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Cheap flights from Chicago Midway Airport to Oregon from $105

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 2/28. 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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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
8:35 am - 11:15 am
MDW
-
PDX
4h 40mnonstop
Southwest Logo
6:30 am - 12:25 pm
PDX
-
MDW
3h 55mnonstop
$227Southwest
Sat, Jan 31 - Mon, Feb 2
Southwest Logo
8:10 am - 3:40 pm
MDW
-
PDX
9h 30m2 stops
Southwest Logo
8:45 am - 6:30 pm
PDX
-
MDW
7h 45m2 stops
$228Southwest
Tue, Jan 27 - Sat, Jan 31
Southwest Logo
8:10 am - 3:40 pm
MDW
-
PDX
9h 30m2 stops
Southwest Logo
6:30 am - 12:25 pm
PDX
-
MDW
3h 55mnonstop
$232Southwest
Tue, Jan 27 - Tue, Feb 3
Southwest Logo
7:00 am - 2:35 pm
MDW
-
PDX
9h 35m1 stop
Southwest Logo
5:05 am - 6:45 pm
PDX
-
MDW
11h 40m2 stops
$233Southwest
Sat, Jan 31 - Tue, Feb 3
Southwest Logo
8:35 am - 2:20 pm
MDW
-
PDX
7h 45m1 stop
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
$234Southwest
Thu, Apr 9 - Sat, Apr 11
Southwest Logo
2:35 pm - 7:55 pm
MDW
-
PDX
7h 20m1 stop
Southwest Logo
6:20 am - 4:45 pm
PDX
-
MDW
8h 25m1 stop
$236Southwest
Sat, Jan 31 - Tue, Feb 3
Delta Logo
1:49 pm - 8:55 pm
MDW
-
BOI
8h 06m1 stop
Delta Logo
1:40 pm - 10:22 pm
BOI
-
MDW
7h 42m1 stop
$269Delta
Thu, Jan 22 - Sun, Jan 25
Delta Logo
9:50 am - 6:28 pm
MDW
-
BOI
9h 38m2 stops
Delta Logo
1:40 pm - 10:22 pm
BOI
-
MDW
7h 42m1 stop
$274Delta
Thu, Jan 22 - Sun, Jan 25
Delta Logo
1:26 pm - 11:45 pm
MDW
-
BOI
11h 19m2 stops
Delta Logo
7:15 pm - 8:54 am
BOI
-
MDW
12h 39m2 stops
$296Delta
Thu, Feb 19 - Mon, Feb 23
Multiple Airlines Logo
2:16 pm - 7:11 pm
MDW
-
EUG
30h 55m1 stop
Multiple Airlines Logo
12:38 pm - 10:19 pm
EUG
-
MDW
31h 41m2 stops
$430Multiple Airlines
Thu, Mar 19 - Sat, Mar 28

Delta flights from Chicago Midway Airport to Oregon

Our best Delta deals on Chicago Midway Airport to Oregon flight tickets
Delta
Jan 22
MDW1:49 pmChicago Midway
8h 43m
1 stop
PDX8:32 pmPortland
Jan 26
PDX9:45 pmPortland
10h 08m
1 stop
MDW9:53 amChicago Midway
$257
Find similar
Delta
Apr 5
MDW2:05 pmChicago Midway
9h 07m
1 stop
PDX9:12 pmPortland
Apr 10
PDX12:30 amPortland
6h 20m
1 stop
MDW8:50 amChicago Midway
$262
Find similar
Delta
Mar 12
MDW2:05 pmChicago Midway
9h 07m
1 stop
PDX9:12 pmPortland
Mar 17
PDX11:15 pmPortland
7h 38m
1 stop
MDW8:53 amChicago Midway
$263
Find similar

Southwest flights from Chicago Midway Airport to Oregon

Our best Southwest deals on Chicago Midway Airport to Oregon flight tickets
Southwest
Jan 31
MDW8:35 amChicago Midway
4h 40m
PDX11:15 amPortland
Feb 2
PDX6:30 amPortland
3h 55m
MDW12:25 pmChicago Midway
$227
Find similar
Southwest
Jan 27
MDW8:10 amChicago Midway
9h 30m
2 stops
PDX3:40 pmPortland
Jan 31
PDX8:45 amPortland
7h 45m
2 stops
MDW6:30 pmChicago Midway
$228
Find similar
Southwest
Jan 27
MDW8:10 amChicago Midway
9h 30m
2 stops
PDX3:40 pmPortland
Feb 3
PDX6:30 amPortland
3h 55m
MDW12:25 pmChicago Midway
$232
Find similar

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 December 28, 2025.
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

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 1/31

8:35 am-11:15 am

Nonstop4h 40m

Portland

Mon 2/2

6:30 am-12:25 pm

Nonstop3h 55m

$227

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 1/27

8:10 am-3:40 pm

2 stops9h 30m

Portland

Sat 1/31

8:45 am-6:30 pm

2 stops7h 45m

$228

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 1/27

8:10 am-3:40 pm

2 stops9h 30m

Portland

Tue 2/3

6:30 am-12:25 pm

Nonstop3h 55m

$232

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 1/31

7:00 am-2:35 pm

1 stop9h 35m

Portland

Tue 2/3

5:05 am-6:45 pm

2 stops11h 40m

$233

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 4/9

8:35 am-2:20 pm

1 stop7h 45m

Portland

Sat 4/11

11:55 pm-5:50 am

Nonstop3h 55m

$234

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 1/31

2:35 pm-7:55 pm

1 stop7h 20m

Portland

Tue 2/3

6:20 am-4:45 pm

1 stop8h 25m

$236

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

Thu 1/22

1:49 pm-8:55 pm

1 stop8h 06m

Boise Air Term. Gowen Fld

Sun 1/25

1:40 pm-10:22 pm

1 stop7h 42m

$269

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

Thu 1/22

9:50 am-6:28 pm

2 stops9h 38m

Boise Air Term. Gowen Fld

Sun 1/25

1:40 pm-10:22 pm

1 stop7h 42m

$274

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

Thu 2/19

1:26 pm-11:45 pm

2 stops11h 19m

Boise Air Term. Gowen Fld

Mon 2/23

7:15 pm-8:54 am

2 stops12h 39m

$296

ChicagoEugene

MDW - EUG

MDWEUG

Chicago Midway

Thu 3/19

2:16 pm-7:11 pm

1 stop30h 55m

Eugene

Sat 3/28

12:38 pm-10:19 pm

2 stops31h 41m

$430

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 January is, on average, the cheapest month to fly to Oregon from Chicago Midway Airport, with most prices found around $238. The month of February is another great option to travel to Oregon, with average flight prices from Chicago Midway Airport averaging around $288.

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 $293. 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 $482.

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 $328. 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 $395. 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?

You could potentially save up to 61% 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

$303

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 $303. The best round-trip flight deal from Chicago Midway Airport to Oregon found on momondo in the last 72 hours is $282.
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?

  • 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 $238Free CancellationRating
8.0
4,256 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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