Cheap flights from Portland to Chicago

Round-trip
Economy
Portland (PDX)
Chicago (CHI)
Sat 10/31
Sat 11/7
Any month
Compare vs. momondo |

Flight information for Portland to Chicago
(PDX to CHI)

Find info about flight duration, direct flights, and airports for your flight from Portland to Chicago
Best Price Found $100 The best flight deal from Portland to Chicago found on momondo in the last 72 hours is $100
Fastest flight time 4h 5m The fastest flight from Portland to Chicago takes 4h 5m.
Direct flights Mo, Tu, Fr, Sa and Su Direct flights go from Portland to Chicago on Monday, Tuesday, Friday, Saturday and Sunday. Airline offering direct flights is American Airlines..
Airports in Chicago 3 airports There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

How to get the cheapest flight ticket from Portland to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Chicago?
January
The cheapest time of year to fly to Chicago from Portland is January. Most expensive is December
What is the cheapest day to fly to Chicago?
Friday
The cheapest day of the week is typically Friday. The most expensive is typically Sunday
When is the cheapest time to fly to Chicago?
in the afternoon
Portland to Chicago flights are approximately 15% more expensive in the morning than in the afternoon
What is the cheapest airline that flies to Chicago?
Frontier
Frontier, Sun Country Air, and Spirit Airlines are the most popular carriers operating from Portland to Chicago
What is the cheapest route?
Portland - Chicago O'Hare Intl
Fly from Portland to Chicago O'Hare Intl for the best Portland - Chicago flight prices
When is the cheapest time to book a flight to Chicago?
57 days before
The cheapest time to buy a flight from Portland to Chicago is approximately 57 days to departure
60
Days before departure
0

Easily compare round-trip flights from Portland to Chicago

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Portland to Chicago by changing tabs
Cheapest
Best
Quickest
Multiple Airlines
Nov 5
PDX
Portland
6h 16m
1 stop
ORD
Chicago O'Hare Intl
Nov 9
ORD
Chicago O'Hare Intl
4h 20m
PDX
Portland
Multiple Airlines
Nov 2
PDX
Portland
13h 09m
1 stop
ORD
Chicago O'Hare Intl
Nov 10
ORD
Chicago O'Hare Intl
4h 23m
PDX
Portland
Multiple Airlines
Nov 2
PDX
Portland
6h 55m
1 stop
ORD
Chicago O'Hare Intl
Nov 10
ORD
Chicago O'Hare Intl
7h 47m
1 stop
PDX
Portland

Find the cheapest one-way flights from Portland to Chicago

If you're looking for one-way flights from Portland to Chicago, view some of our deals below provided by Spirit Airlines
Cheapest
Best
Quickest
Spirit Airlines
Nov 10
PDX
Portland
10h 50m
1 stop
ORD
Chicago O'Hare Intl
Multiple Airlines
Oct 19
PDX
Portland
13h 02m
1 stop
ORD
Chicago O'Hare Intl
Delta
Nov 10
PDX
Portland
8h 58m
2 stops
ORD
Chicago O'Hare Intl

Which airlines flying from Portland to Chicago have COVID-19 safety policies in place?

Airlines such as Alaska Airlines, Southwest, and Delta have taken additional precautions to make sure you’re safer while traveling. When flying from Portland to Chicago, expect masks to be provided - they are required onboard. Aircrafts are also being cleaned thoroughly with enhanced products regularly. Additional policies include the installation of HEPA filters and pre-flight testing. Some airlines are even offering socially-distanced seating for a limited time. Keep in mind that policies will vary by airline.

Are airlines flying from Portland to Chicago offering flexible cancellation due to COVID-19?

To ease the stress of booking flights, some of our airline partners flying from Portland to Chicago are responding to the global pandemic. The following airlines may have a flexible cancellation policy to help accommodate travelers: United Airlines, Alaska Airlines, and American Airlines.


Alternative routes for Portland to Chicago

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Eugene to Chicago Flights
Fastest flight time
9h 00m
Cheapest price
$146

Flights from Portland to:

  • Round-trip
  • One-way
  • Multi-city
  • Economy
  • Premium Economy
  • Business
  • First
  • Multiple
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First