PDX - ORD

$179 Find Cheap Flights from Portland to Chicago O'Hare Airport - Compare and Save

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Everything you should know

Cheapest round-trip
$353
Typical prices: $320-$484
Alaska Airlines
Wed 11/21Thu 11/22
PDX - ORD • 1 stop
Cheapest non-stop
$357
Typical prices: $323-$485
American Airlines
Sun 12/30Wed 1/10
PDX - ORD • Non-stop
Nonstop flights
You can fly direct with United Airlines, American Airlines and Alaska Airlines. Average duration is 4h 07m
Direct flights
+1
Direct flights
+1
When to book
in advance
Our data shows that travelers who book at least 18 weeks in advance save around 40% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 29% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $241 (round-trip)
Shortest trip • 6h 25m (one-way)
Insights
Insights
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We hope you love your trip to Chicago O'Hare Intl Airport!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Portland to O'Hare Intl (PDX-ORD)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Portland to O'Hare Intl

Wed, Dec 16 - Sun, Dec 20
Alaska Airlines Logo
7:30 am - 5:49 pmPDX  Portland-ORD Chicago O'Hare Intl
8h 19m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
8:59 pm - 8:29 amORD  Chicago O'Hare Intl-PDX Portland
13h 30m1 stop Seattle/Tacoma Intl
$353Alaska Airlines
Tue, Dec 8 - Sun, Dec 20
Alaska Airlines Logo
4:03 pm - 11:59 pmPDX  Portland-ORD Chicago O'Hare Intl
5h 56m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
8:59 pm - 8:29 amORD  Chicago O'Hare Intl-PDX Portland
13h 30m1 stop Seattle/Tacoma Intl
$353Alaska Airlines
Thu, Nov 12 - Sun, Nov 15
American Airlines Logo
1:22 pm - 7:44 pmPDX  Portland-ORD Chicago O'Hare Intl
4h 22mnonstop
American Airlines Logo
6:00 am - 1:44 pmORD  Chicago O'Hare Intl-PDX Portland
9h 44m1 stop Dallas/Fort Worth
$354American Airlines
Wed, Feb 24 - Sun, Feb 28
Delta Logo
9:40 am - 9:53 pmPDX  Portland-ORD Chicago O'Hare Intl
10h 13m2 stops Seattle/Tacoma Intl Salt Lake City
Delta Logo
6:59 pm - 11:51 pmORD  Chicago O'Hare Intl-PDX Portland
6h 52m1 stop Salt Lake City
$354Delta
Tue, Jan 12 - Tue, Jan 19
Frontier Logo
4:29 pm - 4:55 pmPDX  Portland-ORD Chicago O'Hare Intl
22h 26m2 stops Denver Intl Dallas/Fort Worth
Frontier Logo
6:21 am - 3:03 pmORD  Chicago O'Hare Intl-PDX Portland
10h 42m1 stop Denver Intl
$355Frontier
Fri, Dec 4 - Sun, Dec 6
Frontier Logo
12:48 pm - 12:53 amPDX  Portland-ORD Chicago O'Hare Intl
10h 05m2 stops Las Vegas Harry Reid Intl Denver Intl
Frontier Logo
7:25 am - 1:03 pmORD  Chicago O'Hare Intl-PDX Portland
7h 38m1 stop Denver Intl
$355Frontier
Mon, Nov 16 - Fri, Nov 20
United Airlines Logo
11:30 pm - 5:19 amPDX  Portland-ORD Chicago O'Hare Intl
3h 49mnonstop
United Airlines Logo
4:25 pm - 7:12 pmORD  Chicago O'Hare Intl-PDX Portland
4h 47mnonstop
$357United Airlines
Sat, Nov 14 - Sat, Nov 21
United Airlines Logo
2:37 pm - 8:45 pmPDX  Portland-ORD Chicago O'Hare Intl
4h 08mnonstop
United Airlines Logo
7:45 pm - 10:27 pmORD  Chicago O'Hare Intl-PDX Portland
4h 42mnonstop
$357United Airlines
Sat, Nov 14 - Mon, Nov 16
American Airlines Logo
11:09 pm - 5:07 amPDX  Portland-ORD Chicago O'Hare Intl
3h 58mnonstop
American Airlines Logo
5:05 pm - 7:47 pmORD  Chicago O'Hare Intl-PDX Portland
4h 42mnonstop
$357American Airlines
Wed, Feb 24 - Sun, Feb 28
Delta Logo
9:40 am - 9:53 pmPDX  Portland-ORD Chicago O'Hare Intl
10h 13m2 stops Seattle/Tacoma Intl Salt Lake City
Delta Logo
6:59 pm - 11:51 pmORD  Chicago O'Hare Intl-PDX Portland
6h 52m1 stop Salt Lake City
$359Delta
Booking Insights

Price, demand and travel trends for Portland to Chicago O'Hare Intl Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Portland to Chicago O'Hare Intl Airport?

Round-trip flights from Portland to Chicago O'Hare Intl Airport typically range from $320 to $484. The lowest price found in the past 5 days was $353, on Alaska Airlines.

What's the cheapest day of the week to fly from Portland to Chicago O'Hare Intl Airport?

Based on deals KAYAK users found in the last 12 months, Saturday is the cheapest day of the week to fly from Portland to Chicago O'Hare Intl Airport. It’s 6% cheaper than the average day, while Sunday is the most expensive, with prices 13% higher.

What’s the cheapest month to fly from Portland to Chicago O'Hare Intl Airport?

•January is the cheapest month to fly from Portland to Chicago O'Hare Intl Airport at $276 round-trip.
•November ($436) and December ($433) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 57% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Portland to Chicago O'Hare Intl Airport the cheapest?

Flights from Portland to Chicago O'Hare Intl Airport are cheapest 18 weeks before departure. Booking in this window typically costs about 40% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

Expert advice for your flight from Portland to O'Hare Intl

 
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 and ORD

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 and Alaska 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.

Gabriel Leigh

Gabriel Leigh

Expert on PDX

Gabriel is a writer and video creator. As senior content producer for Flightradar24 and Monocle’s transport correspondent, he keeps a close eye on aviation in particular. He has also written travel articles for the likes of The New York Times. Born in New York but raised around the world, he now lives in Sweden. He’s been to 75 countries, flying 2.3 million miles on 113 airlines and through 234 airports in the process.

Key details for Portland to Chicago O'Hare Intl Airport flights

Low season

February

Cheapest flight

$179
Beat the crowds with an average 39% drop in travelers.
The most popular month to fly with an average 38% increase in travelers.
One-way flight from Portland to Chicago O'Hare Intl Airport

When to book flights from Portland to O'Hare Intl

Are your dates flexible? Find out the best times to travel from Portland to O'Hare Intl based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Portland to Chicago O'Hare Intl Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Portland to Chicago O'Hare Intl Airport?

    These are the earliest and latest flight times available from Portland to Chicago O'Hare Intl Airport:

    • Earliest: departs at 12:02 am and lands at 4:09 am
    • Latest: departs at 11:59 pm and lands at 4:06 am.

    The flight takes about 4h 07m.

  • What cabin classes can I book on flights from Portland to Chicago O'Hare Intl Airport?

    Three cabin classes are available on flights from Portland to Chicago O'Hare Intl Airport:

    • Economy Class
    • Business Class
    • First Class

  • How long is a flight from Portland to Chicago O'Hare Intl Airport?

    A nonstop flight from Portland to Chicago O'Hare Intl Airport takes 4h 07m, covering 1,733 miles.

  • Do I need a passport to fly from Portland to Chicago O'Hare Intl Airport?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Portland to Chicago O'Hare Intl Airport flight?

    Round-trip flights from Portland to Chicago O'Hare Intl Airport range from $320 to $484, with an average of $387 over the past 12 months. Anything below $320 counts as a good deal.

  • How expensive are last-minute Portland to Chicago O'Hare Intl Airport flights?

    Last-minute fares on this route (booked within two weeks of departure) run 42% above the $387 route average. Book 18 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Portland to Chicago O'Hare Intl Airport?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $241 round-trip via Denver Intl (DEN), compared to $388 for nonstop.

  • What is the standard checked-bag allowance on flights from Portland to Chicago O'Hare Intl Airport?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Portland to Chicago O'Hare Intl Airport?

    The Boeing 737-800 family is used most often on this route, operated mainly by United Airlines and American Airlines. Other aircraft seen on the route include Airbus A321-100/200 variants.

  • How are flight departures from Portland to Chicago O'Hare Intl Airport spread across the day?

    Morning is the busiest departure period on Portland to Chicago O'Hare Intl Airport flights, with 51% of flights leaving in that window. Afternoon departures account for 33%, night flights for 16%, and evening flights for 0%.

  • Have flight prices from Portland to Chicago O'Hare Intl Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $353 to $1,522. That means the highest observed fare was about 4x higher than the lowest one.

  • Which airlines offer Wi-Fi on Portland to Chicago O'Hare Intl Airport flights?

    Three airlines offer in-flight Wi-Fi on Portland to Chicago O'Hare Intl Airport flights:

    • American Airlines
    • Alaska Airlines
    • JetBlue

    Pricing varies by airline and fare class. Some plans are included with the ticket or loyalty program; others are paid add-ons priced by flight length.

  • How are flight prices from Portland to Chicago O'Hare Intl Airport looking right now?

    One-way fares from Portland to Chicago O'Hare Intl Airport are currently lower than usual. Average one-way flight prices are about $180, which is 21% below the typical average for this route.

  • What car rental options are available at Chicago O'Hare Intl Airport (ORD)?

    Chicago O'Hare Intl Airport (ORD) hosts 5 major car rental companies, with daily rates starting from around $17 for economy cars. Top options include:

    • Routes Car & Truck Rentals
    • Europcar
    • Hertz
    • Ace
    • Dollar

  • Which airports can I use when flying from Portland to Chicago O'Hare Intl Airport?

    Flights from Portland to Chicago O'Hare Intl Airport usually depart from Portland (PDX) and arrive at Chicago O'Hare Intl (ORD).

  • Which airports do connecting flights from Portland to Chicago O'Hare Intl Airport pass through?

    One-stop flights from Portland to Chicago O'Hare Intl Airport most commonly connect through:

    • Denver Intl (DEN) - 37% of one-stop connections
    • Seattle/Tacoma Intl (SEA) - 31% of one-stop connections
    • Minneapolis St Paul (MSP) - 13% of one-stop connections
    • San Diego (SAN) - 12% of one-stop connections

  • Can I save money by using flexible dates for flights from Portland to Chicago O'Hare Intl Airport?

    Yes. Flexible dates can save you up to 17% on flights from Portland to Chicago O'Hare Intl Airport. Saturday is the cheapest departure day at $365 round-trip on average, while Sunday is the most expensive at $439, a difference of $74.

    Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • What airlines fly from Portland to Chicago O'Hare Intl Airport?

    3 airlines operate flights between Portland and Chicago O'Hare Intl Airport. The airlines offering nonstop flights on this route include:

    • United Airlines
    • American Airlines
    • Alaska Airlines

  • How much time can I save by choosing a different layover airport from Portland to Chicago O'Hare Intl Airport?

    Flying via Salt Lake City (SLC) gives the shortest average 1-stop total travel time at 6h 25m, compared with 6h 44m via Seattle/Tacoma Intl (SEA) and 7h 34m via Dallas/Fort Worth (DFW).

  • What is the time difference between Portland and Chicago O'Hare Intl Airport?

    Chicago O'Hare Intl Airport is 2 hours ahead of Portland (Central Time vs Pacific Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Chicago O'Hare Intl Airport?

    Some of the most popular sights in Chicago O'Hare Intl Airport are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago O'Hare Intl Airport on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Portland to Chicago O'Hare Intl Airport flights?

    Among airlines operating Portland to Chicago O'Hare Intl Airport flights:

    • United Airlines: offers extra legroom; offers free seat selection
    • American Airlines: offers extra legroom; offers free seat selection
    • Alaska Airlines: offers extra legroom; offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Portland to Chicago O'Hare Intl Airport flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • United Airlines: a cabin bag and a checked bag in Economy Class
    • American Airlines: a cabin bag and a checked bag in Economy Class
    • Alaska Airlines: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

  • How do I get from downtown Portland to PDX?

    Downtown Portland is approximately 30min away from the airport when there's no traffic, and you can take a taxi or use ride-sharing applications like Free2Move, Zipcar, and Turo to get a ride to the airport. You can use other public transport means to get to the airport. Examples include buses, street cars, and MAX light rail service.

  • What is the most convenient way to get to the city center in Chicago from ORD?

    There are various ways to get downtown from ORD. You can use Uber or taxis, book a private transfer, use train services or use public transportation such as a bus or shuttle that departs from the airport every 10 to 15min taking people to Chicago's downtown. Another way includes the Go Airport shuttle, which offers direct transportation to downtown.

  • Are there on-site hotels at ORD?

    Yes, there are various on-site hotels in the airport, like Hilton Chicago O'Hare, that are directly opposite terminals 1, 2, and 3. Some flight delays occur, and you can find yourself arriving in Chicago late. You can book a room in the airport hotels, and you won't have to worry about how you can get to downtown Chicago in the darker hours.

  • Where can you wait for your flight at PDX?

    PDX has several lounges where you can relax while waiting for your flight departure time. Some lounges include Alaska, located in concourse C across from the C5 gate, and Henry's Tavern, found in suite C2192. The lounges are only accessible to adults when they arrive earlier than the departure time or if the flight is delayed for a few hours.

Your guide to booking Portland to Chicago O'Hare Intl Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Saturday departure and avoid flying on Sunday. On this route, Saturday flights average $365, about $74 less than Sunday fares (17% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 18 weeks before you fly. On this route, that window historically saves about 40% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Portland to Chicago O'Hare Intl Airport trip for January. Fares historically average $276 round-trip in that month - typically $160 less than the most expensive month, which is November (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Denver Intl Airport (DEN) can be cheaper than flying direct. The cheapest layover option averages $241 round-trip on this route - about $146 less than direct flights (based on the last 12 months).
  • Are you planning to travel to Chicago on a business trip from Portland International Airport (PDX)? If you do, ensure you are at Portland airport at least 2h before departure time. Early airport arrival gives you enough time to pass the security checkpoints and find the right terminal for your flight.
  • When you drive to the PDX airport when leaving for Chicago, you can consider whether you want long-term or short-term parking. Long-term parking is within walking distance of the terminal entrance, while short-term parking can be found at each terminal entrance.
  • If you wish to travel with your pet or any other animal, you can consult with the airline you are using about their pet rules. Also, PDX offers pet relief areas inside and outside the terminals. They are located at concourse C opposite Alaska Lounge and concourse D across from gate D5.
  • You can keep your mind busy during the flight by engaging in activities like streaming movies and TV shows because some airlines offer free entertainment on board. Some of the airlines like American and Alaska offer Wi-Fi services during long-distance travel.
  • If you need to pick up a rental car at Chicago O'Hare Airport (ORD), you can find car rental centers within the airport. One of them is Avis, where you can follow signs to the lower baggage claim level where the exit for Avis car buses is found. You can board the shuttle that takes you to the car rental customer service a few kilometers from the terminal. Other companies include Budget, Hertz, and Enterprise Rent-a-car.

Prefer to fly direct from Portland to Chicago O'Hare Airport?

 
Find which airlines fly direct from Portland Airport to Chicago O'Hare Intl Airport, which days they fly and book direct flights.

Direct departures

Portland to Chicago O'Hare Intl

Monday

Alaska Airlines,American Airlines,United Airlines

Alaska Airlines,American Airlines, +1 more

Tuesday

Alaska Airlines,American Airlines,United Airlines

Alaska Airlines,American Airlines, +1 more

Wednesday

Alaska Airlines,American Airlines,United Airlines

Alaska Airlines,American Airlines, +1 more

Thursday

Alaska Airlines,American Airlines,United Airlines

Alaska Airlines,American Airlines, +1 more

Friday

Alaska Airlines,American Airlines,United Airlines

Alaska Airlines,American Airlines, +1 more

Saturday

Alaska Airlines,American Airlines,United Airlines

Alaska Airlines,American Airlines, +1 more

Sunday

Alaska Airlines,American Airlines,United Airlines

Alaska Airlines,American Airlines, +1 more

See more direct flights

Direct returns

Chicago O'Hare Intl to Portland

Monday

Alaska Airlines,American Airlines,United Airlines

Alaska Airlines,American Airlines, +1 more

Tuesday

Alaska Airlines,American Airlines,United Airlines

Alaska Airlines,American Airlines, +1 more

Wednesday

Alaska Airlines,American Airlines,United Airlines

Alaska Airlines,American Airlines, +1 more

Thursday

Alaska Airlines,American Airlines,United Airlines

Alaska Airlines,American Airlines, +1 more

Friday

Alaska Airlines,American Airlines,United Airlines

Alaska Airlines,American Airlines, +1 more

Saturday

Alaska Airlines,American Airlines,United Airlines

Alaska Airlines,American Airlines, +1 more

Sunday

Alaska Airlines,American Airlines,United Airlines

Alaska Airlines,American Airlines, +1 more

See more direct flights

More options for your flight from Portland to O'Hare Intl

Complete your trip to Chicago with a hotel stay or car rental