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PWM - CHI

$60 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 6/30. 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
Sat 7/6
Sat 7/13

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, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 44,060,346 times on KAYAK, and here is why:

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

Track pricesNot ready to book? Create a price alert for when prices drop.

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

Bundle and saveSave money when you bundle your flight + hotel.

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

 
These are the cheapest deals for flights from Portland to Chicago currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Portland to Chicago

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

Recent one-way flight deals from Portland to Chicago

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

Recent last minute flight deals from Portland to Chicago

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

Recent direct flight deals from Portland to Chicago

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

Cheap bus & train deals from Portland to Chicago

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

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
10:22 pm - 12:05 amPWM-ORD
2h 43mnonstop
6:03 pm - 9:22 pmORD-PWM
2h 19mnonstop
$85Frontier
Find Deal
Tue, Jul 30 - Tue, Aug 6
10:22 pm - 12:05 amPWM-ORD
2h 43mnonstop
5:53 pm - 9:12 pmORD-PWM
2h 19mnonstop
$88Frontier
Find Deal
Tue, Jul 23 - Thu, Jul 25
5:30 pm - 7:19 pmPWM-ORD
2h 49mnonstop
1:40 pm - 4:59 pmORD-PWM
2h 19mnonstop
$157American Airlines
Find Deal
Wed, Aug 21 - Sun, Aug 25
4:50 pm - 6:38 pmPWM-ORD
2h 48mnonstop
6:00 am - 11:31 amORD-PWM
4h 31m1 stop
$167United Airlines
Find Deal
Wed, Aug 21 - Sun, Aug 25
10:11 pm - 11:57 pmPWM-ORD
2h 46mnonstop
8:05 pm - 11:15 amORD-PWM
14h 10m1 stop
Sun, Aug 18 - Fri, Aug 23
7:09 am - 9:10 amPWM-ORD
3h 01mnonstop
8:20 am - 11:46 amORD-PWM
2h 26mnonstop
$188American Airlines
Find Deal
Wed, Sep 18 - Mon, Sep 23
6:40 pm - 10:46 pmPWM-ORD
5h 06m1 stop
2:40 pm - 10:39 pmORD-PWM
6h 59m1 stop
$196Delta
Find Deal
Wed, Jul 24 - Tue, Jul 30
1:27 pm - 7:10 pmPWM-ORD
6h 43m1 stop
5:53 pm - 9:12 pmORD-PWM
2h 19mnonstop
Mon, Jul 15 - Thu, Jul 18
6:30 am - 10:32 amPWM-ORD
5h 02m1 stop
7:00 am - 2:18 pmORD-PWM
6h 18m1 stop
$227Delta
Find Deal
Tue, Nov 5 - Tue, Nov 12
6:05 am - 7:54 amPWM-ORD
2h 49mnonstop
10:53 am - 2:18 pmORD-PWM
2h 25mnonstop
$260United Airlines
Find Deal
Tue, Jul 9 - Wed, Jul 10
10:05 pm - 11:48 pmPWM-ORD
2h 43mnonstop
$60Frontier
Find Deal
Sun, Jun 30
4:01 pm - 9:25 pmPWM-MDW
6h 24m1 stop
$88Frontier
Find Deal
Tue, Jul 23
6:40 pm - 10:46 pmPWM-ORD
5h 06m1 stop
$98Delta
Find Deal
Tue, Jul 16
9:45 am - 5:43 pmPWM-ORD
8h 58m1 stop
$108JetBlue
Find Deal
Mon, Jul 1
7:17 am - 9:10 amPWM-ORD
2h 53mnonstop
$120American Airlines
Find Deal
Fri, Jun 28
9:45 am - 5:43 pmPWM-ORD
8h 58m1 stop
$128JetBlue
Find Deal
Fri, Jul 5
4:49 pm - 8:56 pmPWM-ORD
5h 07m1 stop
$129American Airlines
Find Deal
Fri, Jun 28
5:37 am - 8:49 amPWM-MDW
4h 12m1 stop
$129Delta
Find Deal
Mon, Jul 1
5:30 am - 9:25 amPWM-ORD
4h 55m1 stop
$134United Airlines
Find Deal
Sun, Jun 30
6:00 am - 7:49 amPWM-ORD
2h 49mnonstop
$215United Airlines
Find Deal
Mon, Jun 10
4:04 pm - 7:56 pmPWM-MDW
4h 52m1 stop
12:57 pm - 12:57 pmMDW-PWM
23h 00m1 stop
$161Frontier
Find Deal
Sun, Jun 9 - Wed, Jun 12
10:05 pm - 11:48 pmPWM-ORD
2h 43mnonstop
5:52 pm - 9:12 pmORD-PWM
2h 20mnonstop
$250Frontier
Find Deal
Thu, Jun 6 - Sun, Jun 9
10:08 am - 6:58 pmPWM-ORD
9h 50m1 stop
5:52 pm - 9:12 pmORD-PWM
2h 20mnonstop
$284Frontier
Find Deal
Thu, Jun 6 - Sun, Jun 9
9:59 am - 6:56 pmPWM-ORD
9h 57m1 stop
5:58 pm - 9:06 amORD-PWM
14h 08m1 stop
$309Frontier
Find Deal
Sun, Jun 9 - Wed, Jun 12
12:29 pm - 2:18 pmPWM-ORD
2h 49mnonstop
7:15 pm - 10:43 pmORD-PWM
2h 28mnonstop
$369American Airlines
Find Deal
Mon, Jun 10 - Sat, Jun 15
12:29 pm - 2:18 pmPWM-ORD
2h 49mnonstop
4:42 pm - 11:53 pmORD-PWM
6h 11m1 stop
$373American Airlines
Find Deal
Mon, Jun 10 - Wed, Jun 12
12:50 pm - 5:04 pmPWM-MDW
5h 14m1 stop
5:45 pm - 11:21 pmMDW-PWM
4h 36m1 stop
$433Delta
Find Deal
Mon, Jun 10 - Sat, Jun 15
6:15 am - 11:55 amPWM-MDW
6h 40m1 stop
3:45 pm - 9:58 pmMDW-PWM
5h 13m1 stop
$448Delta
Find Deal
Fri, Jun 7 - Mon, Jun 10
2:06 pm - 12:55 amPWM-ORD
11h 49m2 stops
8:05 pm - 12:41 pmORD-PWM
15h 36m1 stop
Mon, Jun 10 - Wed, Jun 12
1:16 pm - 8:00 pmPWM-ORD
31h 44m3 stops
8:05 pm - 12:41 pmORD-PWM
15h 36m1 stop
Sun, Jun 9 - Wed, Jun 12
10:22 pm - 12:05 amPWM-ORD
2h 43mnonstop
6:03 pm - 9:22 pmORD-PWM
2h 19mnonstop
$85Frontier
Find Deal
Tue, Jul 30 - Tue, Aug 6
10:22 pm - 12:05 amPWM-ORD
2h 43mnonstop
5:53 pm - 9:12 pmORD-PWM
2h 19mnonstop
$88Frontier
Find Deal
Tue, Jul 23 - Thu, Jul 25
9:55 pm - 11:38 pmPWM-ORD
2h 43mnonstop
5:52 pm - 9:12 pmORD-PWM
2h 20mnonstop
$89Frontier
Find Deal
Tue, Jun 25 - Thu, Jun 27
5:30 pm - 7:19 pmPWM-ORD
2h 49mnonstop
1:40 pm - 4:59 pmORD-PWM
2h 19mnonstop
$157American Airlines
Find Deal
Wed, Aug 21 - Sun, Aug 25
5:30 pm - 7:19 pmPWM-ORD
2h 49mnonstop
1:36 pm - 4:56 pmORD-PWM
2h 20mnonstop
$177American Airlines
Find Deal
Thu, Aug 29 - Sun, Sep 1
7:09 am - 9:10 amPWM-ORD
3h 01mnonstop
8:20 am - 11:46 amORD-PWM
2h 26mnonstop
$188American Airlines
Find Deal
Wed, Sep 18 - Mon, Sep 23
6:05 am - 7:54 amPWM-ORD
2h 49mnonstop
6:05 pm - 9:33 pmORD-PWM
2h 28mnonstop
$247United Airlines
Find Deal
Thu, Jul 11 - Mon, Jul 15
6:05 am - 7:54 amPWM-ORD
2h 49mnonstop
10:53 am - 2:18 pmORD-PWM
2h 25mnonstop
$260United Airlines
Find Deal
Tue, Jul 9 - Wed, Jul 10
6:05 am - 7:54 amPWM-ORD
2h 49mnonstop
6:05 pm - 9:33 pmORD-PWM
2h 28mnonstop
$278United Airlines
Find Deal
Fri, Jul 12 - Mon, Jul 15
6:02 am - 7:51 amPWM-ORD
2h 49mnonstop
6:05 pm - 9:33 pmORD-PWM
2h 28mnonstop
$283United Airlines
Find Deal
Wed, Jul 17 - Wed, Jul 24

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 $89 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 $111.

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.
If you are looking for a flight deal from Portland to Chicago, look for departures on Saturdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Chicago, Tuesday is the cheapest day to fly and Friday is the most expensive.

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 September, where tickets cost $291 on average. On the other hand, the most expensive months are April and December, where the average cost of tickets is $590 and $532 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Portland to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Portland to Chicago, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 89 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.
In the last 3 days, Frontier offered the best one-way deal for that route, at $60. KAYAK users also found Portland to Chicago round-trip flights on Frontier from $85 and on American Airlines from $157.

Which airlines fly most frequently between Portland and Chicago?

American Airlines connects Portland to Chicago with up to 3 flights per day. United Airlines also offers 3 flights per day, while Southwest follows with 1 flight per day.

Which airlines fly non-stop between Portland and Chicago?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Portland to Chicago.
There are 4 airlines that fly nonstop from Portland to Chicago. They are: American Airlines, Frontier, Southwest and United Airlines. The cheapest price of all airlines flying this route was found with Frontier at $40 for a one-way flight. On average, the best prices for this route can be found at Frontier.

How many flights are there between Portland and Chicago per day?

Each day, there are between 8 and 10 nonstop flights that take off from Portland and land in Chicago, with an average flight time of 2h 45m. The most common departure time is 4:00 pm and most flights take off in the morning, while the most flights land at Chicago O'Hare Intl Airport. Each week, there are 61 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 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?

Direct flights take on average 2h 43m to travel the 885 miles between Portland and Chicago.

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

Early birds can take the earliest flight from Portland at 6:00 am and will be landing in Chicago at 7:49 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 10:26 pm and lands at 12:09 am.

Good to know

Low season

January

High season

June

Cheapest flight

$60
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 10% lower on average.
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

  • 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 $60 for a one-way ticket and $85 for a round-trip.

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

    A passport is not required to fly from Portland to Chicago.

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

    On your way to Chicago, you’ll fly out from Portland. You’ll be landing in one of Chicago’s 2 airports: Chicago Midway or Chicago O'Hare Intl.

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

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

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

    The Boeing 737-700 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, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Portland to Chicago are Delta and United Airlines. With an average price for the route of $343 and an overall rating of 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $403 and an overall rating of 7.4.

  • 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 $185 or less one-way and $362 or less round-trip.

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 New Zealand, American Airlines, Emirates, +3 more

Air New Zealand, American Airlines, +4 more

Tuesday

Air New Zealand, American Airlines, Emirates, +4 more

Air New Zealand, American Airlines, +5 more

Wednesday

Air New Zealand, American Airlines, Emirates, +3 more

Air New Zealand, American Airlines, +4 more

Thursday

Air New Zealand, American Airlines, Emirates, +4 more

Air New Zealand, American Airlines, +5 more

Friday

Air New Zealand, American Airlines, Emirates, +3 more

Air New Zealand, American Airlines, +4 more

Saturday

Air New Zealand, American Airlines, Emirates, +3 more

Air New Zealand, American Airlines, +4 more

Sunday

Air New Zealand, American Airlines, Emirates, +4 more

Air New Zealand, American Airlines, +5 more

See more direct flights

Nonstop returns

Chicago to Portland

Monday

Air New Zealand, American Airlines, Qatar Airways, +2 more

Air New Zealand, American Airlines, +3 more

Tuesday

Air New Zealand, American Airlines, Frontier, +3 more

Air New Zealand, American Airlines, +4 more

Wednesday

Air New Zealand, American Airlines, Qatar Airways, +2 more

Air New Zealand, American Airlines, +3 more

Thursday

Air New Zealand, American Airlines, Frontier, +3 more

Air New Zealand, American Airlines, +4 more

Friday

Air New Zealand, American Airlines, Qatar Airways, +2 more

Air New Zealand, American Airlines, +3 more

Saturday

Air New Zealand, American Airlines, Qatar Airways, +2 more

Air New Zealand, American Airlines, +3 more

Sunday

Air New Zealand, American Airlines, Frontier, +3 more

Air New Zealand, American Airlines, +4 more

See more direct flights
See more direct flights

Top 4 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
DeltaOverall score based on 10371 reviews
8.2Boarding
8.0Entertainment
7.9Comfort
7.4Food
8.6Crew
Airline reviews

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

8.0 Excellentmilton, Jun 2024ANC - MSP
Read more about Delta reviews

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

I had a great flight. Everything went smoothly and the flight arrived early.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

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.

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.

Internet service was erratic. Crew service was poor and slow. My luggage on this non-stop flight was lost and not recovered

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 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.

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.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

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.
6/30Sun
nonstopFrontier
2h 43mPWM-ORD
$60
7/23Tue
1 stopFrontier
6h 24mPWM-MDW
$88
7/16Tue
1 stopDelta
5h 06mPWM-ORD
$98
7/1Mon
1 stopJetBlue
8h 58mPWM-ORD
$108
6/28Fri
nonstopAmerican Airlines
2h 53mPWM-ORD
$120
7/5Fri
1 stopJetBlue
8h 58mPWM-ORD
$128
6/28Fri
1 stopAmerican Airlines
5h 07mPWM-ORD
$129
7/1Mon
1 stopDelta
4h 12mPWM-MDW
$129
6/30Sun
1 stopUnited Airlines
4h 55mPWM-ORD
$134
6/10Mon
nonstopUnited Airlines
2h 49mPWM-ORD
$215

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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.
6/9Sun
multi-stopFrontier
4h 52mPWM-MDW
6/12Wed
multi-stopFrontier
23h 00mMDW-PWM
$161
6/6Thu
nonstopFrontier
2h 43mPWM-ORD
6/9Sun
nonstopFrontier
2h 20mORD-PWM
$250
6/6Thu
multi-stopFrontier
9h 50mPWM-ORD
6/9Sun
nonstopFrontier
2h 20mORD-PWM
$284
6/9Sun
multi-stopFrontier
9h 57mPWM-ORD
6/12Wed
multi-stopFrontier
14h 08mORD-PWM
$309
6/10Mon
nonstopAmerican Airlines
2h 49mPWM-ORD
6/15Sat
nonstopAmerican Airlines
2h 28mORD-PWM
$369
6/10Mon
nonstopAmerican Airlines
2h 49mPWM-ORD
6/12Wed
multi-stopAmerican Airlines
6h 11mORD-PWM
$373
6/10Mon
multi-stopDelta
5h 14mPWM-MDW
6/15Sat
multi-stopDelta
4h 36mMDW-PWM
$433
6/7Fri
multi-stopDelta
6h 40mPWM-MDW
6/10Mon
multi-stopDelta
5h 13mMDW-PWM
$448
6/10Mon
multi-stop
11h 49mPWM-ORD
6/12Wed
multi-stop
15h 36mORD-PWM
$519
6/9Sun
multi-stop
31h 44mPWM-ORD
6/12Wed
multi-stop
15h 36mORD-PWM
$624

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Portland - Chicago Flights

Departure:

Portland (PWM)United States

Return flight deals:

Chicago - Portland

Cabin classes:

$787
$1,117
$1,378
$111