CA $135 Cheap Flights from Portland (PWM) to Chicago (ORD)

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Cheap flights from Portland (PWM) to Chicago (ORD)

Prices were available within the past 7 days and start at CA $135 for one-way flights and CA $177 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Tue., Oct. 8 - Thu., Oct. 17
PWM
Portland
ORD
Chicago
CA $177 Roundtrip, found 23 hours ago
CA $177
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Tue., Oct. 8 from Portland to Chicago, returning Thu., Oct. 17, priced at CA $177 found 23 hours ago
Frontier Airlines
Tue., Oct. 8 - Tue., Oct. 15
PWM
Portland
ORD
Chicago
CA $188 Roundtrip, found 23 hours ago
CA $188
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Tue., Oct. 8 from Portland to Chicago, returning Tue., Oct. 15, priced at CA $188 found 23 hours ago
Frontier Airlines
Tue., Oct. 8 - Sun., Oct. 13
PWM
Portland
ORD
Chicago
CA $228 Roundtrip, found 23 hours ago
CA $228
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Tue., Oct. 8 from Portland to Chicago, returning Sun., Oct. 13, priced at CA $228 found 23 hours ago
Delta
Tue., Aug. 27 - Tue., Aug. 27
PWM
Portland
ORD
Chicago
CA $268 Roundtrip, found 2 days ago
CA $268
Roundtrip
found 2 days ago
Select Delta flight, departing Tue., Aug. 27 from Portland to Chicago, returning Tue., Aug. 27, priced at CA $268 found 2 days ago
Delta
Wed., Aug. 28 - Sat., Sep. 7
PWM
Portland
ORD
Chicago
CA $269 Roundtrip, found 2 days ago
CA $269
Roundtrip
found 2 days ago
Select Delta flight, departing Wed., Aug. 28 from Portland to Chicago, returning Sat., Sep. 7, priced at CA $269 found 2 days ago
Frontier Airlines
Wed., Oct. 9 - Thu., Oct. 17
PWM
Portland
ORD
Chicago
CA $273 Roundtrip, found 23 hours ago
CA $273
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Wed., Oct. 9 from Portland to Chicago, returning Thu., Oct. 17, priced at CA $273 found 23 hours ago
JetBlue Airways
Tue., Aug. 27 - Wed., Aug. 28
PWM
Portland
ORD
Chicago
CA $279 Roundtrip, found 2 days ago
CA $279
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue., Aug. 27 from Portland to Chicago, returning Wed., Aug. 28, priced at CA $279 found 2 days ago
Frontier Airlines
Mon., Oct. 14 - Thu., Oct. 17
PWM
Portland
ORD
Chicago
CA $282 Roundtrip, found 23 hours ago
CA $282
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Mon., Oct. 14 from Portland to Chicago, returning Thu., Oct. 17, priced at CA $282 found 23 hours ago
Frontier Airlines
Wed., Oct. 9 - Tue., Oct. 15
PWM
Portland
ORD
Chicago
CA $284 Roundtrip, found 23 hours ago
CA $284
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Wed., Oct. 9 from Portland to Chicago, returning Tue., Oct. 15, priced at CA $284 found 23 hours ago
United
Sun., Sep. 1 - Sat., Sep. 7
PWM
Portland
ORD
Chicago
CA $284 Roundtrip, found 2 days ago
CA $284
Roundtrip
found 2 days ago
Select United flight, departing Sun., Sep. 1 from Portland to Chicago, returning Sat., Sep. 7, priced at CA $284 found 2 days ago
Flight from Portland to Chicago (PWM - ORD) route information
Origin airport
Portland Intl. Jetport
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, Frontier Airlines, JetBlue Airways, United
Roundtrip price
CA $177
Distance
1435 km

Portland to Chicago Flights

Ready for an adventure? Thought so! Prepare to see the sights when you book your trip from Portland to Chicago with Expedia.ca. Whether you’re visiting for business or pleasure, we know how important it is to bring home travel stories. Maybe your tales will include the best dinner of your life, or the weirdest street art you saw in the city, or the concert that turned you into a fan of a new band. Whatever it is, your new favourite anecdote is right around the corner. Book your trip from PWM to ORD and begin your journey!

Getting a cheap deal on your trip sets the tone for the perfect holiday. And with Expedia.ca, you know you can travel from Portland to Chicago on the cheap, with enough money left over for a stellar time in the city. That could mean more tours with the kids, more concerts with the spouse, more dessert amongst co-workers, or even front row seats to a sports game if you’re travelling solo. It’s your holiday! Make it great.

Travelling shouldn’t cost an arm and a leg before you even get to relax on the plane’s armrests. Count on Expedia.ca to get you the best discounts on flights from PWM to ORD. And remember this: You can also save big when you bundle. Add a hotel or car rental deal to your flight and witness those savings add up. Hey, more money for more souvenirs, right? Right! Pack your bags and we’ll see you on the route.

Combine your Chicago flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights from with Expedia Canada. Use us as your top travel destination and have the confidence that you’re getting a bargain!

Frequently asked questions

How much is a flight from Portland Intl. Jetport Airport (PWM) to ORD?
If you’re planning on traveling between Portland Intl. Jetport and ORD, round-trip flights start from CA $177. This price is based on fares listed within the last 7 days on Expedia for flights departing within the next year, so don’t hang about. Book now and save yourself money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Portland Intl. Jetport Airport (PWM) to ORD?
Every airline has its own terms and conditions. If you decide to cancel your trip, head to our Customer Service Portal.
How do I find cheap flights from PWM to ORD that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you’re searching for Portland Intl. Jetport to O’Hare Airport flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from PWM to O'Hare Intl. Airport (ORD)?
A flight distance of just 1,450 kilometers separates Portland and Chicago. Once you’re in the air, you won’t have time to do much more than read the magazine in your seat pocket.
Which airlines fly direct from Portland Intl. Jetport to O'Hare Airport?
United Airlines (UA) is one of the preferred choices for many travelers flying between PWM and ORD. Take your pick of the 60 flights it offers on this route each month. Another airline operating on this route is American Airlines (AA). You’ll have 8 flights each month to take your pick of.
Are PWM to O'Hare Airport flight tickets cheaper when they're purchased at the last minute?
Booking your trip from Portland Intl. Jetport to ORD at the last minute could be your ticket to a cheap deal. However, it could end up costing a great deal more! If you’d prefer not to take any chances, book well ahead of your departure date. In fact, Expedia has some of the best bargains as far ahead as 12 months in advance. If your preferred air carrier hasn’t released tickets yet, check back often as deals are updated on Expedia all the time.
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