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Cheap flights from Chicago to Portland from $77

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 4/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago to Portland

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Portland.
9:02 pm - 4:45 pmORD-PDX
21h 43m1 stop
5:40 pm - 10:55 amPDX-ORD
15h 15m1 stop
$170Spirit Airlines
Find Deal
Mon, May 12 - Tue, May 20
9:02 pm - 4:45 pmORD-PDX
21h 43m1 stop
5:40 pm - 10:55 amPDX-ORD
15h 15m1 stop
$172Spirit Airlines
Find Deal
Wed, May 7 - Mon, May 12
7:00 am - 9:23 amORD-PDX
4h 23mnonstop
5:30 pm - 5:40 amPDX-ORD
10h 10m1 stop
$213Alaska Airlines
Find Deal
Fri, May 30 - Tue, Jun 3
8:20 pm - 11:02 pmORD-PDX
4h 42mnonstop
2:58 pm - 9:04 pmPDX-ORD
4h 06mnonstop
$214American Airlines
Find Deal
Sat, Apr 19 - Thu, Apr 24
8:20 pm - 11:02 pmORD-PDX
4h 42mnonstop
11:52 pm - 5:57 amPDX-ORD
4h 05mnonstop
$218American Airlines
Find Deal
Fri, Apr 18 - Sun, Apr 20
6:20 am - 2:55 pmMDW-PDX
10h 35m1 stop
6:25 pm - 5:00 amPDX-MDW
8h 35m1 stop
$228Southwest
Find Deal
Fri, Jul 4 - Tue, Jul 8
7:59 pm - 10:36 pmORD-PDX
4h 37mnonstop
11:59 pm - 5:56 amPDX-ORD
3h 57mnonstop
$238United Airlines
Find Deal
Fri, May 2 - Sat, May 17
4:15 pm - 6:35 pmMDW-PDX
4h 20mnonstop
11:50 am - 10:15 pmPDX-MDW
8h 25m1 stop
$242Southwest
Find Deal
Sat, Apr 19 - Sat, Apr 26
7:00 am - 9:23 amORD-PDX
4h 23mnonstop
5:51 pm - 11:56 pmPDX-ORD
4h 05mnonstop
$249Alaska Airlines
Find Deal
Thu, Jun 5 - Mon, Jun 9
12:45 pm - 6:17 pmORD-PDX
7h 32m1 stop
11:59 pm - 5:56 amPDX-ORD
3h 57mnonstop
$259United Airlines
Find Deal
Thu, May 8 - Sun, May 11

Spirit Airlines flights from Chicago to Portland

Our best Spirit Airlines deals on Chicago to Portland flight tickets
Spirit Airlines
May 12
ORD9:02 pmChicago O'Hare Intl
21h 43m
1 stop
PDX4:45 pmPortland
May 20
PDX5:40 pmPortland
15h 15m
1 stop
ORD10:55 amChicago O'Hare Intl
Spirit Airlines
May 7
ORD9:02 pmChicago O'Hare Intl
21h 43m
1 stop
PDX4:45 pmPortland
May 12
PDX5:40 pmPortland
15h 15m
1 stop
ORD10:55 amChicago O'Hare Intl
Spirit Airlines
Apr 7
ORD8:09 amChicago O'Hare Intl
11h 46m
1 stop
PDX5:55 pmPortland
Apr 16
PDX7:01 pmPortland
9h 32m
1 stop
ORD6:33 amChicago O'Hare Intl

Hawaiian Airlines flights from Chicago to Portland

Our best Hawaiian Airlines deals on Chicago to Portland flight tickets
Hawaiian Airlines
May 30
ORD7:00 amChicago O'Hare Intl
4h 23m
PDX9:23 amPortland
Jun 4
PDX5:51 pmPortland
4h 05m
ORD11:56 pmChicago O'Hare Intl
Hawaiian Airlines
May 22
ORD7:00 amChicago O'Hare Intl
4h 23m
PDX9:23 amPortland
May 25
PDX5:51 pmPortland
4h 05m
ORD11:56 pmChicago O'Hare Intl
Hawaiian Airlines
Apr 19
ORD2:04 pmChicago O'Hare Intl
4h 32m
PDX4:36 pmPortland
Apr 26
PDX2:30 pmPortland
7h 29m
1 stop
ORD11:59 pmChicago O'Hare Intl

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?

The cheapest month to fly to Portland from Chicago is in September. Flight prices, which tend to average around $267, 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 $304. 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 Monday, with ticket prices averaging around $385.

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 $217. In the afternoon is when there is more demand to fly to Portland, so prices are often more expensive at around $386 per ticket.

What is the cheapest Chicago to Portland flight route?

Fly from Chicago O'Hare Intl 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 5 weeks ahead of your departure date. In general, you can expect to find flights to Portland for around $335 when searching 5 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 $279 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.

How have Chicago to Portland flight prices changed over time?

As of March 2025, prices for Chicago to Portland flights are approximately 35% 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

$77

Fastest flight time

4h 18m

Direct flights

Every day

Airports in Portland

1 airport
The best one-way flight to Portland from Chicago in the past 72 hours is $77. The best round-trip flight deal from Chicago to Portland found on momondo in the last 72 hours is $170.
The fastest flight from Chicago to Portland takes 4h 18m
Direct flights go from Chicago to Portland every day.
There is 1 airport near Portland: Portland (PDX)

  • 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 18m, 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?

  • 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?

  • 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
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $82Free CancellationRating
6.3
7,881 reviews
Search Spirit Airlines flights
FrontierPriceFrom $108Free CancellationRating
6.0
3,271 reviews
Search Frontier flights
Hawaiian AirlinesPriceFrom $173Free CancellationRating
7.9
2,336 reviews
Search Hawaiian Airlines flights
Alaska AirlinesPriceFrom $176Free CancellationRating
8.0
9,798 reviews
Search Alaska Airlines flights
DeltaPriceFrom $176Free CancellationRating
8.0
7,895 reviews
Search Delta flights
American AirlinesPriceFrom $196Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $218Free CancellationRating
7.4
8,603 reviews
Search United Airlines flights
SouthwestPriceFrom $237Free CancellationRating
8.0
4,273 reviews
Search Southwest flights
  • Alaska Airlines Flights From Chicago to Portland

    Alaska Airlines flight deals from Chicago to Portland start from $176 round-trip. Over the 4 Alaska Airlines flights for this route in a normal week, average airfare is usually $288 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, 4,274 ratings). Southwest flies from Chicago to Portland around 8 times per week, with deals starting from $237 round-trip and rising to an average price of around $432.


Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
Lincoln City
Seaside
Cannon Beach
Salem
Vancouver
Astoria
Long Beach
Depoe Bay
Beaverton
Hood River
Hillsboro
Rockaway Beach
Gresham
McMinnville
Tigard
Longview
Pacific City
The Dalles
Clackamas
Troutdale

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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