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Cheap flights from Chicago Midway Airport to Oregon from $88

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 10/16. 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 Chicago Midway Airport to Oregon

Cheap round-trip flights

Frontier Logo
4:48 pm - 12:12 amMDW-PDX
9h 24m1 stop
Frontier Logo
6:05 am - 3:53 pmPDX-MDW
7h 48m1 stop
$176Frontier
Find Deal
Fri, Sep 5 - Mon, Sep 15
Frontier Logo
6:24 pm - 11:48 amMDW-PDX
19h 24m1 stop
Frontier Logo
12:43 pm - 12:24 amPDX-MDW
9h 41m1 stop
$181Frontier
Find Deal
Thu, Oct 23 - Mon, Oct 27
Frontier Logo
4:48 pm - 12:12 amMDW-PDX
9h 24m1 stop
Frontier Logo
6:05 am - 3:53 pmPDX-MDW
7h 48m1 stop
$188Frontier
Find Deal
Fri, Sep 26 - Mon, Sep 29
Frontier Logo
4:48 pm - 12:12 amMDW-PDX
9h 24m1 stop
Frontier Logo
10:34 am - 12:24 amPDX-MDW
11h 50m2 stops
$195Frontier
Find Deal
Fri, Oct 3 - Fri, Oct 10
Southwest Logo
8:20 pm - 10:35 pmMDW-PDX
4h 15mnonstop
Southwest Logo
1:30 pm - 7:30 pmPDX-MDW
4h 00mnonstop
$205Southwest
Find Deal
Sun, Aug 31 - Tue, Sep 9
Southwest Logo
3:45 pm - 6:05 pmMDW-PDX
4h 20mnonstop
Southwest Logo
10:15 am - 9:30 pmPDX-MDW
9h 15m1 stop
$213Southwest
Find Deal
Sat, Oct 25 - Fri, Oct 31
Delta Logo
6:00 am - 1:00 pmMDW-PDX
9h 00m1 stop
Delta Logo
12:40 am - 8:55 amPDX-MDW
6h 15m1 stop
$223Delta
Find Deal
Sat, Oct 25 - Thu, Oct 30
Delta Logo
6:00 am - 12:22 pmMDW-BOI
7h 22m1 stop
Delta Logo
5:25 am - 1:03 pmBOI-MDW
6h 38m1 stop
$234Delta
Find Deal
Sat, Sep 13 - Sat, Sep 20
Logo
7:03 pm - 11:11 amMDW-PDX
18h 08m1 stop
Logo
1:38 pm - 7:23 amPDX-MDW
39h 45m2 stops
$266
Find Deal
Mon, Sep 29 - Sat, Oct 4
Logo
6:24 pm - 11:48 amMDW-PDX
19h 24m1 stop
Logo
7:42 pm - 11:30 amPDX-MDW
13h 48m2 stops
$274
Find Deal
Fri, Oct 24 - Thu, Oct 30

Delta flights from Chicago Midway Airport to Oregon

Our best Delta deals on Chicago Midway Airport to Oregon flight tickets
Delta
Oct 25
MDW6:00 amChicago Midway
9h 00m
1 stop
PDX1:00 pmPortland
Oct 30
PDX12:40 amPortland
6h 15m
1 stop
MDW8:55 amChicago Midway
$223
Find similar
Delta
Sep 13
MDW6:00 amChicago Midway
7h 22m
1 stop
BOI12:22 pmBoise Air Term. Gowen Fld
Sep 20
BOI5:25 amBoise Air Term. Gowen Fld
6h 38m
1 stop
MDW1:03 pmChicago Midway
$234
Find similar
Delta
Oct 22
MDW9:20 amChicago Midway
5h 42m
1 stop
BOI2:02 pmBoise Air Term. Gowen Fld
Oct 26
BOI5:42 amBoise Air Term. Gowen Fld
6h 26m
1 stop
MDW1:08 pmChicago Midway
$245
Find similar

Southwest flights from Chicago Midway Airport to Oregon

Our best Southwest deals on Chicago Midway Airport to Oregon flight tickets
Southwest
Aug 31
MDW8:20 pmChicago Midway
4h 15m
PDX10:35 pmPortland
Sep 9
PDX1:30 pmPortland
4h 00m
MDW7:30 pmChicago Midway
$205
Find similar
Southwest
Oct 25
MDW3:45 pmChicago Midway
4h 20m
PDX6:05 pmPortland
Oct 31
PDX10:15 amPortland
9h 15m
1 stop
MDW9:30 pmChicago Midway
$213
Find similar
Southwest
Aug 31
MDW5:55 amChicago Midway
6h 00m
1 stop
PDX9:55 amPortland
Sep 9
PDX6:00 amPortland
4h 00m
MDW12:00 pmChicago Midway
$215
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 August 18, 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

Fri 9/5

4:48 pm-12:12 am

1 stop9h 24m

Portland

Mon 9/15

6:05 am-3:53 pm

1 stop7h 48m

$176

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 10/23

6:24 pm-11:48 am

1 stop19h 24m

Portland

Mon 10/27

12:43 pm-12:24 am

1 stop9h 41m

$181

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 9/26

4:48 pm-12:12 am

1 stop9h 24m

Portland

Mon 9/29

6:05 am-3:53 pm

1 stop7h 48m

$188

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 10/3

4:48 pm-12:12 am

1 stop9h 24m

Portland

Fri 10/10

10:34 am-12:24 am

2 stops11h 50m

$195

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sun 8/31

8:20 pm-10:35 pm

Nonstop4h 15m

Portland

Tue 9/9

1:30 pm-7:30 pm

Nonstop4h 00m

$205

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 10/25

3:45 pm-6:05 pm

Nonstop4h 20m

Portland

Fri 10/31

10:15 am-9:30 pm

1 stop9h 15m

$213

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 10/25

6:00 am-1:00 pm

1 stop9h 00m

Portland

Thu 10/30

12:40 am-8:55 am

1 stop6h 15m

$223

ChicagoBoise

MDW - BOI

MDWBOI

Chicago Midway

Sat 9/13

6:00 am-12:22 pm

1 stop7h 22m

Boise Air Term. Gowen Fld

Sat 9/20

5:25 am-1:03 pm

1 stop6h 38m

$234

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Mon 9/29

7:03 pm-11:11 am

1 stop18h 08m

Portland

Sat 10/4

1:38 pm-7:23 am

2 stops39h 45m

$266

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 10/24

6:24 pm-11:48 am

1 stop19h 24m

Portland

Thu 10/30

7:42 pm-11:30 am

2 stops13h 48m

$274

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 $266. 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 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 $486.

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 in the afternoon, with an average ticket price of $413. Departure times in the afternoon 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 are 1 cabin classes 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

$88

Fastest flight time

3h 45m

Direct flights

Every day

Airports in Oregon

3 airports
The best one-way flight to Oregon from Chicago Midway Airport in the past 72 hours is $88. The best round-trip flight deal from Chicago Midway Airport to Oregon found on momondo in the last 72 hours is $176.
The fastest flight from Chicago Midway Airport to Oregon takes 3h 45m
Direct flights go from Chicago Midway Airport to Oregon every day.
There are 3 airports near Oregon: Portland (PDX), Eugene (EUG), 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
FrontierPriceFrom $108Free CancellationRating
5.8
3,212 reviews
Search Frontier flights
SouthwestPriceFrom $238Free CancellationRating
8.0
4,246 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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