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Cheap flights from Chicago to Oregon from $54

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 Oregon departing on 2/15. 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 Oregon

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Oregon 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 Oregon.

Cheap last minute flights

Planning a quick getaway from Chicago to Oregon? 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 Oregon, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Oregon

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

All round-trip flight deals to Oregon

The cheapest plane tickets to Oregon found on KAYAK recently.
7:25 am - 11:03 amORD-PDX
29h 38m1 stop
7:35 am - 2:02 pmPDX-ORD
28h 27m1 stop
$109Frontier
Find Deal
Thu, Jan 9 - Wed, Jan 15
6:36 pm - 9:45 amORD-PDX
17h 09m1 stop
6:32 am - 1:25 pmPDX-ORD
28h 53m1 stop
$112Frontier
Find Deal
Thu, Feb 6 - Wed, Feb 12
9:54 pm - 9:21 amORD-PDX
13h 27m1 stop
5:30 pm - 5:31 amPDX-ORD
10h 01m1 stop
$144Spirit Airlines
Find Deal
Wed, Jan 8 - Sun, Jan 12
10:47 pm - 9:21 amORD-PDX
12h 34m1 stop
5:30 pm - 5:31 amPDX-ORD
10h 01m1 stop
$163Spirit Airlines
Find Deal
Sat, Jan 25 - Mon, Jan 27
6:55 pm - 9:41 pmORD-PDX
4h 46mnonstop
7:00 am - 1:07 pmPDX-ORD
4h 07mnonstop
$197Alaska Airlines
Find Deal
Wed, Jan 15 - Wed, Jan 22
3:35 pm - 6:18 pmORD-PDX
4h 43mnonstop
7:00 am - 1:07 pmPDX-ORD
4h 07mnonstop
$206Alaska Airlines
Find Deal
Thu, Jan 9 - Wed, Jan 15
8:20 pm - 10:45 pmORD-PDX
4h 25mnonstop
11:39 pm - 5:45 amPDX-ORD
4h 06mnonstop
$227American Airlines
Find Deal
Tue, May 6 - Tue, May 13
9:10 am - 11:53 amORD-PDX
4h 43mnonstop
7:00 am - 1:01 pmPDX-ORD
4h 01mnonstop
$232United Airlines
Find Deal
Wed, Jan 15 - Wed, Jan 22
6:30 am - 12:24 pmORD-PDX
7h 54m1 stop
11:55 pm - 5:39 amPDX-ORD
3h 44mnonstop
$237United Airlines
Find Deal
Sat, May 3 - Sat, May 10
8:20 pm - 10:45 pmORD-PDX
4h 25mnonstop
11:39 pm - 5:45 amPDX-ORD
4h 06mnonstop
$272American Airlines
Find Deal
Tue, May 6 - Sat, May 10
6:32 pm - 12:37 amORD-PDX
8h 05m1 stop
$54Frontier
Find Deal
Sat, Feb 15
8:44 pm - 8:40 amMDW-PDX
13h 56m1 stop
$60Frontier
Find Deal
Thu, Feb 13
9:54 pm - 9:21 amORD-PDX
13h 27m1 stop
$79Spirit Airlines
Find Deal
Wed, Jan 8
10:47 pm - 9:21 amORD-PDX
12h 34m1 stop
$81Spirit Airlines
Find Deal
Sat, Jan 18
8:15 pm - 10:57 pmORD-PDX
4h 42mnonstop
$87United Airlines
Find Deal
Thu, Jan 30
9:10 am - 11:53 amORD-PDX
4h 43mnonstop
$99United Airlines
Find Deal
Wed, Feb 12
3:35 pm - 6:18 pmORD-PDX
4h 43mnonstop
$107Alaska Airlines
Find Deal
Thu, Jan 23
3:35 pm - 6:18 pmORD-PDX
4h 43mnonstop
$109Alaska Airlines
Find Deal
Thu, Jan 23
5:00 am - 1:16 pmORD-PDX
10h 16m1 stop
$118American Airlines
Find Deal
Thu, Jan 16
5:10 pm - 11:01 pmORD-BOI
6h 51m1 stop
$199American Airlines
Find Deal
Mon, Dec 30
8:34 pm - 6:19 pmORD-PDX
23h 45m1 stop
7:48 pm - 5:30 amPDX-ORD
7h 42m1 stop
Thu, Dec 19 - Tue, Dec 31
6:00 am - 3:44 pmORD-PDX
11h 44m1 stop
12:45 pm - 11:46 pmPDX-ORD
9h 01m1 stop
$308Frontier
Find Deal
Fri, Dec 20 - Wed, Jan 1
2:01 pm - 4:39 pmORD-PDX
4h 38mnonstop
1:52 pm - 11:59 pmPDX-ORD
8h 07m1 stop
$486Alaska Airlines
Find Deal
Thu, Dec 19 - Mon, Jan 6
7:00 am - 9:38 amORD-PDX
4h 38mnonstop
7:00 am - 1:07 pmPDX-ORD
4h 07mnonstop
$493Alaska Airlines
Find Deal
Thu, Dec 19 - Mon, Jan 6
6:00 am - 1:23 pmORD-BOI
8h 23m1 stop
7:03 am - 3:21 pmBOI-ORD
7h 18m1 stop
$518American Airlines
Find Deal
Fri, Dec 20 - Sun, Dec 22
7:35 pm - 10:49 pmORD-BOI
4h 14mnonstop
8:30 am - 1:15 pmBOI-ORD
3h 45mnonstop
$519United Airlines
Find Deal
Mon, Dec 23 - Wed, Dec 25
7:35 pm - 10:49 pmORD-BOI
4h 14mnonstop
8:15 am - 5:05 pmBOI-ORD
7h 50m1 stop
$529United Airlines
Find Deal
Mon, Dec 23 - Wed, Dec 25
7:53 pm - 6:53 pmORD-PDX
25h 00m2 stops
7:19 pm - 5:30 amPDX-ORD
8h 11m1 stop
$590Spirit Airlines
Find Deal
Mon, Dec 23 - Fri, Dec 27
5:10 pm - 11:39 pmORD-BOI
7h 29m1 stop
6:40 am - 8:59 pmBOI-ORD
13h 19m1 stop
$602American Airlines
Find Deal
Fri, Dec 20 - Tue, Dec 24
7:53 pm - 6:22 pmORD-PDX
24h 29m2 stops
7:48 pm - 5:30 amPDX-ORD
7h 42m1 stop
$604Spirit Airlines
Find Deal
Sun, Dec 22 - Tue, Dec 24
9:10 am - 11:53 amORD-PDX
4h 43mnonstop
7:00 am - 1:01 pmPDX-ORD
4h 01mnonstop
$173United Airlines
Find Deal
Wed, Jan 15 - Wed, Jan 22
8:30 am - 10:55 amMDW-PDX
4h 25mnonstop
9:00 am - 2:55 pmPDX-MDW
3h 55mnonstop
$174Southwest
Find Deal
Wed, Jan 15 - Wed, Jan 22
8:10 pm - 10:40 pmMDW-PDX
4h 30mnonstop
9:00 am - 2:55 pmPDX-MDW
3h 55mnonstop
$190Southwest
Find Deal
Mon, Feb 10 - Wed, Feb 12
6:55 pm - 9:41 pmORD-PDX
4h 46mnonstop
7:00 am - 1:07 pmPDX-ORD
4h 07mnonstop
$197Alaska Airlines
Find Deal
Wed, Jan 15 - Wed, Jan 22
8:30 am - 10:55 amMDW-PDX
4h 25mnonstop
9:00 am - 2:55 pmPDX-MDW
3h 55mnonstop
$198Southwest
Find Deal
Tue, Jan 7 - Tue, Jan 14
3:35 pm - 6:18 pmORD-PDX
4h 43mnonstop
7:00 am - 1:07 pmPDX-ORD
4h 07mnonstop
$206Alaska Airlines
Find Deal
Thu, Jan 9 - Wed, Jan 15
6:55 pm - 9:41 pmORD-PDX
4h 46mnonstop
7:00 am - 1:07 pmPDX-ORD
4h 07mnonstop
$207Alaska Airlines
Find Deal
Wed, Jan 15 - Thu, Jan 23
8:10 pm - 10:40 pmMDW-PDX
4h 30mnonstop
9:00 am - 2:55 pmPDX-MDW
3h 55mnonstop
$208Southwest
Find Deal
Thu, Feb 6 - Wed, Feb 12
8:20 pm - 10:45 pmORD-PDX
4h 25mnonstop
11:39 pm - 5:45 amPDX-ORD
4h 06mnonstop
$227American Airlines
Find Deal
Tue, May 6 - Tue, May 13
8:20 pm - 10:45 pmORD-PDX
4h 25mnonstop
11:39 pm - 5:45 amPDX-ORD
4h 06mnonstop
$272American Airlines
Find Deal
Tue, May 6 - Sat, May 10

Frontier flights from Chicago to Oregon

Our best Frontier deals on Chicago to Oregon flight tickets
Frontier
Jan 9
ORD7:25 amChicago O'Hare Intl
29h 38m
1 stop
PDX11:03 amPortland
Jan 15
PDX7:35 amPortland
28h 27m
1 stop
ORD2:02 pmChicago O'Hare Intl
Frontier
Feb 6
ORD6:36 pmChicago O'Hare Intl
17h 09m
1 stop
PDX9:45 amPortland
Feb 12
PDX6:32 amPortland
28h 53m
1 stop
ORD1:25 pmChicago O'Hare Intl
Frontier
Jan 7
MDW8:15 amChicago Midway
18h 00m
1 stop
PDX12:15 amPortland
Jan 14
PDX7:35 amPortland
14h 38m
1 stop
MDW12:13 amChicago Midway

Southwest flights from Chicago to Oregon

Our best Southwest deals on Chicago to Oregon flight tickets
Southwest
Jan 15
MDW8:30 amChicago Midway
4h 25m
PDX10:55 amPortland
Jan 22
PDX9:00 amPortland
3h 55m
MDW2:55 pmChicago Midway
Southwest
Feb 10
MDW8:10 pmChicago Midway
4h 30m
PDX10:40 pmPortland
Feb 12
PDX9:00 amPortland
3h 55m
MDW2:55 pmChicago Midway
Southwest
Jan 16
MDW8:10 pmChicago Midway
4h 30m
PDX10:40 pmPortland
Jan 30
PDX9:00 amPortland
3h 55m
MDW2:55 pmChicago Midway

See travel insights to Oregon from

How to get the cheapest flight ticket from Chicago to Oregon

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 to Oregon?

The month of May is, on average, the cheapest month to fly to Oregon from Chicago, with most prices found around $293. The month of July is another great option to travel to Oregon, with average flight prices from Chicago averaging around $309.

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

On average, the least expensive day to fly to Oregon from Chicago is on a Wednesday. momondo users have found tickets for Wednesday departures for as low as $296. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Oregon is Sunday, with ticket prices averaging around $413.

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

According to our data, the cheapest time of day to fly to Oregon is in the evening. momondo users have found flights departing from Chicago to Oregon in the evening for as low as $207. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights to Oregon are more costly in the afternoon, with an average ticket price of $385. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago to Oregon flight route?

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

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

Most flyers found that booking tickets 4 days in advance of their planned departure date is the best time to get cheap flights to Oregon. During this timeframe, flight prices are around $333. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Oregon from Chicago for as low as $166 on momondo.

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

There are 4 cabin classes available to choose from on Chicago to Oregon 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 Oregon flights?

You could potentially save up to 37% on your flight if you consider stops on a Chicago to Oregon flight.

Cheap Chicago to Oregon flight deals and tips

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

Best Price Found

$54

Fastest flight time

4h 09m

Direct flights

Every day

Airports in Oregon

2 airports
The best one-way flight to Oregon from Chicago in the past 72 hours is $54. The best round-trip flight deal from Chicago to Oregon found on momondo in the last 72 hours is $109.
The fastest flight from Chicago to Oregon takes 4h 09m
Direct flights go from Chicago to Oregon every day.
There are 2 airports near Oregon: Portland (PDX), Boise Air Term. Gowen Fld (BOI)

  • When did momondo last update prices for flights from Chicago to Oregon?

    Prices for flights from Chicago to Oregon were last updated today.

  • How many operators does momondo search for flights from Chicago to Oregon?

  • How old do you have to be to fly from Chicago to Oregon?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Oregon.

  • What documentation or ID do you need to fly to Oregon?

    The travel and health documents required for your trip to Oregon 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 Oregon. 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 Oregon?


Best airlines flying from Chicago to Oregon

Compare and see reviews for airlines that fly from Chicago to Oregon with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $83Free CancellationRating
6.3
8,119 reviews
Search Spirit Airlines flights
FrontierPriceFrom $118Free CancellationRating
6.1
3,479 reviews
Search Frontier flights
Alaska AirlinesPriceFrom $172Free CancellationRating
8.0
9,552 reviews
Search Alaska Airlines flights
DeltaPriceFrom $176Free CancellationRating
8.0
8,604 reviews
Search Delta flights
American AirlinesPriceFrom $193Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $218Free CancellationRating
7.4
9,059 reviews
Search United Airlines flights
SouthwestPriceFrom $237Free CancellationRating
8.1
4,848 reviews
Search Southwest flights

Why use momondo?

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

It is quick and easy to find Chicago to Oregon 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 Oregon that suits you.

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

Flights from Chicago to Oregon with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

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 Oregon.

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

Yes momondo offers price alerts on flights to Oregon from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.


An easier way to manage your Oregon 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.

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Popular cities in Oregon

Popular flights according to clicks in the last 7 days on momondo