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PDX - CHI

$40 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 5/11. 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 6/4
Tue 6/11

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 43,369,418 times on KAYAK, and here is why:

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

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Portland to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
11:30 pm - 5:20 amPDX-ORD
3h 50mnonstop
8:00 pm - 10:30 pmORD-PDX
4h 30mnonstop
$67Spirit Airlines
Find Deal
Wed, May 22 - Wed, May 29
11:30 pm - 5:20 amPDX-ORD
3h 50mnonstop
8:00 pm - 10:30 pmORD-PDX
4h 30mnonstop
$68Spirit Airlines
Find Deal
Wed, May 22 - Wed, May 29
11:30 pm - 5:20 amPDX-ORD
3h 50mnonstop
5:50 pm - 12:07 amORD-PDX
8h 17m1 stop
$79Spirit Airlines
Find Deal
Wed, May 22 - Wed, May 29
7:54 pm - 5:00 amPDX-ORD
31h 06m2 stops
7:59 pm - 7:20 pmORD-PDX
25h 21m2 stops
$137Frontier
Find Deal
Fri, May 17 - Tue, May 21
10:54 pm - 5:50 amPDX-MDW
28h 56m1 stop
5:05 am - 11:43 pmMDW-PDX
20h 38m1 stop
$147Frontier
Find Deal
Thu, May 23 - Sat, Jun 1
11:11 pm - 5:15 amPDX-ORD
4h 04mnonstop
2:25 pm - 4:45 pmORD-PDX
4h 20mnonstop
$194Alaska Airlines
Find Deal
Tue, Aug 6 - Thu, Aug 8
12:15 am - 6:13 amPDX-ORD
3h 58mnonstop
6:30 pm - 8:56 pmORD-PDX
4h 26mnonstop
$203United Airlines
Find Deal
Tue, Jun 11 - Sat, Jun 15
11:41 pm - 5:36 amPDX-ORD
3h 55mnonstop
8:24 pm - 10:49 pmORD-PDX
4h 25mnonstop
$207American Airlines
Find Deal
Sat, Jul 13 - Sat, Jul 20
11:55 pm - 6:00 amPDX-ORD
4h 05mnonstop
8:30 pm - 10:58 pmORD-PDX
4h 28mnonstop
$209American Airlines
Find Deal
Thu, Jun 6 - Tue, Jun 11
7:00 am - 4:19 pmPDX-ORD
7h 19m1 stop
7:00 am - 9:44 amORD-PDX
4h 44mnonstop
$216Alaska Airlines
Find Deal
Tue, Oct 29 - Wed, Nov 6

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 $109 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 $203.

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 January, where tickets cost $297 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is $508 and $462 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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 81 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 $67 on Spirit Airlines, followed by Frontier ($137). One-way flight deals have also been found from as low as $40 on Spirit Airlines and from $70 on Frontier.

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 $113 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 12 and 17 nonstop flights that take off from Portland and land in Chicago, with an average flight time of 4h 03m. The most common departure time is 11:00 pm and most flights take off at night, while the most flights land at Chicago O'Hare Intl Airport. Each week, there are 99 flights. The most frequent day of departure is Wednesday, 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 12:08 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 11:59 pm and lands at 6:05 am.

Good to know

Low season

January

High season

June

Cheapest flight

$40
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 34% 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 $40 for a one-way ticket and $67 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, Delta, Virgin Atlantic, JetBlue, 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 $356 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 $322 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 $198 or less one-way and $388 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, +9 more

Air Canada, Alaska Airlines, +10 more

Tuesday

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

Air Canada, Alaska Airlines, +11 more

Wednesday

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

Air Canada, Alaska Airlines, +12 more

Thursday

Air Canada, Alaska Airlines, American Airlines, +9 more

Air Canada, Alaska Airlines, +10 more

Friday

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

Air Canada, Alaska Airlines, +11 more

Saturday

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

Air Canada, Alaska Airlines, +11 more

Sunday

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

Air Canada, Alaska Airlines, +11 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 9134 reviews
7.9Comfort
7.3Entertainment
8.2Boarding
8.6Crew
7.3Food
Airline reviews

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.

6.0 GoodAnonymous, Apr 2024PDX - SAN
Read more about Alaska Airlines reviews

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 would have rated the entire experience much better were it not for two things: 1. There was inconsistency between what we were told once on the plane vs. the answer I received to the question about "spreading out" from our assigned seats because the flight was sparsely populated, and the entire row we were in was empty but for us. I asked about one of us moving over one seat to make more room for us; before getting on the plane, I was told we could, which seemed like a sensible answer. Once on the plane, it was announced that we needed to stay in our assigned seats despite all of the empty space in our row, which seemed unneccessarily restrictive. 2. To add to the discomfort, we sat on the tarmac once the plane landed in Burbank for over half an hour waiting for a gate to become available. During that time we had to remain seated and buckled in, which was becoming more difficult as time dragged on, especially for my wife. If all of this was due to regulations, that may mitigate the sense of "needless" restriction somewhat, but it points to a need to make regulations less restrictive where it is not appropriate for the current conditions. The crew was not "nasty" about the restrictions, so I do not resent their actions, but it certainly would have been a much more pleasant flight if we had a few more options when it comes to comfort.

The seat side plug ins didn’t work in my row, and I ran out of things to do since my iPad and iPhone ran out of juice. The flight attendant offered me a free drink but I don’t drink. I suggested a free snack box instead and she just shrugged and walked off. Why do us non-drinkers get the short end of the stick?

Flight left two hours late with no real explanation and they inexplicably had the heat running on the flight as well

I like Alaska Air fine. Great crew. Late departure still arrived on time.

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.

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.

Okay, cost of baggage and bidding for a seat is weird.

The flight was delayed almost two hours on the front end, and an hour on the backend once we landed and waited for a gate to open up. We were told to remain in our seats during that whole delay and I had to go to the bathroom badly. I was unable to hold it and was forced to urinate in my pants while in my seat. I then had to sit in it until we finally deboarded and I was able to change my clothes.

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

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.
5/11Sat
nonstopSpirit Airlines
3h 50mPDX-ORD
$40
5/23Thu
nonstopSpirit Airlines
3h 50mPDX-ORD
$41
5/20Mon
1 stopFrontier
18h 32mPDX-ORD
$70
5/12Sun
1 stopFrontier
8h 39mPDX-MDW
$85
6/4Tue
nonstopAlaska Airlines
4h 05mPDX-ORD
$104
6/30Sun
nonstopAlaska Airlines
4h 04mPDX-ORD
$115
6/10Mon
nonstopUnited Airlines
3h 58mPDX-ORD
$140
6/16Sun
nonstopUnited Airlines
3h 58mPDX-ORD
$147
6/30Sun
1 stopAmerican Airlines
8h 03mPDX-ORD
$176
5/23Thu
nonstopAmerican Airlines
4h 05mPDX-ORD
$200

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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.
5/10Fri
nonstopSpirit Airlines
3h 50mPDX-ORD
5/11Sat
nonstopSpirit Airlines
4h 30mORD-PDX
$105
5/10Fri
nonstopSpirit Airlines
3h 50mPDX-ORD
5/13Mon
nonstopSpirit Airlines
4h 30mORD-PDX
$127
5/10Fri
multi-stopFrontier
17h 50mPDX-MDW
5/11Sat
multi-stopFrontier
12h 16mMDW-PDX
$193
5/10Fri
multi-stopFrontier
22h 07mPDX-ORD
5/18Sat
multi-stopFrontier
17h 15mORD-PDX
$199
5/8Wed
nonstopAmerican Airlines
4h 06mPDX-ORD
5/14Tue
nonstopAmerican Airlines
4h 28mORD-PDX
$308
5/8Wed
multi-stopUnited Airlines
11h 44mPDX-ORD
5/18Sat
multi-stopUnited Airlines
6h 32mORD-PDX
$407
5/8Wed
multi-stopUnited Airlines
11h 44mPDX-ORD
5/14Tue
multi-stopUnited Airlines
6h 32mORD-PDX
$422
5/7Tue
nonstopAlaska Airlines
4h 10mPDX-ORD
5/11Sat
nonstopAlaska Airlines
4h 34mORD-PDX
$502
5/7Tue
nonstopAlaska Airlines
4h 21mPDX-ORD
5/8Wed
nonstopAlaska Airlines
4h 34mORD-PDX
$521
5/6Mon
multi-stopAmerican Airlines
7h 26mPDX-ORD
5/8Wed
nonstopAmerican Airlines
4h 28mORD-PDX
$609

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Portland - Chicago Flights

Departure:

Portland (PDX)United States

Return flight deals:

Chicago - Portland

Cabin classes:

$585
$578
$852
$203

Compare transportation modes for Portland to Chicago

Average priceAverage duration
Flights$9553h 50m
Trains$39046h 00m