The Southwest Travel Experience
At Southwest, we know it takes more than great deals on Chicago airfares and convenient scheduling options to make your trip memorable. So from booking to boarding, we offer services and features designed to make your travel from Portland, OR, to Chicago the best it can be. Learn more about the Southwest® travel experience before you book your flight from Portland International Airport to Chicago Midway International Airport.
Flying with Southwest is simple and fun, no matter which of our dozens of exciting destinations you choose. When you search for your next flight to Chicago , know that you wont be surprised at checkout. Low fares and no hidden fees. That’s Transfarency®. And as always, two bags fly free®1. Want the latest news, information, and promotional offers from Southwest? from us. Book your flight today and know that you’ll earn Rapid Rewards® points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
3Failure to cancel a reservation at least 10 minutes prior to departure may result in forfeited Travel Funds.
4Flight credits unexpired on or created on or after July 28, 2022, do not expire and will show an expiration date until our systems are updated. See full details here.
5Available only on WiFi-enabled aircraft. Limited-time offer. Where available.
The Selection Of Cheap Flights From Portland To Chicago
Here you can find and purchase the cheapest flights from Portland to Chicago from $269 and from Portland to Chicago to Portland from $179.
The price of the flight from Portland to Chicago to Portland from $179 .
The average price of the flight from Portland to Chicago to Portland $323 .
The distance between Portland and Chicago 1750 miles .
The time difference between Portland and Chicago is 2 h.
Minimal flight time from Portland to Chicago 3h 40m.
- Destination country: United States
More Than 15k Flights On Friday Already Canceled Due To Storm
Travelers wait in line to check-in for their flights at Terminal 1 ahead of the Christmas Holiday at MSP Airport in Bloomington, Minn., on Thursday, Dec. 22, 2022. AP
Thousands of flights were canceled and homeless shelters were overflowing Thursday amid one of the most treacherous holiday travel seasons the U.S. has seen in decades, with temperatures plummeting 50 degrees Fahrenheit in some areas and forecasters warning of an impending bomb cyclone that could make conditions even worse before Christmas.
The frigid air was moving through the central United States to the east, with windchill advisories affecting about 135 million people over the coming days, weather service meteorologist Ashton Robinson Cook said Thursday. Places like Des Moines, Iowa, will feel like minus 37 degrees, making it possible to suffer frostbite in less than five minutes.
This is not like a snow day when you were a kid, President Joe Biden warned Thursday in the Oval Office after a briefing from federal officials. This is serious stuff.
Forecasters are expecting a bomb cyclone when atmospheric pressure drops very quickly in a strong storm to develop late Thursday and into Friday near the Great Lakes. That will stir up blizzard conditions, including heavy winds and snow, Cook said.
He said five have died in recent storms, including a blizzard from last week.
In Kansas City, Missouri, one person died after a vehicle overturned into an icy creek, police said.
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Plan Your Trip From Portland To Chicago
Portland International Airport
Flights from Portland depart from the Portland International Airport, located at 7000 NE Airport Way. The airport is approximately 22 miles south of downtown Portland and is serviced by 13 airlines, including Delta, Air Canada, Frontier and United. Orbitz.com makes it easy to book domestic and international flights from Portland. You don’t have to scour the Internet to find cheap airline tickets. Orbitz.com searches all of the flights available to get you a ticket with a low fare.
Parking and Transportation
The Portland International Airport offers long-term parking for $19 per day. If you plan to leave your car at the airport for more than 90 days, you need to make prior arrangements with the airport’s parking office. You can take a taxi from downtown Portland to the airport for approximately $32, so if you plan to leave your vehicle for more than two days, taking a taxi to the airport is a cheaper option. Streetcars also run from the downtown area to the airport, and streetcar tickets cost $2.40. If you need transportation when you arrive at your destination, Orbitz.com can reserve a rental car for you.
Dining at the Airport
Airports in Chicago
Transportation from the Airport
Weather in Chicago
Highlights and Attractions
Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.
How To Get The Cheapest Flight Ticket From Portland To Chicago

Look no further. We’ve gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly from Portland to Chicago?
What is the cheapest day to depart Portland for Chicago?
Wednesday. The cheapest day of the week is typically Wednesday. The most expensive is typically Sunday
When is the cheapest time to fly from Portland to Chicago?
in the afternoon. Portland to Chicago flights are approximately 31% more expensive at noon than in the afternoon
What is the cheapest airline that flies to Chicago from Portland?
What is the cheapest Portland to Chicago flight route?
Portland – Chicago O’Hare Intl. Fly from Portland to Chicago O’Hare Intl for the best Portland – Chicago flight prices
How far in advance should you book Portland to Chicago flights?
60 days before. The cheapest time to buy a flight from Portland to Chicago is approximately 60 days to departure
Portland Airport to Chicago O’Hare Intl Airport | $123 |
Search United Airlines flights |
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Portland To Chicago Flight Schedule
Scan through flights from Portland International Airport to O’Hare International Airport for the upcoming week. Sort the list by any column, and click on a dollar sign to see the latest prices available for each flight.
Flights.com only offers pricing for airlines that display a check fare on the days of the week each flight is available. A dot indicates a flight is scheduled, but online booking is not currently available.
Pdx To Ord Flight Details
Distance and aircraft type by airline for flights from Portland International Airport to O’Hare International Airport.
- Alaska Airlines – with 570 direct flights between Portland and Chicago monthly
- Southwest Airlines – with 30 direct flights between PDX and ORD monthly
- United Airlines – with 150 direct flights between Portland and Chicago monthly
- American Airlines – with 30 direct flights between PDX and ORD monthly
- Delta Air Lines – with 150 direct flights between Portland and Chicago monthly
- American Airlines – lists, on average, 1 flights departing before 12:00pm, where the first departure from PDX is at 05:30AM and the last departure before noon is at 10:00AM
- Alaska Airlines – has about 14 flights before noon, starting with the earliest at 05:30AM PST and the latest 10:55AM PST
- Southwest Airlines – has about 1 flights before noon, starting with the earliest at 06:40AM PST and the latest 10:10AM PST
- Delta Air Lines – has about 4 flights before noon, starting with the earliest at 06:00AM PST and the latest 11:30AM PST
- United Airlines – lists, on average, 3 flights departing before 12:00pm, where the first departure from PDX is at 05:30AM and the last departure before noon is at 11:13AM
- Alaska Airlines – with about 3 end of day scheduled flights between PDX and ORD from 6:00pm to 11:00pm.
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The Massive Storm Is Also Taking A Toll On Trains Buses And Roads
A fierce winter storm stranded thousands of passengers in U.S. airports Thursday, leaving some worried their travel misery could persist for days and threaten plans to reach their destinations in time to celebrate with family by Christmas.
The storm has struck during one of the busiest holiday travel seasons in more than 20 years and has also created treacherous conditions on the ground. State highway officials reported jackknifed trucks and closed lanes. Some long-distance rail lines were shuttered. Bus lines were halted.
Im sad, just emotional, and just ready to get out of the airport, said Keri Crutcher, whose layover in Denver with two kids descended into a blur of line waiting and sleeping on the airport floor. Her Southwest flight headed for family in Kentucky was first canceled Wednesday. Shortly before her rescheduled flight was set to board Thursday, she saw her bags rolling toward the cargo hold.
I thought, okay, were getting close! Nope, Crutcher said. Canceled again. Merry Christmas.
By afternoon Thursday, the number of flight cancellations topped 2,300 nationwide and was continuing to grow, according to FlightAware, a website that tracks commercial aviation. More cancellations and delays are expected through Friday.
His best option: getting home late Christmas Day, after an 11-hour flight with stops in San Antonio and Phoenix.
Christmas it is. I guess me and Santa Claus, we just both take a trip that day, Rathbone said.
Fly Portland Or To Chicago And Save Big
**Lowest Fare Guaranteed for fares on Spirit.com and the Spirit Airlines mobile app, for the same flight, on the same day and at the same time, at time of booking, and when SAVER$ CLUB fare is offered along with a standard public fare. Must be a SAVER$ CLUB member. Seats are limited. Additional terms and conditions apply. For general terms and conditions visit Saver$ Club Terms and Conditions*Fares presented below are available at the beginning of each day, but may sell out. Additional baggage fees and fees for other services may apply. Other terms and conditions may apply.
PDX-ORD
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Combina Tu Vuelo A Chicago Con Hoteles Y Renta De Autos
Una vez que tengas asegurado tu boleto de avión de Portland a Chicago, te ayudaremos a encontrar los mejores precios y tarifas exclusivas para hoteles en Chicago o cerca. Y si quieres rentar un auto, también podemos ayudarte. Te permitimos comparar cientos de compañías de renta de autos en una sola búsqueda para encontrar el mejor precio en Chicago.
Airlines Cancel Thousands Of Flights As Massive Winter Storm And Bitter Cold Sweep Us Ahead Of Christmas
- Airlines canceled more than 5,000 flights from Wednesday through Friday, days before Christmas.
- High winds, bitter cold and snow were slowing airline operations this week.
- Airlines are expecting a surge in travelers over the year-end holidays.
Airlines canceled hundreds of flights this week as winter storms, bitter cold and high winds snarled U.S. travel ahead of Christmas weekend.
Carriers scrubbed more than 5,000 U.S. flights from Wednesday through Friday, according to tracking site FlightAware. That period includes what airlines expected to be the busiest travel times before Christmas Day. More than 16,000 U.S. flights were delayed.
Chicago’s two main airports O’Hare and Midway and Denver International Airport had the biggest share of canceled flights on Thursday. New York’s LaGuardia Airport, Detroit and Chicago Midway were set to have the most disruptions on Friday.
Airlines warned that the snow, ice, high winds and cold temperatures could affect travel from Seattle to Boston to North Carolina.
Wednesday’s cancellations accounted for about 2% of U.S. airlines’ schedule, while about 30% of flights were delayed by an average of 47 minutes, FlightAware data showed. Disruptions worsened throughout Thursday.
American, Southwest, United, Delta, Spirit, JetBlue, Alaska and other airlines issued weather waivers for dozens of destinations around the country, allowing travelers to change their departures without paying a change fee or difference in fare.
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Portland To Chicago Flights
Flights from PDX to ORD are operated 14 times a week, with an average of 2 flights per day.Departure times vary between 00:30 – 23:59. The earliest flight departs at 00:30, the last flight departs at 23:59. However, this depends on the date you are flying so please check with the full flight schedule above to see which departure times are available on your preferred date of travel.
You can fly in Economy and Business Class. Premium Economy and First Class are not available on this route .
The fastest direct flight from Portland to Chicago takes 3 hours and 57 minutes.The flight distance between Portland and Chicago is 1,733 miles .
Low Cost Flights From Portland To Chicago

LowCostClub always do a comparison of airfares from Portland to Chicago with several airlines . They will always give you all available options so you can find the cheapest flight to Chicago. In addition, you can choose the platform where you want to place your orders. There are also special offers for air tickets from Portland to Chicago. Last week, for instance, the cheapest round-trip prices stood at $179 while the cheapest one-way price that was available within the last week cost $269
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Reserva Boletos De Avin De Portland Al Chicago Con Tranquilidad
- Encuentra vuelos con fechas flexibles. Es posible que tu aerolínea ofrezca boletos de avión flexibles de Portland a Chicago, lo que significa que no perderás nada si tienes que cambiar o cancelar tu vuelo.
- Agrega protección de viaje. Evita dificultades al viajar y elige la protección de viaje, disponible al pagar la reservación de tu vuelo de Portland a Chicago con nosotros.
- Reduce tu huella de carbono con la opción de vuelo más ecológico. Para saber si hay vuelos con emisiones más bajas disponibles en la ruta de Portland a Chicago, solo tienes que marcar la casilla “solo mostrar vuelos con emisiones más bajas de CO” más adelante en tu búsqueda.
Distance From Portland To Chicago
There are several ways to calculate the distance from Portland to Chicago. Here are two standard methods:
Vincenty’s formula
- 2799.066 kilometers
- 1511.375 nautical miles
Vincenty’s formula calculates the distance between latitude/longitude points on the earth’s surface using an ellipsoidal model of the planet.
Haversine formula
- 2791.659 kilometers
- 1507.376 nautical miles
The haversine formula calculates the distance between latitude/longitude points assuming a spherical earth .
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Related Info For Your Journey
Useful info, stats and facts about Portland to Chicago flights.
What airport do you fly from for flights from Portland to Chicago?
For a flight from Portland to Chicago, you will be flying from Portland. Portland is just 6.0 mi from the center of the city. Portland is the only Portland airport and it handles 12 outbound flights to Chicago per day. 9 airlines have flights to Chicago from Portland on a regular basis.
Which airlines flying from Portland to Chicago have flexible cancellations due to COVID-19?
Some of the carriers operating flights from Portland to Chicago that may be offering flexible cancellation policies are United Airlines, Alaska Airlines, and American Airlines. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.
Can I find flights from Portland to Chicago for under $200 on Cheapflights?
Yes, there are multiple flights from Portland to Chicago for under $200. The cheapest flight booked recently is on Spirit Airlines for just $124, but on average you can expect to pay $144.
Are there nonstop flights from Portland to Chicago for under $300 on Cheapflights?
Cheapflights has at least 20 direct flights from Portland to Chicago under $300. A good price for a nonstop flight from Portland to Chicago is less than $339.
Are there last-minute flights available from Portland to Chicago for under $400?
There are currently 20+ open flights from Portland to Chicago within the next 7 days for less than $400.
Cheap United Airlines Flights From Portland To Chicago
Deal found 12/20
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If youre traveling from Portland to Chicago, one of the more common airlines traveling that route is United Airlines. Flights from United Airlines traveling this route typically cost $505.82 RT. This price is typically 137% more expensive than other airlines that offer Portland to Chicago flights. When booking this route, the cheapest RT price found was $374. The most popular departure airport in Portland when flying to Chicago is Portland Airport. The most popular airport to fly into when visiting Chicago is Chicago O’Hare Intl Airport. When flying from Portland to Chicago, United Airlines flights are 20% more popular than any other airline flying that same route.
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Cheap Flights From Portland To Chicago In December January 2022
The best prices found for PDX to CHI flights for December, January
Deal found 12/20
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If youre traveling from Portland to Chicago, one of the more common airlines traveling that route is Spirit Airlines. Portland to Chicago flights are typically 25% cheaper than other airlines traveling the same route. Flights from Spirit Airlines typically cost $494.45 RT. The cheapest Spirit Airlines flight found for this route was $149. When traveling from Portland to Chicago on Spirit Airlines, the most popular airport to depart from is Portland Airport and the most popular airport to arrive at is Chicago O’Hare Intl Airport. When flying from Portland to Chicago, Spirit Airlines flights are 25% more popular than any other airline flying that same route.
Spirit Airlines Flights From Portland To Chicago
Our best Spirit Airlines deals on Portland to Chicago flight tickets
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Are airlines flying from Portland to Chicago offering flexible cancellation due to COVID-19?
To ease the stress of booking flights, some of our airline partners flying from Portland to Chicago are responding to the global pandemic. The following airlines may have a flexible cancellation policy to help accommodate travelers: United Airlines, Alaska Airlines, and American Airlines.
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How far is Portland to Chicago by plane?
Portland and Chicago are 1753.4 mi apart from one another. A reasonable flight in good conditions will take 6h 23m.
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