Chicago

$60+ Cheap flights from Portland (PWM) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
Nov 5 — Nov 121
1 adult
Tue 11/5
Tue 11/12
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1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
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The best prices from Portland to Chicago are usually found in September or February, booked 65 days in advance, depart on a Thursday or Wednesday and return on a Tuesday

Cheap flight deals from Portland to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 31, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

April

Cheapest in

September

Round-trip from

$138
(CheapOair)

One-way from

$60
(Frontier)
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Portland-Chicago (CHI) flights.
High demand for flights, 32% potential price rise
Best time to find cheap flights, 25% potential price drop
From Portland to Chicago (CHI)
One-way flight from Portland to Chicago (CHI)

Find flight deals from Portland to Chicago

Cheapest flights from Portland to Chicago
Explore the most affordable flight options available from Portland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 31, 2024.

This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/312:30 pmPWM - ORD
1 stop10h 35mAmerican Airlines
Wed 12/186:00 amORD - PWM
1 stop9h 32mAmerican Airlines
Deal found 10/30$293
This CheapOair deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/197:49 pmPWM - MDW
1 stop14h 42mFrontier
Sat 12/216:49 pmMDW - PWM
1 stop23h 02mFrontier
Deal found 10/31$298
This Mytrip deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/165:56 pmPWM - ORD
2 stops23h 10mMultiple Airlines
Thu 12/196:05 amORD - PWM
1 stop9h 30mMultiple Airlines
Deal found 10/30$305
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/255:05 amPWM - MDW
1 stop4h 45mDelta
Sun 1/55:03 pmMDW - PWM
1 stop6h 09mDelta
Deal found 10/31$355
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/241:15 pmPWM - MDW
1 stop9h 00mSouthwest
Fri 12/275:25 amMDW - PWM
1 stop4h 15mSouthwest
Deal found 10/30$375
This United Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/209:30 amPWM - ORD
Nonstop2h 59mUnited Airlines
Sun 11/241:21 pmORD - PWM
1 stop5h 48mUnited Airlines
Deal found 10/30$376
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/126:00 amPWM - ORD
2 stops13h 10mSouthwest
Sun 12/153:10 pmORD - PWM
1 stop7h 45mSouthwest
Deal found 10/31$395
This CheapOair deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/16:02 pmPWM - ORD
1 stop24h 41mFrontier
Sun 11/35:10 amORD - PWM
1 stop12h 35mFrontier
Deal found 10/30$398
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/317:00 amPWM - ORD
1 stop11h 03mDelta
Fri 1/36:20 pmORD - PWM
1 stop15h 59mDelta
Deal found 10/31$403
This Mytrip deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/24:58 pmPWM - MDW
3 stops21h 37mWestJet
Wed 12/42:17 pmMDW - PWM
3 stops20h 54mWestJet
Deal found 10/30$1,074
This Mytrip deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1512:01 pmPWM - MDW
3 stops31h 31mMultiple Airlines
Sun 11/176:46 pmMDW - PWM
3 stops21h 48mMultiple Airlines
Deal found 10/30$1,121

Find flights from Portland to Chicago within your budget

Customize your flight search to find flights from Portland to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,570,725 searches. Data last updated October 31, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 1/30

9:02 pm-9:52 am

1 stop13h 50m

$60

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 12/18

11:54 am-8:49 pm

1 stop9h 55m

$101

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 4/29

6:10 am-10:16 am

1 stop5h 06m

$103

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 2/6

9:02 pm-2:42 pm

1 stop18h 40m

$61

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 1/8

4:10 pm-6:24 pm

Nonstop3h 14m

$123

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 1/28

4:40 pm-8:43 pm

1 stop5h 03m

$132

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 2/22

4:50 pm-9:40 pm

1 stop5h 50m

$152

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 12/31

6:00 am-12:15 pm

1 stop7h 15m

$160

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 1/22

5:40 am-11:59 am

1 stop7h 19m

$132

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 1/1

6:00 am-1:00 pm

2 stops8h 00m

$165

Flights are sorted by cheapest first

Deals found on 10/31

Showing 1-10 of 22 results
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Compare providers for flights from Portland to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Portland to Chicago in October.
ProviderPrice AccuracyTrust Score*Cancellation Policy
ExpediaPrice Accuracy1 starTrust Score*3 stars