$96 Cheap Flights from Portland (PWM) to Chicago (ORD)

Popular airlines from Portland Intl. Jetport Airport (PWM) to Chicago O'Hare Intl. Airport (ORD)

Cheap Flights from Portland to Chicago (PWM-ORD)

Prices were available within the past 7 days and start at $96 for one-way flights and $191 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
JetBlue Airways
JetBlue Airways
JetBlue Airways
JetBlue Airways
JetBlue Airways
Delta
United
American Airlines
Southwest Airlines

Find the cheapest month to fly from Portland (PWM) to Chicago (ORD)

August is typically the cheapest month to fly

From $145 - $355 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Frequently asked questions

How much does a flight from Portland Intl. Jetport Airport (PWM) to O'Hare Intl. Airport (ORD) cost?
Get a cheap one-way flight from $96 or cheap return flight from $191 from Portland Intl. Jetport Airport (PWM) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Portland Intl. Jetport Airport (PWM) to O'Hare Intl. Airport (ORD)?
The cheapest month to fly from PWM to ORD is April, when there's less demand. Off-peak months are often when airlines offer lower prices between these airports.
Which airlines fly direct from Portland Intl. Jetport Airport (PWM) to O'Hare Intl. Airport (ORD)?
When departing from Portland Intl. Jetport Airport (PWM), you can board a direct flight to O'Hare Intl. Airport (ORD) with United Airlines.
What is the cheapest airline that flies from Portland Intl. Jetport Airport (PWM) to O'Hare Intl. Airport (ORD)?
Expedia's filter tool lets you easily compare travel time, airlines and fares all in one place. Customize the search to your preferences, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest PWM to ORD flight.
How many flights per day from Portland Intl. Jetport Airport (PWM) to O'Hare Intl. Airport (ORD)?
On average, you'll only find 1 nonstop flight operating from Portland Intl. Jetport Airport (PWM) to O'Hare Intl. Airport (ORD) each day. If this doesn't fit your plans, check out flights with layovers. Simply filter your search on Expedia to include one or more stops to discover the next best option.
What are the most popular departure times for flights from Portland Intl. Jetport Airport (PWM) to O'Hare Intl. Airport (ORD)?
The 4 PM departures from PWM to ORD are typically the busiest. They can also be more expensive. If you're hoping to save money, choose a less crowded time to fly.
What day of the week has the most flights from PWM to ORD?
If you travel on a Friday, you'll get the biggest range of choices for flights from Portland Intl. Jetport Airport (PWM) to O'Hare Intl. Airport (ORD).
What is the earliest flight from Portland Intl. Jetport Airport (PWM) to O'Hare Intl. Airport (ORD)?
Portland Intl. Jetport Airport (PWM)'s earliest flight to O'Hare Intl. Airport (ORD) takes off at approximately 4:10PM UTC-5. With a total travel time of 3h 14m, you'll arrive at around 6:24PM UTC-6.
How long does it take to fly from Portland Intl. Jetport Airport (PWM) to O'Hare Intl. Airport (ORD)?
The average flight duration from PWM to ORD is 3 hours and 14 minutes, covering a distance of 900 mi.
What airline has the least delays from PWM to ORD?
Consider booking with United Airlines if you'd like to go straight from Portland Intl. Jetport Airport (PWM) to O'Hare Intl. Airport (ORD) without any holdups. This airline has the strongest track record for punctuality, with an on-time score of 82%. Want to be notified if anything changes? You can check your flight status using the Expedia App.
What is the best time to fly from Portland Intl. Jetport Airport (PWM) to O'Hare Intl. Airport (ORD)?
To avoid potential delays on the Portland Intl. Jetport Airport (PWM) to O'Hare Intl. Airport (ORD) route, travel before 3 PM. Later flights have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Portland Intl. Jetport Airport (PWM)?
Compare your flight options from Portland Intl. Jetport Airport (PWM) to O'Hare Intl. Airport (ORD). This is the only airport in Chicago you can fly into if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Portland Intl. Jetport Airport (PWM) to O'Hare Intl. Airport (ORD) last-minute?
Booking your plane ticket from PWM to ORD shortly before your trip is typically more expensive. But if there's some wiggle room with your itinerary, you could land a cheap last-minute fare.
Is it cheaper to book a PWM to ORD flight and hotel package?
Compared with arranging flights and hotels separately, booking a PWM to ORD flight and hotel package with Expedia could result in significant savings. What's more, having it all in one place will take the stress out of planning your trip. Just pick your flights and choose from our extensive range of hotels, then tailor your trip with extras like tours and car rentals.
Can I cancel or change the date of my flight from Portland Intl. Jetport Airport (PWM) to O'Hare Intl. Airport (ORD)?
In most cases, you're able to reschedule or cancel your PWM to ORD flight. However, additional fees may apply, especially if you booked over 24 hours ago. Double-check your itinerary for the airline's guidelines and fees on flight changes, or if you need more information, head to our Customer Service portal.

Travel information

Origin airport
Portland Intl. Jetport
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, JetBlue Airways, Southwest Airlines, United
Roundtrip price
$190
Distance
897 mi
Average flight time
2 hours 7 mins

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