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Cheap flights from Oregon to Chicago from $174

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.
Delta Logo
5:30 am - 4:50 pmPDX  Portland-MDW Chicago Midway
9h 20m2 stops Seattle/Tacoma Intl Minneapolis St Paul
Delta Logo
12:39 pm - 10:06 pmMDW  Chicago Midway-PDX Portland
11h 27m2 stops Minneapolis St Paul Seattle/Tacoma Intl
$313Delta
Thu, Dec 3 - Tue, Dec 8
Delta Logo
5:30 am - 6:01 pmPDX  Portland-MDW Chicago Midway
10h 31m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County
Delta Logo
10:24 am - 8:58 pmMDW  Chicago Midway-PDX Portland
12h 34m2 stops Minneapolis St Paul Seattle/Tacoma Intl
$313Delta
Wed, Dec 9 - Sat, Dec 12
Delta Logo
5:25 pm - 10:03 amMFR  Medford-MDW Chicago Midway
14h 38m2 stops Seattle/Tacoma Intl Atlanta Hartsfield-Jackson
Delta Logo
1:27 pm - 11:18 pmMDW  Chicago Midway-MFR Medford
11h 51m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl
$313Delta
Mon, Oct 26 - Sat, Nov 7
Southwest Logo
6:15 am - 1:25 pmBOI  Boise Air Term. Gowen Fld-MDW Chicago Midway
6h 10m1 stop Las Vegas Harry Reid Intl
Southwest Logo
5:45 am - 11:50 amMDW  Chicago Midway-BOI Boise Air Term. Gowen Fld
7h 05m1 stop Las Vegas Harry Reid Intl
$349Southwest
Wed, Oct 28 - Mon, Nov 2
Southwest Logo
4:40 pm - 11:55 pmBOI  Boise Air Term. Gowen Fld-MDW Chicago Midway
6h 15m1 stop Phoenix Sky Harbor Intl
Southwest Logo
7:25 am - 4:00 pmMDW  Chicago Midway-BOI Boise Air Term. Gowen Fld
9h 35m1 stop Las Vegas Harry Reid Intl
$349Southwest
Tue, Oct 13 - Tue, Oct 20
Delta Logo
5:30 am - 1:20 pmBOI  Boise Air Term. Gowen Fld-MDW Chicago Midway
6h 50m1 stop Minneapolis St Paul
Delta Logo
5:31 pm - 11:59 pmMDW  Chicago Midway-BOI Boise Air Term. Gowen Fld
7h 28m1 stop Minneapolis St Paul
$349Delta
Tue, Sep 22 - Tue, Oct 6
Delta Logo
11:10 pm - 9:49 amBOI  Boise Air Term. Gowen Fld-MDW Chicago Midway
9h 39m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:13 pm - 11:59 pmMDW  Chicago Midway-BOI Boise Air Term. Gowen Fld
5h 46m1 stop Minneapolis St Paul
$349Delta
Mon, Sep 28 - Wed, Sep 30
Southwest Logo
4:40 pm - 11:55 pmBOI  Boise Air Term. Gowen Fld-MDW Chicago Midway
6h 15m1 stop Phoenix Sky Harbor Intl
Southwest Logo
7:25 am - 4:00 pmMDW  Chicago Midway-BOI Boise Air Term. Gowen Fld
9h 35m1 stop Las Vegas Harry Reid Intl
$349Southwest
Tue, Oct 13 - Tue, Oct 20
Southwest Logo
4:55 pm - 12:10 amBOI  Boise Air Term. Gowen Fld-MDW Chicago Midway
6h 15m1 stop Phoenix Sky Harbor Intl
Southwest Logo
6:05 pm - 11:55 pmMDW  Chicago Midway-BOI Boise Air Term. Gowen Fld
6h 50m1 stop Phoenix Sky Harbor Intl
$349Southwest
Sat, Oct 3 - Tue, Oct 20
Southwest Logo
7:05 am - 2:45 pmBOI  Boise Air Term. Gowen Fld-MDW Chicago Midway
6h 40m1 stop Phoenix Sky Harbor Intl
Southwest Logo
5:50 pm - 11:15 pmMDW  Chicago Midway-BOI Boise Air Term. Gowen Fld
6h 25m1 stop Las Vegas Harry Reid Intl
$349Southwest
Tue, Sep 29 - Tue, Oct 6

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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
Oct 28
PDX8:44 pmPortland
10h 00m
2 stops
MDW8:44 amChicago Midway
Nov 3
MDW12:27 pmChicago Midway
9h 33m
2 stops
PDX8:00 pmPortland
$313
Delta
Sep 30
EUG5:51 pmEugene
13h 16m
2 stops
MDW9:07 amChicago Midway
Oct 3
MDW1:19 pmChicago Midway
11h 40m
2 stops
EUG10:59 pmEugene
$361
Delta
Jan 11
PDX7:40 pmPortland
11h 05m
2 stops
MDW8:45 amChicago Midway
Jan 15
MDW1:00 pmChicago Midway
12h 32m
2 stops
PDX11:32 pmPortland
$374

Southwest flights from Oregon to Chicago Midway Airport

Our best Southwest deals on Oregon to Chicago Midway Airport flight tickets
Southwest
Oct 13
BOI4:40 pmBoise Air Term. Gowen Fld
6h 15m
1 stop
MDW11:55 pmChicago Midway
Oct 20
MDW7:25 amChicago Midway
9h 35m
1 stop
BOI4:00 pmBoise Air Term. Gowen Fld
$349
Southwest
Oct 13
BOI4:40 pmBoise Air Term. Gowen Fld
6h 15m
1 stop
MDW11:55 pmChicago Midway
Oct 20
MDW3:35 pmChicago Midway
9h 20m
2 stops
BOI11:55 pmBoise Air Term. Gowen Fld
$354
Southwest
Oct 15
PDX11:35 pmPortland
3h 50m
MDW5:25 amChicago Midway
Oct 19
MDW9:45 pmChicago Midway
4h 30m
PDX12:15 amPortland
$357

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

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Route

Depart

Return

Price

Cheapest round-trip

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Thu 12/3

5:30 am-4:50 pm

2 stops9h 20m

Chicago Midway

Tue 12/8

12:39 pm-10:06 pm

2 stops11h 27m

$313

PortlandChicago

PDX Portland - MDW Chicago Midway

PDXMDW

Portland

Wed 12/9

5:30 am-6:01 pm

2 stops10h 31m

Chicago Midway

Sat 12/12

10:24 am-8:58 pm

2 stops12h 34m

$313

MedfordChicago

MFR Medford - MDW Chicago Midway

MFRMDW

Medford

Mon 10/26

5:25 pm-10:03 am

2 stops14h 38m

Chicago Midway

Sat 11/7

1:27 pm-11:18 pm

2 stops11h 51m

$313

BoiseChicago

BOI Boise Air Term. Gowen Fld - MDW Chicago Midway

BOIMDW

Boise Air Term. Gowen Fld

Wed 10/28

6:15 am-1:25 pm

1 stop6h 10m

Chicago Midway

Mon 11/2

5:45 am-11:50 am

1 stop7h 05m

$349

BoiseChicago

BOI Boise Air Term. Gowen Fld - MDW Chicago Midway

BOIMDW

Boise Air Term. Gowen Fld

Tue 10/13

4:40 pm-11:55 pm

1 stop6h 15m

Chicago Midway

Tue 10/20

7:25 am-4:00 pm

1 stop9h 35m

$349

BoiseChicago

BOI Boise Air Term. Gowen Fld - MDW Chicago Midway

BOIMDW

Boise Air Term. Gowen Fld

Tue 9/22

5:30 am-1:20 pm

1 stop6h 50m

Chicago Midway

Tue 10/6

5:31 pm-11:59 pm

1 stop7h 28m

$349

BoiseChicago

BOI Boise Air Term. Gowen Fld - MDW Chicago Midway

BOIMDW

Boise Air Term. Gowen Fld

Mon 9/28

11:10 pm-9:49 am

1 stop9h 39m

Chicago Midway

Wed 9/30

7:13 pm-11:59 pm

1 stop5h 46m

$349

BoiseChicago

BOI Boise Air Term. Gowen Fld - MDW Chicago Midway

BOIMDW

Boise Air Term. Gowen Fld

Tue 10/13

4:40 pm-11:55 pm

1 stop6h 15m

Chicago Midway

Tue 10/20

7:25 am-4:00 pm

1 stop9h 35m

$349
Quickest round-trip

BoiseChicago

BOI Boise Air Term. Gowen Fld - MDW Chicago Midway

BOIMDW

Boise Air Term. Gowen Fld

Sat 10/3

4:55 pm-12:10 am

1 stop6h 15m

Chicago Midway

Tue 10/20

6:05 pm-11:55 pm

1 stop6h 50m

$349

BoiseChicago

BOI Boise Air Term. Gowen Fld - MDW Chicago Midway

BOIMDW

Boise Air Term. Gowen Fld

Tue 9/29

7:05 am-2:45 pm

1 stop6h 40m

Chicago Midway

Tue 10/6

5:50 pm-11:15 pm

1 stop6h 25m

$349

Flights are sorted by cheapest round-trip flights 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 December is also very affordable. Most momondo users find prices during this month for around $277.

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 $431. 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 $523.

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 $435 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $461. 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 31% 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

$174

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 $174. The best round-trip flight deal from Oregon to Chicago Midway Airport found on momondo in the last 72 hours is $313.
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

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
8.0
4,201 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
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
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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