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Cheap flights from Chicago to Portland from $61

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 1/22. 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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Find the cheapest flights from Chicago to Portland

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Portland that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Portland.

Cheap last minute flights

Planning a quick getaway from Chicago to Portland? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Portland, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Portland

Find recent round-trip train or bus tickets from Chicago to Portland.

All round-trip flight deals to Portland

The cheapest plane tickets to Portland found on KAYAK recently.
12:43 pm - 9:47 amMDW-PDX
23h 04m1 stop
7:35 am - 12:13 amPDX-MDW
14h 38m1 stop
$118Frontier
Find Deal
Thu, Jan 9 - Tue, Jan 14
7:25 am - 11:03 amORD-PDX
29h 38m1 stop
11:39 am - 5:42 amPDX-ORD
16h 03m1 stop
$133Frontier
Find Deal
Thu, Dec 12 - Tue, Dec 17
1:39 pm - 8:46 pmORD-PDX
9h 07m1 stop
10:16 am - 9:52 pmPDX-ORD
9h 36m1 stop
$171Spirit Airlines
Find Deal
Mon, Jan 13 - Thu, Jan 16
3:21 pm - 11:48 pmORD-PDX
10h 27m1 stop
7:16 pm - 5:30 amPDX-ORD
8h 14m1 stop
$185Spirit Airlines
Find Deal
Mon, Dec 9 - Tue, Dec 10
4:05 pm - 6:44 pmORD-PDX
4h 39mnonstop
7:00 am - 1:04 pmPDX-ORD
4h 04mnonstop
$197Alaska Airlines
Find Deal
Tue, Feb 18 - Wed, Feb 19
4:05 pm - 6:44 pmORD-PDX
4h 39mnonstop
7:00 am - 5:00 pmPDX-ORD
8h 00m1 stop
$206Alaska Airlines
Find Deal
Sat, Feb 15 - Sat, Feb 22
2:39 pm - 9:00 pmORD-PDX
8h 21m1 stop
7:00 am - 1:01 pmPDX-ORD
4h 01mnonstop
$207United Airlines
Find Deal
Sat, Jan 18 - Tue, Jan 21
3:25 pm - 5:50 pmMDW-PDX
4h 25mnonstop
9:00 am - 2:55 pmPDX-MDW
3h 55mnonstop
$228Southwest
Find Deal
Sat, Jan 18 - Tue, Jan 21
9:10 am - 11:53 amORD-PDX
4h 43mnonstop
7:00 am - 1:01 pmPDX-ORD
4h 01mnonstop
$237United Airlines
Find Deal
Thu, Jan 23 - Mon, Jan 27
8:10 pm - 10:40 pmMDW-PDX
4h 30mnonstop
9:00 am - 2:55 pmPDX-MDW
3h 55mnonstop
$248Southwest
Find Deal
Fri, Jan 17 - Sun, Jan 19
8:15 am - 12:07 amMDW-PDX
17h 52m1 stop
$61Frontier
Find Deal
Wed, Jan 22
6:36 pm - 9:47 amORD-PDX
17h 11m1 stop
$61Frontier
Find Deal
Thu, Dec 12
12:43 pm - 12:34 pmMDW-PDX
25h 51m1 stop
$62Frontier
Find Deal
Mon, Dec 16
9:54 pm - 1:49 pmORD-PDX
17h 55m1 stop
$89Spirit Airlines
Find Deal
Tue, Jan 7
1:39 pm - 8:46 pmORD-PDX
9h 07m1 stop
$91Spirit Airlines
Find Deal
Sat, Jan 11
4:15 pm - 6:48 pmORD-PDX
4h 33mnonstop
$99United Airlines
Find Deal
Tue, Feb 18
6:50 am - 1:10 pmORD-PDX
8h 20m1 stop
$108United Airlines
Find Deal
Sat, Dec 14
3:21 pm - 5:55 pmORD-PDX
4h 34mnonstop
$114Alaska Airlines
Find Deal
Tue, Mar 25
5:54 pm - 10:56 pmORD-PDX
7h 02m1 stop
$131Alaska Airlines
Find Deal
Thu, Mar 6
6:00 am - 1:03 pmORD-PDX
9h 03m1 stop
$288American Airlines
Find Deal
Sat, Nov 30
12:57 pm - 12:51 amORD-PDX
13h 54m1 stop
9:40 pm - 11:52 amPDX-ORD
12h 12m1 stop
$248Spirit Airlines
Find Deal
Sat, Nov 23 - Mon, Nov 25
12:57 pm - 12:51 amORD-PDX
13h 54m1 stop
11:35 am - 2:07 pmPDX-ORD
24h 32m1 stop
Sat, Nov 23 - Thu, Nov 28
6:00 am - 12:29 amORD-PDX
20h 29m1 stop
6:05 am - 12:15 pmPDX-ORD
28h 10m1 stop
$329Frontier
Find Deal
Tue, Nov 26 - Thu, Nov 28
9:37 pm - 12:29 amMDW-PDX
28h 52m1 stop
6:05 am - 12:13 amPDX-MDW
16h 08m1 stop
$338Frontier
Find Deal
Mon, Nov 25 - Tue, Dec 3
2:25 pm - 4:58 pmORD-PDX
4h 33mnonstop
7:00 am - 1:02 pmPDX-ORD
4h 02mnonstop
$558Alaska Airlines
Find Deal
Sun, Nov 24 - Thu, Dec 5
2:15 pm - 4:50 pmORD-PDX
4h 35mnonstop
9:28 pm - 5:56 amPDX-ORD
6h 28m1 stop
$567Alaska Airlines
Find Deal
Sat, Nov 23 - Thu, Dec 5
2:17 pm - 8:32 pmMDW-PDX
8h 15m1 stop
12:59 am - 8:51 amPDX-MDW
5h 52m1 stop
$592Delta
Find Deal
Tue, Nov 26 - Thu, Nov 28
7:45 am - 12:24 pmORD-PDX
6h 39m1 stop
5:05 am - 1:20 pmPDX-ORD
6h 15m1 stop
$592Delta
Find Deal
Sun, Nov 24 - Thu, Nov 28
4:35 pm - 12:15 amORD-PDX
9h 40m2 stops
2:05 pm - 10:35 pmPDX-ORD
6h 30m1 stop
$651Southwest
Find Deal
Sun, Nov 24 - Mon, Dec 2
12:15 pm - 8:05 pmORD-PDX
9h 50m2 stops
7:45 am - 10:35 pmPDX-ORD
12h 50m2 stops
$656Southwest
Find Deal
Sun, Nov 24 - Tue, Dec 3
4:05 pm - 6:44 pmORD-PDX
4h 39mnonstop
7:00 am - 1:04 pmPDX-ORD
4h 04mnonstop
$197Alaska Airlines
Find Deal
Sat, Feb 15 - Tue, Feb 18
4:05 pm - 6:44 pmORD-PDX
4h 39mnonstop
7:00 am - 1:04 pmPDX-ORD
4h 04mnonstop
$217Alaska Airlines
Find Deal
Sat, Feb 15 - Thu, Feb 20
8:30 am - 10:55 amMDW-PDX
4h 25mnonstop
8:00 am - 1:55 pmPDX-MDW
3h 55mnonstop
$218Southwest
Find Deal
Wed, Jan 8 - Sun, Jan 12
4:05 pm - 6:44 pmORD-PDX
4h 39mnonstop
7:00 am - 1:04 pmPDX-ORD
4h 04mnonstop
$223Alaska Airlines
Find Deal
Fri, Feb 14 - Sat, Feb 22
3:21 pm - 5:55 pmORD-PDX
4h 34mnonstop
7:00 am - 1:03 pmPDX-ORD
4h 03mnonstop
$227Alaska Airlines
Find Deal
Tue, Apr 8 - Tue, Apr 15
3:25 pm - 5:50 pmMDW-PDX
4h 25mnonstop
9:00 am - 2:55 pmPDX-MDW
3h 55mnonstop
$228Southwest
Find Deal
Sat, Jan 18 - Tue, Jan 21
9:10 am - 11:52 amORD-PDX
4h 42mnonstop
7:00 am - 12:57 pmPDX-ORD
3h 57mnonstop
$230United Airlines
Find Deal
Wed, Dec 11 - Sat, Dec 14
2:01 pm - 4:39 pmORD-PDX
4h 38mnonstop
11:29 pm - 5:30 amPDX-ORD
4h 01mnonstop
$232Alaska Airlines
Find Deal
Tue, Dec 24 - Tue, Dec 31
9:10 am - 11:53 amORD-PDX
4h 43mnonstop
7:00 am - 1:01 pmPDX-ORD
4h 01mnonstop
$237United Airlines
Find Deal
Thu, Jan 23 - Mon, Jan 27
9:55 am - 12:26 pmORD-PDX
4h 31mnonstop
1:42 pm - 7:40 pmPDX-ORD
3h 58mnonstop
$435American Airlines
Find Deal
Thu, Apr 10 - Sun, Apr 13

Frontier flights from Chicago to Portland

Our best Frontier deals on Chicago to Portland flight tickets
Frontier
Jan 9
MDW12:43 pmChicago Midway
23h 04m
1 stop
PDX9:47 amPortland
Jan 14
PDX7:35 amPortland
14h 38m
1 stop
MDW12:13 amChicago Midway
Frontier
Dec 12
ORD7:25 amChicago O'Hare Intl
29h 38m
1 stop
PDX11:03 amPortland
Dec 17
PDX11:39 amPortland
16h 03m
1 stop
ORD5:42 amChicago O'Hare Intl
Frontier
Feb 4
MDW8:15 amChicago Midway
17h 52m
1 stop
PDX12:07 amPortland
Feb 7
PDX12:03 pmPortland
10h 14m
1 stop
MDW12:17 amChicago Midway

Spirit Airlines flights from Chicago to Portland

Our best Spirit Airlines deals on Chicago to Portland flight tickets
Spirit Airlines
Jan 13
ORD1:39 pmChicago O'Hare Intl
9h 07m
1 stop
PDX8:46 pmPortland
Jan 16
PDX10:16 amPortland
9h 36m
1 stop
ORD9:52 pmChicago O'Hare Intl
Spirit Airlines
Dec 9
ORD3:21 pmChicago O'Hare Intl
10h 27m
1 stop
PDX11:48 pmPortland
Dec 10
PDX7:16 pmPortland
8h 14m
1 stop
ORD5:30 amChicago O'Hare Intl
Spirit Airlines
Dec 10
ORD9:10 pmChicago O'Hare Intl
25h 18m
1 stop
PDX8:28 pmPortland
Dec 14
PDX7:16 pmPortland
8h 14m
1 stop
ORD5:30 amChicago 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 cheapest month to fly from Chicago to Portland?

September. The cheapest time of year to fly to Portland from Chicago is September. Most expensive is March

What is the cheapest day to depart Chicago for Portland?

Wednesday. The cheapest day of the week is typically Wednesday. The most expensive is typically Monday

When is the cheapest time to fly from Chicago to Portland?

In the evening. Chicago to Portland flights are approximately 46% more expensive in the afternoon than in the evening

What is the cheapest Chicago to Portland flight route?

Chicago O'Hare Intl - Portland. Fly from Chicago O'Hare Intl to Portland for the best Chicago - Portland flight prices

How far in advance should you book Chicago to Portland flights?

24 days before. The cheapest time to buy a flight from Chicago to Portland is approximately 24 days to departure

Can stopping save me money on Chicago to Portland flights?

You could potentially save up to 38% on your flight if you consider stops on a Chicago to Portland flight.

How have Chicago to Portland flight prices changed over time?

As of November 2024, prices for Chicago to Portland flights are approximately 0% more expensive 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

$61

Fastest flight time

4h 20m

Direct flights

Every day

Airports in Portland

1 airport
The best one-way flight to Portland from Chicago in the past 72 hours is $61. The best round-trip flight deal from Chicago to Portland found on momondo in the last 72 hours is $118.
The fastest flight from Chicago to Portland takes 4h 20m
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 20m, 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 $83Free CancellationRating
6.3
8,175 reviews
Search Spirit Airlines flights
FrontierPriceFrom $118Free CancellationRating
6.1
3,539 reviews
Search Frontier flights
Alaska AirlinesPriceFrom $172Free CancellationRating
8.0
9,458 reviews
Search Alaska Airlines flights
DeltaPriceFrom $176Free CancellationRating
8.0
8,758 reviews
Search Delta flights
American AirlinesPriceFrom $193Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $218Free CancellationRating
7.4
9,172 reviews
Search United Airlines flights
SouthwestPriceFrom $237Free CancellationRating
8.1
5,015 reviews
Search Southwest flights
  • Southwest Flights From Chicago to Portland

    Southwest flight deals from Chicago to Portland start from $237 round-trip. Over the 8 Southwest flights for this route in a normal week, average airfare is usually $420 round-trip - but some users have found much cheaper deals with momondo.

  • Alaska Airlines Flights From Chicago to Portland

    Another popular option for Chicago to Portland flights is Alaska Airlines (8.0/10, 9,458 ratings). Alaska Airlines flies from Chicago to Portland around 2 times per week, with deals starting from $172 round-trip and rising to an average price of around $313.


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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