Cheap flights from Chicago to Portland

Chicago FSS
CHI
Portland
PDX

Flight deals from Chicago to Portland

Below you can see the best deals on flights Chicago — Portland for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 1 September, from $102.

Top 10 cheap flights from Chicago to Portland

F9
F9
$ 102

Chicago — Portland

14:41—17:11
1 Sep 2026
28 h 30 m
1 stop
F9
F9
F9
$ 134

Chicago — Portland

14:41—12:52
2 Sep 2026
24 h 11 m
2 stops
F9
F9
F9
$ 144

Chicago — Portland

21:10—17:11
4 Sep 2026
22 h 1 m
2 stops
F9
F9
AS
$ 146

Chicago — Portland

06:30—20:35
9 Sep 2026
16 h 5 m
2 stops
F9
F9
DL
DL
$ 147

Chicago — Portland

06:30—22:31
9 Sep 2026
18 h 1 m
3 stops
F9
F9
$ 151

Chicago — Portland

06:30—11:43
9 Sep 2026
31 h 13 m
1 stop
F9
F9
$ 160

Chicago — Portland

20:55—11:36
11 Sep 2026
16 h 41 m
1 stop
F9
F9
$ 168

Chicago — Portland

14:41—17:11
2 Sep 2026
28 h 30 m
1 stop
F9
F9
AS
$ 168

Chicago — Portland

06:30—16:26
12 Sep 2026
11 h 56 m
2 stops
F9
F9
AS
$ 168

Chicago — Portland

06:30—20:33
12 Sep 2026
16 h 3 m
2 stops

Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the Chicago — Portland flight

Looking for cheap flights from Chicago to Portland? Compare fares from different airlines, check the flight schedule and travel time — and book your Chicago — Portland ticket online at the best price.

The route has direct flights — around 138 flights per week, flights are operated by United Airlines, American Airlines, Alaska Airlines, a nonstop flight takes about 4 h 25 min, the distance between the cities is around 2,831 km.

Planning your trip? You may find our Portland travel guide, how to get from the airport into town and Portland weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

Facts about this route

from $102Min. price
SeptemberCheapest
MayPeak season
YesDirect flights
2,831 kmDistance
4 h 25 minTravel time
3Airlines
138 / wkFlights

Flight schedule from Chicago to Portland

The table shows direct flights from Chicago to Portland on the selected date. The flight takes approximately 4 h 25 min. Regular flights are operated by United Airlines, American Airlines and Alaska Airlines. Departures from O'Hare International Airport, Chicago Midway International Airport and Midway International Airport airports, arrivals at Portland International Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

Today
Any time
Last update: 15 Aug 2026

Flight ticket prices by day: Chicago — Portland

Below is a calendar of the lowest flight ticket prices for Chicago — Portland by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $102 in September, and the most expensive are around $194 in May. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--

Prices by month

Average one-way fares from Chicago to Portland by month. Tickets are usually cheapest in September (around $175) and priciest in July (about $232) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$185lowMay$190mediumSep$175low
Feb$180lowJun$228highOct$180low
Mar$194mediumJul$232highNov$213high
Apr$194mediumAug$180lowDec$199medium

Some values are estimated based on seasonality.

When to fly

Weather in Portland: it is warmest in August (up to 29 °C on average) and coolest in December (around 8 °C). The driest month is July.

Tickets are usually cheapest in September and most expensive in May. Compare prices and weather by month in the charts below to pick the best time to fly.

Temperature · Portland

Dry and wet days · Portland

Wind speed and direction · Portland

We'll let you know if you need a visa

Enter your destination or
Your nationality
Destination

How to get the best deal on a Chicago — Portland ticket

  • Book ahead: fares for Chicago — Portland are usually lower 3–8 weeks before departure than at the last minute.
  • Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
  • Chicago is served by more than one airport — compare fares and travel time to each before you book.
  • The cheapest month to fly to Portland is usually September — plan your trip around it if your dates are flexible.
  • Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
  • Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
  • Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
  • Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Airlines

Flights on the Chicago — Portland route are operated by 3 airlines; United Airlines runs the most flights (around 47% of all flights). Compare carriers, flight shares and schedules below.

  • United AirlinesUA
    22x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight ORD → PDX22x/week
      Duration
      4h 32m
      Days
      MTWTFSS
    47.1%Open →
  • American AirlinesAA
    15x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight ORD → PDX15x/week
      Duration
      4h 34m
      Days
      MTWTFSS
    32.6%Open →
  • Alaska AirlinesAS
    9x/week
    WebsiteFleet: 31545M pax/year
    • Direct flight ORD → PDX9x/week
      Duration
      4h 27m
      Days
      MTWTFSS
    20.3%Open →

Cities and airports on the Chicago — Portland route

Flights Chicago — Portland depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport and arrive at Portland International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Arrival

Portland

PDX
United States
About the cityHow to get thereWeatherAll about the country United States
Departure airports
Arrival airports

Interesting articles about Portland

5 Reasons to Travel Beyond LondonTips for Travelers

5 Reasons to Travel Beyond London

England is not just London, Oxford’s library, and a flock of wizards on Baker Street with pipes in their teeth. Getting a British visa is not easy, so if you’re going, you should see all corners. Afte…

Free Public Transport AbroadUseful information

Free Public Transport Abroad

How to get around abroad is always a tricky question. Some simply buy a day pass and spare no expense, while others prefer to walk to avoid spending extra money on “it’s only a ten-minute walk!”. But…

Did you know that some airports have beds?Interesting

Did you know that some airports have beds?

Did you know that some airports have beds? They are intended for passengers whose flights were canceled due to bad weather or other force majeure circumstances. These unfortunate travelers are offered…

Graffiti: Where to go for street artInteresting

Graffiti: Where to go for street art

Long gone are the days when graffiti was considered solely vandalism. Today, street art is a powerful and vibrant direction of contemporary art, transforming gray city walls into open-air galleries. A…

The World’s Largest CitiesInteresting

The World’s Largest Cities

If you prefer non-stop action to quiet solitude somewhere by the sea or in the mountains—this article is for you. We’ve already told you about the oldest cities in the world, and now it’s time to delv…

Useful information

The most delicious dishes for economy class passengers.

Sometimes, even in economy, you can feel like a business class passenger. Don’t believe it? Just take a look at the dishes offered by some airlines in their economy classes. Alaska Airlines Chili bris…

Frequently asked questions about the Chicago — Portland flight

How long is the flight from Chicago to Portland?

A nonstop Chicago — Portland flight takes about 4 h 25 min — the distance between the cities is around 2,831 km.

How far is it from Chicago to Portland?

The distance from Chicago to Portland is about 2,831 km, which a nonstop flight covers in around 4 h 25 min.

Are there direct flights from Chicago to Portland?

Yes, there are nonstop flights Chicago — Portland — around 138 flights per week.

Which airlines fly from Chicago to Portland?

Airlines operating Chicago — Portland include United Airlines, American Airlines, Alaska Airlines. See the full list with schedules in the "Airlines" section on this page.

Which airports do Chicago — Portland flights use?

Flights from Chicago depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport, and arrive at Portland International Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from Chicago to Portland?

The price of a Chicago — Portland ticket depends on your travel date, season and demand: it is usually cheapest to fly in September, and most expensive in May. Tickets typically cost between $102 and $194. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights Chicago — Portland?

Flights Chicago — Portland are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is September. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from Chicago to Portland?

To catch a low fare Chicago — Portland, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually September.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

Where else you can fly from Chicago

See all
New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverLondonNashvilleIndianapolisSan DiegoMontrealMilwaukeeSt. LouisCharlottePhiladelphiaColumbusKansas CityMiamiPhoenixLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochester

Where else you can fly from Portland

See all
SeattleLos AngelesSan FranciscoDenverSalt Lake CitySan JoseNew York CitySan DiegoPhoenixAnchorageLas VegasBoiseVancouverMinneapolisSanta AnaSpokaneSacramentoRedmondSanta RosaHonoluluMedfordDallasAtlantaFresnoOaklandEugeneBurbankBostonRenoWashington, D.C.PascoHoustonAustinPhiladelphiaFairbanksMissoulaCharlotteBozemanPalm SpringsCalgary

We use cookies and services to collect user information. This is essential for the functioning of the site and for marketing purposes. You can find out more in .