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Cheap flights from Oregon to Illinois from $111

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 Illinois departing on 6/8. 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 Illinois

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
8:42 pm - 2:06 pm
PDX
-
STL
15h 24m
1 stop
Frontier Logo
7:46 pm - 7:47 pm
STL
-
PDX
26h 01m
1 stop
$299Frontier
Thu, Jun 11 - Wed, Jun 17
United Airlines Logo
7:00 am - 1:13 pm
PDX
-
ORD
4h 13mnonstop
United Airlines Logo
7:55 pm - 10:29 pm
ORD
-
PDX
4h 34mnonstop
$305United Airlines
Wed, May 27 - Thu, May 28
Southwest Logo
11:30 pm - 5:20 am
PDX
-
MDW
3h 50mnonstop
Southwest Logo
9:35 pm - 11:55 pm
MDW
-
PDX
4h 20mnonstop
$305Southwest
Sat, Jun 27 - Fri, Jul 3
American Airlines Logo
10:59 pm - 5:00 am
PDX
-
ORD
4h 01mnonstop
American Airlines Logo
7:20 pm - 9:50 pm
ORD
-
PDX
4h 30mnonstop
$309American Airlines
Sat, Jun 27 - Fri, Jul 3
Southwest Logo
4:25 pm - 12:35 am
PDX
-
STL
6h 10m
1 stop
Southwest Logo
5:35 pm - 7:40 pm
STL
-
PDX
4h 05mnonstop
$309Southwest
Sat, Jul 11 - Sat, Jul 25
American Airlines Logo
10:59 pm - 5:00 am
PDX
-
ORD
4h 01mnonstop
American Airlines Logo
8:00 am - 10:36 am
ORD
-
PDX
4h 36mnonstop
$311American Airlines
Sat, Jun 27 - Fri, Jul 3
Delta Logo
12:33 am - 8:37 am
PDX
-
MDW
6h 04m
1 stop
Delta Logo
7:16 pm - 11:18 pm
MDW
-
PDX
6h 02m
1 stop
$330Delta
Fri, Jun 26 - Fri, Jul 3
Alaska Airlines Logo
12:34 pm - 5:00 am
EUG
-
ORD
14h 26m
1 stop
Alaska Airlines Logo
7:20 am - 11:57 am
ORD
-
EUG
6h 37m
1 stop
$334Alaska Airlines
Tue, Jul 7 - Thu, Jul 9
Delta Logo
5:30 am - 1:09 pm
BOI
-
MDW
6h 39m
1 stop
Delta Logo
7:06 pm - 11:46 pm
MDW
-
BOI
5h 40m
1 stop
$335Delta
Wed, Jul 8 - Tue, Jul 14
Alaska Airlines Logo
7:35 pm - 6:20 am
EUG
-
ORD
8h 45m
1 stop
Alaska Airlines Logo
9:00 am - 1:37 pm
ORD
-
EUG
6h 37m
1 stop
$343Alaska Airlines
Tue, Sep 1 - Wed, Sep 2

Delta flights from Oregon to Illinois

Our best Delta deals on Oregon to Illinois flight tickets
Delta
Jun 26
PDX12:33 amPortland
6h 02m
1 stop
ORD8:35 amChicago O'Hare Intl
Jul 3
ORD5:57 pmChicago O'Hare Intl
7h 21m
1 stop
PDX11:18 pmPortland
$330
Delta
Jul 8
BOI5:30 amBoise Air Term. Gowen Fld
6h 39m
1 stop
MDW1:09 pmChicago Midway
Jul 14
MDW7:06 pmChicago Midway
5h 40m
1 stop
BOI11:46 pmBoise Air Term. Gowen Fld
$335
Delta
May 29
BOI9:16 pmBoise Air Term. Gowen Fld
10h 20m
2 stops
ORD8:36 amChicago O'Hare Intl
Jul 14
ORD5:54 pmChicago O'Hare Intl
6h 52m
1 stop
BOI11:46 pmBoise Air Term. Gowen Fld
$340

American Airlines flights from Oregon to Illinois

Our best American Airlines deals on Oregon to Illinois flight tickets
American Airlines
Jun 30
PDX6:15 amPortland
4h 06m
ORD12:21 pmChicago O'Hare Intl
Jul 4
ORD12:10 pmChicago O'Hare Intl
4h 30m
PDX2:40 pmPortland
$305
American Airlines
Jun 27
PDX10:59 pmPortland
4h 01m
ORD5:00 amChicago O'Hare Intl
Jul 3
ORD7:20 pmChicago O'Hare Intl
4h 30m
PDX9:50 pmPortland
$309
American Airlines
Jun 27
PDX10:59 pmPortland
4h 01m
ORD5:00 amChicago O'Hare Intl
Jul 3
ORD8:00 amChicago O'Hare Intl
4h 36m
PDX10:36 amPortland
$311

momondo Fare Finder

 
Customize your flight search to find flights from Oregon to Illinois 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 22, 2026.
Use the filters below to find and compare flights from Oregon to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandSt. Louis

PDX - STL

PDXSTL

Portland

Thu 6/11

8:42 pm-2:06 pm

1 stop15h 24m

Lambert-St Louis

Wed 6/17

7:46 pm-7:47 pm

1 stop26h 01m

$299

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 5/27

7:00 am-1:13 pm

Nonstop4h 13m

Chicago O'Hare Intl

Thu 5/28

7:55 pm-10:29 pm

Nonstop4h 34m

$305
Quickest round-trip

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 6/27

11:30 pm-5:20 am

Nonstop3h 50m

Chicago Midway

Fri 7/3

9:35 pm-11:55 pm

Nonstop4h 20m

$305

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 6/27

10:59 pm-5:00 am

Nonstop4h 01m

Chicago O'Hare Intl

Fri 7/3

7:20 pm-9:50 pm

Nonstop4h 30m

$309

PortlandSt. Louis

PDX - STL

PDXSTL

Portland

Sat 7/11

4:25 pm-12:35 am

1 stop6h 10m

Lambert-St Louis

Sat 7/25

5:35 pm-7:40 pm

Nonstop4h 05m

$309

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 6/27

10:59 pm-5:00 am

Nonstop4h 01m

Chicago O'Hare Intl

Fri 7/3

8:00 am-10:36 am

Nonstop4h 36m

$311

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 6/26

12:33 am-8:37 am

1 stop6h 04m

Chicago Midway

Fri 7/3

7:16 pm-11:18 pm

1 stop6h 02m

$330

EugeneChicago

EUG - ORD

EUGORD

Eugene

Tue 7/7

12:34 pm-5:00 am

1 stop14h 26m

Chicago O'Hare Intl

Thu 7/9

7:20 am-11:57 am

1 stop6h 37m

$334

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Wed 7/8

5:30 am-1:09 pm

1 stop6h 39m

Chicago Midway

Tue 7/14

7:06 pm-11:46 pm

1 stop5h 40m

$335

EugeneChicago

EUG - ORD

EUGORD

Eugene

Tue 9/1

7:35 pm-6:20 am

1 stop8h 45m

Chicago O'Hare Intl

Wed 9/2

9:00 am-1:37 pm

1 stop6h 37m

$343

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Illinois from

How to get the cheapest flight ticket from Oregon to Illinois

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 Illinois?

The cheapest month to fly to Illinois from Oregon is in December. Flight prices, which tend to average around $108, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of December, then flying in April is also cheap. Prices for this month can be found on momondo for an average of $108.

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

The cheapest day to depart from Oregon to Illinois is on a Wednesday when prices can be found for as low as $426. Flights from Oregon to Illinois on a Monday will generally be more expensive and average around $523. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

Our most recent data shows that the best time of day to fly to Illinois is in the afternoon. Flights from Oregon to Illinois during this time can be as low as $328. Flights in the morning are often more expensive with an average ticket price of $468.

What is the cheapest Oregon to Illinois flight route?

Fly from Portland to Chicago Midway for the best Oregon - Illinois flight prices

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

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

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

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

You could potentially save up to 14% on your flight if you consider stops on a Oregon to Illinois flight.

Cheap Oregon to Illinois flight deals and tips

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

Best Price Found

$152

Fastest flight time

3h 20m

Direct flights

Every day

Airports in Illinois

98 airports
The best one-way flight to Illinois from Oregon in the past 72 hours is $152. The best round-trip flight deal from Oregon to Illinois found on momondo in the last 72 hours is $373.
The fastest flight from Oregon to Illinois takes 3h 20m
Direct flights go from Oregon to Illinois every day.
There are 98 airports in Illinois. From Oregon there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Lambert-St Louis (STL).
Search flight deals

Frequently asked questions about flying from Oregon to Illinois

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

    Prices for flights from Oregon to Illinois are updated daily.

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

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

    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 Illinois.

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

    The necessary travel and health documents for your Illinois trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Oregon to Illinois?

Best airlines flying from Oregon to Illinois

Compare and see reviews for airlines that fly from Oregon to Illinois with momondo
Airline
Rating
Free Cancellation
Price
Hawaiian AirlinesPriceFrom $93Free CancellationRating
7.8
2,835 reviews
Search Hawaiian Airlines flights
FrontierPriceFrom $96Free CancellationRating
5.6
2,944 reviews
Search Frontier flights
DeltaPriceFrom $108Free CancellationRating
7.9
8,445 reviews
Search Delta flights
American AirlinesPriceFrom $171Free CancellationRating
7.1
11,645 reviews
Search American Airlines flights
SouthwestPriceFrom $179Free CancellationRating
7.9
4,277 reviews
Search Southwest flights
Alaska AirlinesPriceFrom $198Free CancellationRating
7.9
12,398 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $217Free CancellationRating
7.4
9,752 reviews
Search United Airlines flights

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Oregon to Illinois. momondo saves you time and could save you money on your trip.

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

Flights from Oregon to Illinois 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 Oregon to Illinois?

Once you have performed a search for Oregon to Illinois flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes momondo offers price alerts on flights to Illinois from Oregon. 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 Illinois trip

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