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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 6/13
Thu 6/20

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Portland.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Portland.
In the last 7 days travelers have searched 41,771,603 times on KAYAK, and here is why:

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

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Portland 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
8:00 pm - 10:30 pmORD-PDX
4h 30mnonstop
11:53 pm - 6:00 amPDX-ORD
4h 07mnonstop
$67Spirit Airlines
Find Deal
Wed, May 29 - Wed, Jun 5
8:00 pm - 10:30 pmORD-PDX
4h 30mnonstop
11:53 pm - 6:00 amPDX-ORD
4h 07mnonstop
$68Spirit Airlines
Find Deal
Wed, May 29 - Wed, Jun 5
8:26 pm - 10:53 pmORD-PDX
4h 27mnonstop
11:53 pm - 6:00 amPDX-ORD
4h 07mnonstop
$83Spirit Airlines
Find Deal
Wed, Jun 12 - Sat, Jun 15
4:18 pm - 3:28 pmMDW-PDX
25h 10m1 stop
7:43 am - 11:08 amPDX-MDW
25h 25m1 stop
$167Frontier
Find Deal
Wed, May 29 - Wed, Jun 5
6:45 pm - 6:48 amORD-PDX
14h 03m1 stop
12:49 am - 8:48 pmPDX-ORD
17h 59m1 stop
$167Frontier
Find Deal
Wed, May 29 - Tue, Jun 4
7:10 am - 9:38 amORD-PDX
4h 28mnonstop
12:20 am - 6:18 amPDX-ORD
3h 58mnonstop
$207United Airlines
Find Deal
Wed, Jun 19 - Fri, Jun 28
2:25 pm - 4:45 pmORD-PDX
4h 20mnonstop
11:11 pm - 5:15 amPDX-ORD
4h 04mnonstop
$209Alaska Airlines
Find Deal
Thu, Aug 8 - Mon, Aug 12
7:00 am - 9:32 amORD-PDX
4h 32mnonstop
11:29 pm - 5:28 amPDX-ORD
3h 59mnonstop
$218Alaska Airlines
Find Deal
Tue, Oct 29 - Mon, Nov 4
8:30 pm - 10:58 pmORD-PDX
4h 28mnonstop
11:55 pm - 6:00 amPDX-ORD
4h 05mnonstop
$228American Airlines
Find Deal
Tue, Jun 18 - Mon, Jun 24
7:10 am - 9:38 amORD-PDX
4h 28mnonstop
12:20 am - 6:18 amPDX-ORD
3h 58mnonstop
$229United Airlines
Find Deal
Fri, Jul 12 - Thu, Jul 18

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 $69 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 $109.

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 June and July, where the average cost of tickets is $418 and $418 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 2 weeks 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 ($67) and Frontier ($167). Spirit Airlines proposed the cheapest one-way flight at $49.

Which airlines fly most frequently between Chicago and Portland?

The airlines most regularly connecting Chicago to Portland are United Airlines (7 flights per day), Southwest (4 flights per day), and American Airlines (3 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 $88 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 15 and 19 nonstop flights that take off from Chicago and land in Portland, with an average flight time of 4h 24m. The most common departure time is 8:00 pm and most flights take off in the morning. Each week, there are 119 flights. The most frequent day of departure is Thursday, when 16% of all weekly flights depart. The fewest flights depart on a Saturday.

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 6% drop in price.
Most popular time to fly with an average 17% 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 $67 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 $342 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 $341 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 $204 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 9144 reviews
8.6Crew
7.3Entertainment
8.2Boarding
7.3Food
7.9Comfort
Airline reviews

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

4.0 OkayAnonymous, May 2024EWR - PDX
Read more about Alaska Airlines reviews

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.

I appreciated the ability to choose between multiple flights both into and out of Portland from Burbank on the same day, so we were able to attend an event and return without spending the night. I am unable to appreciate what Alaska Air calls "streamlining" the checkin/boarding process at Burbank Airport. If you have a smartphone and the Alaska Air app, it is probably fine, but removing the option of using onsite kiosks to print boarding passes does not meet my definition of "streamlined". I also found it challenging that both Portland and Burbank airports required the plane to sit on the runway for some time due to lack of an open gate at which to disembark. It would not be so bad if we could at least remove our seat belts and move a little bit while we waited, but that is not an option. I honestly don't know whether this is because of how Alaska Air operates, or just the circumstances of the particular day and airports we were using, but I normally do not experience these kinds of delays to reach a gate using Southwest Air.

I was not given a seat when I bought the ticket. I know airlines are trying to squeeze every penny out ot the customer, but we are buying a seat on the airplane, right? I find this irritating with all airlines, but especially Alaska because I fly it so often. No sense of customer use and loyalty.

It was adequate nothing special no entertain because flight was short. Crew pleasant.

All employees were very nice and I was very comfortable

Loved the gate agent and flight attendants. All were extremely helpful.

It was a good flight, wish they would have handed out snacks though.

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.

The control panel for the seat back screen did not work at all after takeoff.

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.

They stuck us with multiple extra fees. I will never fly spirit again

Arrived 3 hours early and never made it past baggage drop

Flight delayed then canceled! I will NEVER fly Spirit Airlines again and will tell all my friends!

Absolutely terrible. The boarding process had zero organization. Mobs of people trying to board. People were climbing over my child's stroller with her in it. No families were boarded first. Boarding was delayed with no reasoning or notification that it would be late. We were then stuck on the plane for 45 minutes after landing. Then waited over two hours for our luggage. There was zero communication with the travelers. Never have I experienced such I professionalism and disgrace of others. Extremely disappointed.

For it to have left on time! Instead of two hours early with zero notice

Flight kept delayed from morning to late afternoon so I had to make other arrangements

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.

Terrible… missed our flight due to ridiculously long time to go thru baggage check-in!

The crew was not great or professional. It seemed like they didn't really want to be there. A true lack of effort for accommodating customers.

Everything was really good but the seats are not very comfortable.

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

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.

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
6/3Mon
nonstopSpirit Airlines
4h 30mORD-PDX
$50
6/3Mon
1 stopFrontier
6h 50mORD-PDX
$85
6/26Wed
1 stopFrontier
9h 55mMDW-PDX
$90
7/4Thu
nonstopAlaska Airlines
4h 20mORD-PDX
$95
7/13Sat
nonstopUnited Airlines
4h 28mORD-PDX
$104
6/4Tue
nonstopAmerican Airlines
4h 28mORD-PDX
$115
5/28Tue
nonstopAmerican Airlines
4h 28mORD-PDX
$127
7/7Sun
nonstopUnited Airlines
4h 28mORD-PDX
$204
6/19Wed
2 stopsAlaska Airlines
11h 25mORD-PDX
$258

Search by stops

Search by airline

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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.
5/17Fri
nonstopSpirit Airlines
4h 30mORD-PDX
5/23Thu
nonstopSpirit Airlines
3h 50mPDX-ORD
$106
5/17Fri
nonstopSpirit Airlines
4h 30mORD-PDX
5/20Mon
nonstopSpirit Airlines
3h 50mPDX-ORD
$107
5/15Wed
multi-stop
14h 21mORD-PDX
5/18Sat
nonstop
3h 50mPDX-ORD
$159
5/19Sun
nonstop
4h 30mORD-PDX
5/22Wed
multi-stop
30h 40mPDX-ORD
$176
5/16Thu
multi-stopFrontier
11h 07mMDW-PDX
5/27Mon
multi-stopFrontier
11h 13mPDX-MDW
$189
5/19Sun
multi-stopFrontier
12h 28mMDW-PDX
5/22Wed
multi-stopFrontier
31h 30mPDX-MDW
$200
5/15Wed
nonstopUnited Airlines
4h 32mORD-PDX
5/28Tue
nonstopUnited Airlines
4h 05mPDX-ORD
$293
5/15Wed
multi-stopUnited Airlines
6h 32mORD-PDX
5/27Mon
nonstopUnited Airlines
3h 58mPDX-ORD
$302
5/16Thu
multi-stopDelta
6h 30mORD-PDX
5/20Mon
multi-stopDelta
6h 50mPDX-ORD
$327
5/15Wed
multi-stopDelta
6h 32mORD-PDX
5/17Fri
multi-stopDelta
8h 45mPDX-ORD
$352

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Flights to Portland

Destination:

Portland (PDX)United States

Return flight deals:

Portland - Chicago

Cabin classes:

$588
$1,338
$717
$109

Compare transportation modes for Chicago to Portland

Average priceAverage duration
Flights$4654h 20m
Trains$24646h 12m