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Cheap flights from Oregon to Chicago from $163

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Oregon to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
11:15 am - 10:00 pmEUG  Eugene-MDW Chicago Midway
8h 45m1 stop San Diego
Southwest Logo
5:55 am - 10:20 amMDW  Chicago Midway-EUG Eugene
6h 25m1 stop Denver Intl
$272Southwest
Thu, Dec 10 - Thu, Dec 17
Southwest Logo
1:40 pm - 10:45 pmEUG  Eugene-MDW Chicago Midway
7h 05m1 stop Denver Intl
Southwest Logo
5:00 am - 11:45 amMDW  Chicago Midway-EUG Eugene
8h 45m1 stop Las Vegas Harry Reid Intl
$319Southwest
Wed, Jan 27 - Sun, Jan 31
Southwest Logo
6:00 am - 3:50 pmEUG  Eugene-MDW Chicago Midway
7h 50m1 stop Sacramento Intl
Southwest Logo
5:20 am - 1:55 pmMDW  Chicago Midway-EUG Eugene
10h 35m2 stops Phoenix Sky Harbor Intl San Diego
$325Southwest
Wed, Jan 27 - Sun, Jan 31
Southwest Logo
6:00 am - 4:40 pmEUG  Eugene-MDW Chicago Midway
8h 40m2 stops Sacramento Intl Denver Intl
Southwest Logo
5:20 am - 1:55 pmMDW  Chicago Midway-EUG Eugene
10h 35m2 stops Phoenix Sky Harbor Intl San Diego
$330Southwest
Wed, Jan 27 - Sun, Jan 31
Southwest Logo
5:45 am - 5:50 pmEUG  Eugene-MDW Chicago Midway
10h 05m2 stops Denver Intl Lambert-St Louis
Southwest Logo
5:55 am - 10:20 amMDW  Chicago Midway-EUG Eugene
6h 25m1 stop Denver Intl
$351Southwest
Thu, Dec 10 - Thu, Dec 17
Southwest Logo
11:30 pm - 5:15 amPDX  Portland-MDW Chicago Midway
3h 45mnonstop
Southwest Logo
7:40 pm - 10:15 pmMDW  Chicago Midway-PDX Portland
4h 35mnonstop
$357Southwest
Wed, Dec 30 - Sun, Jan 10
Southwest Logo
11:20 am - 5:05 pmPDX  Portland-MDW Chicago Midway
3h 45mnonstop
Southwest Logo
8:40 pm - 11:25 pmMDW  Chicago Midway-PDX Portland
4h 45mnonstop
$357Southwest
Fri, Dec 25 - Thu, Dec 31
Southwest Logo
11:20 am - 5:05 pmPDX  Portland-MDW Chicago Midway
3h 45mnonstop
Southwest Logo
10:00 am - 12:35 pmMDW  Chicago Midway-PDX Portland
4h 35mnonstop
$357Southwest
Tue, Nov 17 - Wed, Nov 18
Delta Logo
6:04 am - 4:25 pmPDX  Portland-MDW Chicago Midway
8h 21m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:35 pm - 11:43 pmMDW  Chicago Midway-PDX Portland
8h 08m1 stop Minneapolis St Paul
$359Delta
Tue, Mar 2 - Sun, Mar 7
Delta Logo
6:20 am - 4:53 pmPDX  Portland-MDW Chicago Midway
8h 33m1 stop Minneapolis St Paul
Delta Logo
9:38 am - 6:58 pmMDW  Chicago Midway-PDX Portland
11h 20m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl
$359Delta
Sun, Jan 10 - Sat, Jan 16

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Delta flights from Oregon to Chicago Midway Airport

Our best Delta deals on Oregon to Chicago Midway Airport flight tickets
Delta
Nov 21
PDX12:35 amPortland
6h 15m
1 stop
MDW8:50 amChicago Midway
Nov 26
MDW11:05 amChicago Midway
9h 50m
2 stops
PDX6:55 pmPortland
$369
Delta
Nov 18
PDX12:35 amPortland
6h 15m
1 stop
MDW8:50 amChicago Midway
Dec 1
MDW12:39 pmChicago Midway
11h 27m
2 stops
PDX10:06 pmPortland
$372
Delta
Nov 14
PDX11:20 pmPortland
8h 26m
1 stop
MDW9:46 amChicago Midway
Nov 21
MDW5:29 pmChicago Midway
8h 17m
1 stop
PDX11:46 pmPortland
$377

Southwest flights from Oregon to Chicago Midway Airport

Our best Southwest deals on Oregon to Chicago Midway Airport flight tickets
Southwest
Dec 10
EUG11:15 amEugene
8h 45m
1 stop
MDW10:00 pmChicago Midway
Dec 17
MDW5:55 amChicago Midway
6h 25m
1 stop
EUG10:20 amEugene
$272
Southwest
Jan 27
EUG1:40 pmEugene
7h 05m
1 stop
MDW10:45 pmChicago Midway
Jan 31
MDW5:00 amChicago Midway
8h 45m
1 stop
EUG11:45 amEugene
$319
Southwest
Jan 27
EUG6:00 amEugene
7h 50m
1 stop
MDW3:50 pmChicago Midway
Jan 31
MDW5:20 amChicago Midway
10h 35m
2 stops
EUG1:55 pmEugene
$325

momondo Fare Finder

 
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

Cheapest round-trip

EugeneChicago

EUG Eugene - MDW Chicago Midway

EUGMDW

Eugene

Thu 12/10

11:15 am-10:00 pm

1 stop8h 45m

Chicago Midway

Thu 12/17

5:55 am-10:20 am

1 stop6h 25m

$272

EugeneChicago

EUG Eugene - MDW Chicago Midway

EUGMDW

Eugene

Wed 1/27

1:40 pm-10:45 pm

1 stop7h 05m

Chicago Midway

Sun 1/31

5:00 am-11:45 am

1 stop8h 45m

$319

EugeneChicago

EUG Eugene - MDW Chicago Midway

EUGMDW

Eugene

Wed 1/27

6:00 am-3:50 pm

1 stop7h 50m

Chicago Midway

Sun 1/31

5:20 am-1:55 pm

2 stops10h 35m

$325

EugeneChicago

EUG Eugene - MDW Chicago Midway

EUGMDW

Eugene

Wed 1/27

6:00 am-4:40 pm

2 stops8h 40m

Chicago Midway

Sun 1/31

5:20 am-1:55 pm

2 stops10h 35m

$330

EugeneChicago

EUG Eugene - MDW Chicago Midway

EUGMDW

Eugene

Thu 12/10

5:45 am-5:50 pm

2 stops10h 05m

Chicago Midway

Thu 12/17

5:55 am-10:20 am

1 stop6h 25m

$351
Quickest round-trip

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Wed 12/30

11:30 pm-5:15 am

Nonstop3h 45m

Chicago Midway

Sun 1/10

7:40 pm-10:15 pm

Nonstop4h 35m

$357

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Fri 12/25

11:20 am-5:05 pm

Nonstop3h 45m

Chicago Midway

Thu 12/31

8:40 pm-11:25 pm

Nonstop4h 45m

$357

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Tue 11/17

11:20 am-5:05 pm

Nonstop3h 45m

Chicago Midway

Wed 11/18

10:00 am-12:35 pm

Nonstop4h 35m

$357

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Tue 3/2

6:04 am-4:25 pm

1 stop8h 21m

Chicago Midway

Sun 3/7

5:35 pm-11:43 pm

1 stop8h 08m

$359

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Sun 1/10

6:20 am-4:53 pm

1 stop8h 33m

Chicago Midway

Sat 1/16

9:38 am-6:58 pm

2 stops11h 20m

$359

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 February is, on average, the cheapest month to fly to Chicago Midway Airport from Oregon, with most prices found around $293. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Oregon during the month April is also very affordable. Most momondo users find prices during this month for around $297.

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

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Oregon. The lowest ticket price found for a Tuesday departure recently was $436. 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 $567.

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

Flying to Chicago Midway Airport from Oregon in the evening is the least expensive time of day to depart. momondo users have found prices as low as $457 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $468. 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 Airport flights?

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

You could potentially save up to 43% on your flight if you consider stops on a Oregon to Chicago Midway Airport flight.

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

$163

Fastest flight time

3h 45m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Oregon in the past 72 hours is $163. The best round-trip flight deal from Oregon to Chicago Midway Airport found on momondo in the last 72 hours is $272.
The fastest flight from Oregon to Chicago Midway Airport takes 3h 45m
Direct flights go from Oregon to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Oregon to Chicago Midway Airport

  • 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 $266Free CancellationRating
7.9
4,219 reviews
Search Southwest flights

Traveling to a place near Chicago?

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