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Cheap flights from Oregon to Chicago from $154

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 8/6. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Oregon to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
12:35 am - 8:39 am
PDX
-
MDW
6h 04m
1 stop
Delta Logo
2:00 pm - 8:16 pm
MDW
-
PDX
8h 16m
1 stop
$327Delta
Thu, Aug 27 - Tue, Sep 8
Southwest Logo
12:40 pm - 11:45 pm
PDX
-
MDW
9h 05m
2 stops
Southwest Logo
6:00 am - 11:20 am
MDW
-
PDX
7h 20m
1 stop
$328Southwest
Fri, Aug 21 - Tue, Aug 25
Southwest Logo
12:20 pm - 8:15 pm
EUG
-
MDW
5h 55m
1 stop
Southwest Logo
4:25 pm - 10:40 pm
MDW
-
EUG
8h 15m
1 stop
$329Southwest
Fri, Aug 14 - Fri, Aug 21
Southwest Logo
1:15 pm - 12:25 am
EUG
-
MDW
9h 10m
1 stop
Southwest Logo
6:15 am - 12:40 pm
MDW
-
EUG
8h 25m
2 stops
$330Southwest
Fri, Aug 14 - Fri, Aug 21
Southwest Logo
7:55 pm - 5:00 am
PDX
-
MDW
7h 05m
1 stop
Southwest Logo
10:30 am - 5:50 pm
MDW
-
PDX
9h 20m
2 stops
$332Southwest
Mon, Sep 14 - Tue, Sep 15
Southwest Logo
1:35 pm - 4:30 am
PDX
-
MDW
12h 55m
2 stops
Southwest Logo
8:20 am - 3:00 pm
MDW
-
PDX
8h 40m
2 stops
$333Southwest
Sat, Sep 5 - Tue, Sep 15
Southwest Logo
12:20 pm - 9:55 pm
EUG
-
MDW
7h 35m
2 stops
Southwest Logo
6:15 am - 12:40 pm
MDW
-
EUG
8h 25m
2 stops
$335Southwest
Fri, Aug 14 - Fri, Aug 21
Delta Logo
12:35 am - 8:39 am
PDX
-
MDW
6h 04m
1 stop
Delta Logo
6:05 am - 12:58 pm
MDW
-
PDX
8h 53m
1 stop
$337Delta
Sat, Aug 29 - Sun, Sep 6
Southwest Logo
12:40 pm - 11:45 pm
PDX
-
MDW
9h 05m
2 stops
Southwest Logo
4:25 pm - 9:15 pm
MDW
-
PDX
6h 50m
1 stop
$338Southwest
Fri, Sep 11 - Mon, Sep 14
Southwest Logo
12:10 pm - 4:30 pm
BOI
-
MDW
3h 20mnonstop
Southwest Logo
6:40 am - 10:55 am
MDW
-
BOI
5h 15m
1 stop
$340Southwest
Thu, Sep 17 - Tue, Sep 29

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Delta flights from Oregon to Chicago Midway Airport

Our best Delta deals on Oregon to Chicago Midway Airport flight tickets
Delta
Aug 27
PDX12:35 amPortland
6h 04m
1 stop
MDW8:39 amChicago Midway
Sep 8
MDW2:00 pmChicago Midway
8h 16m
1 stop
PDX8:16 pmPortland
$327
Delta
Aug 29
PDX12:35 amPortland
6h 04m
1 stop
MDW8:39 amChicago Midway
Sep 6
MDW6:05 amChicago Midway
8h 53m
1 stop
PDX12:58 pmPortland
$337
Delta
Sep 2
BOI1:59 pmBoise Air Term. Gowen Fld
7h 37m
1 stop
MDW10:36 pmChicago Midway
Sep 6
MDW6:05 amChicago Midway
7h 44m
1 stop
BOI12:49 pmBoise Air Term. Gowen Fld
$341

Southwest flights from Oregon to Chicago Midway Airport

Our best Southwest deals on Oregon to Chicago Midway Airport flight tickets
Southwest
Aug 21
PDX12:40 pmPortland
9h 05m
2 stops
MDW11:45 pmChicago Midway
Aug 25
MDW6:00 amChicago Midway
7h 20m
1 stop
PDX11:20 amPortland
$328
Southwest
Aug 14
EUG12:20 pmEugene
5h 55m
1 stop
MDW8:15 pmChicago Midway
Aug 21
MDW4:25 pmChicago Midway
8h 15m
1 stop
EUG10:40 pmEugene
$329
Southwest
Aug 14
EUG1:15 pmEugene
9h 10m
1 stop
MDW12:25 amChicago Midway
Aug 21
MDW6:15 amChicago Midway
8h 25m
2 stops
EUG12:40 pmEugene
$330

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 July 17, 2026.
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

Cheapest round-trip

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 8/27

12:35 am-8:39 am

1 stop6h 04m

Chicago Midway

Tue 9/8

2:00 pm-8:16 pm

1 stop8h 16m

$327

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 8/21

12:40 pm-11:45 pm

2 stops9h 05m

Chicago Midway

Tue 8/25

6:00 am-11:20 am

1 stop7h 20m

$328

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Fri 8/14

12:20 pm-8:15 pm

1 stop5h 55m

Chicago Midway

Fri 8/21

4:25 pm-10:40 pm

1 stop8h 15m

$329

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Fri 8/14

1:15 pm-12:25 am

1 stop9h 10m

Chicago Midway

Fri 8/21

6:15 am-12:40 pm

2 stops8h 25m

$330

PortlandChicago

PDX - MDW

PDXMDW

Portland

Mon 9/14

7:55 pm-5:00 am

1 stop7h 05m

Chicago Midway

Tue 9/15

10:30 am-5:50 pm

2 stops9h 20m

$332

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 9/5

1:35 pm-4:30 am

2 stops12h 55m

Chicago Midway

Tue 9/15

8:20 am-3:00 pm

2 stops8h 40m

$333

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Fri 8/14

12:20 pm-9:55 pm

2 stops7h 35m

Chicago Midway

Fri 8/21

6:15 am-12:40 pm

2 stops8h 25m

$335

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 8/29

12:35 am-8:39 am

1 stop6h 04m

Chicago Midway

Sun 9/6

6:05 am-12:58 pm

1 stop8h 53m

$337

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 9/11

12:40 pm-11:45 pm

2 stops9h 05m

Chicago Midway

Mon 9/14

4:25 pm-9:15 pm

1 stop6h 50m

$338
Quickest round-trip

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Thu 9/17

12:10 pm-4:30 pm

Nonstop3h 20m

Chicago Midway

Tue 9/29

6:40 am-10:55 am

1 stop5h 15m

$340

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 December is also very affordable. Most momondo users find prices during this month for around $277.

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 $435. 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 $520.

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 $350 when looking at flights departing at noon. Try not to purchase tickets in the evening because they tend to be around $454. 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 Airport flights?

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

You could potentially save up to 35% on your flight if you consider stops on a Oregon to Chicago Midway Airport flight.

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

$228

Fastest flight time

3h 20m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Oregon in the past 72 hours is $228. The best round-trip flight deal from Oregon to Chicago Midway Airport found on momondo in the last 72 hours is $377.
The fastest flight from Oregon to Chicago Midway Airport takes 3h 20m
Direct flights go from Oregon to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Oregon to Chicago Midway Airport

  • 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
SouthwestPriceFrom $231Free CancellationRating
8.0
4,241 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
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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