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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 6/19. 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
Wed 7/10
Wed 7/17

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Portland.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Portland.
In the last 7 days travelers have searched 42,898,604 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

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Filter your dealsChoose cabin class, free Wi-Fi and more.

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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
9:08 pm - 11:31 pmORD-PDX
4h 23mnonstop
12:37 am - 6:38 amPDX-ORD
4h 01mnonstop
$84Spirit Airlines
Find Deal
Wed, Aug 21 - Mon, Aug 26
9:08 pm - 11:31 pmORD-PDX
4h 23mnonstop
12:37 am - 6:38 amPDX-ORD
4h 01mnonstop
$88Spirit Airlines
Find Deal
Wed, Aug 14 - Mon, Aug 26
9:08 pm - 11:31 pmORD-PDX
4h 23mnonstop
12:37 am - 6:38 amPDX-ORD
4h 01mnonstop
$98Spirit Airlines
Find Deal
Thu, Aug 15 - Sun, Aug 18
10:11 pm - 8:45 amORD-PDX
12h 34m1 stop
11:53 pm - 6:00 amPDX-ORD
4h 07mnonstop
Sat, Jun 22 - Sat, Jun 29
8:23 pm - 3:20 pmORD-PDX
20h 57m2 stops
11:53 pm - 6:00 amPDX-ORD
4h 07mnonstop
Tue, Jun 25 - Mon, Jul 1
12:23 pm - 9:31 pmMDW-PDX
11h 08m1 stop
3:40 pm - 3:14 pmPDX-MDW
21h 34m1 stop
$176Frontier
Find Deal
Mon, Aug 12 - Fri, Aug 23
5:54 am - 4:06 pmMDW-PDX
12h 12m1 stop
9:26 pm - 10:42 amPDX-MDW
11h 16m1 stop
$177Frontier
Find Deal
Thu, Sep 19 - Wed, Sep 25
7:00 am - 9:30 amORD-PDX
4h 30mnonstop
11:28 pm - 5:30 amPDX-ORD
4h 02mnonstop
$189Alaska Airlines
Find Deal
Fri, Sep 6 - Mon, Sep 9
7:00 am - 9:32 amORD-PDX
4h 32mnonstop
11:29 pm - 5:30 amPDX-ORD
4h 01mnonstop
$197Alaska Airlines
Find Deal
Sun, Oct 6 - Wed, Oct 9
6:00 am - 12:40 pmORD-PDX
8h 40m1 stop
12:50 am - 11:27 amPDX-ORD
8h 37m1 stop
$216Delta
Find Deal
Sat, Nov 2 - Fri, Nov 8

Flights from Chicago to Portland - Travel Insights & Trends

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

What is the cheapest Chicago to Portland flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Chicago to Portland.
Our data shows that the cheapest route for a one-way flight from Chicago to Portland cost $50 and was between Chicago O'Hare Intl Airport and Portland. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $99.

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

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

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

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

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

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

Which airlines provide the cheapest flights from Chicago to Portland?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the best return deals on flights connecting Chicago to Portland were found on Spirit Airlines ($84) and Frontier ($176). 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 (2 flights per day).

Which airlines fly non-stop between Chicago and Portland?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Chicago to Portland.
There are 5 airlines that fly nonstop from Chicago to Portland. They are: Alaska Airlines, American Airlines, Southwest, Spirit Airlines and United Airlines. The cheapest price of all airlines flying this route was found with Spirit Airlines at $67 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 14 and 18 nonstop flights that take off from Chicago and land in Portland, with an average flight time of 4h 23m. The most common departure time is 8:00 pm and most flights take off in the morning. Each week, there are 112 flights. The most frequent day of departure is Friday, 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 5% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Chicago O'Hare Airport to Portland

When to book flights from Chicago to Portland

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

FAQs for booking flights from Chicago to Portland

  • Can I fly out of Chicago with pets?

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

  • Which airport is best for people with disability needs?

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

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

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

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

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

  • What is the cheapest flight from Chicago to Portland?

    In the last 3 days, the lowest price for a flight from Chicago to Portland was $49 for a one-way ticket and $84 for a round-trip.

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

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

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

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

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

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

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

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

  • Which airline alliances offer flights from Chicago to Portland?

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

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

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

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

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

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

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

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

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

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

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

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

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

See more FAQs

Top tips for finding a cheap flight from Chicago to Portland

  • Looking for a cheap flight? 25% of our users found flights on this route for $114 or less one-way and $180 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 9254 reviews
8.2Boarding
7.3Entertainment
7.3Food
7.9Comfort
8.6Crew
Airline reviews

Everything was great but there were no entertainment options available.

6.0 GoodKyndra Homuth, Jun 2024SFO - PDX
Read more about Alaska Airlines reviews

Everything was great but there were no entertainment options available.

No prob with entertainment-would have selected n/a if it had been an option. No entertainment-flight was only a short hop. Great flight,

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Flight was canceled less than 6 hours before takeoff, rebooked on a flight that was twice as long and left earlier so we couldn’t make it, when using text support option took over 2 hours to speak with someone.

Not enough help at airport during boarding process. Flight was delayed. Overall WORST flying experience I’ve ever had. Will NEVER FLT SPIRIT AGAIN

Terrible legroom, seats do not recline, tray table the size of an iPhone, delayed flight, have to pay 5$ to get a cup of water onboard.

Could have TV/Movie and some water ou soda free

Flight was good and clean but delayed over an hour on the return flight.

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

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

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

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

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

I strongly dislike Frontier. I find them barebones, the seats not particularly comfortable, the nickel and diming is maddening, the app is TERRIBLE - super confusing to navigate, and the last 4 frontier flights I have flown have been on AVERAGE 2 hours late, one ruining a fancy night out in Vegas with reservations made well in advance, which was nodded to with a measly 5000 miles, which translates to almost nothing. At least credit a free checked bag or something.

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

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

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

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

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

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.
6/19Wed
nonstopSpirit Airlines
4h 27mORD-PDX
$49
6/19Wed
nonstopSpirit Airlines
4h 27mORD-PDX
$50
6/16Sun
1 stopFrontier
26h 45mORD-PDX
$74
6/18Tue
2 stopsFrontier
20h 57mORD-PDX
$79
9/7Sat
nonstopUnited Airlines
4h 25mORD-PDX
$89
10/15Tue
1 stopAlaska Airlines
8h 21mORD-PDX
$98
9/9Mon
nonstopAlaska Airlines
4h 30mORD-PDX
$100
10/15Tue
nonstopUnited Airlines
4h 29mORD-PDX
$104
10/15Tue
nonstopAmerican Airlines
4h 32mORD-PDX
$139
6/17Mon
nonstopAmerican Airlines
4h 28mORD-PDX
$142

Search by stops

Search by airline

Search by price

Last minute flights from Chicago to Portland

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Portland that are departing in the next 10 days.
6/15Sat
nonstopSpirit Airlines
4h 27mORD-PDX
6/29Sat
nonstopSpirit Airlines
4h 07mPDX-ORD
$114
6/15Sat
multi-stopSpirit Airlines
13h 36mORD-PDX
6/22Sat
nonstopSpirit Airlines
4h 07mPDX-ORD
$120
6/15Sat
multi-stopFrontier
29h 05mMDW-PDX
6/22Sat
multi-stopFrontier
8h 09mPDX-MDW
$204
6/15Sat
multi-stopFrontier
29h 05mMDW-PDX
6/22Sat
multi-stopFrontier
8h 56mPDX-MDW
$209
6/11Tue
nonstopAmerican Airlines
4h 28mORD-PDX
6/12Wed
nonstopAmerican Airlines
4h 05mPDX-ORD
$333
6/13Thu
nonstopAmerican Airlines
4h 28mORD-PDX
6/13Thu
multi-stopAmerican Airlines
7h 56mPDX-ORD
$337
6/11Tue
nonstopAlaska Airlines
4h 20mORD-PDX
6/12Wed
nonstopAlaska Airlines
4h 05mPDX-ORD
$373
6/11Tue
nonstopAlaska Airlines
4h 20mORD-PDX
6/14Fri
nonstopAlaska Airlines
4h 04mPDX-ORD
$398
6/12Wed
nonstopUnited Airlines
4h 28mORD-PDX
6/24Mon
nonstopUnited Airlines
3h 58mPDX-ORD
$408
6/12Wed
multi-stopUnited Airlines
8h 30mORD-PDX
6/24Mon
nonstopUnited Airlines
3h 58mPDX-ORD
$418

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Flights to Portland

Destination:

Portland (PDX)United States

Return flight deals:

Portland - Chicago

Cabin classes:

$682
$932
$598
$103

Compare transportation modes for Chicago to Portland

Average priceAverage duration
Flights$5274h 22m
Trains$36546h 12m