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Cheap flights from Chicago Midway Airport to Oregon from $129

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Oregon departing on 6/4. 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

Find the cheapest flights from Chicago Midway Airport to Oregon

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:00 am - 2:05 pm
MDW
-
EUG
10h 05m
1 stop
Southwest Logo
10:15 am - 11:25 pm
EUG
-
MDW
11h 10m
1 stop
$212Southwest
Tue, Jul 14 - Mon, Jul 20
Southwest Logo
5:30 am - 1:00 pm
MDW
-
EUG
9h 30m
2 stops
Southwest Logo
10:15 am - 11:25 pm
EUG
-
MDW
11h 10m
1 stop
$218Southwest
Tue, Jul 14 - Mon, Jul 20
Southwest Logo
6:05 pm - 8:25 pm
MDW
-
PDX
4h 20mnonstop
Southwest Logo
7:05 pm - 5:40 am
PDX
-
MDW
8h 35m
1 stop
$249Southwest
Sat, May 9 - Sat, May 16
Southwest Logo
6:05 pm - 8:25 pm
MDW
-
PDX
4h 20mnonstop
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
$251Southwest
Sat, May 9 - Sat, May 16
Southwest Logo
6:00 am - 2:05 pm
MDW
-
EUG
10h 05m
1 stop
Southwest Logo
6:40 pm - 5:00 am
EUG
-
MDW
8h 20m
1 stop
$257Southwest
Tue, Jul 14 - Mon, Jul 20
Southwest Logo
6:05 pm - 8:25 pm
MDW
-
PDX
4h 20mnonstop
Southwest Logo
7:05 pm - 5:40 am
PDX
-
MDW
8h 35m
1 stop
$261Southwest
Sat, May 9 - Sat, May 16
Southwest Logo
6:30 am - 10:45 am
MDW
-
EUG
6h 15m
1 stop
Southwest Logo
3:40 pm - 4:35 am
EUG
-
MDW
10h 55m
1 stop
$262Southwest
Tue, May 5 - Sat, May 16
Delta Logo
1:22 pm - 11:48 pm
MDW
-
EUG
12h 26m
2 stops
Delta Logo
6:13 am - 6:31 pm
EUG
-
MDW
10h 18m
2 stops
$267Delta
Wed, Jun 3 - Sun, Jun 7
Southwest Logo
6:55 am - 12:00 pm
MDW
-
PDX
7h 05m
1 stop
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
$271Southwest
Sat, May 9 - Wed, May 13
Delta Logo
9:20 am - 2:03 pm
MDW
-
BOI
5h 43m
1 stop
Delta Logo
5:40 am - 1:11 pm
BOI
-
MDW
6h 31m
1 stop
$335Delta
Wed, Sep 23 - Sat, Oct 3

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Delta flights from Chicago Midway Airport to Oregon

Our best Delta deals on Chicago Midway Airport to Oregon flight tickets
Delta
Jun 3
MDW1:22 pmChicago Midway
12h 26m
2 stops
EUG11:48 pmEugene
Jun 7
EUG6:13 amEugene
10h 18m
2 stops
MDW6:31 pmChicago Midway
$267
Delta
Jun 4
MDW1:22 pmChicago Midway
12h 21m
2 stops
EUG11:43 pmEugene
Jun 6
EUG6:15 amEugene
9h 41m
2 stops
MDW5:56 pmChicago Midway
$313
Delta
Aug 15
MDW9:20 amChicago Midway
8h 38m
1 stop
PDX3:58 pmPortland
Aug 24
PDX12:40 amPortland
5h 58m
1 stop
MDW8:38 amChicago Midway
$325

Southwest flights from Chicago Midway Airport to Oregon

Our best Southwest deals on Chicago Midway Airport to Oregon flight tickets
Southwest
Jul 14
MDW6:00 amChicago Midway
10h 05m
1 stop
EUG2:05 pmEugene
Jul 20
EUG10:15 amEugene
11h 10m
1 stop
MDW11:25 pmChicago Midway
$212
Southwest
Jul 14
MDW5:30 amChicago Midway
9h 30m
2 stops
EUG1:00 pmEugene
Jul 20
EUG10:15 amEugene
11h 10m
1 stop
MDW11:25 pmChicago Midway
$218
Southwest
May 9
MDW6:05 pmChicago Midway
4h 20m
PDX8:25 pmPortland
May 16
PDX7:05 pmPortland
8h 35m
1 stop
MDW5:40 amChicago Midway
$249

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Oregon 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 18, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Oregon that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoEugene

MDW - EUG

MDWEUG

Chicago Midway

Tue 7/14

6:00 am-2:05 pm

1 stop10h 05m

Eugene

Mon 7/20

10:15 am-11:25 pm

1 stop11h 10m

$212

ChicagoEugene

MDW - EUG

MDWEUG

Chicago Midway

Tue 7/14

5:30 am-1:00 pm

2 stops9h 30m

Eugene

Mon 7/20

10:15 am-11:25 pm

1 stop11h 10m

$218

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 5/9

6:05 pm-8:25 pm

Nonstop4h 20m

Portland

Sat 5/16

7:05 pm-5:40 am

1 stop8h 35m

$249
Quickest round-trip

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 5/9

6:05 pm-8:25 pm

Nonstop4h 20m

Portland

Sat 5/16

11:55 pm-5:50 am

Nonstop3h 55m

$251

ChicagoEugene

MDW - EUG

MDWEUG

Chicago Midway

Tue 7/14

6:00 am-2:05 pm

1 stop10h 05m

Eugene

Mon 7/20

6:40 pm-5:00 am

1 stop8h 20m

$257

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 5/9

6:05 pm-8:25 pm

Nonstop4h 20m

Portland

Sat 5/16

7:05 pm-5:40 am

1 stop8h 35m

$261

ChicagoEugene

MDW - EUG

MDWEUG

Chicago Midway

Tue 5/5

6:30 am-10:45 am

1 stop6h 15m

Eugene

Sat 5/16

3:40 pm-4:35 am

1 stop10h 55m

$262

ChicagoEugene

MDW - EUG

MDWEUG

Chicago Midway

Wed 6/3

1:22 pm-11:48 pm

2 stops12h 26m

Eugene

Sun 6/7

6:13 am-6:31 pm

2 stops10h 18m

$267

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 5/9

6:55 am-12:00 pm

1 stop7h 05m

Portland

Wed 5/13

11:55 pm-5:50 am

Nonstop3h 55m

$271

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

Wed 9/23

9:20 am-2:03 pm

1 stop5h 43m

Boise Air Term. Gowen Fld

Sat 10/3

5:40 am-1:11 pm

1 stop6h 31m

$335

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 Oregon from

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

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 Oregon?

The month of March is, on average, the cheapest month to fly to Oregon from Chicago Midway Airport, with most prices found around $227. The month of December is another great option to travel to Oregon, with average flight prices from Chicago Midway Airport averaging around $313.

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

On average, the least expensive day to fly to Oregon from Chicago Midway Airport is on a Saturday. momondo users have found tickets for Saturday departures for as low as $314. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Oregon is Sunday, with ticket prices averaging around $460.

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

According to our data, the cheapest time of day to fly to Oregon is in the afternoon. momondo users have found flights departing from Chicago Midway Airport to Oregon in the afternoon for as low as $316. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights to Oregon are more costly in the morning, with an average ticket price of $338. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago Midway to Oregon flight route?

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

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

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

You could potentially save up to 22% on your flight if you consider stops on a Chicago Midway Airport to Oregon flight.

Cheap Chicago Midway Airport to Oregon flight deals and tips

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

Best Price Found

$152

Fastest flight time

3h 30m

Direct flights

Every day

Airports in Oregon

64 airports
The best one-way flight to Oregon from Chicago Midway Airport in the past 72 hours is $152. The best round-trip flight deal from Chicago Midway Airport to Oregon found on momondo in the last 72 hours is $316.
The fastest flight from Chicago Midway Airport to Oregon takes 3h 30m
Direct flights go from Chicago Midway Airport to Oregon every day.
There are 64 airports in Oregon. From Chicago Midway Airport there are direct flights to Portland (PDX), Boise Air Term. Gowen Fld (BOI).
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Oregon

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

    Prices for flights from Chicago Midway Airport to Oregon are refreshed on a daily basis.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Oregon.

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

    The travel and health documents required for your trip to Oregon can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Oregon. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Chicago Midway Airport to Oregon?

Best airlines flying from Chicago Midway Airport to Oregon

Compare and see reviews for airlines that fly from Chicago Midway Airport to Oregon with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $227Free CancellationRating
8.0
4,330 reviews
Search Southwest flights

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Oregon. Millions of users trust and use momondo every year so you are in good hands.

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

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

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

Once you have performed a search for Chicago to Oregon 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 Chicago to Oregon right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Oregon from Chicago. 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.

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