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

The number of flights available between Chicago and Portland is 23 per day as of July 2025. The most frequent departure time is 7:00AM, with 43% of daily flights leaving in the afternoon.

What airlines fly to Portland?

United Airlines, Alaska Airlines and American Airlines are the top three most popular airlines that fly to Portland from Chicago according to our data. United Airlines is the first choice among our users, with 42% of people opting to fly with this airline when traveling to Portland. Keep in mind that there are 8 different airlines that fly to Portland on a routine basis, so you have a few additional options to choose from.

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

As of July 2025, there are 167 flights per week flying from Chicago to Portland. The most common day of the week flights depart is Thu, with 17% of flights taking off on this day.

What is the cheapest airline that flies from Chicago to Portland?

Hawaiian Airlines, Southwest, and United Airlines are the most popular carriers operating from Chicago to Portland

When did momondo last update prices for flights from Chicago to Portland Airport?

Prices for flights from Chicago to Portland Airport refresh daily.

How many operators does momondo search for flights from Chicago to Portland Airport?

As of July 2025, there are 8 operators available to choose from for flights from Chicago to Portland Airport.

How old do you have to be to fly from Chicago to Portland Airport?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Portland Airport.

What documentation or ID do you need to fly to Portland Airport?

The travel and health documents required for your trip to Portland Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Portland Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$52 Cheap Flights from Chicago to Portland in 2025

Q: What is the typical price of a round-trip flight between Chicago and Portland?

Prices are currently low for flights on this route. Typical prices usually range from $220 to $373. The lowest price recently found on this route was $99.

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Find the cheapest flights from Chicago to Portland

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

7:00 am - 9:25 amORD-PDX

4h 25mnonstop

5:35 pm - 11:39 pmPDX-ORD

4h 04mnonstop

$99Hawaiian Airlines

Find Deal

Sat, Aug 9 - Tue, Aug 12

7:00 am - 9:25 amORD-PDX

4h 25mnonstop

5:35 pm - 11:39 pmPDX-ORD

4h 04mnonstop

$100Hawaiian Airlines

Find Deal

Sat, Aug 9 - Tue, Aug 12

7:00 am - 9:25 amORD-PDX

4h 25mnonstop

5:35 pm - 11:39 pmPDX-ORD

4h 04mnonstop

$104Hawaiian Airlines

Find Deal

Thu, Aug 7 - Wed, Aug 13

7:00 am - 9:25 amORD-PDX

4h 25mnonstop

5:35 pm - 11:39 pmPDX-ORD

4h 04mnonstop

$105Alaska Airlines

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Thu, Aug 7 - Thu, Aug 14

8:25 pm - 10:50 pmMDW-PDX

4h 25mnonstop

1:25 pm - 7:20 pmPDX-MDW

3h 55mnonstop

$105Southwest

Find Deal

Tue, Oct 21 - Wed, Oct 29

8:49 pm - 11:26 pmORD-PDX

4h 37mnonstop

1:20 pm - 7:18 pmPDX-ORD

3h 58mnonstop

$106American Airlines

Find Deal

Sat, Aug 23 - Sat, Aug 30

7:00 pm - 11:20 pmMDW-PDX

6h 20m1 stop

6:00 am - 11:55 amPDX-MDW

3h 55mnonstop

$115Southwest

Find Deal

Tue, Oct 21 - Wed, Oct 29

7:00 am - 9:25 amORD-PDX

4h 25mnonstop

5:35 pm - 11:39 pmPDX-ORD

4h 04mnonstop

$118Alaska Airlines

Find Deal

Fri, Aug 15 - Tue, Aug 19

4:13 pm - 6:45 pmORD-PDX

4h 32mnonstop

10:55 pm - 4:56 amPDX-ORD

4h 01mnonstop

$134United Airlines

Find Deal

Wed, Aug 6 - Sat, Aug 9

12:46 pm - 3:14 pmORD-PDX

4h 28mnonstop

11:59 pm - 6:00 amPDX-ORD

4h 01mnonstop

$139United Airlines

Find Deal

Mon, Aug 4 - Mon, Aug 11

Delta flights from Chicago to Portland

Our best Delta deals on Chicago to Portland flight tickets

Delta

Aug 22

MDW6:04 amChicago Midway

8h 37m

1 stop

PDX12:41 pmPortland

Aug 29

PDX11:32 amPortland

8h 12m

1 stop

MDW9:44 pmChicago Midway

$177

Find similar

Delta

Jul 23

MDW1:46 pmChicago Midway

8h 37m

1 stop

PDX8:23 pmPortland

Jul 29

PDX12:40 amPortland

6h 05m

1 stop

MDW8:45 amChicago Midway

$469

Find similar

Delta

Jul 16

MDW6:00 amChicago Midway

8h 55m

1 stop

PDX12:55 pmPortland

Jul 18

PDX12:40 amPortland

6h 05m

1 stop

MDW8:45 amChicago Midway

$477

Find similar

United Airlines flights from Chicago to Portland

Our best United Airlines deals on Chicago to Portland flight tickets

United Airlines

Aug 6

ORD4:13 pmChicago O'Hare Intl

4h 32m

PDX6:45 pmPortland

Aug 9

PDX10:55 pmPortland

4h 01m

ORD4:56 amChicago O'Hare Intl

$134

Find similar

United Airlines

Aug 4

ORD12:46 pmChicago O'Hare Intl

4h 28m

PDX3:14 pmPortland

Aug 11

PDX11:59 pmPortland

4h 01m

ORD6:00 amChicago O'Hare Intl

$139

Find similar

United Airlines

Sep 7

ORD7:50 pmChicago O'Hare Intl

4h 35m

PDX10:25 pmPortland

Sep 13

PDX8:30 amPortland

4h 08m

ORD2:38 pmChicago O'Hare Intl

$148

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How to get the cheapest flight ticket from Chicago to Portland

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

Prices

Airlines

Other information

What is the typical price of a round-trip flight between Chicago and Portland?

What is the cheapest month to fly to Portland?

The cheapest month to fly to Portland from Chicago is in September. Flight prices, which tend to average around $268, are often lower during this time because this is during the off-season. If you don’t want to visit Portland in September, then you should wait until January to fly from Chicago, when ticket prices are also cheap, with an average price of $274.

What is the cheapest day to depart on your flight to Portland?

The cheapest day to depart on your flight to Portland is on a Wednesday when prices can be found for as low as $327. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Portland is Sunday, with ticket prices averaging around $397.

What is the cheapest time of day to depart on your flight to Portland?

The cheapest time of day to fly to Portland is in the evening when flights can be purchased for as low as $289. At noon is when there is more demand to fly to Portland, so prices are often more expensive at around $399 per ticket.

What is the cheapest Chicago to Portland flight route?

Fly from Chicago Midway to Portland for the best Chicago - Portland flight prices

How far in advance should I book a flight to Portland?

You are more likely to see cheaper flights to Portland from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Portland for around $332 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Portland from Chicago for as low as $287 on momondo.

What cabin class options are available on Chicago to Portland flights?

There are 4 cabin classes available to choose from on Chicago to Portland flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Portland flights?

No. A direct flight is the cheapest option for a flight between Chicago to Portland.

How have Chicago to Portland flight prices changed over time?

As of July 2025, prices for Chicago to Portland flights are approximately 70% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Portland

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Portland according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago to Portland (CHI to PDX) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Portland

Best Price Found	$52
Fastest flight time	4h 15m
Direct flights	Every day
Airports in Portland	1 airport

The best one-way flight to Portland from Chicago in the past 72 hours is $52. The best round-trip flight deal from Chicago to Portland found on momondo in the last 72 hours is $99.

The fastest flight from Chicago to Portland takes 4h 15m

Direct flights go from Chicago to Portland every day.

There is 1 airport near Portland: Portland (PDX)

Search flight deals

How far is Chicago to Portland by plane?
A flight from Chicago to Portland will travel around 1753.4 mi. Flights usually cover this in 4h 15m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Chicago to Portland Airport?
Prices for flights from Chicago to Portland Airport refresh daily.
How many operators does momondo search for flights from Chicago to Portland Airport?
As of July 2025, there are 8 operators available to choose from for flights from Chicago to Portland Airport.
How old do you have to be to fly from Chicago to Portland Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Portland Airport.
What documentation or ID do you need to fly to Portland Airport?
The travel and health documents required for your trip to Portland Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Portland Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to Portland?
momondo data reveals that the most frequently booked plane model on the route from Chicago to Portland is Boeing 737-800, representing 20.11% of all bookings. The subsequent popular models are Boeing 737 MAX 9 at 15.93%, Boeing 737-900 at 12.95%, and Airbus A321-100/200 at 10.64%.
What is the most popular airline from Chicago to Portland?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago to Portland is United Airlines (35% of total bookings). The next most popular airlines are Alaska Airlines (27%), American Airlines (16%), and Spirit Airlines (7%).

Best airlines flying from Chicago to Portland

Compare and see reviews for airlines that fly from Chicago to Portland with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $84	Free Cancellation	Rating 6.3 8,055 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $108	Free Cancellation	Rating 5.9 3,267 reviews	Search Frontier flights
Delta	PriceFrom $123	Free Cancellation	Rating 8.0 7,951 reviews	Search Delta flights
Hawaiian Airlines	PriceFrom $138	Free Cancellation	Rating 7.8 2,562 reviews	Search Hawaiian Airlines flights
Alaska Airlines	PriceFrom $179	Free Cancellation	Rating 8.0 10,000 reviews	Search Alaska Airlines flights
United Airlines	PriceFrom $226	Free Cancellation	Rating 7.4 8,846 reviews	Search United Airlines flights
American Airlines	PriceFrom $227	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Southwest	PriceFrom $238	Free Cancellation	Rating 8.0 4,249 reviews	Search Southwest flights

Alaska Airlines Flights From Chicago to Portland
Alaska Airlines flight deals from Chicago to Portland start from $179 round-trip. Over the 12 Alaska Airlines flights for this route in a normal week, average airfare is usually $287 round-trip - but some users have found much cheaper deals with momondo.
Southwest Flights From Chicago to Portland
Another popular option for Chicago to Portland flights is Southwest (8.0/10, 4,250 ratings). Southwest flies from Chicago to Portland around 15 times per week, with deals starting from $238 round-trip and rising to an average price of around $440.

Lincoln City

Seaside

Cannon Beach

Salem

Vancouver

Astoria

Long Beach

Depoe Bay

Rockaway Beach

Beaverton

Hood River

Gresham

Hillsboro

Tigard

McMinnville

Longview

Pacific City

Manzanita

The Dalles

Clackamas

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Portland?

It is quick and easy to find Chicago to Portland flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Portland that suits you.

Can I find flights from Chicago to Portland with flexible booking policies on momondo?

All flight searches from Chicago to Portland on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Portland?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Portland.

I’m not ready to book a flight from Chicago to Portland right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Portland flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Cheap flights from Chicago to Portland from $52

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Portland departing on 8/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names and deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Chicago to Portland

Cheap round-trip flights

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Cheap last minute flights

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Delta flights from Chicago to Portland

Our best Delta deals on Chicago to Portland flight tickets

United Airlines flights from Chicago to Portland

Our best United Airlines deals on Chicago to Portland flight tickets

See travel insights to Portland from

How to get the cheapest flight ticket from Chicago to Portland

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 typical price of a round-trip flight between Chicago and Portland?

What is the cheapest month to fly to Portland?

What is the cheapest day to depart on your flight to Portland?

The cheapest day to depart on your flight to Portland is on a Wednesday when prices can be found for as low as $327. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Portland is Sunday, with ticket prices averaging around $397.

What is the cheapest time of day to depart on your flight to Portland?

The cheapest time of day to fly to Portland is in the evening when flights can be purchased for as low as $289. At noon is when there is more demand to fly to Portland, so prices are often more expensive at around $399 per ticket.

What is the cheapest Chicago to Portland flight route?

Fly from Chicago Midway to Portland for the best Chicago - Portland flight prices

How far in advance should I book a flight to Portland?

What cabin class options are available on Chicago to Portland flights?

There are 4 cabin classes available to choose from on Chicago to Portland flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Portland flights?

No. A direct flight is the cheapest option for a flight between Chicago to Portland.

How have Chicago to Portland flight prices changed over time?

As of July 2025, prices for Chicago to Portland flights are approximately 70% cheaper when compared to flights at the same time last year.

What is the cheapest airline that flies from Chicago to Portland?

Hawaiian Airlines, Southwest, and United Airlines are the most popular carriers operating from Chicago to Portland

What airlines fly to Portland?

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

The number of flights available between Chicago and Portland is 23 per day as of July 2025. The most frequent departure time is 7:00AM, with 43% of daily flights leaving in the afternoon.

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

As of July 2025, there are 167 flights per week flying from Chicago to Portland. The most common day of the week flights depart is Thu, with 17% of flights taking off on this day.

When to book flights from Chicago to Portland

Cheap Chicago to Portland (CHI to PDX) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Portland

Best Price Found

Fastest flight time

Direct flights

Airports in Portland

How far is Chicago to Portland by plane?

When did momondo last update prices for flights from Chicago to Portland Airport?

How many operators does momondo search for flights from Chicago to Portland Airport?

How old do you have to be to fly from Chicago to Portland Airport?

What documentation or ID do you need to fly to Portland Airport?

What is the most popular plane model from Chicago to Portland?

What is the most popular airline from Chicago to Portland?

Best airlines flying from Chicago to Portland

Compare and see reviews for airlines that fly from Chicago to Portland with momondo

Alaska Airlines Flights From Chicago to Portland

Southwest Flights From Chicago to Portland

Traveling to a place near Portland?

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Portland?

Can I find flights from Chicago to Portland with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to Portland?

I’m not ready to book a flight from Chicago to Portland right now. Can momondo alert me if prices change?

An easier way to manage your Portland trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Airports servicing Oregon