Cheap Flights from Portland to Chicago
We've found these cheap flights for you. You can book one-way or return flight tickets.
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Flights from Portland to Chicago Starting at £37
We've found these cheap flights for you. You can book one-way or return flight tickets.
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Round-trip
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One way
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Cheapest nonstop
PDX 23:524h 5mNonstopORD 05:57Portland - Chicago | Sat, Apr 12 | American Airlines
ORD 20:204h 42mNonstopPDX 23:02Chicago - Portland | Sat, Apr 19 | American Airlines£157 £1729% OFF9% OFF£172 £157 -
PDX 23:524h 5mNonstopORD 05:57Portland - Chicago | Sat, Apr 19 | American Airlines
ORD 20:204h 42mNonstopPDX 23:02Chicago - Portland | Sat, Apr 26 | American Airlines£157 £1729% OFF9% OFF£172 £157
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PDX 10:0612h 11m1 stopsMDW 00:17Portland - Chicago | Tue, Mar 18 | Frontier Airlines
MDW 06:4019h 57m1 stopsPDX 00:37Chicago - Portland | Tue, Mar 25 | Frontier Airlines£86 £17250% OFF50% OFF£172 £86 -
PDX 06:4015h 41m1 stopsMDW 00:21Portland - Chicago | Mon, Apr 7 | Frontier Airlines
MDW 06:4519h 52m1 stopsPDX 00:37Chicago - Portland | Tue, Apr 15 | Frontier Airlines£9644% OFF£172 £96
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PDX 09:5412h 27m1 stopsMDW 00:21Portland - Chicago | Tue, Apr 1 | Frontier Airlines
MDW 06:4519h 52m1 stopsPDX 00:37Chicago - Portland | Wed, Apr 9 | Frontier Airlines£9744% OFF£172 £97
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PDX 06:4015h 41m1 stopsMDW 00:21Portland - Chicago | Thu, Apr 10 | Frontier Airlines
MDW 20:5013h 57m1 stopsPDX 08:47Chicago - Portland | Thu, Apr 17 | Frontier Airlines£9943% OFF£172 £99
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PDX 07:0015h 44m1 stopsORD 00:44Portland - Chicago | Wed, Mar 26 | Frontier Airlines
ORD 19:3915h 8m1 stopsPDX 08:47Chicago - Portland | Thu, Apr 3 | Frontier Airlines£10142% OFF£172 £101
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PDX 15:227h 41m1 stopsORD 01:03Portland - Chicago | Wed, Apr 16 | Frontier Airlines
ORD 06:4519h 38m1 stopsPDX 00:23Chicago - Portland | Sat, Apr 19 | Frontier Airlines£10340% OFF£172 £103
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PDX 14:3318h 22m1 stopsORD 10:55Portland - Chicago | Tue, May 6 | Spirit Airlines
ORD 21:0221h 43m1 stopsPDX 16:45Chicago - Portland | Tue, May 13 | Spirit Airlines£10440% OFF£172 £104 -
PDX 14:3214h 1m1 stopsORD 06:33Portland - Chicago | Wed, Apr 30 | Spirit Airlines
ORD 21:0217h 37m1 stopsPDX 12:39Chicago - Portland | Wed, May 7 | Spirit Airlines£10440% OFF£172 £104
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PDX 09:018h 40m1 stopsMDW 19:41Portland - Chicago | Fri, Apr 11 | Frontier Airlines
MDW 06:4519h 52m1 stopsPDX 00:37Chicago - Portland | Tue, Apr 15 | Frontier Airlines£10638% OFF£172 £106
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PDX 21:5111h 32m1 stopsMDW 11:23Portland - Chicago | Mon, May 5 | Frontier Airlines
MDW 20:036h 35m1 stopsPDX 00:38Chicago - Portland | Mon, May 12 | Frontier Airlines£10738% OFF£172 £107
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PDX 13:0017h 25m1 stopsCHI Invalid DatePortland - Chicago | Tue, Mar 18 | Normal Airline
CHI 15:006hNonstopPDX 16:00Chicago - Portland | Thu, Mar 20 | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstop
PDX 07:004h 5mNonstopORD 13:05Portland - Chicago | Tue, Apr 8 | Hawaiian Airlines£73 £8918% OFF18% OFF£89 £73 -
PDX 07:004h 5mNonstopORD 13:05Portland - Chicago | Sat, Apr 5 | Hawaiian Airlines£81 £899% OFF9% OFF£89 £81
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PDX 09:019h 13m1 stopsMDW 20:14Portland - Chicago | Mon, Apr 7 | Frontier Airlines£37 £8959% OFF59% OFF£89 £37
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PDX 10:0412h 17m1 stopsMDW 00:21Portland - Chicago | Wed, Apr 16 | Frontier Airlines£4451% OFF£89 £44
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PDX 10:0612h 17m1 stopsORD 00:23Portland - Chicago | Tue, Mar 18 | Frontier Airlines£4550% OFF£89 £45
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PDX 15:227h 41m1 stopsORD 01:03Portland - Chicago | Wed, Apr 9 | Frontier Airlines£4549% OFF£89 £45
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PDX 09:5412h 21m1 stopsORD 00:15Portland - Chicago | Tue, Apr 8 | Frontier Airlines£4648% OFF£89 £46
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PDX 06:4015h 35m1 stopsORD 00:15Portland - Chicago | Thu, Apr 17 | Frontier Airlines£4846% OFF£89 £48
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PDX 21:5111h 32m1 stopsMDW 11:23Portland - Chicago | Mon, May 5 | Frontier Airlines£4945% OFF£89 £49
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PDX 10:1612h 47m1 stopsORD 01:03Portland - Chicago | Thu, Apr 3 | Frontier Airlines£5044% OFF£89 £50
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PDX 17:1628h 24m1 stopsORD 23:40Portland - Chicago | Thu, Apr 24 | Frontier Airlines£5044% OFF£89 £50
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PDX 09:5013h 7m1 stopsORD 00:57Portland - Chicago | Mon, Mar 17 | Frontier Airlines£5044% OFF£89 £50
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PDX 13:0017h 25m1 stopsCHI Invalid DatePortland - Chicago | Tue, Mar 18 | 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.
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Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Airlines Flying from Portland to Chicago
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FAQ
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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 date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays. -
How much are flights from Portland (PDX) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around £271. -
How long is the flight from Portland (PDX) to Chicago (CHI)?
It takes about 9 hours 45 minutes to fly from Portland (PDX) to Chicago (CHI). -
What is the transportation method from the main airport to downtown in Chicago?
- The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
- The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
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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, Hawaiian Airlines, United Airlines, Lufthansa, Air Canada and Southwest Airlines. -
What's the most popular airline for direct flights from Portland (PDX) to Chicago (CHI)?
American Airlines operates 1 direct flights from Portland (PDX) to Chicago (CHI). -
How many airports in Chicago (CHI)?
There are 3 airport(s) in Chicago (CHI): Midway International Airport, O'Hare International Airport and Chicago Rockford International Airport.
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.
Be flexible with your travel dates to get the cheapest flight from Portland to Chicago.
Simply tap "Date" on the flight search bar to browse through the calendar and check out airfare from Portland to Chicago over the next 6 months in 2025. If you're planning to fly within the next three months, it looks like the most affordable option is on Tue, Apr 8, with one-way flights priced at just £73.
Compare cheap flight deals from Portland to Chicago across hundreds of airlines.
With our extensive search, you can compare prices from over 500 airlines to find the cheapest flight tickets from Portland to Chicago. The cheapest airline for this route is Hawaiian Airlines.
Set up a Price Alert
By setting up a Price Alert for your journey from Portland to Chicago, you can easily keep an eye on ticket prices without having to check every day.
Don't miss out on cheap flight deals and promo codes from Portland to Chicago.
You can always find the latest offers through Trip.com Deals and Promo Codes for cheap flights. By signing up for a free membership, you'll get access to even more deals for your flights.
Book early or wait until the last minute.
It's usually best to book early. Flight tickets are often cheapest when they're first released, typically about a year before the departure date. So, have a look online as soon as the flights you're interested in become available. If you miss the cheapest time, you might still find some good deals as the departure date gets closer.
Search for flights on the go.
For the best travel flight booking experience, download the Trip.com app. You can search for cheap flights from Portland to Chicago and snag some exclusive deals just for you.
Flight Information from Portland to Chicago
| Cheapest direct flight price | £36 |
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| Cheapest return ticket price | £140 |
| Off-season travel month | March |
| Peak season for travel | June |
| Flight distance | 2,816.22km |
| Average flight time | 9 hours 45 minutes |
| Popular airline | Alaska Airlines |
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