Cheap flight from Portland to Chicago from $78
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Flights from Portland to Chicago
Find cheap airlines flights from Portland to Chicago
Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.
Cheap flight deals from Portland to Chicago
We've found these cheap flights for you. You can book one-way or round-trip flight tickets.
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Round-trip
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One way
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Cheapest nonstop
PDX 5:51 PM4h 5mNonstopORD 11:56 PMPortland - Chicago | Sat, May 17 | Hawaiian Airlines
ORD 7:00 AM4h 23mNonstopPDX 9:23 AMChicago - Portland | Sat, May 24 | Hawaiian Airlines$169 $19614% OFF14% OFF$196 $169 -
PDX 5:51 PM4h 5mNonstopORD 11:56 PMPortland - Chicago | Sat, May 24 | Hawaiian Airlines
ORD 7:00 AM4h 23mNonstopPDX 9:23 AMChicago - Portland | Fri, May 30 | Hawaiian Airlines$169 $19614% OFF14% OFF$196 $169
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PDX 5:51 PM4h 5mNonstopORD 11:56 PMPortland - Chicago | Mon, May 19 | Hawaiian Airlines
ORD 7:00 AM4h 23mNonstopPDX 9:23 AMChicago - Portland | Tue, May 27 | Hawaiian Airlines$169 $19614% OFF14% OFF$196 $169
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PDX 5:51 PM4h 5mNonstopORD 11:56 PMPortland - Chicago | Sat, May 17 | Alaska Airlines
ORD 7:00 AM4h 23mNonstopPDX 9:23 AMChicago - Portland | Sat, May 24 | Hawaiian Airlines$17013% OFF$196 $170 -
PDX 5:51 PM4h 5mNonstopORD 11:56 PMPortland - Chicago | Sat, May 24 | Alaska Airlines
ORD 7:00 AM4h 23mNonstopPDX 9:23 AMChicago - Portland | Fri, May 30 | Hawaiian Airlines$17113% OFF$196 $171
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PDX 2:33 PM18h 22m1 stopsORD 10:55 AMPortland - Chicago | Tue, May 6 | Spirit Airlines
ORD 9:02 PM21h 43m1 stopsPDX 4:45 PMChicago - Portland | Tue, May 13 | Spirit Airlines$13531% OFF$196 $135 -
PDX 5:40 PM9h 45m1 stopsORD 5:25 AMPortland - Chicago | Sun, May 11 | Spirit Airlines
ORD 9:02 PM21h 43m1 stopsPDX 4:45 PMChicago - Portland | Tue, May 13 | Spirit Airlines$16019% OFF$196 $160
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PDX 5:51 PM4h 5mNonstopORD 11:56 PMPortland - Chicago | Tue, May 27 | Alaska Airlines
ORD 11:50 AM6h 55m1 stopsPDX 4:45 PMChicago - Portland | Wed, May 28 | Spirit Airlines$16417% OFF$196 $164
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PDX 5:40 PM15h 15m1 stopsORD 10:55 AMPortland - Chicago | Mon, May 12 | Spirit Airlines
ORD 9:02 PM17h 38m1 stopsPDX 12:40 PMChicago - Portland | Tue, May 20 | Spirit Airlines$16715% OFF$196 $167
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PDX 5:40 PM9h 45m1 stopsORD 5:25 AMPortland - Chicago | Tue, May 27 | Spirit Airlines
ORD 11:50 AM6h 55m1 stopsPDX 4:45 PMChicago - Portland | Wed, May 28 | Spirit Airlines$17013% OFF$196 $170
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PDX 1:00 PM17h 25m1 stopsCHI Invalid DatePortland - Chicago | Thu, May 8 | Normal Airline
CHI 3:00 PM6hNonstopPDX 4:00 PMChicago - Portland | Sat, May 10 | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstop
PDX 7:00 AM4h 8mNonstopORD 1:08 PMPortland - Chicago | Mon, May 26 | Alaska Airlines$84 $40679% OFF79% OFF$406 $84
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PDX 5:51 PM4h 5mNonstopORD 11:56 PMPortland - Chicago | Sat, May 31 | Alaska Airlines$84 $40679% OFF79% OFF$406 $84
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PDX 7:00 AM4h 8mNonstopORD 1:08 PMPortland - Chicago | Mon, May 26 | Hawaiian Airlines$87 $40679% OFF79% OFF$406 $87
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PDX 7:00 AM4h 7mNonstopORD 1:07 PMPortland - Chicago | Sat, May 10 | Hawaiian Airlines$35313% OFF$406 $353
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PDX 7:00 AM4h 7mNonstopORD 1:07 PMPortland - Chicago | Sun, May 11 | Hawaiian Airlines$35313% OFF$406 $353
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PDX 5:40 PM9h 45m1 stopsORD 5:25 AMPortland - Chicago | Fri, May 16 | Spirit Airlines$7881% OFF$406 $78
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PDX 5:40 PM9h 45m1 stopsORD 5:25 AMPortland - Chicago | Wed, May 28 | Spirit Airlines$8080% OFF$406 $80
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PDX 5:40 PM15h 15m1 stopsORD 10:55 AMPortland - Chicago | Wed, Jun 4 | Spirit Airlines$8380% OFF$406 $83
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PDX 5:40 PM9h 45m1 stopsORD 5:25 AMPortland - Chicago | Tue, May 13 | Spirit Airlines$8479% OFF$406 $84
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PDX 1:37 PM14h 35m1 stopsORD 6:12 AMPortland - Chicago | Wed, Jun 11 | Spirit Airlines$9676% OFF$406 $96
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PDX 1:00 PM17h 25m1 stopsCHI Invalid DatePortland - Chicago | Thu, May 8 | Normal AirlineFind More FlightsFind More Flights
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Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.
Flight Info | Portland to Chicago
| Cheapest one-way flight price | $77 |
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| Cheapest round-trip ticket price | $163 |
| Off-season for travel | March |
| Peak season for travel | June |
| Flight distance | 2,816.22 km |
| Average flight time | 4 hours 43 minutes |
| Popular airline | Alaska Airlines |
When is the cheapest time to fly from Portland to Chicago?
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Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Frequently Asked Questions
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When are flight tickets from Portland (PDX) to Chicago (CHI) the cheapest?
Airlines adjust prices for flights from Portland to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays. -
How much do flights from Portland (PDX) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around $350. -
How long does it take to fly from Portland (PDX) to Chicago (CHI) and what is the distance?
It takes around 4 hours 43 minutes to fly from Portland (PDX) to Chicago (CHI). -
What are the most popular airlines that fly from Portland (PDX) to Chicago (CHI)?
Airlines with flights from Portland (PDX) to Chicago (CHI): Brussels Airlines, Alaska Airlines, American Airlines, United Airlines, Lufthansa, Air Canada, Gulf Air, Iberia, Qatar Airways and Finnair.
How to find a cheap flight from Portland to Chicago
Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Portland to Chicago. Book your flights at the right time and save more.
Book Early
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Compare Flight Prices
Compare prices on travel agency and airline websites.
Look Out for Deals
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Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
Try Different Dates
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