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

View $96 flight on Wed, Apr 8, 2026Opens in a new window

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
Mon, Apr 6 - Wed, Apr 15
PWM
Portland
ORD
Chicago
$191 Roundtrip, found 1 day ago
$191
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Apr 6 from Portland to Chicago, returning Wed, Apr 15, priced at $191 found 1 day ago
JetBlue Airways
Mon, Apr 6 - Fri, Apr 10
PWM
Portland
ORD
Chicago
$202 Roundtrip, found 23 hours ago
$202
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Mon, Apr 6 from Portland to Chicago, returning Fri, Apr 10, priced at $202 found 23 hours ago
JetBlue Airways
Mon, Mar 30 - Tue, Mar 31
PWM
Portland
ORD
Chicago
$208 Roundtrip, found 4 days ago
$208
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Mon, Mar 30 from Portland to Chicago, returning Tue, Mar 31, priced at $208 found 4 days ago
JetBlue Airways
Mon, Mar 30 - Thu, Apr 2
PWM
Portland
ORD
Chicago
$213 Roundtrip, found 4 days ago
$213
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Mon, Mar 30 from Portland to Chicago, returning Thu, Apr 2, priced at $213 found 4 days ago
JetBlue Airways
Mon, Apr 6 - Tue, Apr 14
PWM
Portland
ORD
Chicago
$214 Roundtrip, found 3 days ago
$214
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Mon, Apr 6 from Portland to Chicago, returning Tue, Apr 14, priced at $214 found 3 days ago
JetBlue Airways
Tue, Mar 31 - Fri, Apr 3
PWM
Portland
ORD
Chicago
$225 Roundtrip, found 14 hours ago
$225
Roundtrip
found 14 hours ago
Select JetBlue Airways flight, departing Tue, Mar 31 from Portland to Chicago, returning Fri, Apr 3, priced at $225 found 14 hours ago
Delta
Mon, Nov 24 - Thu, Nov 27
PWM
Portland
ORD
Chicago
$267 Roundtrip, found 18 hours ago
$267
Roundtrip
found 18 hours ago
Select Delta flight, departing Mon, Nov 24 from Portland to Chicago, returning Thu, Nov 27, priced at $267 found 18 hours ago
United
Wed, Feb 11 - Sun, Feb 15
PWM
Portland
ORD
Chicago
$289 Roundtrip, found 1 hour ago
$289
Roundtrip
found 1 hour ago
Select United flight, departing Wed, Feb 11 from Portland to Chicago, returning Sun, Feb 15, priced at $289 found 1 hour ago
American Airlines
Sat, Nov 22 - Thu, Nov 27
PWM
Portland
ORD
Chicago
$294 Roundtrip, found 1 day ago
$294
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Nov 22 from Portland to Chicago, returning Thu, Nov 27, priced at $294 found 1 day ago
Southwest Airlines
Fri, Oct 31 - Sat, Nov 1
PWM
Portland
ORD
Chicago
$434 Roundtrip, found 2 hours ago
$434
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Fri, Oct 31 from Portland to Chicago, returning Sat, Nov 1, priced at $434 found 2 hours ago

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.

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $431
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $431

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

Book with confidence

Portland to Chicago Flights

The cheapest times to fly from Portland to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Portland to Chicago are during the month of April. You can find some of the cheapest flights from Portland to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Portland to Chicago

Sunday is one of the best days to book for cheap flights from Portland to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Portland to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Portland to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $96 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Portland to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Portland to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Portland to Chicago Flights

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*Available to One Key members.