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Cheap flights from Oregon to Chicago from $102

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 3/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Oregon to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
1:35 pm - 9:15 pm
EUG
-
MDW
5h 40m1 stop
Southwest Logo
5:55 am - 10:10 am
MDW
-
EUG
6h 15m1 stop
$181Southwest
Tue, Mar 10 - Tue, Mar 17
Southwest Logo
10:45 am - 9:15 pm
EUG
-
MDW
8h 30m2 stops
Southwest Logo
5:55 am - 10:10 am
MDW
-
EUG
6h 15m1 stop
$186Southwest
Tue, Mar 10 - Tue, Mar 17
Delta Logo
5:50 am - 6:40 pm
BOI
-
MDW
11h 50m2 stops
Delta Logo
9:50 am - 8:15 pm
MDW
-
BOI
11h 25m2 stops
$192Delta
Fri, Feb 20 - Tue, Feb 24
Southwest Logo
7:45 am - 3:25 pm
BOI
-
MDW
6h 40m1 stop
Southwest Logo
8:10 am - 3:20 pm
MDW
-
BOI
8h 10m1 stop
$204Southwest
Tue, Jan 27 - Tue, Feb 3
Southwest Logo
6:10 am - 4:40 pm
EUG
-
MDW
8h 30m2 stops
Southwest Logo
5:40 pm - 10:35 pm
MDW
-
EUG
6h 55m1 stop
$206Southwest
Wed, Apr 1 - Mon, Apr 6
Southwest Logo
7:45 am - 4:45 pm
BOI
-
MDW
8h 00m1 stop
Southwest Logo
8:15 am - 4:50 pm
MDW
-
BOI
9h 35m2 stops
$209Southwest
Tue, Jan 27 - Tue, Feb 3
Delta Logo
5:15 am - 6:40 pm
EUG
-
MDW
11h 25m2 stops
Delta Logo
1:29 pm - 10:55 pm
MDW
-
EUG
11h 26m2 stops
$210Delta
Fri, Mar 6 - Sat, Mar 7
Southwest Logo
6:10 am - 4:10 pm
EUG
-
MDW
8h 00m2 stops
Southwest Logo
2:35 pm - 10:35 pm
MDW
-
EUG
10h 00m2 stops
$211Southwest
Wed, Apr 1 - Mon, Apr 6
Southwest Logo
11:50 am - 9:50 pm
BOI
-
MDW
9h 00m2 stops
Southwest Logo
8:10 am - 3:20 pm
MDW
-
BOI
8h 10m2 stops
$214Southwest
Tue, Jan 27 - Tue, Feb 3
Southwest Logo
2:50 pm - 11:40 pm
EUG
-
MDW
6h 50m1 stop
Southwest Logo
10:00 am - 4:40 pm
MDW
-
EUG
8h 40m2 stops
$215Southwest
Thu, May 7 - Wed, May 13

Southwest flights from Oregon to Chicago Midway Airport

Our best Southwest deals on Oregon to Chicago Midway Airport flight tickets
Southwest
Mar 10
EUG1:35 pmEugene
5h 40m
1 stop
MDW9:15 pmChicago Midway
Mar 17
MDW5:55 amChicago Midway
6h 15m
1 stop
EUG10:10 amEugene
$181
Southwest
Mar 10
EUG10:45 amEugene
8h 30m
2 stops
MDW9:15 pmChicago Midway
Mar 17
MDW5:55 amChicago Midway
6h 15m
1 stop
EUG10:10 amEugene
$186
Southwest
Jan 27
BOI7:45 amBoise Air Term. Gowen Fld
6h 40m
1 stop
MDW3:25 pmChicago Midway
Feb 3
MDW8:10 amChicago Midway
8h 10m
1 stop
BOI3:20 pmBoise Air Term. Gowen Fld
$204

Delta flights from Oregon to Chicago Midway Airport

Our best Delta deals on Oregon to Chicago Midway Airport flight tickets
Delta
Feb 20
BOI5:50 amBoise Air Term. Gowen Fld
11h 50m
2 stops
MDW6:40 pmChicago Midway
Feb 23
MDW1:28 pmChicago Midway
9h 28m
2 stops
BOI9:56 pmBoise Air Term. Gowen Fld
$192
Delta
Mar 6
EUG5:15 amEugene
11h 25m
2 stops
MDW6:40 pmChicago Midway
Mar 7
MDW1:29 pmChicago Midway
11h 26m
2 stops
EUG10:55 pmEugene
$210
Delta
Jan 28
PDX11:59 amPortland
8h 23m
1 stop
MDW10:22 pmChicago Midway
Jan 30
MDW9:33 amChicago Midway
11h 17m
2 stops
PDX6:50 pmPortland
$220

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 January 8, 2026.
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

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Tue 3/10

1:35 pm-9:15 pm

1 stop5h 40m

Chicago Midway

Tue 3/17

5:55 am-10:10 am

1 stop6h 15m

$181

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Tue 3/10

10:45 am-9:15 pm

2 stops8h 30m

Chicago Midway

Tue 3/17

5:55 am-10:10 am

1 stop6h 15m

$186

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Fri 2/20

5:50 am-6:40 pm

2 stops11h 50m

Chicago Midway

Tue 2/24

9:50 am-8:15 pm

2 stops11h 25m

$192

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Tue 1/27

7:45 am-3:25 pm

1 stop6h 40m

Chicago Midway

Tue 2/3

8:10 am-3:20 pm

1 stop8h 10m

$204

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Wed 4/1

6:10 am-4:40 pm

2 stops8h 30m

Chicago Midway

Mon 4/6

5:40 pm-10:35 pm

1 stop6h 55m

$206

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Tue 1/27

7:45 am-4:45 pm

1 stop8h 00m

Chicago Midway

Tue 2/3

8:15 am-4:50 pm

2 stops9h 35m

$209

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Fri 3/6

5:15 am-6:40 pm

2 stops11h 25m

Chicago Midway

Sat 3/7

1:29 pm-10:55 pm

2 stops11h 26m

$210

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Wed 4/1

6:10 am-4:10 pm

2 stops8h 00m

Chicago Midway

Mon 4/6

2:35 pm-10:35 pm

2 stops10h 00m

$211

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Tue 1/27

11:50 am-9:50 pm

2 stops9h 00m

Chicago Midway

Tue 2/3

8:10 am-3:20 pm

2 stops8h 10m

$214

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Thu 5/7

2:50 pm-11:40 pm

1 stop6h 50m

Chicago Midway

Wed 5/13

10:00 am-4:40 pm

2 stops8h 40m

$215

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 September is also very affordable. Most momondo users find prices during this month for around $242.

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 $415. 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 $474.

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 $388 when looking at flights departing at noon. Try not to purchase tickets in the evening because they tend to be around $527. 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

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.

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

$148

Fastest flight time

3h 20m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Oregon in the past 72 hours is $148. The best round-trip flight deal from Oregon to Chicago Midway Airport found on momondo in the last 72 hours is $303.
The fastest flight from Oregon to Chicago Midway Airport takes 3h 20m
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
SouthwestPriceFrom $238Free CancellationRating
8.0
4,250 reviews
Search Southwest flights
DeltaPriceFrom $268Free CancellationRating
7.9
8,025 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
Munster
Crown Point
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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