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Cheap flights from Oregon to Chicago from $90

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 8/31. 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

Delta Logo
1:30 pm - 9:44 pmBOI-MDW
7h 14m1 stop
Delta Logo
7:17 pm - 11:56 pmMDW-BOI
5h 39m1 stop
$197Delta
Find Deal
Tue, Aug 26 - Sat, Sep 6
Southwest Logo
10:35 am - 4:35 pmPDX-MDW
4h 00mnonstop
Southwest Logo
2:10 pm - 4:25 pmMDW-PDX
4h 15mnonstop
$197Southwest
Find Deal
Sat, Sep 6 - Sat, Sep 13
Southwest Logo
1:35 pm - 7:35 pmPDX-MDW
4h 00mnonstop
Southwest Logo
8:20 pm - 10:35 pmMDW-PDX
4h 15mnonstop
$198Southwest
Find Deal
Fri, Aug 29 - Sun, Aug 31
Delta Logo
5:25 am - 1:03 pmBOI-MDW
6h 38m1 stop
Delta Logo
1:43 pm - 11:57 pmMDW-BOI
11h 14m2 stops
$202Delta
Find Deal
Sat, Sep 13 - Sat, Sep 20
Southwest Logo
6:55 am - 12:55 pmPDX-MDW
4h 00mnonstop
Southwest Logo
3:50 pm - 6:05 pmMDW-PDX
4h 15mnonstop
$203Southwest
Find Deal
Sun, Aug 31 - Wed, Sep 3
Southwest Logo
6:10 am - 12:10 pmPDX-MDW
4h 00mnonstop
Southwest Logo
2:10 pm - 4:25 pmMDW-PDX
4h 15mnonstop
$207Southwest
Find Deal
Thu, Sep 4 - Sat, Sep 6
Delta Logo
10:57 pm - 8:35 amPDX-MDW
7h 38m1 stop
Delta Logo
1:43 pm - 8:56 pmMDW-PDX
9h 13m1 stop
$208Delta
Find Deal
Sat, Aug 30 - Tue, Sep 23
Frontier Logo
6:35 am - 8:54 pmPDX-MDW
12h 19m1 stop
Frontier Logo
2:44 pm - 11:24 pmMDW-PDX
10h 40m1 stop
$248Frontier
Find Deal
Thu, Aug 14 - Sat, Aug 16
Frontier Logo
6:05 am - 3:53 pmPDX-MDW
7h 48m1 stop
Frontier Logo
4:48 pm - 12:12 amMDW-PDX
9h 24m1 stop
$257Frontier
Find Deal
Mon, Sep 15 - Mon, Sep 22
Frontier Logo
11:08 am - 10:01 pmPDX-MDW
8h 53m1 stop
Frontier Logo
4:29 pm - 12:16 amMDW-PDX
9h 47m1 stop
$258Frontier
Find Deal
Thu, Oct 9 - Thu, Oct 16

Southwest flights from Oregon to Chicago Midway Airport

Our best Southwest deals on Oregon to Chicago Midway Airport flight tickets
Southwest
Sep 6
PDX10:35 amPortland
4h 00m
MDW4:35 pmChicago Midway
Sep 13
MDW2:10 pmChicago Midway
4h 15m
PDX4:25 pmPortland
$197
Find similar
Southwest
Aug 29
PDX1:35 pmPortland
4h 00m
MDW7:35 pmChicago Midway
Aug 31
MDW8:20 pmChicago Midway
4h 15m
PDX10:35 pmPortland
$198
Find similar
Southwest
Aug 31
PDX6:55 amPortland
4h 00m
MDW12:55 pmChicago Midway
Sep 3
MDW3:50 pmChicago Midway
4h 15m
PDX6:05 pmPortland
$203
Find similar

Delta flights from Oregon to Chicago Midway Airport

Our best Delta deals on Oregon to Chicago Midway Airport flight tickets
Delta
Aug 26
BOI1:30 pmBoise Air Term. Gowen Fld
7h 14m
1 stop
MDW9:44 pmChicago Midway
Sep 6
MDW7:17 pmChicago Midway
5h 39m
1 stop
BOI11:56 pmBoise Air Term. Gowen Fld
$197
Find similar
Delta
Sep 13
BOI5:25 amBoise Air Term. Gowen Fld
6h 38m
1 stop
MDW1:03 pmChicago Midway
Sep 20
MDW1:43 pmChicago Midway
11h 14m
2 stops
BOI11:57 pmBoise Air Term. Gowen Fld
$202
Find similar
Delta
Aug 30
PDX10:57 pmPortland
7h 38m
1 stop
MDW8:35 amChicago Midway
Sep 23
MDW1:43 pmChicago Midway
9h 13m
1 stop
PDX8:56 pmPortland
$208
Find similar

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 August 2, 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

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Tue 8/26

1:30 pm-9:44 pm

1 stop7h 14m

Chicago Midway

Sat 9/6

7:17 pm-11:56 pm

1 stop5h 39m

$197

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 9/6

10:35 am-4:35 pm

Nonstop4h 00m

Chicago Midway

Sat 9/13

2:10 pm-4:25 pm

Nonstop4h 15m

$197

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 8/29

1:35 pm-7:35 pm

Nonstop4h 00m

Chicago Midway

Sun 8/31

8:20 pm-10:35 pm

Nonstop4h 15m

$198

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Sat 9/13

5:25 am-1:03 pm

1 stop6h 38m

Chicago Midway

Sat 9/20

1:43 pm-11:57 pm

2 stops11h 14m

$202

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sun 8/31

6:55 am-12:55 pm

Nonstop4h 00m

Chicago Midway

Wed 9/3

3:50 pm-6:05 pm

Nonstop4h 15m

$203

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 9/4

6:10 am-12:10 pm

Nonstop4h 00m

Chicago Midway

Sat 9/6

2:10 pm-4:25 pm

Nonstop4h 15m

$207

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 8/30

10:57 pm-8:35 am

1 stop7h 38m

Chicago Midway

Tue 9/23

1:43 pm-8:56 pm

1 stop9h 13m

$208

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 8/14

6:35 am-8:54 pm

1 stop12h 19m

Chicago Midway

Sat 8/16

2:44 pm-11:24 pm

1 stop10h 40m

$248

PortlandChicago

PDX - MDW

PDXMDW

Portland

Mon 9/15

6:05 am-3:53 pm

1 stop7h 48m

Chicago Midway

Mon 9/22

4:48 pm-12:12 am

1 stop9h 24m

$257

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 10/9

11:08 am-10:01 pm

1 stop8h 53m

Chicago Midway

Thu 10/16

4:29 pm-12:16 am

1 stop9h 47m

$258

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 $253. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Oregon during the month September is also very affordable. Most momondo users find prices during this month for around $289.

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

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Oregon. The lowest ticket price found for a Friday departure recently was $428. 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 $525.

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 afternoon is the least expensive time of day to depart. momondo users have found prices as low as $289 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $451. 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 are 1 cabin classes 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

$90

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 $90. The best round-trip flight deal from Oregon to Chicago Midway Airport found on momondo in the last 72 hours is $197.
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
FrontierPriceFrom $108Free CancellationRating
5.8
3,237 reviews
Search Frontier flights
SouthwestPriceFrom $249Free CancellationRating
8.0
4,246 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Hammond
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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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