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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0 bags

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Cheap round-trip flights

Hawaiian Airlines Logo
7:00 am - 9:25 amORD-PDX
4h 25mnonstop
Hawaiian Airlines Logo
5:35 pm - 11:39 pmPDX-ORD
4h 04mnonstop
$99Hawaiian Airlines
Find Deal
Sat, Aug 9 - Tue, Aug 12
Hawaiian Airlines Logo
7:00 am - 9:25 amORD-PDX
4h 25mnonstop
Hawaiian Airlines Logo
5:35 pm - 11:39 pmPDX-ORD
4h 04mnonstop
$100Hawaiian Airlines
Find Deal
Sat, Aug 9 - Tue, Aug 12
Hawaiian Airlines Logo
7:00 am - 9:25 amORD-PDX
4h 25mnonstop
Hawaiian Airlines Logo
5:35 pm - 11:39 pmPDX-ORD
4h 04mnonstop
$104Hawaiian Airlines
Find Deal
Thu, Aug 7 - Wed, Aug 13
Alaska Airlines Logo
7:00 am - 9:25 amORD-PDX
4h 25mnonstop
Alaska Airlines Logo
5:35 pm - 11:39 pmPDX-ORD
4h 04mnonstop
$105Alaska Airlines
Find Deal
Thu, Aug 7 - Thu, Aug 14
Southwest Logo
8:25 pm - 10:50 pmMDW-PDX
4h 25mnonstop
Southwest Logo
1:25 pm - 7:20 pmPDX-MDW
3h 55mnonstop
$105Southwest
Find Deal
Tue, Oct 21 - Wed, Oct 29
American Airlines Logo
8:49 pm - 11:26 pmORD-PDX
4h 37mnonstop
American Airlines Logo
1:20 pm - 7:18 pmPDX-ORD
3h 58mnonstop
$106American Airlines
Find Deal
Sat, Aug 23 - Sat, Aug 30
Southwest Logo
7:00 pm - 11:20 pmMDW-PDX
6h 20m1 stop
Southwest Logo
6:00 am - 11:55 amPDX-MDW
3h 55mnonstop
$115Southwest
Find Deal
Tue, Oct 21 - Wed, Oct 29
Alaska Airlines Logo
7:00 am - 9:25 amORD-PDX
4h 25mnonstop
Alaska Airlines Logo
5:35 pm - 11:39 pmPDX-ORD
4h 04mnonstop
$118Alaska Airlines
Find Deal
Fri, Aug 15 - Tue, Aug 19
United Airlines Logo
4:13 pm - 6:45 pmORD-PDX
4h 32mnonstop
United Airlines Logo
10:55 pm - 4:56 amPDX-ORD
4h 01mnonstop
$134United Airlines
Find Deal
Wed, Aug 6 - Sat, Aug 9
United Airlines Logo
12:46 pm - 3:14 pmORD-PDX
4h 28mnonstop
United Airlines Logo
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
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
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

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
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
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

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 $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)

  • 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?

  • 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 $84Free CancellationRating
6.3
8,055 reviews
Search Spirit Airlines flights
FrontierPriceFrom $108Free CancellationRating
5.9
3,267 reviews
Search Frontier flights
DeltaPriceFrom $123Free CancellationRating
8.0
7,951 reviews
Search Delta flights
Hawaiian AirlinesPriceFrom $138Free CancellationRating
7.8
2,562 reviews
Search Hawaiian Airlines flights
Alaska AirlinesPriceFrom $179Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $226Free CancellationRating
7.4
8,846 reviews
Search United Airlines flights
American AirlinesPriceFrom $227Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $238Free CancellationRating
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.


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
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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1 adult
Tue 7/15
Tue 7/22

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