PWM - CHI

$97 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 6/10. 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
1 adult, Economy, 0 bags

KAYAK searches 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

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

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

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

Everything you should know

Cheapest round-trip
$248
Overall average: $319
American Airlines
Fri 4/3Sun 4/5
PWM - ORD • Non-stop
Cheapest one-way
$97
Typical prices: $176-$288
JetBlue
Wed 6/10
PWM - ORD • 1 stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
American's Basic Economy is carry-on only, budget-friendly.
United's Economy Plus offers extra legroom for comfort.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $248 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines and United Airlines. Average duration is 3h 07m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 19% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $192 (round-trip)
Shortest trip • 4h 59m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 30% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 17% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Portland to Chicago (PWM-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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Portland to Chicago

Fri, Apr 3 - Sun, Apr 5
American Airlines Logo
5:40 pm - 7:50 pm
PWM
-
ORD
3h 10mnonstop
American Airlines Logo
1:45 pm - 5:07 pm
ORD
-
PWM
2h 22mnonstop
$248American Airlines
Fri, May 22 - Sun, May 24
United Airlines Logo
6:00 am - 8:00 am
PWM
-
ORD
3h 00mnonstop
United Airlines Logo
6:18 pm - 9:51 pm
ORD
-
PWM
2h 33mnonstop
$249United Airlines
Thu, Jun 4 - Sun, Jun 7
Southwest Logo
7:40 am - 9:15 am
PWM
-
MDW
2h 35mnonstop
Southwest Logo
7:55 pm - 11:10 pm
MDW
-
PWM
2h 15mnonstop
$249Southwest
Thu, Jun 4 - Sat, Jun 6
Southwest Logo
7:40 am - 9:15 am
PWM
-
MDW
2h 35mnonstop
Southwest Logo
1:10 pm - 9:00 pm
MDW
-
PWM
6h 50m
1 stop
$259Southwest
Fri, May 22 - Sun, May 24
United Airlines Logo
4:51 pm - 6:51 pm
PWM
-
ORD
3h 00mnonstop
United Airlines Logo
6:12 pm - 11:51 pm
ORD
-
PWM
4h 39m
1 stop
$259United Airlines
Thu, Jun 4 - Sat, Jun 6
Southwest Logo
7:40 am - 9:15 am
PWM
-
MDW
2h 35mnonstop
Southwest Logo
2:10 pm - 11:40 pm
MDW
-
PWM
8h 30m
2 stops
$264Southwest
Thu, Jun 4 - Sat, Jun 6
American Airlines Logo
7:19 pm - 9:45 pm
PWM
-
ORD
3h 26mnonstop
American Airlines Logo
7:28 am - 11:03 am
ORD
-
PWM
2h 35mnonstop
$268American Airlines
Fri, May 22 - Mon, May 25
Delta Logo
12:55 pm - 6:05 pm
PWM
-
ORD
6h 10m
1 stop
Delta Logo
7:00 am - 12:00 pm
ORD
-
PWM
4h 00m
1 stop
$269Delta
Mon, Apr 13 - Tue, Apr 14
Southwest Logo
4:50 pm - 10:20 pm
PWM
-
MDW
6h 30m
1 stop
Southwest Logo
5:00 pm - 10:35 pm
MDW
-
PWM
4h 35m
1 stop
$269Southwest
Wed, Apr 29 - Mon, May 4
Delta Logo
2:51 pm - 11:59 pm
PWM
-
ORD
10h 08m
2 stops
Delta Logo
6:21 pm - 12:46 am
ORD
-
PWM
5h 25m
1 stop
$274Delta
Booking Insights

KAYAK's insights & trends for Portland to Chicago flights

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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Portland to Chicago costs $246 on the route between Portland (PWM) and Chicago O'Hare Intl Airport (ORD). Over the past month, this route was, on average, 19% cheaper than other Portland-Chicago routes. It is also the most popular route.

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

The average price of all round-trip flights from Portland to Chicago clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Chicago on a Tuesday and more expensive on a Sunday. On your return trip to Portland, you should consider flying back on a Tuesday, and avoid Thursdays for better deals.

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 round-trip 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 $281 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $420 and $391 respectively.

Can I save money by flying with a layover from Portland to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $337 on average.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip 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 week.

To get a below average price on the flight from Portland to Chicago, you should book around 5 weeks before departure, which saves you about 30% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Expert advice

Expert advice for your flight from Portland to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Good to know

Low seasonJanuary
Cheapest flight$97
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 2% 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 $97 for a one-way ticket and $248 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, and Delta offer inflight Wi-Fi service on the Portland to Chicago flight route.

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

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Portland to Chicago flight route.

  • Which airline alliances offer flights from Portland to Chicago?

    SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between Portland and Chicago, with SkyTeam 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, Southwest or United Airlines?

    The two airlines most popular with KAYAK users for flights from Portland to Chicago are Southwest and United Airlines. With an average price for the route of $385 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $347 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.

KAYAK’s 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 $208 or less one-way and $419 or less round-trip.

Prefer to fly direct from Portland to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Portland to Chicago.
Find which airlines fly direct from Portland Airport to Chicago, which days they fly and book direct flights.

Direct departures

Portland to Chicago

Monday

American Airlines,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines,United Airlines

American Airlines,United Airlines

See more direct flights

Direct returns

Chicago to Portland

Monday

American Airlines,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines,United Airlines

American Airlines,United Airlines

See more direct flights

Reviews of the top 3 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
SouthwestOverall score based on 4320 reviews
8.1Boarding
7.5Entertainment
7.0Food
8.0Comfort
8.6Crew
Airline reviews

We had a 5 hour delay on the tarmac in Baltimore

2.0 MediocreDavid, Mar 2026
ALB - BWI
Read more Southwest reviews

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

Everything you need to know for your flight from Portland to Chicago

Information on your arrival and departure airports