Cheap Flights from Portland to Chicago
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Cheap Flights from Portland to Chicago
Cheap Flights from Portland to Chicago starting at S$ 64
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 17:514h 5mNonstopORD 23:56Portland - Chicago | Sat, May 17 | Hawaiian Airlines
ORD 07:004h 23mNonstopPDX 09:23Chicago - Portland | Sun, May 25 | Alaska AirlinesS$ 264 S$ 33120% OFF20% OFFS$ 331 S$ 264 -
PDX 17:514h 5mNonstopORD 23:56Portland - Chicago | Sat, May 17 | Alaska Airlines
ORD 07:004h 23mNonstopPDX 09:23Chicago - Portland | Sun, May 25 | Hawaiian AirlinesS$ 265 S$ 33120% OFF20% OFFS$ 331 S$ 265 -
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 AirlinesS$ 167 S$ 33150% OFF50% OFFS$ 331 S$ 167 -
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 AirlinesS$ 16749% OFFS$ 331 S$ 167
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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 AirlinesS$ 17049% OFFS$ 331 S$ 170
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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 AirlinesS$ 17447% OFFS$ 331 S$ 174
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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 AirlinesS$ 17746% OFFS$ 331 S$ 177
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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 AirlinesS$ 18046% OFFS$ 331 S$ 180 -
PDX 15:227h 41m1 stopsORD 01:03Portland - Chicago | Wed, Apr 9 | Frontier Airlines
ORD 06:4519h 52m1 stopsPDX 00:37Chicago - Portland | Sun, Apr 13 | Frontier AirlinesS$ 18444% OFFS$ 331 S$ 184
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PDX 09:019h 13m1 stopsMDW 20:14Portland - Chicago | Mon, Apr 14 | Frontier Airlines
MDW 06:4519h 52m1 stopsPDX 00:37Chicago - Portland | Tue, Apr 15 | Frontier AirlinesS$ 18544% OFFS$ 331 S$ 185
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PDX 09:5412h 21m1 stopsORD 00:15Portland - Chicago | Tue, Apr 8 | Frontier Airlines
MDW 20:5013h 57m1 stopsPDX 08:47Chicago - Portland | Fri, Apr 11 | Frontier AirlinesS$ 19242% OFFS$ 331 S$ 192
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PDX 10:0011h 59m1 stopsORD 23:59Portland - Chicago | Sat, Apr 12 | Frontier Airlines
ORD 19:3915h 8m1 stopsPDX 08:47Chicago - Portland | Sun, Apr 13 | Frontier AirlinesS$ 20139% OFFS$ 331 S$ 201
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PDX 13:0017h 25m1 stopsCHI Invalid DatePortland - Chicago | Thu, Mar 27 | Normal Airline
CHI 15:006hNonstopPDX 16:00Chicago - Portland | Sat, Mar 29 | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstop
PDX 06:004hNonstopMDW 12:00Portland - Chicago | Sun, Apr 20 | Southwest AirlinesS$ 119 S$ 15825% OFF25% OFFS$ 158 S$ 119 -
PDX 07:004h 5mNonstopORD 13:05Portland - Chicago | Tue, Apr 8 | Hawaiian AirlinesS$ 126 S$ 15820% OFF20% OFFS$ 158 S$ 126
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PDX 09:019h 13m1 stopsMDW 20:14Portland - Chicago | Mon, Apr 7 | Frontier AirlinesS$ 64 S$ 15860% OFF60% OFFS$ 158 S$ 64
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PDX 10:0412h 17m1 stopsMDW 00:21Portland - Chicago | Wed, Apr 16 | Frontier AirlinesS$ 7652% OFFS$ 158 S$ 76
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PDX 15:227h 41m1 stopsORD 01:03Portland - Chicago | Wed, Apr 9 | Frontier AirlinesS$ 7851% OFFS$ 158 S$ 78
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PDX 09:5412h 21m1 stopsORD 00:15Portland - Chicago | Tue, Apr 8 | Frontier AirlinesS$ 8049% OFFS$ 158 S$ 80
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PDX 06:4015h 35m1 stopsORD 00:15Portland - Chicago | Thu, Apr 17 | Frontier AirlinesS$ 8447% OFFS$ 158 S$ 84
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PDX 21:5111h 32m1 stopsMDW 11:23Portland - Chicago | Mon, May 5 | Frontier AirlinesS$ 8546% OFFS$ 158 S$ 85
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PDX 10:1612h 47m1 stopsORD 01:03Portland - Chicago | Thu, Apr 3 | Frontier AirlinesS$ 8646% OFFS$ 158 S$ 86
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PDX 17:1628h 24m1 stopsORD 23:40Portland - Chicago | Thu, Apr 24 | Frontier AirlinesS$ 8646% OFFS$ 158 S$ 86
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PDX 19:019h 32m1 stopsORD 06:33Portland - Chicago | Wed, Apr 16 | Spirit AirlinesS$ 9441% OFFS$ 158 S$ 94
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PDX 21:2129h 44m1 stopsORD 05:05Portland - Chicago | Sat, Apr 5 | Frontier AirlinesS$ 9739% OFFS$ 158 S$ 97
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PDX 13:0017h 25m1 stopsCHI Invalid DatePortland - Chicago | Thu, Mar 27 | 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.
Cheapest time to fly from Portland to Chicago
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Displayed prices are calculated based on the lowest average weekly prices of the corresponding route on Trip.com.
Cheapest Airlines flying from Portland to Chicago
Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.
Frequently Asked Questions
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When to buy 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 is a flight from Portland (PDX) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around S$ 468. -
How long is a flight from Portland (PDX) to Chicago (CHI)?
It takes about 7 hours 37 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, 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?
There are 3 airports near Chicago: O'Hare International Airport, Midway 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.
Choose your dates flexibly and get the best deals on flights from Portland to Chicago.
Tap 'Date' on the flight search bar to browse the calendar for Portland to Chicago airfare over the next 6 months in 2025. If you're looking to fly within the next 3 months, the cheapest date seems to be Sun, Apr 20, with one-way flights starting at S$ 119.
Compare cheap flight deals from hundreds of airlines for Portland to Chicago flights.
Our extensive search lets you compare prices from over 500 airlines to find the cheapest flights from Portland to Chicago. The cheapest flight at the moment is with Southwest Airlines.
Set up a Price Alert
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Don't miss out on cheap deals and promo codes for Portland to Chicago flights.
You can always get the latest deals through Trip.com Deals and Promo Codes for cheap flights. Sign up for a free membership for more exclusive flight deals.
Book early or wait for last-minute deals.
It's always better to book early. Flight tickets are often at their lowest when first released, usually a year ahead of departure. Keep an eye out as soon as your desired flights open for booking. If you miss the early deals, you may still find lower prices closer to your travel date.
Search for flights on the go.
For the best flight booking experience on the go, download Trip.com and search for cheap flights from Portland to Chicago to get your exclusive deals.
Find cheapest flight ticket from Portland to Chicago
| Cheapest one-way flight price | S$ 63 |
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| Cheapest return ticket price | S$ 207 |
| Off-season for travel | March |
| Peak season for travel | December |
| Flight distance | 2,816.22km |
| Average flight time | 7 hours 37 minutes |
| Popular airline | Alaska Airlines |
Plan Your Trip Around Chicago
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