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Cheap flights from Oregon to Chicago from $126

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 4/29. 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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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
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
6:05 pm - 8:25 pm
MDW
-
PDX
4h 20mnonstop
$251Southwest
Sat, Apr 25 - Sat, May 2
Southwest Logo
5:20 pm - 5:00 am
EUG
-
MDW
9h 40m
1 stop
Southwest Logo
6:15 am - 2:55 pm
MDW
-
EUG
10h 40m
1 stop
$257Southwest
Tue, Apr 28 - Sat, May 2
Southwest Logo
10:25 am - 9:20 pm
PDX
-
MDW
8h 55m
1 stop
Southwest Logo
10:15 am - 12:35 pm
MDW
-
PDX
4h 20mnonstop
$261Southwest
Sat, Apr 25 - Sat, May 2
Southwest Logo
5:20 pm - 5:00 am
EUG
-
MDW
9h 40m
1 stop
Southwest Logo
12:45 pm - 9:40 pm
MDW
-
EUG
10h 55m
2 stops
$262Southwest
Tue, Apr 28 - Sat, May 2
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
4:00 pm - 11:10 pm
MDW
-
PDX
9h 10m
2 stops
$266Southwest
Wed, Apr 29 - Wed, May 6
Southwest Logo
5:15 pm - 5:25 am
EUG
-
MDW
10h 10m
2 stops
Southwest Logo
10:10 am - 4:40 pm
MDW
-
EUG
8h 30m
2 stops
$267Southwest
Sat, Apr 18 - Tue, Apr 21
Southwest Logo
5:00 pm - 5:00 am
EUG
-
MDW
10h 00m
1 stop
Southwest Logo
6:55 am - 2:10 pm
MDW
-
EUG
9h 15m
2 stops
$268Southwest
Mon, May 4 - Thu, May 7
Delta Logo
12:30 am - 9:06 am
PDX
-
MDW
6h 36m
1 stop
Delta Logo
2:12 pm - 8:07 pm
MDW
-
PDX
7h 55m
1 stop
$271Delta
Fri, Apr 24 - Sat, May 2
Southwest Logo
7:25 pm - 5:45 am
PDX
-
MDW
8h 20m
1 stop
Southwest Logo
4:00 pm - 11:10 pm
MDW
-
PDX
9h 10m
2 stops
$276Southwest
Wed, Apr 29 - Wed, May 6
Delta Logo
5:10 am - 6:33 pm
EUG
-
MDW
11h 23m
2 stops
Delta Logo
1:22 pm - 11:50 pm
MDW
-
EUG
12h 28m
2 stops
$313Delta
Sat, May 23 - Wed, May 27

Delta flights from Oregon to Chicago Midway Airport

Our best Delta deals on Oregon to Chicago Midway Airport flight tickets
Delta
Apr 24
PDX12:30 amPortland
6h 36m
1 stop
MDW9:06 amChicago Midway
May 2
MDW2:12 pmChicago Midway
7h 55m
1 stop
PDX8:07 pmPortland
$271
Delta
May 23
EUG5:10 amEugene
11h 23m
2 stops
MDW6:33 pmChicago Midway
May 27
MDW1:22 pmChicago Midway
12h 28m
2 stops
EUG11:50 pmEugene
$313
Delta
Jun 29
PDX12:31 amPortland
6h 06m
1 stop
MDW8:37 amChicago Midway
Jun 30
MDW1:49 pmChicago Midway
8h 28m
1 stop
PDX8:17 pmPortland
$325

Southwest flights from Oregon to Chicago Midway Airport

Our best Southwest deals on Oregon to Chicago Midway Airport flight tickets
Southwest
Apr 25
PDX11:55 pmPortland
3h 55m
MDW5:50 amChicago Midway
May 2
MDW6:05 pmChicago Midway
4h 20m
PDX8:25 pmPortland
$251
Southwest
Apr 28
EUG5:20 pmEugene
9h 40m
1 stop
MDW5:00 amChicago Midway
May 2
MDW6:15 amChicago Midway
10h 40m
1 stop
EUG2:55 pmEugene
$257
Southwest
Apr 25
PDX10:25 amPortland
8h 55m
1 stop
MDW9:20 pmChicago Midway
May 2
MDW10:15 amChicago Midway
4h 20m
PDX12:35 pmPortland
$261

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 April 1, 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
Quickest round-trip

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 4/25

11:55 pm-5:50 am

Nonstop3h 55m

Chicago Midway

Sat 5/2

6:05 pm-8:25 pm

Nonstop4h 20m

$251

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Tue 4/28

5:20 pm-5:00 am

1 stop9h 40m

Chicago Midway

Sat 5/2

6:15 am-2:55 pm

1 stop10h 40m

$257

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 4/25

10:25 am-9:20 pm

1 stop8h 55m

Chicago Midway

Sat 5/2

10:15 am-12:35 pm

Nonstop4h 20m

$261

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Tue 4/28

5:20 pm-5:00 am

1 stop9h 40m

Chicago Midway

Sat 5/2

12:45 pm-9:40 pm

2 stops10h 55m

$262

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 4/29

11:55 pm-5:50 am

Nonstop3h 55m

Chicago Midway

Wed 5/6

4:00 pm-11:10 pm

2 stops9h 10m

$266

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Sat 4/18

5:15 pm-5:25 am

2 stops10h 10m

Chicago Midway

Tue 4/21

10:10 am-4:40 pm

2 stops8h 30m

$267

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Mon 5/4

5:00 pm-5:00 am

1 stop10h 00m

Chicago Midway

Thu 5/7

6:55 am-2:10 pm

2 stops9h 15m

$268

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 4/24

12:30 am-9:06 am

1 stop6h 36m

Chicago Midway

Sat 5/2

2:12 pm-8:07 pm

1 stop7h 55m

$271

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 4/29

7:25 pm-5:45 am

1 stop8h 20m

Chicago Midway

Wed 5/6

4:00 pm-11:10 pm

2 stops9h 10m

$276

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Sat 5/23

5:10 am-6:33 pm

2 stops11h 23m

Chicago Midway

Wed 5/27

1:22 pm-11:50 pm

2 stops12h 28m

$313

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, Thursday is the cheapest day to fly to Chicago Midway Airport from Oregon. The lowest ticket price found for a Thursday departure recently was $404. 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 $472.

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 $364 when looking at flights departing at noon. Try not to purchase tickets in the evening because they tend to be around $435. 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?

You could potentially save up to 33% 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

$192

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 $192. The best round-trip flight deal from Oregon to Chicago Midway Airport found on momondo in the last 72 hours is $385.
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
4,334 reviews
Search Southwest flights
DeltaPriceFrom $268Free CancellationRating
7.9
8,367 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
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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