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Cheap flights from Chicago to Portland from $81

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 5/5. 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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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.
Spirit Airlines Logo
11:50 am - 4:45 pmORD-PDX
6h 55m1 stop
Spirit Airlines Logo
1:37 pm - 5:25 amPDX-ORD
13h 48m1 stop
$166Spirit Airlines
Find Deal
Fri, May 16 - Sun, May 18
Spirit Airlines Logo
11:50 am - 4:45 pmORD-PDX
6h 55m1 stop
Spirit Airlines Logo
5:40 pm - 10:55 amPDX-ORD
15h 15m1 stop
$169Spirit Airlines
Find Deal
Wed, May 7 - Mon, May 12
Alaska Airlines Logo
7:00 am - 9:23 amORD-PDX
4h 23mnonstop
Alaska Airlines Logo
7:00 am - 1:08 pmPDX-ORD
4h 08mnonstop
$179Alaska Airlines
Find Deal
Wed, May 28 - Sat, May 31
Southwest Logo
4:15 pm - 6:35 pmMDW-PDX
4h 20mnonstop
Southwest Logo
6:45 am - 12:45 pmPDX-MDW
4h 00mnonstop
$179Southwest
Find Deal
Sat, May 24 - Sat, May 31
Alaska Airlines Logo
8:00 am - 12:18 pmORD-PDX
6h 18m1 stop
Alaska Airlines Logo
5:51 pm - 11:56 pmPDX-ORD
4h 05mnonstop
$209Alaska Airlines
Find Deal
Wed, May 28 - Sat, May 31
Southwest Logo
4:15 pm - 6:35 pmMDW-PDX
4h 20mnonstop
Southwest Logo
6:35 pm - 5:20 amPDX-MDW
8h 45m1 stop
$213Southwest
Find Deal
Fri, May 30 - Tue, Jun 3
American Airlines Logo
8:20 pm - 11:02 pmORD-PDX
4h 42mnonstop
American Airlines Logo
12:07 am - 6:03 amPDX-ORD
3h 56mnonstop
$283American Airlines
Find Deal
Fri, Jun 13 - Mon, Jun 16
American Airlines Logo
8:00 am - 10:24 amORD-PDX
4h 24mnonstop
American Airlines Logo
11:49 pm - 5:54 amPDX-ORD
4h 05mnonstop
$288American Airlines
Find Deal
Wed, May 14 - Sun, May 18
United Airlines Logo
7:59 pm - 10:36 pmORD-PDX
4h 37mnonstop
United Airlines Logo
2:24 pm - 12:15 amPDX-ORD
7h 51m1 stop
$292United Airlines
Find Deal
Fri, May 9 - Thu, May 15
United Airlines Logo
7:10 am - 9:42 amORD-PDX
4h 32mnonstop
United Airlines Logo
2:12 pm - 8:25 pmPDX-ORD
4h 13mnonstop
$303United Airlines
Find Deal
Sat, Jun 21 - Fri, Jul 4

Delta flights from Chicago to Portland

Our best Delta deals on Chicago to Portland flight tickets
Delta
May 28
ORD2:25 pmChicago O'Hare Intl
8h 27m
1 stop
PDX8:52 pmPortland
May 31
PDX11:15 pmPortland
8h 36m
1 stop
ORD9:51 amChicago O'Hare Intl
Delta
May 14
ORD7:15 amChicago O'Hare Intl
9h 35m
1 stop
PDX2:50 pmPortland
May 25
PDX2:00 pmPortland
7h 59m
1 stop
ORD11:59 pmChicago O'Hare Intl
Delta
Jul 5
ORD7:09 amChicago O'Hare Intl
7h 41m
1 stop
PDX12:50 pmPortland
Jul 13
PDX1:38 pmPortland
8h 06m
1 stop
ORD11:44 pmChicago O'Hare Intl

American Airlines flights from Chicago to Portland

Our best American Airlines deals on Chicago to Portland flight tickets
American Airlines
Jun 13
ORD8:20 pmChicago O'Hare Intl
4h 42m
PDX11:02 pmPortland
Jun 16
PDX12:07 amPortland
3h 56m
ORD6:03 amChicago O'Hare Intl
American Airlines
May 14
ORD8:00 amChicago O'Hare Intl
4h 24m
PDX10:24 amPortland
May 18
PDX11:49 pmPortland
4h 05m
ORD5:54 amChicago O'Hare Intl
American Airlines
Jul 26
ORD7:17 amChicago O'Hare Intl
4h 18m
PDX9:35 amPortland
Jul 29
PDX6:00 amPortland
7h 52m
1 stop
ORD3:52 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 $264, 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 $384.

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 $219. In the afternoon is when there is more demand to fly to Portland, so prices are often more expensive at around $388 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 5 weeks ahead of your departure date. In general, you can expect to find flights to Portland for around $329 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 $277 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 April 2025, prices for Chicago to Portland flights are approximately 34% 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

$81

Fastest flight time

4h 10m

Direct flights

Every day

Airports in Portland

1 airport
The best one-way flight to Portland from Chicago in the past 72 hours is $81. The best round-trip flight deal from Chicago to Portland found on momondo in the last 72 hours is $166.
The fastest flight from Chicago to Portland takes 4h 10m
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 10m, 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 $81Free CancellationRating
6.3
7,926 reviews
Search Spirit Airlines flights
FrontierPriceFrom $108Free CancellationRating
6.0
3,281 reviews
Search Frontier flights
Hawaiian AirlinesPriceFrom $134Free CancellationRating
7.9
2,380 reviews
Search Hawaiian Airlines flights
DeltaPriceFrom $176Free CancellationRating
8.0
7,916 reviews
Search Delta flights
Alaska AirlinesPriceFrom $177Free CancellationRating
8.0
9,887 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $197Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $215Free CancellationRating
7.4
8,667 reviews
Search United Airlines flights
SouthwestPriceFrom $238Free CancellationRating
8.0
4,280 reviews
Search Southwest flights
  • Alaska Airlines Flights From Chicago to Portland

    Alaska Airlines flight deals from Chicago to Portland start from $177 round-trip. Over the 2 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, 4,280 ratings). Southwest flies from Chicago to Portland around 10 times per week, with deals starting from $238 round-trip and rising to an average price of around $433.


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
Rockaway Beach
Gresham
Hillsboro
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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