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Cheap flights from Midway (MDW) to Portland (PDX) 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 7/17. 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.
MDW — PDX
Jun 12 — Jun 191
From?
To?
Wed 6/12
Wed 6/19
1 adult, Economy
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Cheap flight deals from Midway to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Portland (PDX). 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 7, 2024.

Popular in

April

Cheapest in

January

Round-trip from

$274

One-way from

$86
High demand for flights, 25% potential price rise
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Best time to find cheap flights, 42% potential price drop
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From Chicago Midway to Portland
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One-way flight from Chicago Midway to Portland
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What is the cheapest day to fly round-trip from Chicago Midway Airport to Portland?

Travelers have found that booking a Sunday departure is the best way to save up to 86% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.

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

To save up to 115% on this flight, we recommend booking at least 11 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Chicago Midway Airport to Portland from $253 1-2 weeks out and tickets from $558 for flights departing within the next 72 hours.

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

Due to multiple factors, expect to potentially pay more when booking in July. For low rates, January can be a great choice for travel to Portland. Flights to Portland from Chicago Midway Airport in January are about $352 on average during January, but can be found for as low as $158.

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

One of the essential ways to save on airfare from Chicago Midway Airport to Portland is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 50% on airfare.

Cheap Midway to Portland flights in June & July 2024

Find cheap flight options from Midway to Portland specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,050,429 searches. Prices were last updated on June 7, 2024.
Listed are some of the best fares we've found on flights departing from Chicago to Portland in 2024. Check back soon for alternative fares.
Tue 7/169:45 pmMDW - PDX
1 stop11h 04mFrontier
Tue 7/2311:43 amPDX - MDW
1 stop15h 02mFrontier
Deal found 6/6$175
Wed 7/1712:23 pmMDW - PDX
1 stop9h 09mFrontier
Fri 8/210:21 pmPDX - MDW
1 stop10h 52mFrontier
Deal found 6/5$178
Mon 7/15:55 amMDW - PDX
1 stop26h 55mFrontier
Mon 7/86:44 pmPDX - MDW
1 stop8h 49mFrontier
Deal found 6/6$180
Mon 7/15:55 amMDW - PDX
1 stop26h 55mFrontier
Mon 7/86:44 pmPDX - MDW
1 stop8h 49mFrontier
Deal found 6/6$188
Thu 6/66:35 amMDW - PDX
1 stop11h 51mFrontier
Sat 6/88:39 amPDX - MDW
1 stop24h 33mFrontier
Deal found 6/5$190
Sun 7/145:20 amMDW - PDX
1 stop12h 46mFrontier
Thu 7/184:28 pmPDX - MDW
1 stop10h 17mFrontier
Deal found 6/6$191
Mon 7/18:58 pmMDW - PDX
2 stops21h 40mFrontier
Mon 7/86:44 pmPDX - MDW
1 stop8h 49mFrontier
Deal found 6/6$193
Thu 7/48:43 pmMDW - PDX
1 stop22h 53mFrontier
Thu 7/114:28 pmPDX - MDW
1 stop10h 17mFrontier
Deal found 6/6$197
Wed 6/198:58 pmMDW - PDX
2 stops22h 27mFrontier
Sat 6/227:12 pmPDX - MDW
1 stop8h 09mFrontier
Deal found 6/7$198

Midway to Portland 2024 flight deals

Discover exclusive flight deals for travel between Midway and Portland in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated June 7, 2024.
Listed are some of the best fares we've found on flights departing from Chicago to Portland in 2024. Check back soon for alternative fares.
Wed 9/1811:32 amMDW - PDX
1 stop11h 04mFrontier
Mon 9/2312:48 amPDX - MDW
1 stop9h 04mFrontier
Deal found 6/6$172
Wed 9/411:32 amMDW - PDX
1 stop11h 04mFrontier
Tue 9/104:30 pmPDX - MDW
1 stop12h 03mFrontier
Deal found 6/6$173
Tue 7/169:45 pmMDW - PDX
1 stop11h 04mFrontier
Tue 7/2311:43 amPDX - MDW
1 stop15h 02mFrontier
Deal found 6/6$175
Tue 8/135:54 amMDW - PDX
1 stop12h 12mFrontier
Tue 8/204:30 pmPDX - MDW
1 stop12h 03mFrontier
Deal found 6/6$177
Wed 7/1712:23 pmMDW - PDX
1 stop9h 09mFrontier
Fri 8/210:21 pmPDX - MDW
1 stop10h 52mFrontier
Deal found 6/5$178
Sat 8/1010:20 amMDW - PDX
1 stop8h 14mFrontier
Wed 8/149:26 pmPDX - MDW
1 stop11h 16mFrontier
Deal found 6/5$179
Thu 8/155:54 amMDW - PDX
1 stop12h 12mFrontier
Mon 8/199:26 pmPDX - MDW
1 stop11h 16mFrontier
Deal found 6/6$180
Sun 9/15:54 amMDW - PDX
1 stop12h 12mFrontier
Tue 9/312:48 amPDX - MDW
1 stop9h 04mFrontier
Deal found 6/6$184
Mon 8/1212:23 pmMDW - PDX
1 stop11h 08mFrontier
Thu 8/1512:48 amPDX - MDW
1 stop9h 04mFrontier
Deal found 6/6$187

Midway to Portland flights leaving soon

Find last-minute flight options from Midway to Portland 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 3,050,429 searches. Data last updated June 7, 2024.
Have a look at some of the flights available from Chicago to Portland departing last-minute. Tip: verify your flight details before completing your reservation.
Fri 6/1411:26 amMDW - PDX
1 stop12h 04mFrontier
Sat 6/227:12 pmPDX - MDW
1 stop8h 09mFrontier
Deal found 6/6$227
Fri 6/1411:26 amMDW - PDX
1 stop12h 04mFrontier
Sat 6/226:25 pmPDX - MDW
2 stops8h 56mFrontier
Deal found 6/6$228
Fri 6/1411:26 amMDW - PDX
1 stop12h 04mFrontier
Wed 7/174:50 pmPDX - MDW
2 stops10h 43mFrontier
Deal found 6/6$231
Sat 6/1511:56 amMDW - PDX
1 stop12h 11mFrontier
Sat 6/226:25 pmPDX - MDW
2 stops8h 56mFrontier
Deal found 6/6$252
Fri 6/1411:26 amMDW - PDX
1 stop12h 04mFrontier
Fri 6/2110:22 pmPDX - MDW
1 stop10h 39mFrontier
Deal found 6/6$257
Sat 6/155:40 amMDW - PDX
1 stop20h 18mFrontier
Fri 6/2112:49 amPDX - MDW
1 stop18h 41mFrontier
Deal found 6/6$269
Fri 6/1411:26 amMDW - PDX
1 stop12h 04mFrontier
Tue 7/1612:49 amPDX - MDW
2 stops12h 19mFrontier
Deal found 6/6$277
Mon 6/178:58 pmMDW - PDX
1 stop21h 01mFrontier
Thu 6/204:02 pmPDX - MDW
1 stop11h 12mFrontier
Deal found 6/6$279
Sat 6/1511:56 amMDW - PDX
1 stop12h 11mFrontier
Thu 6/204:02 pmPDX - MDW
1 stop11h 12mFrontier
Deal found 6/6$284

One-way flights to Portland from Midway

Search for one-way flight options from Midway to Portland. 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 3,050,429 searches. Data last updated June 7, 2024.
Users in need of a one-way flight from Chicago to Portland can choose from these deals. Those seeking round-trip flights from Chicago to Portland should utilize the search form at the the top of the page.
Wed 7/1712:23 pmMDW - PDX
1 stop9h 09mFrontier
Deal found 6/6$86
Sun 6/165:05 amMDW - PDX
1 stop20h 51mFrontier
Deal found 6/6$89
Tue 8/67:00 amMDW - PDX
1 stop11h 06mFrontier
Deal found 6/6$92
Sat 6/2210:26 pmMDW - PDX
1 stop12h 19mFrontier
Deal found 6/6$93
Sun 9/225:54 amMDW - PDX
1 stop12h 12mFrontier
Deal found 6/6$96
Mon 7/15:55 amMDW - PDX
1 stop26h 55mFrontier
Deal found 6/6$99
Sun 6/308:20 pmMDW - PDX
1 stop23h 26mFrontier
Deal found 6/6$100
Tue 7/239:45 pmMDW - PDX
1 stop11h 04mFrontier
Deal found 6/5$103
Mon 8/1910:00 pmMDW - PDX
1 stop19h 54mFrontier
Deal found 6/7$104

Find flights from Midway to Portland within your budget

Customize your flight search to find flights from Midway to Portland 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 3,050,429 searches. Data last updated June 7, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$172 - $307

Route

Depart

Return

Price

Chicago MidwayPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 9/18

1 stop11h 04m

Portland

Mon 9/23

1 stop9h 04m

$172

Chicago MidwayPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 9/4

1 stop11h 04m

Portland

Tue 9/10

1 stop12h 03m

$173

Chicago MidwayPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 7/16

1 stop11h 04m

Portland

Tue 7/23

1 stop15h 02m

$175

Chicago MidwayPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 8/13

1 stop12h 12m

Portland

Tue 8/20

1 stop12h 03m

$177

Chicago MidwayPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 7/17

1 stop9h 09m

Portland

Fri 8/2

1 stop10h 52m

$178

Chicago MidwayPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 8/10

1 stop8h 14m

Portland

Wed 8/14

1 stop11h 16m

$179

Chicago MidwayPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 8/15

1 stop12h 12m

Portland

Mon 8/19

1 stop11h 16m

$180

Chicago MidwayPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 8/20

1 stop6h 09m

Portland

Thu 8/22

1 stop6h 03m

$276

Chicago MidwayPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 10/23

1 stop7h 58m

Portland

Fri 11/1

1 stop7h 41m

$307

Flights are sorted by cheapest first

Deals found on 6/6

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

Use this chart to determine the cheapest time to fly round-trip from Midway to Portland. Price data was last updated on June 2, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Chicago Midway Airport to Portland flight should consider departing on Sunday evenings when fares are most often at their lowest. Sunday 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 Midway to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Midway 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 Portland by month

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

PDX

Temperature

41 - 69.8 °F

If weather is an important factor for your trip to Portland, 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 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 41.0 F).

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated June 7, 2024.
Get a feel of what it's like to fly with Frontier and Delta from Chicago to Portland by reading reviews from past customers. 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
10,363 reviews

Comfort

7.9

Crew

8.6

Boarding

8.2

Entertainment

8.0

Food

7.4

Overall

8.0

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
10,363 reviews
Delta
8.0
Very good
10,363 reviews

Comfort

7.9

Crew

8.6

Boarding

8.2

Entertainment

8.0

Food

7.4

Overall

8.0

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
2,853 reviews
Delta
8.0
Very good
10,363 reviews

Comfort

7.9

Crew

8.6

Boarding

8.2

Entertainment

8.0

Food

7.4

Overall

8.0

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
3,977 reviews
Delta
8.0
Very good
10,363 reviews

Comfort

7.9

Crew

8.6

Boarding

8.2

Entertainment

8.0

Food

7.4

Overall

8.0

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 Midway to Portland. 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 into for flights to Portland from Chicago Midway?

    Most people fly into Portland (PDX) if they book a flight to Portland from Chicago Midway. On average, Portland has 1 inbound flight from Chicago Midway per day from 3 airlines. Portland is conveniently located just 6.0 mi from Portland’s city center.

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

    Yes, there are multiple flights from Chicago Midway Airport to Portland for under $200. The cheapest flight booked recently is on Frontier for just $172, but on average you can expect to pay $188.

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

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

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

    According to our current data, Frontier ($172), offers the cheapest pricing from Chicago Midway Airport to Portland. Frontier is currently priced 46% below the average price you’ll pay for this route.

  • What does MDW to PDX mean?

    This is defined as Chicago Midway Airport (MDW) and Portland Airport (PDX). Codes like Portland Airport are often used to just call airports uniquely.

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

    The amount of baggage you can bring on your Midway to Portland 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 Midway to Portland with specific airlines?

    Yes, Cheapflights allows you to browse and filter Midway to Portland 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 Midway to Portland that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Portland 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 Midway to Portland that allow pets onboard?

    Many airlines flying from Midway to Portland 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 Midway to Portland?

    Yes, you can often find last-minute deals on Midway to Portland 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 Chicago Midway Airport to Portland flight deals updated?

    The Chicago Midway Airport to Portland flight deals you see on this page were last updated on 6/6.

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

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

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

    Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Portland (average of $274). Flying from Chicago Midway Airport to Portland in July is currently the most expensive (average of $394). 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 Midway to Portland
See prices for flight routes from nearby airports that may be better suited for you.

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Top 3 airlines flying from Midway to Portland

Discover the top 3 airlines that operate flights from Midway to Portland. 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 3,050,429 searches. Data last updated June 7, 2024.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$139Average$387FlexibilityNo cancel feeOn-time69%
FrontierCheapest$167Average$218FlexibilityNo cancel feeOn-time62%
DeltaCheapest$296Average$639FlexibilityNo cancel feeOn-timeN/A
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Search flights from Midway to Portland by cabin class

Find flights from Midway to Portland, 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 Midway to Portland

Find hourly flight availability from Midway to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 7, 2024.
1%of flight departuresEarly morningMidnight to 6 am
44%of flight departuresMorning6 am to noon
33%of flight departuresAfternoonNoon to 6 pm
22%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Midway to Portland

Explore weekly flight availability from Midway to Portland. 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 7, 2024.
Sunday1daily flight
Monday1daily flight
Tuesday1daily flight
Wednesday1daily flight
Thursday1daily flight
Friday1daily flight
Saturday1daily flight

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