Cheap flights from Chicago (CHI) to Portland (PWM) from $116

This is the cheapest one-way flight price, found on 5/31. Prices may vary by date and flight preferences.
CHI — PWM
Jun 6 — Jun 131

The best prices from Chicago to Portland are usually found in September or January, booked 38 days in advance, depart on a Tuesday or Wednesday and return on a Saturday

How to find the cheapest flight from Chicago (CHI) to Portland (PWM)

All the information you need to plan the best CHI to PWM flight in 2023: compare Chicago to Portland flight prices with the expected peak season, weather and rainfall in Portland.

Popular in

November

Cheapest in

September

Round-trip from

$317

One-way from

$153
High demand for flights, 22% potential price rise
Best time to find cheap flights, 27% potential price drop
From Chicago (CHI) to Portland
One-way flight from Chicago (CHI) to Portland

CHI - PWM

Price

$317 - $557

PWM

Temperature

23 - 68 °F

PWM

Rainfall

2.9 - 4.5 inches

Cheap flights from Chicago to Portland in June, July 2023

The best prices found for CHI to PWM flights for June, July
Check out some of the best flight deals from Chicago to Portland in 2023. Check back in a little while for more flight options.

Chicago to Portland 2023 flight deals

Cheap flights to Portland from Chicago found for this year
Check out some of the best flight deals from Chicago to Portland in 2023. Check back in a little while for more flight options.

Cheap United Airlines flights from Chicago to Portland

Find some of the cheapest United Airlines flights traveling from Chicago to Portland. Come back soon if you're not finding the exact deal you're looking for.

Cheap Delta flights from Chicago to Portland

Browse through some of the cheapest Delta flights traveling from Chicago to Portland. Check back soon if you're not seeing flights that suit your needs.

Non-stop flights to Portland from Chicago

Save time with Chicago to Portland direct flight deals
Take a look at some of the direct flights traveling from Chicago to Portland in the near future. Those looking to potentially save on 1 or 2-stop flights from Chicago to Portland should utilize the search form at the the top of the page.

Last minute flights from Chicago to Portland

Late deals on return flights to Portland from Chicago, departing today and this week
Have a look at some of the flights available from Chicago to Portland departing last-minute. Users should be sure to double check the price, date, and time of their last-minute flight.

One-way flights to Portland from Chicago

The cheapest one-way flights from Chicago to Portland
Users traveling one-way from Chicago to Portland can select one of these great deals. For those needing a return trip from Chicago, there is a search form available above.

Find flights from Chicago to Portland within your budget

Use the slider to find flights from Chicago to Portland that fit your budget.

Fly from

Any airport

Fly to

Any airport

Budget

$233 - $353

Route

Depart

Return

Price

Chicago O'Hare IntlPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 8/30

1 stop10h 52m

Portland

Tue 9/5

1 stop9h 27m

Chicago O'Hare IntlPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 8/30

Nonstop2h 25m

Portland

Wed 9/6

1 stop10h 50m

Chicago O'Hare IntlPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 8/30

Nonstop2h 25m

Portland

Tue 9/5

Nonstop2h 50m

Chicago MidwayPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 8/15

1 stop5h 32m

Portland

Wed 8/23

1 stop8h 11m

Chicago MidwayPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 8/29

2 stops7h 40m

Portland

Wed 9/6

1 stop4h 07m

Chicago O'Hare IntlPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 7/11

1 stop4h 57m

Portland

Tue 7/18

Nonstop2h 47m

Chicago O'Hare IntlPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 8/31

1 stop8h 16m

Portland

Fri 9/8

1 stop6h 15m

Chicago MidwayPortland

MDW - PWM

MDWPWM

Chicago Midway

Fri 6/16

1 stop8h 54m

Portland

Mon 6/19

2 stops27h 18m

Chicago MidwayPortland

MDW - PWM

MDWPWM

Chicago Midway

Fri 6/23

1 stop8h 27m

Portland

Wed 6/28

2 stops12h 38m

Flights are sorted by cheapest first

Deals found on 5/31

Reviews of Airlines Servicing Portland

Read reviews from past customers who have flown United Airlines, Delta and American Airlines from Chicago to Portland. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
2,370 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.8

Boarding

8.1

Food

7.2

Reviews

1 / 10

Flights were on time with no delays, luggage arrived with the flight. I know the flights were short, but the only drinks offered were water, tea and coffee. It would’ve been nice to have the option to choose a soda, especially since I was in comfort class. The snacks were very small.

Delta
8.0
Very good
2,370 reviews
Delta
8.0
Very good
2,370 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.8

Boarding

8.1

Food

7.2

Reviews

1 / 10

Flights were on time with no delays, luggage arrived with the flight. I know the flights were short, but the only drinks offered were water, tea and coffee. It would’ve been nice to have the option to choose a soda, especially since I was in comfort class. The snacks were very small.

United Airlines
7.6
Good
1,535 reviews
Delta
8.0
Very good
2,370 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.8

Boarding

8.1

Food

7.2

Reviews

1 / 10

Flights were on time with no delays, luggage arrived with the flight. I know the flights were short, but the only drinks offered were water, tea and coffee. It would’ve been nice to have the option to choose a soda, especially since I was in comfort class. The snacks were very small.

JetBlue
7.5
Good
609 reviews
Delta
8.0
Very good
2,370 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.8

Boarding

8.1

Food

7.2

Reviews

1 / 10

Flights were on time with no delays, luggage arrived with the flight. I know the flights were short, but the only drinks offered were water, tea and coffee. It would’ve been nice to have the option to choose a soda, especially since I was in comfort class. The snacks were very small.

Sun Country Air
7.4
Good
84 reviews
Delta
8.0
Very good
2,370 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.8

Boarding

8.1

Food

7.2

Reviews

1 / 10

Flights were on time with no delays, luggage arrived with the flight. I know the flights were short, but the only drinks offered were water, tea and coffee. It would’ve been nice to have the option to choose a soda, especially since I was in comfort class. The snacks were very small.

American Airlines
7.3
Good
2,149 reviews
Delta
8.0
Very good
2,370 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.8

Boarding

8.1

Food

7.2

Reviews

1 / 10

Flights were on time with no delays, luggage arrived with the flight. I know the flights were short, but the only drinks offered were water, tea and coffee. It would’ve been nice to have the option to choose a soda, especially since I was in comfort class. The snacks were very small.

Related info for your journey

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

Top 3 airlines flying from Chicago to Portland

The chart below displays the airlines Cheapflights users traveling from Chicago to Portland choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
American AirlinesCheapest$131Average$366FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
United AirlinesCheapest$206Average$384FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
DeltaCheapest$246Average$399FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights

Hourly flight availability from Chicago to Portland

See what time of day planes typically take off from Chicago to Portland
0%of flight departuresEarly morningMidnight to 6 am
0%of flight departuresMorning6 am to noon
100%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Chicago to Portland

See how many times per day planes take to the skies headed from Chicago to Portland
Sunday4daily flights
Monday5daily flights
Tuesday5daily flights
Wednesday5daily flights
Thursday5daily flights
Friday5daily flights
Saturday6daily flights
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