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Cheap flights from Oregon to Chicago from $101

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Oregon to Chicago departing on 12/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Frontier Logo
12:52 pm - 11:30 amPDX-MDW
20h 38m1 stop
Frontier Logo
12:30 pm - 11:56 amMDW-PDX
25h 26m1 stop
$204Frontier
Find Deal
Thu, Nov 6 - Mon, Nov 10
Frontier Logo
12:43 pm - 12:36 amPDX-MDW
9h 53m1 stop
Frontier Logo
6:24 pm - 11:48 amMDW-PDX
19h 24m1 stop
$223Frontier
Find Deal
Thu, Oct 16 - Mon, Oct 20
Delta Logo
12:40 am - 10:30 amPDX-MDW
7h 50m1 stop
Delta Logo
4:23 pm - 10:08 pmMDW-PDX
7h 45m1 stop
$224Delta
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Fri, Oct 24 - Fri, Oct 31
Frontier Logo
12:03 pm - 1:57 pmPDX-MDW
23h 54m1 stop
Frontier Logo
12:30 pm - 11:56 amMDW-PDX
25h 26m1 stop
$229Frontier
Find Deal
Fri, Nov 7 - Mon, Nov 10
Southwest Logo
1:25 pm - 7:20 pmPDX-MDW
3h 55mnonstop
Southwest Logo
3:45 pm - 6:05 pmMDW-PDX
4h 20mnonstop
$231Southwest
Find Deal
Tue, Oct 21 - Sat, Oct 25
Delta Logo
10:58 pm - 8:40 amPDX-MDW
7h 42m1 stop
Delta Logo
4:23 pm - 10:08 pmMDW-PDX
7h 45m1 stop
$237Delta
Find Deal
Thu, Oct 23 - Fri, Oct 31
Southwest Logo
1:25 pm - 7:20 pmPDX-MDW
3h 55mnonstop
Southwest Logo
5:00 am - 10:30 amMDW-PDX
7h 30m1 stop
$241Southwest
Find Deal
Tue, Oct 21 - Sat, Oct 25
Frontier Logo
12:43 pm - 12:24 amPDX-MDW
9h 41m1 stop
Frontier Logo
7:50 am - 9:39 amMDW-PDX
27h 49m1 stop
$247Frontier
Find Deal
Fri, Oct 17 - Sun, Oct 19
Delta Logo
12:40 am - 8:55 amPDX-MDW
6h 15m1 stop
Delta Logo
6:00 am - 1:00 pmMDW-PDX
9h 00m1 stop
$251Delta
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Tue, Oct 21 - Wed, Oct 29
Multiple Airlines Logo
1:18 pm - 12:37 pmPDX-MDW
21h 19m2 stops
Multiple Airlines Logo
9:00 am - 9:18 amMDW-PDX
26h 18m1 stop
$341Multiple Airlines
Find Deal
Thu, Oct 30 - Sun, Nov 2

Southwest flights from Oregon to Chicago Midway Airport

Our best Southwest deals on Oregon to Chicago Midway Airport flight tickets
Southwest
Oct 21
PDX1:25 pmPortland
3h 55m
MDW7:20 pmChicago Midway
Oct 25
MDW3:45 pmChicago Midway
4h 20m
PDX6:05 pmPortland
$231
Find similar
Southwest
Oct 21
PDX1:25 pmPortland
3h 55m
MDW7:20 pmChicago Midway
Oct 25
MDW5:00 amChicago Midway
7h 30m
1 stop
PDX10:30 amPortland
$241
Find similar
Southwest
Oct 21
PDX5:30 pmPortland
9h 45m
1 stop
MDW5:15 amChicago Midway
Oct 25
MDW5:15 amChicago Midway
6h 35m
1 stop
PDX9:50 amPortland
$256
Find similar

Delta flights from Oregon to Chicago Midway Airport

Our best Delta deals on Oregon to Chicago Midway Airport flight tickets
Delta
Oct 24
PDX12:40 amPortland
7h 50m
1 stop
MDW10:30 amChicago Midway
Oct 31
MDW4:23 pmChicago Midway
7h 45m
1 stop
PDX10:08 pmPortland
$224
Find similar
Delta
Oct 23
PDX10:58 pmPortland
7h 42m
1 stop
MDW8:40 amChicago Midway
Oct 31
MDW4:23 pmChicago Midway
7h 45m
1 stop
PDX10:08 pmPortland
$237
Find similar
Delta
Oct 21
PDX12:40 amPortland
6h 15m
1 stop
MDW8:55 amChicago Midway
Oct 29
MDW6:00 amChicago Midway
9h 00m
1 stop
PDX1:00 pmPortland
$251
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momondo Fare Finder

 
Customize your flight search to find flights from Oregon to Chicago Midway Airport 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 September 29, 2025.
Use the filters below to find and compare flights from Oregon to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 11/6

12:52 pm-11:30 am

1 stop20h 38m

Chicago Midway

Mon 11/10

12:30 pm-11:56 am

1 stop25h 26m

$204

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 10/16

12:43 pm-12:36 am

1 stop9h 53m

Chicago Midway

Mon 10/20

6:24 pm-11:48 am

1 stop19h 24m

$223

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 10/24

12:40 am-10:30 am

1 stop7h 50m

Chicago Midway

Fri 10/31

4:23 pm-10:08 pm

1 stop7h 45m

$224

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 11/7

12:03 pm-1:57 pm

1 stop23h 54m

Chicago Midway

Mon 11/10

12:30 pm-11:56 am

1 stop25h 26m

$229

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 10/21

1:25 pm-7:20 pm

Nonstop3h 55m

Chicago Midway

Sat 10/25

3:45 pm-6:05 pm

Nonstop4h 20m

$231

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 10/23

10:58 pm-8:40 am

1 stop7h 42m

Chicago Midway

Fri 10/31

4:23 pm-10:08 pm

1 stop7h 45m

$237

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 10/21

1:25 pm-7:20 pm

Nonstop3h 55m

Chicago Midway

Sat 10/25

5:00 am-10:30 am

1 stop7h 30m

$241

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 10/17

12:43 pm-12:24 am

1 stop9h 41m

Chicago Midway

Sun 10/19

7:50 am-9:39 am

1 stop27h 49m

$247

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 10/21

12:40 am-8:55 am

1 stop6h 15m

Chicago Midway

Wed 10/29

6:00 am-1:00 pm

1 stop9h 00m

$251

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 10/30

1:18 pm-12:37 pm

2 stops21h 19m

Chicago Midway

Sun 11/2

9:00 am-9:18 am

1 stop26h 18m

$341

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 Chicago from

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

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 Chicago Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Oregon, with most prices found around $197. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Oregon during the month February is also very affordable. Most momondo users find prices during this month for around $253.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Oregon. The lowest ticket price found for a Thursday departure recently was $423. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Oregon because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $490.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Oregon at noon is the least expensive time of day to depart. momondo users have found prices as low as $398 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $438. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Oregon to Chicago Midway flight route?

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

How far in advance should I book a flight to Chicago Midway Airport?

You are more likely to see cheaper flights to Chicago Midway Airport from Oregon when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $379 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Oregon for as low as $260 on momondo.

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

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

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

Cheap Oregon to Chicago Midway Airport flight deals and tips

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

Best Price Found

$204

Fastest flight time

3h 50m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Oregon in the past 72 hours is $204. The best round-trip flight deal from Oregon to Chicago Midway Airport found on momondo in the last 72 hours is $349.
The fastest flight from Oregon to Chicago Midway Airport takes 3h 50m
Direct flights go from Oregon to Chicago Midway Airport every day.
Search flight deals

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

    Prices for flights from Oregon to Chicago Midway Airport refresh daily.

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Oregon to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

Best airlines flying from Oregon to Chicago Midway Airport

Compare and see reviews for airlines that fly from Oregon to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $128Free CancellationRating
5.8
3,158 reviews
Search Frontier flights
Alaska AirlinesPriceFrom $197Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $238Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
DeltaPriceFrom $256Free CancellationRating
7.9
7,964 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Oregon to Chicago for you.

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

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

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

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

Yes. momondo can track prices for Oregon to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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