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Cheap flights from Oregon to Chicago from $105

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Oregon to Chicago departing on 6/30. 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 Oregon to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
12:35 pm - 8:32 pm
PDX
-
ORD
29h 57m
1 stop
Frontier Logo
9:48 pm - 7:47 pm
ORD
-
PDX
23h 59m
2 stops
$287Frontier
Sun, May 31 - Wed, Jun 17
Multiple Airlines Logo
12:26 pm - 8:52 pm
PDX
-
ORD
6h 26m
1 stop
Multiple Airlines Logo
7:20 am - 9:45 am
ORD
-
PDX
4h 25mnonstop
$289Multiple Airlines
Mon, Jul 20 - Fri, Jul 31
United Airlines Logo
5:46 pm - 12:44 am
BOI
-
ORD
5h 58m
1 stop
United Airlines Logo
8:40 am - 11:32 am
ORD
-
BOI
3h 52mnonstop
$325United Airlines
Wed, Jun 10 - Sat, Jun 13
United Airlines Logo
12:25 pm - 6:34 pm
EUG
-
ORD
4h 09mnonstop
United Airlines Logo
8:45 am - 11:13 am
ORD
-
EUG
4h 28mnonstop
$329United Airlines
Thu, Sep 3 - Sun, Sep 6
Alaska Airlines Logo
8:28 pm - 5:00 am
BOI
-
ORD
7h 32m
1 stop
Alaska Airlines Logo
7:00 am - 1:22 pm
ORD
-
BOI
7h 22m
1 stop
$329Alaska Airlines
Tue, Aug 18 - Wed, Aug 19
Delta Logo
10:29 am - 7:30 pm
BOI
-
ORD
8h 01m
1 stop
Delta Logo
7:40 pm - 12:05 am
ORD
-
BOI
5h 25m
1 stop
$335Delta
Wed, Jul 8 - Tue, Jul 14
American Airlines Logo
1:59 pm - 11:00 pm
BOI
-
ORD
8h 01m
1 stop
American Airlines Logo
5:00 am - 11:18 am
ORD
-
BOI
7h 18m
1 stop
$336American Airlines
Sat, Jun 6 - Sat, Jun 13
Delta Logo
2:23 pm - 9:20 pm
BOI
-
ORD
5h 57m
1 stop
Delta Logo
8:36 am - 7:05 pm
ORD
-
BOI
11h 29m
2 stops
$340Delta
Sat, Jun 6 - Sat, Jun 13
Alaska Airlines Logo
7:35 pm - 6:22 am
EUG
-
ORD
8h 47m
1 stop
Alaska Airlines Logo
9:00 am - 1:44 pm
ORD
-
EUG
6h 44m
1 stop
$343Alaska Airlines
Tue, Sep 22 - Wed, Sep 23
American Airlines Logo
3:10 pm - 7:59 pm
BOI
-
ORD
3h 49mnonstop
American Airlines Logo
11:30 am - 2:20 pm
ORD
-
BOI
3h 50mnonstop
$345American Airlines
Thu, Jul 9 - Tue, Jul 14

United Airlines flights from Oregon to Chicago O'Hare Intl Airport

Our best United Airlines deals on Oregon to Chicago O'Hare Intl Airport flight tickets
United Airlines
Jun 27
PDX10:40 pmPortland
4h 05m
ORD4:45 amChicago O'Hare Intl
Jul 1
ORD7:00 amChicago O'Hare Intl
4h 34m
PDX9:34 amPortland
$305
United Airlines
Jun 2
PDX12:50 pmPortland
7h 04m
1 stop
ORD9:54 pmChicago O'Hare Intl
Jun 9
ORD4:15 pmChicago O'Hare Intl
4h 32m
PDX6:47 pmPortland
$311
United Airlines
Jun 13
PDX10:40 pmPortland
4h 05m
ORD4:45 amChicago O'Hare Intl
Jun 16
ORD5:00 amChicago O'Hare Intl
6h 47m
1 stop
PDX9:47 amPortland
$323

Alaska Airlines flights from Oregon to Chicago O'Hare Intl Airport

Our best Alaska Airlines deals on Oregon to Chicago O'Hare Intl Airport flight tickets
Alaska Airlines
Jul 15
PDX10:59 pmPortland
4h 01m
ORD5:00 amChicago O'Hare Intl
Jul 29
ORD6:20 amChicago O'Hare Intl
9h 23m
1 stop
PDX1:43 pmPortland
$315
Alaska Airlines
Jun 26
PDX10:59 pmPortland
4h 01m
ORD5:00 amChicago O'Hare Intl
Jul 3
ORD7:20 amChicago O'Hare Intl
4h 25m
PDX9:45 amPortland
$316
Alaska Airlines
Jun 26
PDX10:59 pmPortland
4h 01m
ORD5:00 amChicago O'Hare Intl
Jul 3
ORD7:20 amChicago O'Hare Intl
4h 25m
PDX9:45 amPortland
$321

momondo Fare Finder

 
Customize your flight search to find flights from Oregon to Chicago O'Hare Intl Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated May 9, 2026.
Use the filters below to find and compare flights from Oregon to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandChicago

PDX - ORD

PDXORD

Portland

Sun 5/31

12:35 pm-8:32 pm

1 stop29h 57m

Chicago O'Hare Intl

Wed 6/17

9:48 pm-7:47 pm

2 stops23h 59m

$287

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 7/20

12:26 pm-8:52 pm

1 stop6h 26m

Chicago O'Hare Intl

Fri 7/31

7:20 am-9:45 am

Nonstop4h 25m

$289

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Wed 6/10

5:46 pm-12:44 am

1 stop5h 58m

Chicago O'Hare Intl

Sat 6/13

8:40 am-11:32 am

Nonstop3h 52m

$325

EugeneChicago

EUG - ORD

EUGORD

Eugene

Thu 9/3

12:25 pm-6:34 pm

Nonstop4h 09m

Chicago O'Hare Intl

Sun 9/6

8:45 am-11:13 am

Nonstop4h 28m

$329

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Tue 8/18

8:28 pm-5:00 am

1 stop7h 32m

Chicago O'Hare Intl

Wed 8/19

7:00 am-1:22 pm

1 stop7h 22m

$329

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Wed 7/8

10:29 am-7:30 pm

1 stop8h 01m

Chicago O'Hare Intl

Tue 7/14

7:40 pm-12:05 am

1 stop5h 25m

$335

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Sat 6/6

1:59 pm-11:00 pm

1 stop8h 01m

Chicago O'Hare Intl

Sat 6/13

5:00 am-11:18 am

1 stop7h 18m

$336

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Sat 6/6

2:23 pm-9:20 pm

1 stop5h 57m

Chicago O'Hare Intl

Sat 6/13

8:36 am-7:05 pm

2 stops11h 29m

$340

EugeneChicago

EUG - ORD

EUGORD

Eugene

Tue 9/22

7:35 pm-6:22 am

1 stop8h 47m

Chicago O'Hare Intl

Wed 9/23

9:00 am-1:44 pm

1 stop6h 44m

$343
Quickest round-trip

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Thu 7/9

3:10 pm-7:59 pm

Nonstop3h 49m

Chicago O'Hare Intl

Tue 7/14

11:30 am-2:20 pm

Nonstop3h 50m

$345

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Oregon to Chicago O'Hare Intl Airport

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 Chicago O'Hare Intl Airport?

The month of August is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Oregon averaging around $105.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $421. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Oregon because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $533.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Oregon in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $322 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $476. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Oregon to Chicago O'Hare Intl flight route?

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

How far in advance should I book a flight from Oregon to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Oregon when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $339 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Oregon for as low as $274 on momondo.

Can stopping save me money on Oregon to Chicago O'Hare Intl Airport flights?

You could potentially save up to 18% on your flight if you consider stops on a Oregon to Chicago O'Hare Intl Airport flight.

Cheap Oregon to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Oregon to Chicago O'Hare Intl Airport

Best Price Found

$143

Fastest flight time

3h 24m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Oregon in the past 72 hours is $143. The best round-trip flight deal from Oregon to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $366.
The fastest flight from Oregon to Chicago O'Hare Intl Airport takes 3h 24m
Direct flights go from Oregon to Chicago O'Hare Intl Airport every day.
Search flight deals

Frequently asked questions about flying from Oregon to Chicago O'Hare Intl Airport

  • When did momondo last update prices for flights from Oregon to Chicago O'Hare Intl Airport?

    Prices for flights from Oregon to Chicago O'Hare Intl Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Oregon to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Oregon to Chicago O'Hare Intl 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 Oregon to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Oregon to Chicago O'Hare Intl Airport?

Best airlines flying from Oregon to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Oregon to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $96Free CancellationRating
5.6
2,961 reviews
Search Frontier flights
DeltaPriceFrom $99Free CancellationRating
7.9
8,456 reviews
Search Delta flights
Hawaiian AirlinesPriceFrom $113Free CancellationRating
7.8
2,837 reviews
Search Hawaiian Airlines flights
American AirlinesPriceFrom $169Free CancellationRating
7.1
11,667 reviews
Search American Airlines flights
SouthwestPriceFrom $179Free CancellationRating
7.9
4,302 reviews
Search Southwest flights
United AirlinesPriceFrom $204Free CancellationRating
7.4
9,693 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $212Free CancellationRating
7.9
12,345 reviews
Search Alaska Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Rosemont
Naperville
New Buffalo
Orland Park
Oak Brook
Kenosha
Joliet
Aurora
Janesville
Racine
Hammond
Tinley Park
Elgin
Evanston

Why use momondo?

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

Finding the right flight to Chicago from Oregon is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

Yes. momondo enables you to select and highlight flights to Chicago from Oregon with this policy.

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

Once all potential Oregon to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Yes. momondo can track prices for Oregon to Chicago 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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