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Cheap flights from Portland (PDX) to Midway (MDW) from $86

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 7/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
PDX — MDW
Jun 11 — Jun 181
From?
To?
Tue 6/11
Tue 6/18
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 June 6, 2024.

Popular in

January

Cheapest in

October

Round-trip from

$223

One-way from

$86
High demand for flights, 34% potential price rise
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Best time to find cheap flights, 26% 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 59 days before your planned departure. Booking around this time can save you about 23% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $332 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $615.

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 $361. You can even find prices in November for less than $361, as users have found deals to Chicago Midway Airport from as low as $127. The month of June 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 26%.

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 afternoon. Doing so could potentially save you 52% on the flight price compared to flying at noon, which is usually more expensive.

Cheap Portland to Midway flights in June & July 2024

Find cheap flight options from Portland to Midway specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,009,960 searches. Prices were last updated on June 6, 2024.
These are some of the most attractive deals on flights from Portland to Chicago in 2024. Check back regularly for other flight deals.
Thu 7/184:28 pmPDX - MDW
1 stop10h 17mFrontier
Tue 7/307:00 amMDW - PDX
1 stop11h 06mFrontier
Deal found 6/6$171
Tue 7/3011:43 amPDX - MDW
1 stop15h 02mFrontier
Wed 7/3112:23 pmMDW - PDX
2 stops31h 14mFrontier
Deal found 6/5$185
Mon 6/1012:49 amPDX - MDW
1 stop10h 20mFrontier
Thu 6/1310:41 pmMDW - PDX
1 stop27h 18mFrontier
Deal found 6/5$187
Thu 7/184:28 pmPDX - MDW
1 stop10h 17mFrontier
Mon 7/296:15 amMDW - PDX
1 stop19h 38mFrontier
Deal found 6/6$188
Thu 7/184:28 pmPDX - MDW
1 stop10h 17mFrontier
Sun 7/285:20 amMDW - PDX
1 stop12h 46mFrontier
Deal found 6/6$191
Thu 7/184:28 pmPDX - MDW
1 stop10h 17mFrontier
Tue 7/307:55 pmMDW - PDX
2 stops22h 05mFrontier
Deal found 6/6$193
Mon 6/1012:49 amPDX - MDW
1 stop10h 20mFrontier
Tue 6/187:00 amMDW - PDX
1 stop12h 11mFrontier
Deal found 6/4$200
Tue 7/911:43 amPDX - MDW
1 stop15h 02mFrontier
Fri 7/194:06 pmMDW - PDX
1 stop27h 40mFrontier
Deal found 6/5$209
Fri 7/2610:21 pmPDX - MDW
1 stop10h 52mFrontier
Wed 7/3112:23 pmMDW - PDX
1 stop9h 09mFrontier
Deal found 6/5$213

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 3,009,960 searches. Data last updated June 6, 2024.
These are some of the most attractive deals on flights from Portland to Chicago in 2024. Check back regularly for other flight deals.
Thu 7/184:28 pmPDX - MDW
1 stop10h 17mFrontier
Tue 7/307:00 amMDW - PDX
1 stop11h 06mFrontier
Deal found 6/6$171
Fri 9/612:48 amPDX - MDW
1 stop9h 04mFrontier
Wed 9/1111:32 amMDW - PDX
1 stop11h 04mFrontier
Deal found 6/5$172
Tue 8/204:30 pmPDX - MDW
1 stop12h 03mFrontier
Fri 8/2311:32 amMDW - PDX
1 stop11h 04mFrontier
Deal found 6/5$173
Mon 9/912:48 amPDX - MDW
1 stop9h 04mFrontier
Tue 9/175:54 amMDW - PDX
1 stop12h 12mFrontier
Deal found 6/5$178
Tue 9/1712:48 amPDX - MDW
1 stop9h 04mFrontier
Sun 9/225:54 amMDW - PDX
1 stop12h 12mFrontier
Deal found 6/4$180
Tue 7/3011:43 amPDX - MDW
1 stop15h 02mFrontier
Wed 7/3112:23 pmMDW - PDX
2 stops31h 14mFrontier
Deal found 6/5$185
Mon 6/1012:49 amPDX - MDW
1 stop10h 20mFrontier
Thu 6/1310:41 pmMDW - PDX
1 stop27h 18mFrontier
Deal found 6/5$187
Thu 7/184:28 pmPDX - MDW
1 stop10h 17mFrontier
Mon 7/296:15 amMDW - PDX
1 stop19h 38mFrontier
Deal found 6/6$188
Mon 8/2612:48 amPDX - MDW
1 stop9h 04mFrontier
Sat 8/316:00 amMDW - PDX
1 stop19h 40mFrontier
Deal found 6/6$189

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 3,009,960 searches. Data last updated June 6, 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.
Tue 6/1112:49 amPDX - MDW
1 stop9h 11mFrontier
Sat 6/1511:56 amMDW - PDX
1 stop12h 11mFrontier
Deal found 6/5$223
Tue 6/117:53 amPDX - MDW
1 stop7h 17mFrontier
Thu 6/1310:41 pmMDW - PDX
1 stop27h 18mFrontier
Deal found 6/5$224
Tue 6/115:41 pmPDX - MDW
2 stops8h 52mFrontier
Thu 6/1310:41 pmMDW - PDX
1 stop27h 18mFrontier
Deal found 6/5$230
Tue 6/117:53 amPDX - MDW
1 stop7h 17mFrontier
Tue 6/187:00 amMDW - PDX
1 stop12h 11mFrontier
Deal found 6/4$233
Tue 6/115:41 pmPDX - MDW
2 stops8h 52mFrontier
Tue 6/187:00 amMDW - PDX
1 stop12h 11mFrontier
Deal found 6/4$238
Tue 6/117:53 amPDX - MDW
1 stop7h 17mFrontier
Tue 7/99:45 pmMDW - PDX
1 stop11h 04mFrontier
Deal found 6/5$239
Tue 6/115:41 pmPDX - MDW
2 stops8h 52mFrontier
Mon 6/1711:26 amMDW - PDX
1 stop12h 04mFrontier
Deal found 6/5$251
Thu 6/1312:32 amPDX - MDW
1 stop9h 28mFrontier
Sun 6/165:54 amMDW - PDX
1 stop12h 12mFrontier
Deal found 6/5$276
Thu 6/138:52 amPDX - MDW
1 stop25h 08mFrontier
Mon 6/1711:26 amMDW - PDX
1 stop12h 04mFrontier
Deal found 6/5$281

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 3,009,960 searches. Data last updated June 6, 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.
Mon 7/16:36 pmPDX - MDW
1 stop8h 53mFrontier
Deal found 6/6$86
Tue 7/2311:43 amPDX - MDW
1 stop15h 02mFrontier
Deal found 6/6$92
Mon 9/212:48 amPDX - MDW
1 stop9h 04mFrontier
Deal found 6/5$93
Mon 7/86:44 pmPDX - MDW
1 stop8h 49mFrontier
Deal found 6/5$94
Fri 8/239:26 pmPDX - MDW
1 stop11h 16mFrontier
Deal found 6/5$96
Wed 6/1212:52 amPDX - MDW
1 stop8h 16mFrontier
Deal found 6/4$98
Fri 8/169:26 pmPDX - MDW
1 stop11h 16mFrontier
Deal found 6/5$101
Thu 8/1512:48 amPDX - MDW
1 stop9h 04mFrontier
Deal found 6/5$104
Mon 7/16:36 pmPDX - MDW
1 stop8h 53mFrontier
Deal found 6/5$107

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 3,009,960 searches. Data last updated June 6, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$171 - $307

Route

Depart

Return

Price

PortlandChicago Midway

PDX - MDW

PDXMDW

Portland

Tue 7/30

1 stop15h 02m

Chicago Midway

Wed 7/31

1 stop9h 09m

$171

PortlandChicago Midway

PDX - MDW

PDXMDW

Portland

Fri 9/6

1 stop9h 04m

Chicago Midway

Wed 9/11

1 stop11h 04m

$172

PortlandChicago Midway

PDX - MDW

PDXMDW

Portland

Tue 8/20

1 stop12h 03m

Chicago Midway

Fri 8/23

1 stop11h 04m

$173

PortlandChicago Midway

PDX - MDW

PDXMDW

Portland

Mon 9/9

1 stop9h 04m

Chicago Midway

Tue 9/17

1 stop12h 12m

$178

PortlandChicago Midway

PDX - MDW

PDXMDW

Portland

Tue 9/17

1 stop9h 04m

Chicago Midway

Sun 9/22

1 stop12h 12m

$180

PortlandChicago Midway

PDX - MDW

PDXMDW

Portland

Tue 7/30

1 stop15h 02m

Chicago Midway

Wed 7/31

2 stops31h 14m

$185

PortlandChicago Midway

PDX - MDW

PDXMDW

Portland

Mon 9/9

1 stop12h 03m

Chicago Midway

Wed 9/18

1 stop11h 04m

$187

PortlandChicago Midway

PDX - MDW

PDXMDW

Portland

Thu 7/18

1 stop10h 17m

Chicago Midway

Mon 7/29

1 stop19h 38m

$188

PortlandChicago Midway

PDX - MDW

PDXMDW

Portland

Thu 9/5

1 stop6h 03m

Chicago Midway

Sun 9/15

1 stop6h 22m

$307

Flights are sorted by cheapest first

Deals found on 6/5

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 June 2, 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 Friday mornings 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 June 6, 2024.
To help decide which airline to fly from Portland to Chicago, see what other customers have to say about Delta, Frontier and Southwest. 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
10,371 reviews

Entertainment

8.0

Boarding

8.2

Food

7.4

Overall

8.0

Crew

8.6

Comfort

7.9

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Delta
8.0
Very good
10,371 reviews
Delta
8.0
Very good
10,371 reviews

Entertainment

8.0

Boarding

8.2

Food

7.4

Overall

8.0

Crew

8.6

Comfort

7.9

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

WestJet
7.5
Good
2,856 reviews
Delta
8.0
Very good
10,371 reviews

Entertainment

8.0

Boarding

8.2

Food

7.4

Overall

8.0

Crew

8.6

Comfort

7.9

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Volaris
6.6
Okay
1,463 reviews
Delta
8.0
Very good
10,371 reviews

Entertainment

8.0

Boarding

8.2

Food

7.4

Overall

8.0

Crew

8.6

Comfort

7.9

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Frontier
6.2
Okay
3,982 reviews
Delta
8.0
Very good
10,371 reviews

Entertainment

8.0

Boarding

8.2

Food

7.4

Overall

8.0

Crew

8.6

Comfort

7.9

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

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 $171, but on average you can expect to pay $195.

  • Are there nonstop flights from Portland to Chicago Midway Airport for under $600 on Cheapflights?

    Cheapflights has at least 1 direct flight from Portland to Chicago Midway Airport under $600. A good price for a nonstop flight from Portland to Chicago Midway Airport is less than $572.

  • 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 $171, 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 50% 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 6/6.

  • 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, December is the cheapest month in which you can book a flight from Portland to Chicago Midway Airport (average of $141). Flying from Portland to Chicago Midway Airport in July is currently the most expensive (average of $249). 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.

See more FAQs

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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.

Portland to O'Hare Intl flights
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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 3,009,960 searches. Data last updated June 6, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$149Average$266FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$247Average$368FlexibilityNo cancel feeOn-time69%
DeltaCheapest$322Average$584FlexibilityNo 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.
First Class
Business Class
Prem Econ Class
Economy Class

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 June 6, 2024.
43%of flight departuresEarly morningMidnight to 6 am
29%of flight departuresMorning6 am to noon
28%of flight departuresAfternoonNoon to 6 pm
0%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 June 6, 2024.
Sunday3daily flights
Monday2daily flights
Tuesday2daily flights
Wednesday2daily flights
Thursday2daily flights
Friday2daily flights
Saturday1daily flight

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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Portland to Midway?

Deals for Portland to Midway flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Portland to Midway?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Midway from Portland.

Can Cheapflights find flights from Portland to Midway with no change fees?

Need flexible booking options for your flight to Midway from Portland? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Portland to Midway become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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