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$73+ Cheap flights from Portland (PDX) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MDW
Jul 31 — Aug 71
From?
To?
Wed 7/31
Wed 8/7
1 adult, Economy
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Cheap flight deals from Portland to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 26, 2024.

Popular in

January

Cheapest in

September

Round-trip from

$142
(mytrip.com)

One-way from

$73
(mytrip.com)
High demand for flights, 36% potential price rise
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Best time to find cheap flights, 24% potential price drop
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From Portland to Chicago Midway
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One-way flight from Portland to Chicago Midway
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What is the cheapest day to fly round-trip from Portland to Chicago Midway Airport?

Users have found that flying from Portland to Chicago Midway Airport on a Sunday typically leans towards higher prices. However, this doesn’t mean you still can’t find a deal. Flexibility with other aspects of your flight can still land a great price for your trip.

How far in advance should I book a flight from Portland to Chicago Midway Airport?

To save on the cost of your flight from Portland to Chicago Midway Airport, book at least 13 days before your planned departure. Booking around this time can save you about 51% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $195 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $413.

What is the cheapest month to fly from Portland to Chicago Midway Airport?

The best pricing can be found in the month of November. Prices to Chicago Midway Airport from Portland average $337. You can even find prices in November for less than $337, as users have found deals to Chicago Midway Airport from as low as $128. The month of March appears to be one of the more expensive times to travel to Chicago Midway Airport from Portland. Flying in the targeted month can save you up to 23%.

What is the cheapest time of day to fly from PDX to MDW?

It’s typically best to fly out from Portland to Chicago Midway Airport in the evening. Doing so could potentially save you 50% on the flight price compared to flying at noon, which is usually more expensive.

Cheap Portland to Midway flights in July & August 2024

Find cheap flight options from Portland to Midway specifically for the months of July and August 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,752,877 searches. Prices were last updated on July 26, 2024.
These are some of the most attractive deals on flights from Portland to Chicago in 2024. Check back regularly for other flight deals.
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1812:49 amPDX - MDW
1 stop16h 14mFrontier
Sat 8/2410:38 pmMDW - PDX
1 stop27h 21mFrontier
Deal found 7/25$145
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1910:53 amPDX - MDW
1 stop8h 18mFrontier
Sat 8/2410:38 pmMDW - PDX
1 stop27h 21mFrontier
Deal found 7/25$146
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2112:49 amPDX - MDW
1 stop8h 17mFrontier
Thu 8/298:44 pmMDW - PDX
1 stop15h 19mFrontier
Deal found 7/25$147
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2312:49 amPDX - MDW
1 stop6h 33mFrontier
Sat 8/2410:38 pmMDW - PDX
1 stop27h 21mFrontier
Deal found 7/25$150
This mytrip.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2012:49 amPDX - MDW
1 stop9h 25mFrontier
Sat 8/2410:38 pmMDW - PDX
1 stop27h 21mFrontier
Deal found 7/24$152
This CheapOair deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1612:49 amPDX - MDW
1 stop6h 33mFrontier
Mon 8/199:22 amMDW - PDX
1 stop16h 31mFrontier
Deal found 7/25$158
This CheapOair deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/151:20 pmPDX - MDW
1 stop29h 51mFrontier
Wed 8/216:15 amMDW - PDX
1 stop19h 34mFrontier
Deal found 7/25$161
This mytrip.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/188:20 pmPDX - MDW
1 stop10h 07mFrontier
Tue 8/276:00 amMDW - PDX
1 stop19h 49mFrontier
Deal found 7/24$162
This Gotogate deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1812:49 amPDX - MDW
1 stop16h 14mFrontier
Fri 8/2310:06 pmMDW - PDX
1 stop23h 45mFrontier
Deal found 7/25$163

Portland to Midway 2024 flight deals

Discover exclusive flight deals for travel between Portland and Midway in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,752,877 searches. Data last updated July 26, 2024.
These are some of the most attractive deals on flights from Portland to Chicago in 2024. Check back regularly for other flight deals.
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1611:18 amPDX - MDW
1 stop8h 52mFrontier
Mon 9/236:05 amMDW - PDX
1 stop6h 23mFrontier
Deal found 7/25$142
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1812:49 amPDX - MDW
1 stop16h 14mFrontier
Sat 8/2410:38 pmMDW - PDX
1 stop27h 21mFrontier
Deal found 7/25$145
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1910:53 amPDX - MDW
1 stop8h 18mFrontier
Sat 8/2410:38 pmMDW - PDX
1 stop27h 21mFrontier
Deal found 7/25$146
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2112:49 amPDX - MDW
1 stop8h 17mFrontier
Thu 8/298:44 pmMDW - PDX
1 stop15h 19mFrontier
Deal found 7/25$147
This Frontier deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/116:05 amPDX - MDW
1 stop7h 47mFrontier
Thu 9/127:45 pmMDW - PDX
1 stop6h 14mFrontier
Deal found 7/25$148
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2312:49 amPDX - MDW
1 stop6h 33mFrontier
Sat 8/2410:38 pmMDW - PDX
1 stop27h 21mFrontier
Deal found 7/25$150
This mytrip.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2012:49 amPDX - MDW
1 stop9h 25mFrontier
Sat 8/2410:38 pmMDW - PDX
1 stop27h 21mFrontier
Deal found 7/24$152
This CheapOair deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1612:49 amPDX - MDW
1 stop6h 33mFrontier
Mon 8/199:22 amMDW - PDX
1 stop16h 31mFrontier
Deal found 7/25$158
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/911:18 amPDX - MDW
1 stop8h 52mFrontier
Fri 9/135:02 pmMDW - PDX
1 stop9h 07mFrontier
Deal found 7/25$159

Portland to Midway flights leaving soon

Find last-minute flight options from Portland to Midway for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,752,877 searches. Data last updated July 26, 2024.
Have a look at some of the flights available from Portland to Chicago departing last-minute. Tip: verify your flight details before completing your reservation.
This CheapOair deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/59:49 pmPDX - MDW
1 stop28h 56mFrontier
Sun 8/116:00 amMDW - PDX
1 stop28h 23mFrontier
Deal found 7/25$238
This CheapOair deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/412:49 amPDX - MDW
1 stop9h 25mFrontier
Sun 8/116:00 amMDW - PDX
1 stop28h 23mFrontier
Deal found 7/25$268
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/59:49 pmPDX - MDW
1 stop28h 56mFrontier
Wed 8/78:59 pmMDW - PDX
1 stop23h 29mFrontier
Deal found 7/25$271
This Frontier deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/14:28 pmPDX - MDW
1 stop10h 17mFrontier
Sat 8/37:05 amMDW - PDX
1 stop11h 29mFrontier
Deal found 7/25$298
This Frontier deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/3112:49 amPDX - MDW
1 stop8h 13mFrontier
Sat 8/312:08 pmMDW - PDX
1 stop11h 56mFrontier
Deal found 7/25$328
This CheapOair deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/317:39 amPDX - MDW
1 stop25h 23mFrontier
Fri 8/28:59 pmMDW - PDX
1 stop26h 28mFrontier
Deal found 7/25$344
This CheapOair deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/3112:49 amPDX - MDW
1 stop19h 11mFrontier
Sat 8/312:08 pmMDW - PDX
1 stop11h 56mFrontier
Deal found 7/26$364
This Frontier deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/314:50 pmPDX - MDW
2 stops10h 43mFrontier
Fri 8/212:23 pmMDW - PDX
1 stop11h 08mFrontier
Deal found 7/25$369
This Gotogate deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/210:21 pmPDX - MDW
1 stop10h 52mFrontier
Mon 8/512:23 pmMDW - PDX
1 stop11h 08mFrontier
Deal found 7/25$373

One-way flights to Midway from Portland

Search for one-way flight options from Portland to Midway. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,752,877 searches. Data last updated July 26, 2024.
If you're seeking multiple options on one-way flights from Portland to Chicago, be sure to check out these deals, which are updated often. Those needing a return flight from Portland to Chicago can use the search form above.
This mytrip.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2610:53 amPDX - MDW
1 stop8h 18mFrontier
Deal found 7/24$73
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1812:49 amPDX - MDW
1 stop5h 38mFrontier
Deal found 7/25$74
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/312:49 amPDX - MDW
1 stop9h 25mFrontier
Deal found 7/25$78
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/248:22 amPDX - MDW
1 stop13h 27mFrontier
Deal found 7/25$79
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1912:49 amPDX - MDW
1 stop14h 21mFrontier
Deal found 7/25$80
This mytrip.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2012:49 amPDX - MDW
1 stop9h 25mFrontier
Deal found 7/24$81
This Trip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/291:20 pmPDX - MDW
1 stop29h 51mFrontier
Deal found 7/25$82
This Trip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/151:20 pmPDX - MDW
1 stop13h 53mFrontier
Deal found 7/25$85
This Frontier deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/162:03 pmPDX - MDW
1 stop8h 54mFrontier
Deal found 7/25$90

Find flights from Portland to Midway within your budget

Customize your flight search to find flights from Portland to Midway 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, Cheapflights users made 2,752,877 searches. Data last updated July 26, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$142 - $256

Route

Depart

Return

Price

PortlandChicago Midway

PDX - MDW

PDXMDW

Portland

Mon 9/16

1 stop8h 52m

Chicago Midway

Mon 9/23

1 stop6h 23m

$142

PortlandChicago Midway

PDX - MDW

PDXMDW

Portland

Thu 8/22

1 stop22h 01m

Chicago Midway

Thu 8/29

1 stop15h 19m

$145

PortlandChicago Midway

PDX - MDW

PDXMDW

Portland

Sun 8/18

1 stop5h 38m

Chicago Midway

Sat 8/31

1 stop23h 00m

$146

PortlandChicago Midway

PDX - MDW

PDXMDW

Portland

Wed 8/21

1 stop8h 17m

Chicago Midway

Thu 8/29

1 stop15h 19m

$147

PortlandChicago Midway

PDX - MDW

PDXMDW

Portland

Wed 9/11

1 stop7h 47m

Chicago Midway

Thu 9/12

1 stop6h 14m

$148

PortlandChicago Midway

PDX - MDW

PDXMDW

Portland

Tue 8/20

1 stop9h 25m

Chicago Midway

Sat 8/24

1 stop27h 21m

$152

PortlandChicago Midway

PDX - MDW

PDXMDW

Portland

Fri 8/16

1 stop6h 33m

Chicago Midway

Mon 8/19

1 stop16h 31m

$158

PortlandChicago Midway

PDX - MDW

PDXMDW

Portland

Mon 9/9

1 stop8h 52m

Chicago Midway

Fri 9/13

1 stop9h 07m

$159

PortlandChicago Midway

PDX - MDW

PDXMDW

Portland

Sat 9/7

1 stop5h 57m

Chicago Midway

Fri 9/13

1 stop6h 19m

$256

Flights are sorted by cheapest first

Deals found on 7/25

What is the cheapest day to fly from Portland to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Portland to Midway. Price data was last updated on July 21, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Portland to Chicago Midway Airport flight should consider departing on Wednesday evenings when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Best time to book a flight from Portland to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Portland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Temperature and rainfall in Midway by month

Plan your trip to Midway by taking into account the average temperature and rainfall totals by month.

CHI

Temperature

23 - 73.4 °F

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated July 26, 2024.
To help decide which airline to fly from Portland to Chicago, see what other customers have to say about Frontier and Delta. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
9,630 reviews

Crew

8.6

Food

7.4

Overall

8.0

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

Delta
8.0
Very good
9,630 reviews
Delta
8.0
Very good
9,630 reviews

Crew

8.6

Food

7.4

Overall

8.0

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

WestJet
7.4
Good
2,761 reviews
Delta
8.0
Very good
9,630 reviews

Crew

8.6

Food

7.4

Overall

8.0

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

Frontier
6.2
Okay
3,835 reviews
Delta
8.0
Very good
9,630 reviews

Crew

8.6

Food

7.4

Overall

8.0

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

Related info for your journey

Find useful and relevant information for your journey from Portland to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Portland to Chicago Midway?

    If you book a flight to Chicago Midway from Portland, you will be flying from Portland, which is the city’s only airport. Portland (PDX) is located 6.0 mi from the center of Portland. There are 2 flights from Portland to Chicago Midway per day from 3 different airlines.

  • Can I find flights from Portland to Chicago Midway Airport for under $200 on Cheapflights?

    Yes, there are multiple flights from Portland to Chicago Midway Airport for under $200. The cheapest flight booked recently is on Frontier for just $142, but on average you can expect to pay $160.

  • Are there last-minute flights available from Portland to Chicago Midway Airport for under $300?

    There are currently 20+ open flights from Portland to Chicago Midway Airport within the next 7 days for less than $300.

  • What is the cheapest airline to fly from Portland to Chicago Midway Airport round-trip?

    Currently priced at $142, Frontier will fly you from Portland to Chicago Midway Airport and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. This flight start at 58% lower than the current average price 3 months from now.

  • What does PDX to MDW mean?

    Great question - PDX to MDW just means Portland Airport to Chicago Midway Airport. Now you’ll know what these unique codes when you look for flights!

  • Can I find deals for flights from Portland to Midway that include extra baggage allowance?

    The amount of baggage you can bring on your Portland to Midway flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Portland to Midway with specific airlines?

    Yes, Cheapflights allows you to browse and filter Portland to Midway flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Portland to Midway that include hotel bookings?

    Yes. In addition to deals on Portland to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Midway.

  • Can I find deals for business class flights from Portland to Midway?

    Yes. Cheapflights offers flight deals from Portland to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Portland to Midway that allow pets onboard?

    Many airlines flying from Portland to Midway offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Portland to Midway?

    Yes, you can often find last-minute deals on Portland to Midway flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Portland to Chicago Midway Airport flight deals updated?

    The Portland to Chicago Midway Airport flight deals you see on this page were last updated on 7/25.

  • What are the most popular airlines that fly from Portland to Chicago Midway Airport?

    Consider Delta, Frontier or United Airlines when booking your flight. These represent the most popular airlines when flying from Portland to Chicago Midway Airport.

  • What is the cheapest month to book a flight from Portland to Chicago Midway Airport?

    Currently, September is the cheapest month in which you can book a flight from Portland to Chicago Midway Airport (average of $137). Flying from Portland to Chicago Midway Airport in July is currently the most expensive (average of $231). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for Portland to Midway
See prices for flight routes from nearby airports that may be better suited for you.

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Top 3 airlines flying from Portland to Midway

Discover the top 3 airlines that operate flights from Portland to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,752,877 searches. Data last updated July 26, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$150Average$258FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$247Average$368FlexibilityNo cancel feeOn-time69%
DeltaCheapest$326Average$551FlexibilityNo cancel feeOn-timeN/A
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Search flights from Portland to Midway by cabin class

Find flights from Portland to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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Hourly flight availability from Portland to Midway

Find hourly flight availability from Portland to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 26, 2024.
34%of flight departuresEarly morningMidnight to 6 am
13%of flight departuresMorning6 am to noon
33%of flight departuresAfternoonNoon to 6 pm
20%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Portland to Midway

Explore weekly flight availability from Portland to Midway. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 26, 2024.
Sunday3daily flights
Monday2daily flights
Tuesday2daily flights
Wednesday2daily flights
Thursday2daily flights
Friday2daily flights
Saturday1daily flight

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