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Cheap flights from Portland to Chicago (PWM - CHI)

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The best prices from Portland to Chicago are usually found in June or May, booked 60 days in advance, depart on a Saturday or Tuesday and return on a Wednesday

PWM - CHI
Price
$309 - $399
CHI
Temperature
33.8 - 84.2 °F
CHI
Rainfall
0.7 - 4.3 inches
Popular in March High demand for flights, 10% potential price rise
Cheapest in June Best time to find cheap flights, 14% potential price drop
Average price $321 Average for round-trip flights in April 2020
Round-trip from $309 From Portland to Chicago

Cheap flights from Portland to Chicago in April 2020

The best prices found for PWM to ORD flights for April
24 Apr - 27 Apr
$89pp
PWM
Portland
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
PWM
Portland
21 Apr - 25 Apr
$94pp
PWM
Portland
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
PWM
Portland
25 Apr - 27 Apr
$95pp
PWM
Portland
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
PWM
Portland

Portland to Chicago 2020 flight deals

Cheap flights to Chicago from Portland found for this year
9 Jun - 11 Jun
$90pp
PWM
Portland
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
PWM
Portland
22 May - 26 May
$95pp
PWM
Portland
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
PWM
Portland
25 Jun - 5 Jul
$105pp
PWM
Portland
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
PWM
Portland

Non-stop flights to Chicago from Portland

Save time with Portland to Chicago direct flight deals
9 Jun - 11 Jun
$90pp
PWM
Portland
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
PWM
Portland
25 Jun - 5 Jul
$105pp
PWM
Portland
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
PWM
Portland

Last minute flights from Portland to Chicago

Late deals on round-trip flights to Chicago from Portland, departing today and this week
7 Apr - 12 May
$117pp
PWM
Portland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
PWM
Portland
9 Apr - 14 Apr
$126pp
PWM
Portland
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
PWM
Portland
5 Apr - 8 Apr
$140pp
PWM
Portland
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
PWM
Portland

Alternative routes for Portland to Chicago

Destination information for Chicago

Things to know before you go. Useful info for your trip from Portland to Chicago
Flight duration
2h 36m
Average temperature for April in Chicago
62.6 °F
Avg rainfall for April in Chicago
2.3 ″

Airports servicing Portland

Airports servicing Chicago

Chicago-O'Hare Intl (ORD)
Rockford (RFD)
Weekly flight availability
from Portland to Chicago
Sunday
4 daily flights
Monday
4 daily flights
Tuesday
4 daily flights
Wednesday
3 daily flights
Thursday
4 daily flights
Friday
4 daily flights
Saturday
4 daily flights

Related info for your journey

Useful info, stats and facts about Portland to Chicago flights.

Flight FAQs

From Portland to Chicago

Are flight prices decreasing from Portland to Chicago due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Portland and Chicago for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

Are there nonstop flights from Portland to Chicago for under $100 on Cheapflights?

There are no nonstop flights from Portland to Chicago, but Cheapflights can provide you with all the information you need to find the fastest route with the fewest stops.

Are there last-minute flights available from Portland to Chicago for under $200?

There are currently just 3 open flights from Portland to Chicago within the next 7 days for less than $200.

What days are nonstop flights available from Portland to Chicago?

Nonstop flights can be found on the following days: Sunday, Monday, Tuesday, Wednesday, Thursday, Friday, Saturday.

How popular is this flight route?

The Portland to Chicago flight path was viewed by 148 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

What percent of flights are delayed?

Airlines departing from Portland to Chicago can be delayed by up to 22min. or more hours.

What is the cheapest airline for this route?

When searching, try setting your filters to view flights for Pinnacle Airlines, Inc. D/B/A Delta Connection, as currently they have the cheapest options available from Portland to Chicago. On average you can find 78 flights for this flight path daily.

How long does the flight from Portland to Chicago take?

A typical nonstop flight can take about 3 hours, covering about 560 miles.

How many flights depart from Portland to Chicago on average per day?

6 flight departures from Portland to Chicago per day on average.
Morning (6am - Noon) - 50% of flight departures
Afternoon (Noon - 6pm) - 50% of flight departures

Is Portland weather warmer or cooler than Chicago?

Temperatures around the 84 °F's can be experienced in July. The weather in Chicago is hotter than in Portland. Plan for potential changes in flight availability as peak weather approaches in this location.