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Cheap flights from Oregon to Chicago Midway Airport from $55

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 Midway Airport departing on 4/7. 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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Find the cheapest flights from Oregon to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Oregon to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Oregon to Chicago.

Cheap last minute flights

Planning a quick getaway from Oregon to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Oregon to Chicago

Find recent round-trip train or bus tickets from Oregon to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
12:03 pm - 12:17 amPDX-MDW
10h 14m1 stop
8:44 pm - 8:40 amMDW-PDX
13h 56m1 stop
$110Frontier
Find Deal
Mon, Feb 10 - Sat, Feb 22
7:35 am - 12:17 amPDX-MDW
14h 42m1 stop
7:05 am - 12:37 amMDW-PDX
19h 32m1 stop
$120Frontier
Find Deal
Wed, Feb 5 - Wed, Feb 12
7:35 am - 12:17 amPDX-MDW
14h 42m1 stop
7:05 am - 12:37 amMDW-PDX
19h 32m1 stop
$127Frontier
Find Deal
Tue, Feb 11 - Tue, Feb 18
6:32 am - 12:17 amPDX-MDW
15h 45m1 stop
8:44 pm - 8:40 amMDW-PDX
13h 56m1 stop
$129Frontier
Find Deal
Wed, Feb 19 - Sat, Feb 22
10:16 am - 12:17 amPDX-MDW
36h 01m2 stops
6:40 am - 12:37 amMDW-PDX
19h 57m1 stop
Mon, Feb 10 - Sat, Feb 22
5:30 pm - 12:17 amPDX-MDW
28h 47m2 stops
5:10 am - 7:31 pmMDW-PDX
16h 21m2 stops
Mon, Feb 10 - Sat, Feb 22
9:00 am - 2:55 pmPDX-MDW
3h 55mnonstop
8:30 am - 10:55 amMDW-PDX
4h 25mnonstop
$197Southwest
Find Deal
Wed, Feb 5 - Wed, Feb 12
9:00 am - 2:55 pmPDX-MDW
3h 55mnonstop
8:10 pm - 10:40 pmMDW-PDX
4h 30mnonstop
$207Southwest
Find Deal
Wed, Feb 5 - Mon, Feb 10
1:39 pm - 10:20 pmBOI-MDW
7h 41m1 stop
6:00 am - 12:28 pmMDW-BOI
7h 28m1 stop
$229Delta
Find Deal
Fri, Feb 7 - Sun, Feb 9
5:30 am - 12:46 pmBOI-MDW
6h 16m1 stop
2:08 pm - 11:58 pmMDW-BOI
10h 50m2 stops
$234Delta
Find Deal
Fri, Jan 31 - Mon, Feb 3
9:01 am - 8:14 pmPDX-MDW
9h 13m1 stop
$55Frontier
Find Deal
Mon, Apr 7
7:35 am - 12:17 amPDX-MDW
14h 42m1 stop
$58Frontier
Find Deal
Wed, Jan 29
9:00 am - 2:55 pmPDX-MDW
3h 55mnonstop
$99Southwest
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Tue, Feb 4
9:00 am - 2:55 pmPDX-MDW
3h 55mnonstop
$109Southwest
Find Deal
Sat, Feb 8
1:39 pm - 10:20 pmBOI-MDW
7h 41m1 stop
$115Delta
Find Deal
Fri, Feb 7
12:45 pm - 10:20 pmPDX-MDW
7h 35m1 stop
$119Delta
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Sat, Feb 8
11:16 am - 10:09 amPDX-MDW
20h 53m2 stops
$140Allegiant Air
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Thu, Mar 6
12:45 pm - 10:09 amPDX-MDW
19h 24m2 stops
$153Allegiant Air
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Thu, Mar 13
2:33 pm - 1:32 pmPDX-MDW
20h 59m3 stops
Wed, Mar 5
2:33 pm - 1:32 pmPDX-MDW
20h 59m3 stops
Wed, Mar 12
10:37 am - 11:48 amPDX-MDW
23h 11m1 stop
7:15 am - 11:01 amMDW-PDX
29h 46m1 stop
$348Frontier
Find Deal
Sun, Jan 12 - Thu, Jan 16
12:03 pm - 12:13 amPDX-MDW
10h 10m1 stop
8:15 am - 12:15 amMDW-PDX
18h 00m1 stop
$350Frontier
Find Deal
Sun, Jan 12 - Tue, Jan 14
5:30 am - 12:46 pmBOI-MDW
6h 16m1 stop
6:59 pm - 11:58 pmMDW-BOI
5h 59m1 stop
$439Delta
Find Deal
Fri, Jan 10 - Mon, Jan 13
5:30 am - 12:46 pmBOI-MDW
6h 16m1 stop
1:26 pm - 11:46 pmMDW-BOI
11h 20m2 stops
$444Delta
Find Deal
Fri, Jan 10 - Mon, Jan 13
11:25 am - 10:20 pmBOI-MDW
9h 55m2 stops
2:08 pm - 12:18 amMDW-BOI
11h 10m2 stops
$449Delta
Find Deal
Fri, Jan 10 - Mon, Jan 13
5:15 am - 12:00 pmBOI-MDW
5h 45m1 stop
2:30 pm - 10:45 pmMDW-BOI
9h 15m2 stops
$518Southwest
Find Deal
Fri, Jan 10 - Fri, Jan 10
11:50 am - 9:45 pmBOI-MDW
8h 55m1 stop
5:30 am - 12:00 pmMDW-BOI
7h 30m1 stop
$519Southwest
Find Deal
Fri, Jan 10 - Sun, Jan 12
6:25 am - 3:40 pmBOI-MDW
8h 15m1 stop
10:10 am - 10:55 pmMDW-BOI
13h 45m2 stops
$524Southwest
Find Deal
Fri, Jan 10 - Sun, Jan 12
9:00 am - 2:55 pmPDX-MDW
3h 55mnonstop
8:10 pm - 10:40 pmMDW-PDX
4h 30mnonstop
$627Southwest
Find Deal
Sat, Jan 11 - Fri, Jan 17
12:45 pm - 10:20 pmPDX-MDW
7h 35m1 stop
1:26 pm - 8:36 pmMDW-PDX
9h 10m1 stop
$692Delta
Find Deal
Wed, Jan 15 - Mon, Jan 20
9:00 am - 2:55 pmPDX-MDW
3h 55mnonstop
8:30 am - 10:55 amMDW-PDX
4h 25mnonstop
$197Southwest
Find Deal
Wed, Feb 5 - Wed, Feb 12
9:00 am - 2:55 pmPDX-MDW
3h 55mnonstop
8:10 pm - 10:40 pmMDW-PDX
4h 30mnonstop
$207Southwest
Find Deal
Wed, Feb 5 - Mon, Feb 10
8:00 am - 1:55 pmPDX-MDW
3h 55mnonstop
8:30 am - 10:55 amMDW-PDX
4h 25mnonstop
$217Southwest
Find Deal
Fri, Feb 7 - Sun, Feb 9
6:35 am - 12:30 pmPDX-MDW
3h 55mnonstop
8:30 am - 10:55 amMDW-PDX
4h 25mnonstop
$227Southwest
Find Deal
Thu, Feb 27 - Wed, Mar 5
8:00 am - 1:55 pmPDX-MDW
3h 55mnonstop
8:10 pm - 10:40 pmMDW-PDX
4h 30mnonstop
$237Southwest
Find Deal
Thu, Feb 20 - Mon, Feb 24
8:00 am - 1:55 pmPDX-MDW
3h 55mnonstop
8:05 pm - 10:30 pmMDW-PDX
4h 25mnonstop
$247Southwest
Find Deal
Thu, Feb 20 - Thu, Feb 27
9:00 am - 2:55 pmPDX-MDW
3h 55mnonstop
10:25 am - 12:45 pmMDW-PDX
4h 20mnonstop
$272Southwest
Find Deal
Tue, Mar 4 - Sun, Mar 9
9:00 am - 2:55 pmPDX-MDW
3h 55mnonstop
8:30 am - 10:55 amMDW-PDX
4h 25mnonstop
$308Southwest
Find Deal
Mon, Jan 27 - Wed, Jan 29
9:00 am - 2:55 pmPDX-MDW
3h 55mnonstop
8:10 pm - 10:40 pmMDW-PDX
4h 30mnonstop
$318Southwest
Find Deal
Sat, Jan 25 - Sun, Feb 2
12:55 pm - 6:50 pmPDX-MDW
3h 55mnonstop
10:25 am - 12:45 pmMDW-PDX
4h 20mnonstop
$327Southwest
Find Deal
Thu, Mar 6 - Sun, Mar 9

Southwest flights from Oregon to Chicago Midway Airport

Our best Southwest deals on Oregon to Chicago Midway Airport flight tickets
Southwest
Feb 5
PDX9:00 amPortland
3h 55m
MDW2:55 pmChicago Midway
Feb 12
MDW8:30 amChicago Midway
4h 25m
PDX10:55 amPortland
Southwest
Feb 5
PDX9:00 amPortland
3h 55m
MDW2:55 pmChicago Midway
Feb 10
MDW8:10 pmChicago Midway
4h 30m
PDX10:40 pmPortland
Southwest
Feb 7
PDX8:00 amPortland
3h 55m
MDW1:55 pmChicago Midway
Feb 9
MDW8:30 amChicago Midway
4h 25m
PDX10:55 amPortland

Frontier flights from Oregon to Chicago Midway Airport

Our best Frontier deals on Oregon to Chicago Midway Airport flight tickets
Frontier
Feb 10
PDX12:03 pmPortland
10h 14m
1 stop
MDW12:17 amChicago Midway
Feb 22
MDW8:44 pmChicago Midway
13h 56m
1 stop
PDX8:40 amPortland
Frontier
Feb 5
PDX7:35 amPortland
14h 42m
1 stop
MDW12:17 amChicago Midway
Feb 12
MDW7:05 amChicago Midway
19h 32m
1 stop
PDX12:37 amPortland
Frontier
Feb 11
PDX7:35 amPortland
14h 42m
1 stop
MDW12:17 amChicago Midway
Feb 18
MDW7:05 amChicago Midway
19h 32m
1 stop
PDX12:37 amPortland

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 May is, on average, the cheapest month to fly to Chicago Midway Airport from Oregon, with most prices found around $267. If you are unable to visit Chicago Midway Airport during the month of May, then departing from Oregon during the month July is also very affordable. Most momondo users find prices during this month for around $282.

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

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Oregon. The lowest ticket price found for a Wednesday departure recently was $285. 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 $559.

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 $318 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $455. 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.

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

$55

Fastest flight time

3h 55m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Oregon in the past 72 hours is $55. The best round-trip flight deal from Oregon to Chicago Midway Airport found on momondo in the last 72 hours is $110.
The fastest flight from Oregon to Chicago Midway Airport takes 3h 55m
Direct flights go from Oregon to Chicago Midway Airport every day.

  • 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 $134Free CancellationRating
6.0
3,429 reviews
Search Frontier flights
DeltaPriceFrom $216Free CancellationRating
8.0
8,501 reviews
Search Delta flights
SouthwestPriceFrom $233Free CancellationRating
8.1
4,650 reviews
Search Southwest flights

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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