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Flights to Chicago
All fares Portland (PDX) to Chicago (CHI) found by travelers in past 72 hours¤

Today's lowest fares
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Jun
$216
Jul
$249
Aug
$249
About TripAdvisor Flights

Your one-stop shop for finding the best flights from Portland to Chicago. Simply tell us where and when you want to travel and we'll do all the legwork for you. Featuring the most powerful shopping tools on the web, we search the largest online travel websites, established airfare discounters, plus the world's leading airlines and low-cost carriers to bring back thousands of flight options.

Travel information for Portland, OR to Chicago

Route information
  • Portland, OR is 1734 miles from Chicago
  • There are 20 daily flights from Portland, OR to Chicago
  • There are 65 weekly flights from Portland, OR to Chicago
  • 40 non-stop flights are operating from Portland, OR to Chicago today
  • United has the most nonstop flights between Portland, OR and Chicago
  • 3 direct flights are operating from Portland, OR to Chicago today
  • US Airways has the most direct flights between Portland, OR and Chicago
  • Seattle, WA - Seattle/Tacoma International Airport is the most popular connection for one stop flights between Portland, OR and Chicago
In-Flight Information
  • The average flying time for a direct flight from Portland, OR to Chicago is 3 hours 57 minutes
  • Most direct flights leave around 7:00 PDT
Arrival information
  • Chicago is 16 mi from O'Hare Intl Airport (Chicago, IL).
  • O'Hare Intl Airport (Chicago, IL)
    • Right now, 95 airlines operate out of O'Hare Intl Airport.
    • O'Hare Intl Airport offers nonstop flights to 239 cities.
    • Every week, at least 26,600 domestic flights and 2,807 international flights depart from O'Hare Intl Airport.
  • Chicago is 9 mi from Midway Airport (Chicago, IL).
  • Midway Airport (Chicago, IL)
    • Right now, 8 airlines operate out of Midway Airport.
    • Midway Airport offers nonstop flights to 73 cities.
    • Every week, at least 2,807 domestic flights and 126 international flights depart from Midway Airport.

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