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Cheap flights from Oregon to Chicago from $72

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 1/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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.
Southwest Logo
10:50 am - 8:05 pmPDX-MDW
7h 15m1 stop
Southwest Logo
5:15 am - 11:25 amMDW-PDX
8h 10m1 stop
$246Southwest
Find Deal
Wed, Dec 10 - Thu, Dec 11
Southwest Logo
6:00 am - 11:55 amPDX-MDW
3h 55mnonstop
Southwest Logo
8:35 am - 11:15 amMDW-PDX
4h 40mnonstop
$248Southwest
Find Deal
Sat, Jan 10 - Sat, Jan 17
Southwest Logo
8:55 pm - 9:20 amPDX-MDW
10h 25m1 stop
Southwest Logo
5:35 pm - 10:15 pmMDW-PDX
6h 40m1 stop
$252Southwest
Find Deal
Mon, Dec 22 - Tue, Jan 6
Delta Logo
11:44 am - 10:07 pmPDX-MDW
8h 23m1 stop
Delta Logo
1:49 pm - 8:12 pmMDW-PDX
8h 23m1 stop
$257Delta
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Fri, Jan 9 - Sun, Jan 11
Southwest Logo
6:00 am - 11:55 amPDX-MDW
3h 55mnonstop
Southwest Logo
4:05 pm - 8:30 pmMDW-PDX
6h 25m1 stop
$258Southwest
Find Deal
Sat, Jan 10 - Sat, Jan 17
Delta Logo
5:30 am - 5:55 pmEUG-MDW
10h 25m2 stops
Delta Logo
1:26 pm - 11:59 pmMDW-EUG
12h 33m2 stops
$261Delta
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Tue, Jan 27 - Tue, Feb 3
Delta Logo
6:00 am - 4:16 pmPDX-MDW
8h 16m1 stop
Delta Logo
1:49 pm - 10:07 amMDW-PDX
22h 18m2 stops
$266Delta
Find Deal
Sat, Jan 17 - Wed, Jan 21
Southwest Logo
6:30 am - 12:25 pmPDX-MDW
3h 55mnonstop
Southwest Logo
8:35 am - 11:15 amMDW-PDX
4h 40mnonstop
$267Southwest
Find Deal
Thu, Jan 8 - Sat, Jan 10
Delta Logo
1:00 pm - 11:40 pmPDX-MDW
8h 40m1 stop
Delta Logo
10:49 am - 7:35 pmMDW-PDX
10h 46m1 stop
$268Delta
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Thu, Nov 27 - Wed, Dec 3
Southwest Logo
2:30 pm - 10:40 pmEUG-MDW
6h 10m1 stop
Southwest Logo
6:10 am - 11:30 amMDW-EUG
7h 20m1 stop
$270Southwest
Find Deal
Tue, Jan 27 - Tue, Feb 3

Southwest flights from Oregon to Chicago Midway Airport

Our best Southwest deals on Oregon to Chicago Midway Airport flight tickets
Southwest
Dec 10
PDX10:50 amPortland
7h 15m
1 stop
MDW8:05 pmChicago Midway
Dec 12
MDW6:35 pmChicago Midway
7h 40m
1 stop
PDX12:15 amPortland
$246
Find similar
Southwest
Jan 10
PDX6:00 amPortland
3h 55m
MDW11:55 amChicago Midway
Jan 17
MDW8:35 amChicago Midway
4h 40m
PDX11:15 amPortland
$248
Find similar
Southwest
Dec 22
PDX8:55 pmPortland
10h 25m
1 stop
MDW9:20 amChicago Midway
Jan 6
MDW5:35 pmChicago Midway
6h 40m
1 stop
PDX10:15 pmPortland
$252
Find similar

Delta flights from Oregon to Chicago Midway Airport

Our best Delta deals on Oregon to Chicago Midway Airport flight tickets
Delta
Jan 20
PDX12:40 amPortland
6h 28m
1 stop
MDW9:08 amChicago Midway
Jan 25
MDW1:49 pmChicago Midway
8h 43m
1 stop
PDX8:32 pmPortland
$247
Find similar
Delta
Jan 9
PDX11:44 amPortland
8h 23m
1 stop
MDW10:07 pmChicago Midway
Jan 11
MDW1:49 pmChicago Midway
8h 23m
1 stop
PDX8:12 pmPortland
$257
Find similar
Delta
Jan 17
PDX6:00 amPortland
8h 16m
1 stop
MDW4:16 pmChicago Midway
Jan 21
MDW1:49 pmChicago Midway
22h 18m
2 stops
PDX10:07 amPortland
$266
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Oregon to Chicago Midway 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 November 18, 2025.
Use the filters below to find and compare flights from Oregon to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 12/10

10:50 am-8:05 pm

1 stop7h 15m

Chicago Midway

Thu 12/11

5:15 am-11:25 am

1 stop8h 10m

$246

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 1/10

6:00 am-11:55 am

Nonstop3h 55m

Chicago Midway

Sat 1/17

8:35 am-11:15 am

Nonstop4h 40m

$248

PortlandChicago

PDX - MDW

PDXMDW

Portland

Mon 12/22

8:55 pm-9:20 am

1 stop10h 25m

Chicago Midway

Tue 1/6

5:35 pm-10:15 pm

1 stop6h 40m

$252

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 1/9

11:44 am-10:07 pm

1 stop8h 23m

Chicago Midway

Sun 1/11

1:49 pm-8:12 pm

1 stop8h 23m

$257

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 1/10

6:00 am-11:55 am

Nonstop3h 55m

Chicago Midway

Sat 1/17

4:05 pm-8:30 pm

1 stop6h 25m

$258

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Tue 1/27

5:30 am-5:55 pm

2 stops10h 25m

Chicago Midway

Tue 2/3

1:26 pm-11:59 pm

2 stops12h 33m

$261

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 1/17

6:00 am-4:16 pm

1 stop8h 16m

Chicago Midway

Wed 1/21

1:49 pm-10:07 am

2 stops22h 18m

$266

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 1/8

6:30 am-12:25 pm

Nonstop3h 55m

Chicago Midway

Sat 1/10

8:35 am-11:15 am

Nonstop4h 40m

$267

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 11/27

1:00 pm-11:40 pm

1 stop8h 40m

Chicago Midway

Wed 12/3

10:49 am-7:35 pm

1 stop10h 46m

$268

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Tue 1/27

2:30 pm-10:40 pm

1 stop6h 10m

Chicago Midway

Tue 2/3

6:10 am-11:30 am

1 stop7h 20m

$270

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 Chicago from

How to get the cheapest flight ticket from Oregon to Chicago Midway 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 Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Oregon, with most prices found around $197. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Oregon during the month September is also very affordable. Most momondo users find prices during this month for around $242.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Oregon. The lowest ticket price found for a Friday departure recently was $418. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday 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 $490.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Oregon at noon is the least expensive time of day to depart. momondo users have found prices as low as $391 when looking at flights departing at noon. Try not to purchase tickets in the evening because they tend to be around $636. 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 Midway flight route?

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

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

There is only 1 cabin class available to choose from on Oregon to Chicago Midway 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 Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Oregon to Chicago Midway Airport.

Cheap Oregon to Chicago Midway Airport flight deals and tips

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

Best Price Found

$186

Fastest flight time

3h 50m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Oregon in the past 72 hours is $186. The best round-trip flight deal from Oregon to Chicago Midway Airport found on momondo in the last 72 hours is $287.
The fastest flight from Oregon to Chicago Midway Airport takes 3h 50m
Direct flights go from Oregon to Chicago Midway Airport every day.
Search flight deals

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

    Prices for flights from Oregon to Chicago Midway Airport refresh daily.

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Oregon to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport 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 Chicago Midway Airport?

Best airlines flying from Oregon to Chicago Midway Airport

Compare and see reviews for airlines that fly from Oregon to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $128Free CancellationRating
5.8
3,105 reviews
Search Frontier flights
Alaska AirlinesPriceFrom $197Free CancellationRating
8.0
11,316 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $246Free CancellationRating
8.0
4,248 reviews
Search Southwest flights
DeltaPriceFrom $268Free CancellationRating
7.9
8,003 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Porter
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Saint John

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Oregon to Chicago for you.

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

Yes. All flights to Chicago from Oregon on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once you have performed a search for Oregon to Chicago 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 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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