago

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

Recent one-way flight deals from Portland to Chicago

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

Recent last minute flight deals from Portland to Chicago

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

Recent direct flight deals from Portland to Chicago

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

Cheap bus & train deals from Portland to Chicago

Find recent round-trip train or bus tickets from Portland to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
11:51 pm - 5:41 amPDX-ORD
3h 50mnonstop
8:26 pm - 10:56 pmORD-PDX
4h 30mnonstop
$83Spirit Airlines
Find Deal
Sat, Sep 7 - Wed, Sep 11
11:51 pm - 5:41 amPDX-ORD
3h 50mnonstop
8:26 pm - 10:56 pmORD-PDX
4h 30mnonstop
$84Spirit Airlines
Find Deal
Sat, Sep 7 - Wed, Sep 11
11:51 pm - 5:41 amPDX-ORD
3h 50mnonstop
8:26 pm - 10:56 pmORD-PDX
4h 30mnonstop
$88Spirit Airlines
Find Deal
Wed, Aug 28 - Sun, Sep 1
11:51 pm - 5:41 amPDX-ORD
3h 50mnonstop
8:26 pm - 10:56 pmORD-PDX
4h 30mnonstop
$89Spirit Airlines
Find Deal
Thu, Sep 5 - Mon, Sep 9
11:51 pm - 5:41 amPDX-ORD
3h 50mnonstop
8:26 pm - 10:56 pmORD-PDX
4h 30mnonstop
$94Spirit Airlines
Find Deal
Thu, Aug 22 - Wed, Aug 28
12:48 am - 11:52 amPDX-MDW
9h 04m1 stop
10:00 pm - 3:54 pmMDW-PDX
19h 54m1 stop
$178Frontier
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Tue, Sep 10 - Wed, Sep 18
11:58 pm - 6:00 amPDX-ORD
4h 02mnonstop
6:30 pm - 9:08 pmORD-PDX
4h 38mnonstop
$179American Airlines
Find Deal
Tue, Aug 20 - Tue, Aug 27
12:48 am - 11:52 amPDX-MDW
9h 04m1 stop
11:32 am - 8:36 pmMDW-PDX
11h 04m1 stop
$179Frontier
Find Deal
Wed, Aug 21 - Wed, Aug 28
11:11 pm - 5:15 amPDX-ORD
4h 04mnonstop
2:18 pm - 4:48 pmORD-PDX
4h 30mnonstop
$189Alaska Airlines
Find Deal
Mon, Aug 19 - Tue, Aug 27
11:11 pm - 8:48 amPDX-MDW
7h 37m1 stop
7:19 pm - 11:17 pmMDW-PDX
5h 58m1 stop
$352Delta
Find Deal
Fri, Jun 7 - Mon, Jun 10
11:51 pm - 5:41 amPDX-ORD
3h 50mnonstop
$48Spirit Airlines
Find Deal
Sat, Sep 7
11:53 pm - 6:00 amPDX-ORD
4h 07mnonstop
$49Spirit Airlines
Find Deal
Sat, Jun 8
11:29 pm - 5:30 amPDX-ORD
4h 01mnonstop
$88Alaska Airlines
Find Deal
Tue, Oct 8
8:07 am - 5:12 pmPDX-MDW
7h 05m1 stop
$90Frontier
Find Deal
Tue, Jun 4
10:54 pm - 5:50 amPDX-MDW
28h 56m1 stop
$95Frontier
Find Deal
Sun, Jun 2
2:25 pm - 8:26 pmPDX-ORD
4h 01mnonstop
$104American Airlines
Find Deal
Sat, Oct 12
11:29 pm - 5:30 amPDX-ORD
4h 01mnonstop
$114Alaska Airlines
Find Deal
Thu, Oct 10
11:55 pm - 6:00 amPDX-ORD
4h 05mnonstop
$127American Airlines
Find Deal
Tue, Jun 11
12:15 am - 6:13 amPDX-ORD
3h 58mnonstop
$145United Airlines
Find Deal
Thu, Aug 15
12:15 am - 6:13 amPDX-ORD
3h 58mnonstop
$146United Airlines
Find Deal
Mon, Jun 24
11:30 pm - 5:20 amPDX-ORD
3h 50mnonstop
8:00 pm - 10:30 pmORD-PDX
4h 30mnonstop
$141Spirit Airlines
Find Deal
Thu, May 30 - Mon, Jun 3
11:30 pm - 5:20 amPDX-ORD
3h 50mnonstop
8:26 pm - 10:53 pmORD-PDX
4h 27mnonstop
$142Spirit Airlines
Find Deal
Fri, May 31 - Thu, Jun 6
7:48 am - 9:15 pmPDX-ORD
11h 27m1 stop
8:26 pm - 10:53 pmORD-PDX
4h 27mnonstop
Thu, May 30 - Wed, Jun 5
7:48 am - 9:15 pmPDX-ORD
11h 27m1 stop
9:53 pm - 7:50 amORD-PDX
11h 57m1 stop
$180Frontier
Find Deal
Thu, May 30 - Wed, Jun 5
12:48 am - 11:09 amPDX-MDW
8h 21m1 stop
5:55 am - 11:56 pmMDW-PDX
20h 01m1 stop
$182Frontier
Find Deal
Sun, Jun 2 - Mon, Jun 10
11:30 pm - 5:20 amPDX-ORD
3h 50mnonstop
6:45 pm - 11:35 pmORD-PDX
6h 50m1 stop
Sat, Jun 1 - Mon, Jun 3
12:40 am - 11:25 amPDX-ORD
8h 45m1 stop
1:45 pm - 6:17 pmORD-PDX
6h 32m1 stop
$327Delta
Find Deal
Fri, May 31 - Wed, Jun 5
12:40 am - 8:39 amPDX-ORD
5h 59m1 stop
5:44 pm - 11:23 pmORD-PDX
7h 39m1 stop
$352Delta
Find Deal
Wed, May 29 - Mon, Jun 3
12:15 am - 6:13 amPDX-ORD
3h 58mnonstop
8:00 pm - 10:26 pmORD-PDX
4h 26mnonstop
$358United Airlines
Find Deal
Thu, May 30 - Fri, Jun 7
12:15 am - 6:13 amPDX-ORD
3h 58mnonstop
4:10 pm - 6:35 pmORD-PDX
4h 25mnonstop
$373United Airlines
Find Deal
Sun, Jun 2 - Thu, Jun 6
11:51 pm - 5:41 amPDX-ORD
3h 50mnonstop
8:26 pm - 10:56 pmORD-PDX
4h 30mnonstop
$83Spirit Airlines
Find Deal
Sat, Sep 7 - Wed, Sep 11
11:51 pm - 5:41 amPDX-ORD
3h 50mnonstop
8:26 pm - 10:56 pmORD-PDX
4h 30mnonstop
$84Spirit Airlines
Find Deal
Sat, Sep 7 - Wed, Sep 11
11:51 pm - 5:41 amPDX-ORD
3h 50mnonstop
7:00 am - 9:30 amORD-PDX
4h 30mnonstop
Thu, Sep 19 - Tue, Sep 24
11:53 pm - 6:00 amPDX-ORD
4h 07mnonstop
8:00 am - 10:20 amORD-PDX
4h 20mnonstop
Sat, Jun 8 - Tue, Jun 11
11:58 pm - 6:00 amPDX-ORD
4h 02mnonstop
6:30 pm - 9:08 pmORD-PDX
4h 38mnonstop
$179American Airlines
Find Deal
Tue, Aug 20 - Tue, Aug 27
11:11 pm - 5:15 amPDX-ORD
4h 04mnonstop
2:18 pm - 4:48 pmORD-PDX
4h 30mnonstop
$189Alaska Airlines
Find Deal
Mon, Aug 19 - Tue, Aug 27
11:29 pm - 5:30 amPDX-ORD
4h 01mnonstop
7:00 am - 9:32 amORD-PDX
4h 32mnonstop
$193Alaska Airlines
Find Deal
Tue, Oct 8 - Sat, Oct 12
12:20 am - 6:18 amPDX-ORD
3h 58mnonstop
7:10 am - 9:38 amORD-PDX
4h 28mnonstop
$204United Airlines
Find Deal
Tue, Jul 16 - Mon, Jul 22
12:20 am - 6:18 amPDX-ORD
3h 58mnonstop
7:10 am - 9:38 amORD-PDX
4h 28mnonstop
$214United Airlines
Find Deal
Tue, Aug 6 - Sun, Aug 11
11:58 pm - 6:00 amPDX-ORD
4h 02mnonstop
10:12 am - 12:43 pmORD-PDX
4h 31mnonstop
$228American Airlines
Find Deal
Tue, Aug 20 - Sat, Aug 24
5:09 pm - 4:45 pmVancouver-
Chicago Union
45h 36mnonstop
3:05 pm - 10:35 amChicago Union-
Vancouver
45h 30mnonstop
$354Amtrak
Find Deal
Mon, Jun 3 - Mon, Jun 10
4:45 pm - 4:45 pmPortland Union Station-
Chicago Union
46h 00mnonstop
3:05 pm - 11:17 amChicago Union-
Portland Union Station
46h 12mnonstop
$354Amtrak
Find Deal
Thu, Jun 6 - Mon, Jun 10
4:45 pm - 4:45 pmPortland Union Station-
Chicago Union
46h 00mnonstop
3:05 pm - 11:17 amChicago Union-
Portland Union Station
46h 12mnonstop
$354Amtrak
Find Deal
Mon, Jun 3 - Mon, Jun 10
5:09 pm - 4:45 pmVancouver-
Chicago Union
45h 36mnonstop
3:05 pm - 10:35 amChicago Union-
Vancouver
45h 30mnonstop
$354Amtrak
Find Deal
Thu, Jun 6 - Mon, Jun 10
5:09 pm - 4:45 pmVancouver-
Chicago Union
45h 36mnonstop
3:05 pm - 10:35 amChicago Union-
Vancouver
45h 30mnonstop
$396Amtrak
Find Deal
Mon, Jun 3 - Thu, Jun 6
4:45 pm - 4:45 pmPortland Union Station-
Chicago Union
46h 00mnonstop
3:05 pm - 11:17 amChicago Union-
Portland Union Station
46h 12mnonstop
$396Amtrak
Find Deal
Mon, Jun 3 - Fri, Jun 7
5:09 pm - 4:45 pmVancouver-
Chicago Union
45h 36mnonstop
3:05 pm - 10:35 amChicago Union-
Vancouver
45h 30mnonstop
$396Amtrak
Find Deal
Mon, Jun 3 - Fri, Jun 7
4:45 pm - 4:45 pmPortland Union Station-
Chicago Union
46h 00mnonstop
3:05 pm - 11:17 amChicago Union-
Portland Union Station
46h 12mnonstop
$396Amtrak
Find Deal
Mon, Jun 3 - Thu, Jun 6
4:45 pm - 4:45 pmPortland Union Station-
Chicago Union
46h 00mnonstop
3:05 pm - 11:17 amChicago Union-
Portland Union Station
46h 12mnonstop
$420Amtrak
Find Deal
Wed, Jun 19 - Sat, Jun 22
4:45 pm - 4:45 pmPortland Union Station-
Chicago Union
46h 00mnonstop
3:05 pm - 11:17 amChicago Union-
Portland Union Station
46h 12mnonstop
$420Amtrak
Find Deal
Wed, Jun 19 - Sun, Jun 23

Flights from Portland to Chicago - Travel Insights & Trends

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

What is the cheapest Portland to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Portland to Chicago.
Our data shows that the cheapest route for a one-way flight from Portland to Chicago cost $73 and was between Portland and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $142.

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

The average price of all flights from Portland to Chicago clicked on KAYAK for each day over the last 12 months.
When flying from Portland to Chicago, you should consider leaving on a Saturday and avoid Mondays if you are looking for the best rates. For your return to Portland, you’ll find the best rates on Tuesdays and the most expensive ones on Mondays.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Portland to Chicago, 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 Portland to Chicago is November, where tickets cost $298 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is $458 and $418 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Portland to Chicago, 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 Portland to Chicago, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 58 days before departure.

Which airlines provide the cheapest flights from Portland to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Portland to Chicago found by KAYAK users in the last 72 hours was for $83 on Spirit Airlines, followed by Frontier ($178). One-way flight deals have also been found from as low as $48 on Spirit Airlines and from $88 on Alaska Airlines.

Which airlines fly most frequently between Portland and Chicago?

United Airlines connects Portland to Chicago 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 Portland and Chicago?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Portland to Chicago.
There are 5 airlines that fly nonstop from Portland to Chicago. 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 $73 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 Portland and Chicago per day?

Each day, there are between 11 and 16 nonstop flights that take off from Portland and land in Chicago, with an average flight time of 4h 00m. The most common departure time is 2:00 pm and most flights take off at night, while the most flights land at Chicago O'Hare Intl Airport. Each week, there are 94 flights. The most frequent day of departure is Friday, when 17% of all weekly flights depart. The fewest flights depart on a Sunday.

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

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 Portland to Chicago take?

Nonstop flights from Portland generally make it to Chicago in 3h 50m. The flying distance between the two cities is 1,749 miles.

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

Early birds can take the earliest flight from Portland at 12:15 am and will be landing in Chicago at 6:13 am.

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

If you prefer to fly at night, the latest flight from Portland to Chicago jets off at 11:55 pm and lands at 6:00 am.

Good to know

Low season

February

High season

June

Cheapest flight

$48
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 26% increase in price.
Flight from Portland to Chicago O'Hare Airport

When to book flights from Portland to Chicago

Are your dates flexible? Find out the best times to travel from Portland to Chicago 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 Portland to Chicago

  • Where can I park my car at PDX long-term before my flight to Chicago?

    Near the tunnels that connect the north and south terminals, PDX has long-term parking lots. Further away, PDX has an economy lot. This economy lot is less expensive and there is a 24h shuttle service for free that will take you to your terminal.

  • Is there a USO lounge for US military at PDX?

    The USO lounge at PDX is before security on the mezzanine level. It is open Monday to Friday 9 am to 5 pm. The USO is closed on Saturday and Sunday. This lounge is available to active-duty military service members and their families. Local and transportation information is available here. Amenities at the lounge include TV, Xbox 30, Wi-Fi, computers, laptops, toiletries, free drinks, and lounge seating.

  • What are the major airports in Chicago?

    The two major airports in Chicago are Chicago O'Hare International Airport (ORD) and Midway International Airport (MDW). ORD is a hub for United Airlines and American Airlines and the airport has four terminals. Midway, a hub for Southwest Airlines, is much smaller, with just one terminal and three concourses.

  • How can I fly from PDX to the Chicago airports?

    United Airlines and Alaska Airlines operate non-stop flights from PDX into Chicago. All of these flights tend to land at ORD airport. Southwest operates non-stop flights from PDX that land at MDW. Alaska Airlines, Delta, Spirit, and United Airlines operate one stop flights from PDX to ORD. Some layover cities include Las Vegas (LAS), Seattle (SEA) and Denver (DEN). Delta operates one stop flights from PDX that land in MDW. These flights tend to stop at cities such as Atlanta (ATL) and Detroit (DTW).

  • What is the cheapest flight from Portland to Chicago?

    In the last 3 days, the lowest price for a flight from Portland to Chicago was $48 for a one-way ticket and $83 for a round-trip.

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

    All the following airlines offer inflight Wi-Fi service on the Portland to Chicago flight route: American Airlines, Alaska Airlines, JetBlue, Delta, Virgin Atlantic, Air France, and KLM.

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

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

  • Which airline alliances offer flights from Portland to Chicago?

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Portland to Chicago are Alaska Airlines and Delta. With an average price for the route of $345 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 Portland to Chicago?

    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 Portland to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Portland 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 Portland to Chicago?

    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 Chicago with an airline and back to Portland with another airline.

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

    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 Chicago from Portland 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 Portland to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $168 or less one-way and $335 or less round-trip.
  • Portland International Airport (PDX) has designated areas where children can play as they wait for their plane. This area is also very convenient for parents to relax. One of these kid-play areas is at gate C-17. The other is before security at terminals D/E.
  • Both major airports in Chicago provide private spaces for nursing mothers. Chicago O'Hare International Airport (ORD) provides Mothers Rooms for nursing mothers to breastfeed or pump. These private, sanitized spaces are located in terminals 1, 2, 3, 5, and in the Multi-Modal Facility. ORD also provides lactation pods, free standing privacy units for nursing mothers, in terminals 1, 2, and 3. Midway International Airport (MDW) provides a Mothers Room on Concourse C, next to the yoga room. MDW also provides a free-standing lactation pod on Concourse A at gate A5.
  • PDX has partnered with DoveLewis to make therapy dogs available throughout the airport in order to comfort confused, bereaved, or anxious travelers. Retired Guide Dogs for the Blind wear gray DoveLewis vests and passengers are encouraged to smooch, hug, pet, and cuddle these dogs. The dog handlers are trained to spot people in emotional need of assistance in stressful situations.
  • The Hollywood Theater on Concourse C of PDX shows short films that are 10min or shorter, made by Oregon filmmakers. If you have some time before your flight, consider stopping into this 22-seat theater. It is open 24h a day, and it is free.
  • If you want to stay near the airport the night before your flight to Chicago, PDX has many comfortable hotels nearby that offer free airport shuttles to your terminal. Some examples of these hotels are the Red Lion Hotel Portland Airport, The Howard Johnson By Wyndham Portland Airport, and The Ramada By Wyndham Portland Airport.
See more tips

Prefer to fly non-stop from Portland to Chicago?

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

Nonstop departures

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

Nonstop returns

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
See more direct flights

Top 5 airlines serving from Portland to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Portland to Chicago. 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 Portland to Chicago? 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 9194 reviews
7.9Comfort
8.6Crew
7.3Food
8.2Boarding
7.3Entertainment
Airline reviews

The one stewardess was rude about helping me put my bag in overhead….she said “ Is it heavy ?” (I am 73 yrs old)

8.0 ExcellentAnonymous, May 2024PDX - SAN
Read more about Alaska Airlines reviews

The one stewardess was rude about helping me put my bag in overhead….she said “ Is it heavy ?” (I am 73 yrs old)

That flight was a terrible experience. Flying to Portland was not much better. I will not ever fly Alaska Airlines again. I have a temporary disability due to recent neurocervical surgery. I cannot lift heavy things, I cannot walk long distances without vertigo and fainting, and I required wheelchair assistance. I showed up an hour and a half before my flight. The wheelchair queue assistance person was rude and chastised me for showing up so late. An older couple showed up almost an half an hour AFTER me, and she was sweet as pie to them. There was a long wait for wheelchair assistance as they were backed up. When I got to the gate, the gate attendants were rude and again, I got chastised for being late, even though it was not my fault they were backed up. When I asked for help with my bags and boarding the plane, they told me it was my fault and they were not obligated to help me. I was treated like a big inconvenience because I had a wheelchair and I couldn't "just walk." One of them literally rolled her eyes at me. I kept silent, because I just wanted to get home and I felt like they would not let me on if I complained, but I was practically crying. When I got down to the door to board, the wheelchair person left, and I asked the flight attendants for help. They said, well, you'll have to stand there and wait, even though I said I couldn't stand very long, and another passenger said, "Oh just let me do it" and helped me down. I tried not to bother the inflight attendants, because everytime you did, they acted exasperated and stressed out. I paid $7.50 for a bag of Pirate Booty and a tiny turkey beef stick for dinner. I needed wifi to work during the flight, and it kept crashing on me repeatedly and resetting my online work, costing me valuable time. I had to pay twice to get it on my laptop and phone, but I did get a refund when I returned. When I got to NY, the Portland agents had not arranged for a wheelchair to meet me and I had to stand for fifteen minutes waiting for the very nice young man who found an empty chair and had to wheel me and another passenger with carry on luggage to the front of JFK all by himself. Never, ever again. You all should be ashamed of how you treat people with disabilities. The other people who needed assistance to get on this flight did not fare much better than me, from what I could see.

My experience for a sort flight was perfect and hassle free.

I didn’t like not knowing my seat till I got to the airport - and my boarding group was F (last).

My boarding pass birthdate was printed incorrectly causing me to spend an extra hour in a check-in and then again TSA line and to miss a chance to have dinner pre-flight. My window seat was given away and was replaced with a middle seat. I would have liked an opportunity to charge my phone and take advantage of movies but many of the departure gate chargers weren’t operational and I don’t know of an in-flight charging option, The flight left 45 late after trouble with unruly passengers, and I was glad staff removed them.

Horrible. I likely will have to spend several thousand dollars to rebook my international flights, due to their delays, plus a hotel in SF. I can’t wait to never fly them again!

Quick easy boarding. Airport was unprepared for early landing and we were waiting in the plane for 20 minutes before getting a gate.

It was so easy to board using my boarding pass on my iPhone, and I liked what I was given on the plane for food and drink, and everyone was very friendly.

dont re-route to San Jose. Re-route to closer airport. Provide shuttle bus to go to SFO, not just LYFT vouchers.

Staff seemed genuinely nice, not just going through the motions.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

This was a Lufthansa flight. Disappointing main meal. Very rough over Canada and arrival at FRA. IFE was almost unusable.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Poor seating comfort, seat cushion too thin, very uncomfortable. My luggage didi not make the flight due to equipment change. At least. United had it delivered the next day. I was without my toilet items for one day.

The CX617 from HK to BKK was delayed more than 1.5 hours.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight boarded without pilots. Sat on plane for 3 hrs. after over an hour late boarding. Plane never took off. Had to deplane near midnight. Line for rebooking was 3 hours + long. I had to leave.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

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.

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Had to board plan 2x due to lack of security check after 1st boarding

Miserable. The crew was rude, the flight was delayed 5 hours for mechanical reasons and then “weather” even though other planes were leaving.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

Flight was delayed...not horribly late. Just before push back engine shut down for a quick replacement item that took about five minutes. After that, everything was smooth and the pilot was able to make up time in the air so that our arrival time was not too far off the original anticipated arrival time.

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 Portland to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Portland to Chicago found on KAYAK in the last 72 hours.
9/7Sat
nonstopSpirit Airlines
3h 50mPDX-ORD
$48
6/8Sat
nonstopSpirit Airlines
4h 07mPDX-ORD
$49
10/8Tue
nonstopAlaska Airlines
4h 01mPDX-ORD
$88
6/4Tue
1 stopFrontier
7h 05mPDX-MDW
$90
6/2Sun
1 stopFrontier
28h 56mPDX-MDW
$95
10/12Sat
nonstopAmerican Airlines
4h 01mPDX-ORD
$104
10/10Thu
nonstopAlaska Airlines
4h 01mPDX-ORD
$114
6/11Tue
nonstopAmerican Airlines
4h 05mPDX-ORD
$127
8/15Thu
nonstopUnited Airlines
3h 58mPDX-ORD
$145
6/24Mon
nonstopUnited Airlines
3h 58mPDX-ORD
$146

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Last minute flights from Portland to Chicago

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 Portland to Chicago that are departing in the next 10 days.
5/30Thu
nonstopSpirit Airlines
3h 50mPDX-ORD
6/3Mon
nonstopSpirit Airlines
4h 30mORD-PDX
$141
5/31Fri
nonstopSpirit Airlines
3h 50mPDX-ORD
6/6Thu
nonstopSpirit Airlines
4h 27mORD-PDX
$142
5/30Thu
multi-stop
11h 27mPDX-ORD
6/5Wed
nonstop
4h 27mORD-PDX
$152
5/30Thu
multi-stopFrontier
11h 27mPDX-ORD
6/5Wed
multi-stopFrontier
11h 57mORD-PDX
$180
6/2Sun
multi-stopFrontier
8h 21mPDX-MDW
6/10Mon
multi-stopFrontier
20h 01mMDW-PDX
$182
6/1Sat
nonstop
3h 50mPDX-ORD
6/3Mon
multi-stop
6h 50mORD-PDX
$187
5/31Fri
multi-stopDelta
8h 45mPDX-ORD
6/5Wed
multi-stopDelta
6h 32mORD-PDX
$327
5/29Wed
multi-stopDelta
5h 59mPDX-ORD
6/3Mon
multi-stopDelta
7h 39mORD-PDX
$352
5/30Thu
nonstopUnited Airlines
3h 58mPDX-ORD
6/7Fri
nonstopUnited Airlines
4h 26mORD-PDX
$358
6/2Sun
nonstopUnited Airlines
3h 58mPDX-ORD
6/6Thu
nonstopUnited Airlines
4h 25mORD-PDX
$373

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Portland - Chicago Flights

Departure:

Portland (PDX)United States

Return flight deals:

Chicago - Portland

Cabin classes:

$412
$954
$615
$142

Compare transportation modes for Portland to Chicago

Average priceAverage duration
Flights$1,1343h 50m
Trains$39346h 00m