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?

3 flights are operational weekly from Chicago Midway Airport to Oregon as of September 2026. The most popular departure day for this route is Tue, with 67% 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 September 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.

$179 Cheap Flights from Chicago Midway Airport to Oregon in 2026/27

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.

9:15 pm - 11:55 pmMDW Chicago Midway-PDX Portland

4h 40mnonstop

11:30 pm - 5:15 amPDX Portland-MDW Chicago Midway

3h 45mnonstop

$357Southwest

Thu, Nov 5 - Mon, Nov 9

9:45 pm - 12:15 amMDW Chicago Midway-PDX Portland

4h 30mnonstop

11:35 pm - 5:25 amPDX Portland-MDW Chicago Midway

3h 50mnonstop

$357Southwest

Thu, Oct 22 - Wed, Oct 28

10:00 am - 12:35 pmMDW Chicago Midway-PDX Portland

4h 35mnonstop

6:00 am - 11:50 amPDX Portland-MDW Chicago Midway

3h 50mnonstop

$357Southwest

Wed, Nov 11 - Mon, Nov 16

11:00 am - 1:25 pmMDW Chicago Midway-PDX Portland

4h 25mnonstop

11:35 pm - 5:25 amPDX Portland-MDW Chicago Midway

3h 50mnonstop

$357Southwest

Sat, Oct 17 - Sat, Oct 24

10:10 am - 12:35 pmMDW Chicago Midway-PDX Portland

4h 25mnonstop

5:35 am - 11:25 amPDX Portland-MDW Chicago Midway

3h 50mnonstop

$357Southwest

Thu, Feb 11 - Mon, Feb 15

9:45 pm - 12:15 amMDW Chicago Midway-PDX Portland

4h 30mnonstop

11:35 pm - 5:25 amPDX Portland-MDW Chicago Midway

3h 50mnonstop

$357Southwest

Thu, Oct 22 - Mon, Oct 26

9:15 pm - 11:55 pmMDW Chicago Midway-PDX Portland

4h 40mnonstop

6:00 am - 11:50 amPDX Portland-MDW Chicago Midway

3h 50mnonstop

$357Southwest

Mon, Nov 2 - Tue, Nov 10

6:04 am - 1:38 pmMDW Chicago Midway-PDX Portland

9h 34m1 stop Atlanta Hartsfield-Jackson

6:00 am - 4:47 pmPDX Portland-MDW Chicago Midway

8h 47m1 stop Minneapolis St Paul

$377Delta

Tue, Oct 20 - Sat, Oct 24

12:49 pm - 9:49 pmMDW Chicago Midway-PDX Portland

11h 00m1 stop Atlanta Hartsfield-Jackson

6:00 am - 4:47 pmPDX Portland-MDW Chicago Midway

8h 47m1 stop Minneapolis St Paul

$377Delta

Tue, Oct 20 - Sat, Oct 24

5:29 pm - 11:46 pmMDW Chicago Midway-PDX Portland

8h 17m1 stop Minneapolis St Paul

6:00 am - 4:50 pmPDX Portland-MDW Chicago Midway

8h 50m1 stop Minneapolis St Paul

$377Delta

Mon, Nov 23 - Thu, Dec 3

Cheap last minute flights

Enter your travel dates to find the best prices.

8:55 pm - 11:15 pmMDW Chicago Midway-PDX Portland

4h 20mnonstop

11:35 pm - 5:25 amPDX Portland-MDW Chicago Midway

3h 50mnonstop

$497Southwest

Wed, Sep 30 - Sat, Oct 3

10:20 am - 12:35 pmMDW Chicago Midway-PDX Portland

4h 15mnonstop

2:25 pm - 11:50 pmPDX Portland-MDW Chicago Midway

7h 25m1 stop Dallas Love Field

$507Southwest

Wed, Sep 30 - Wed, Oct 7

8:55 pm - 11:15 pmMDW Chicago Midway-PDX Portland

4h 20mnonstop

10:40 am - 8:55 pmPDX Portland-MDW Chicago Midway

8h 15m1 stop Denver Intl

$507Southwest

Wed, Sep 30 - Sat, Oct 3

8:55 pm - 11:15 pmMDW Chicago Midway-PDX Portland

4h 20mnonstop

5:50 am - 6:05 pmPDX Portland-MDW Chicago Midway

10h 15m2 stops Las Vegas Harry Reid Intl Detroit Metropolitan Wayne County

$512Southwest

Wed, Sep 30 - Sat, Oct 3

10:20 am - 12:35 pmMDW Chicago Midway-PDX Portland

4h 15mnonstop

6:00 am - 4:40 pmPDX Portland-MDW Chicago Midway

8h 40m2 stops Las Vegas Harry Reid Intl Tucson

$512Southwest

Wed, Sep 30 - Wed, Oct 7

11:35 am - 6:59 pmMDW Chicago Midway-PDX Portland

9h 24m1 stop Atlanta Hartsfield-Jackson

6:00 am - 4:47 pmPDX Portland-MDW Chicago Midway

8h 47m1 stop Minneapolis St Paul

$517Delta

Sat, Oct 3 - Wed, Oct 7

11:35 am - 6:59 pmMDW Chicago Midway-PDX Portland

9h 24m1 stop Atlanta Hartsfield-Jackson

6:00 am - 4:47 pmPDX Portland-MDW Chicago Midway

8h 47m1 stop Minneapolis St Paul

$517Delta

Sat, Oct 3 - Tue, Oct 13

6:05 am - 1:00 pmMDW Chicago Midway-PDX Portland

8h 55m1 stop Atlanta Hartsfield-Jackson

6:00 am - 4:47 pmPDX Portland-MDW Chicago Midway

8h 47m1 stop Minneapolis St Paul

$517Delta

Sat, Oct 3 - Sat, Oct 10

9:45 pm - 12:10 amMDW Chicago Midway-PDX Portland

4h 25mnonstop

11:35 pm - 5:25 amPDX Portland-MDW Chicago Midway

3h 50mnonstop

$520Southwest

Thu, Oct 1 - Sat, Oct 3

9:45 pm - 12:15 amMDW Chicago Midway-PDX Portland

4h 30mnonstop

11:35 pm - 5:25 amPDX Portland-MDW Chicago Midway

3h 50mnonstop

$520Southwest

Mon, Oct 5 - Tue, Oct 6

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Southwest flights from Chicago Midway Airport to Oregon

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

Southwest

Oct 27

MDW10:05 amChicago Midway

4h 25m

PDX12:30 pmPortland

Nov 3

PDX6:00 amPortland

3h 50m

MDW11:50 amChicago Midway

$357

Southwest

Oct 27

MDW6:05 amChicago Midway

6h 30m

1 stop

PDX10:35 amPortland

Nov 3

PDX6:00 amPortland

3h 50m

MDW11:50 amChicago Midway

$367

Southwest

Oct 30

MDW9:45 amChicago Midway

4h 25m

PDX12:10 pmPortland

Nov 2

PDX11:30 pmPortland

3h 45m

MDW5:15 amChicago Midway

$371

Delta flights from Chicago Midway Airport to Oregon

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

Delta

Oct 28

MDW12:49 pmChicago Midway

8h 20m

1 stop

PDX7:09 pmPortland

Nov 4

PDX6:00 amPortland

8h 47m

1 stop

MDW4:47 pmChicago Midway

$377

Delta

Oct 24

MDW12:27 pmChicago Midway

9h 33m

2 stops

PDX8:00 pmPortland

Oct 26

PDX8:44 pmPortland

10h 00m

2 stops

MDW8:44 amChicago Midway

$387

Delta

Dec 4

MDW12:39 pmChicago Midway

8h 19m

2 stops

PDX6:58 pmPortland

Dec 7

PDX11:17 pmPortland

8h 20m

1 stop

MDW9:37 amChicago Midway

$396

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

Cheapest round-trip

ChicagoPortland

MDW Chicago Midway - PDX Portland

MDWPDX

Chicago Midway

Thu 11/5

9:15 pm-11:55 pm

Nonstop4h 40m

Portland

Mon 11/9

11:30 pm-5:15 am

Nonstop3h 45m

$357

ChicagoPortland

MDW Chicago Midway - PDX Portland

MDWPDX

Chicago Midway

Thu 10/22

9:45 pm-12:15 am

Nonstop4h 30m

Portland

Wed 10/28

11:35 pm-5:25 am

Nonstop3h 50m

$357

ChicagoPortland

MDW Chicago Midway - PDX Portland

MDWPDX

Chicago Midway

Wed 11/11

10:00 am-12:35 pm

Nonstop4h 35m

Portland

Mon 11/16

6:00 am-11:50 am

Nonstop3h 50m

$357

Quickest round-trip

ChicagoPortland

MDW Chicago Midway - PDX Portland

MDWPDX

Chicago Midway

Sat 10/17

11:00 am-1:25 pm

Nonstop4h 25m

Portland

Sat 10/24

11:35 pm-5:25 am

Nonstop3h 50m

$357

ChicagoPortland

MDW Chicago Midway - PDX Portland

MDWPDX

Chicago Midway

Thu 2/11

10:10 am-12:35 pm

Nonstop4h 25m

Portland

Mon 2/15

5:35 am-11:25 am

Nonstop3h 50m

$357

ChicagoPortland

MDW Chicago Midway - PDX Portland

MDWPDX

Chicago Midway

Thu 10/22

9:45 pm-12:15 am

Nonstop4h 30m

Portland

Mon 10/26

11:35 pm-5:25 am

Nonstop3h 50m

$357

ChicagoPortland

MDW Chicago Midway - PDX Portland

MDWPDX

Chicago Midway

Mon 11/2

9:15 pm-11:55 pm

Nonstop4h 40m

Portland

Tue 11/10

6:00 am-11:50 am

Nonstop3h 50m

$357

ChicagoPortland

MDW Chicago Midway - PDX Portland

MDWPDX

Chicago Midway

Tue 10/20

6:04 am-1:38 pm

1 stop9h 34m

Portland

Sat 10/24

6:00 am-4:47 pm

1 stop8h 47m

$377

ChicagoPortland

MDW Chicago Midway - PDX Portland

MDWPDX

Chicago Midway

Tue 10/20

12:49 pm-9:49 pm

1 stop11h 00m

Portland

Sat 10/24

6:00 am-4:47 pm

1 stop8h 47m

$377

ChicagoPortland

MDW Chicago Midway - PDX Portland

MDWPDX

Chicago Midway

Mon 11/23

5:29 pm-11:46 pm

1 stop8h 17m

Portland

Thu 12/3

6:00 am-4:50 pm

1 stop8h 50m

$377

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 March is, on average, the cheapest month to fly to Oregon from Chicago Midway Airport, with most prices found around $227. The month of November is another great option to travel to Oregon, with average flight prices from Chicago Midway Airport averaging around $285.

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 $316. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Oregon is Friday, with ticket prices averaging around $412.

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 $338. 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 $388. 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 Airport to Oregon flights?

There is only 1 cabin class available to choose from on Chicago Midway Airport 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	$179
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 $179. The best round-trip flight deal from Chicago Midway Airport to Oregon found on momondo in the last 72 hours is $357.

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).

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?
As of September 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 737-800, making up 25.42% of the total bookings. Other popular models include Boeing 737 MAX 8 with 17.63%, Boeing 737-900 Passenger/BBJ3 (winglets) with 10.85%, and Boeing 737 MAX 9 with 9.83%.

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 $239	Free Cancellation	Rating 8.0 4,202 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.