What is the cheapest airline that flies from Chicago Midway to Oregon?

Southwest and Delta are the most popular carriers operating from Chicago Midway to Oregon

How many flights depart from Chicago Midway Airport to Oregon on average per week?

2 flights are operational weekly from Chicago Midway Airport to Oregon as of March 2026. The most popular departure day for this route is Tue, with 50% of flights per week taking off on this day.

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?

As of March 2026, there is 1 operator available to choose from 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.

$99 Cheap Flights from Chicago Midway Airport to Oregon in 2026

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Find the cheapest flights from Chicago Midway Airport to Oregon

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:30 am - 10:45 am

MDW

EUG

6h 15m

1 stop

2:50 pm - 11:40 pm

EUG

MDW

6h 50m

1 stop

$197Southwest

Tue, Apr 14 - Thu, Apr 23

9:50 pm - 12:10 am

MDW

PDX

4h 20mnonstop

11:55 pm - 5:50 am

PDX

MDW

3h 55mnonstop

$200Southwest

Thu, Apr 23 - Tue, Apr 28

6:05 pm - 8:25 pm

MDW

PDX

4h 20mnonstop

7:05 pm - 5:40 am

PDX

MDW

8h 35m

1 stop

$201Southwest

Sat, Apr 18 - Sat, Apr 25

2:10 pm - 10:00 pm

MDW

EUG

9h 50m

2 stops

2:50 pm - 11:40 pm

EUG

MDW

6h 50m

1 stop

$202Southwest

Tue, Apr 14 - Thu, Apr 23

10:15 am - 6:45 pm

MDW

PDX

10h 30m

2 stops

11:55 pm - 5:50 am

PDX

MDW

3h 55mnonstop

$206Southwest

Sat, Apr 18 - Sat, Apr 25

4:05 pm - 10:45 pm

MDW

EUG

8h 40m

2 stops

6:35 am - 4:35 pm

EUG

MDW

8h 00m

2 stops

$207Southwest

Fri, Apr 17 - Tue, Apr 21

9:50 pm - 12:10 am

MDW

PDX

4h 20mnonstop

6:10 pm - 6:00 am

PDX

MDW

9h 50m

1 stop

$210Southwest

Thu, Apr 23 - Tue, Apr 28

8:50 pm - 11:10 pm

MDW

PDX

4h 20mnonstop

11:55 pm - 5:50 am

PDX

MDW

3h 55mnonstop

$211Southwest

Wed, Apr 22 - Sat, Apr 25

9:29 am - 2:26 pm

MDW

BOI

5h 57m

1 stop

11:35 pm - 9:56 am

BOI

MDW

9h 21m

1 stop

$229Delta

Wed, Apr 22 - Tue, Apr 28

9:29 am - 2:26 pm

MDW

BOI

5h 57m

1 stop

6:00 am - 1:32 pm

BOI

MDW

6h 32m

2 stops

$234Delta

Wed, Apr 22 - Tue, Apr 28

Southwest flights from Chicago Midway Airport to Oregon

Our best Southwest deals on Chicago Midway Airport to Oregon flight tickets

Southwest

Apr 14

MDW6:30 amChicago Midway

6h 15m

1 stop

EUG10:45 amEugene

Apr 23

EUG2:50 pmEugene

6h 50m

1 stop

MDW11:40 pmChicago Midway

$197

Southwest

Apr 23

MDW9:50 pmChicago Midway

4h 20m

PDX12:10 amPortland

Apr 28

PDX11:55 pmPortland

3h 55m

MDW5:50 amChicago Midway

$200

Southwest

Apr 18

MDW6:05 pmChicago Midway

4h 20m

PDX8:25 pmPortland

Apr 25

PDX7:05 pmPortland

8h 35m

1 stop

MDW5:40 amChicago Midway

$201

Delta flights from Chicago Midway Airport to Oregon

Our best Delta deals on Chicago Midway Airport to Oregon flight tickets

Delta

Apr 22

MDW9:29 amChicago Midway

5h 57m

1 stop

BOI2:26 pmBoise Air Term. Gowen Fld

Apr 28

BOI11:35 pmBoise Air Term. Gowen Fld

9h 21m

1 stop

MDW9:56 amChicago Midway

$229

Delta

Apr 22

MDW9:29 amChicago Midway

5h 57m

1 stop

BOI2:26 pmBoise Air Term. Gowen Fld

Apr 28

BOI6:00 amBoise Air Term. Gowen Fld

6h 32m

2 stops

MDW1:32 pmChicago Midway

$234

Delta

Apr 8

MDW2:05 pmChicago Midway

8h 20m

1 stop

PDX8:25 pmPortland

Apr 12

PDX11:15 pmPortland

7h 32m

1 stop

MDW8:47 amChicago Midway

$243

momondo Fare Finder

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

ChicagoEugene

MDW - EUG

MDWEUG

Chicago Midway

Tue 4/14

6:30 am-10:45 am

1 stop6h 15m

Eugene

Thu 4/23

2:50 pm-11:40 pm

1 stop6h 50m

$197

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 4/23

9:50 pm-12:10 am

Nonstop4h 20m

Portland

Tue 4/28

11:55 pm-5:50 am

Nonstop3h 55m

$200

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 4/18

6:05 pm-8:25 pm

Nonstop4h 20m

Portland

Sat 4/25

7:05 pm-5:40 am

1 stop8h 35m

$201

ChicagoEugene

MDW - EUG

MDWEUG

Chicago Midway

Tue 4/14

2:10 pm-10:00 pm

2 stops9h 50m

Eugene

Thu 4/23

2:50 pm-11:40 pm

1 stop6h 50m

$202

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 4/18

10:15 am-6:45 pm

2 stops10h 30m

Portland

Sat 4/25

11:55 pm-5:50 am

Nonstop3h 55m

$206

ChicagoEugene

MDW - EUG

MDWEUG

Chicago Midway

Fri 4/17

4:05 pm-10:45 pm

2 stops8h 40m

Eugene

Tue 4/21

6:35 am-4:35 pm

2 stops8h 00m

$207

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 4/23

9:50 pm-12:10 am

Nonstop4h 20m

Portland

Tue 4/28

6:10 pm-6:00 am

1 stop9h 50m

$210

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 4/22

8:50 pm-11:10 pm

Nonstop4h 20m

Portland

Sat 4/25

11:55 pm-5:50 am

Nonstop3h 55m

$211

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

Wed 4/22

9:29 am-2:26 pm

1 stop5h 57m

Boise Air Term. Gowen Fld

Tue 4/28

11:35 pm-9:56 am

1 stop9h 21m

$229

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

Wed 4/22

9:29 am-2:26 pm

1 stop5h 57m

Boise Air Term. Gowen Fld

Tue 4/28

6:00 am-1:32 pm

2 stops6h 32m

$234

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

What is the cheapest month to fly to Oregon?

The month of December is, on average, the cheapest month to fly to Oregon from Chicago Midway Airport, with most prices found around $313. The month of February is another great option to travel to Oregon, with average flight prices from Chicago Midway Airport averaging around $350.

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 Monday. momondo users have found tickets for Monday departures for as low as $282. 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 evening. momondo users have found flights departing from Chicago Midway Airport to Oregon in the evening for as low as $325. 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 at noon, with an average ticket price of $393. Departure times at noon 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?

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

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	$133
Fastest flight time	3h 35m
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 $133. The best round-trip flight deal from Chicago Midway Airport to Oregon found on momondo in the last 72 hours is $231.

The fastest flight from Chicago Midway Airport to Oregon takes 3h 35m

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

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?
As of March 2026, there is 1 operator available to choose from 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?
Based on momondo bookings for flights between Chicago Midway Airport and Oregon, the leading plane model is Boeing 737 MAX 8, making up 30.59% of the total bookings. Other popular models include Boeing 737-800 with 28.82%, Boeing 737 MAX 9 with 7.65%, and Boeing 737-900 Passenger/BBJ3 (winglets) with 7.65%.

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
Southwest	PriceFrom $227	Free Cancellation	Rating 8.0 4,302 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.