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Cheap flights from Portland (PWM) to Midway (MDW) from $52

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 5/21. 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.
PWM — MDW
May 13 — May 201
From?
To?
Mon 5/13
Mon 5/20
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 (PWM) 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 May 8, 2024.

Popular in

August

Cheapest in

January

Average price

$611

Round-trip from

$223
High demand for flights, 34% potential price rise
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Best time to find cheap flights, 53% potential price drop
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Average for round-trip flights in May 2024
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From Portland to Chicago Midway
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What is the cheapest day to fly round-trip from Portland, Maine to Chicago Midway Airport?

Leaving on a Saturday is a viable option for saving on travel. Heavily demanded days of the week can typically drive up the prices you see. Booking your travel for a less competitive day can save up to 30% on the overall cost on flights from Portland, Maine to Chicago Midway Airport.

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

To save on the cost of your flight from Portland, Maine to Chicago Midway Airport, book at least 44 days before your planned departure. Booking around this time can save you about 101% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $329 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $539.

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

September is one of the best times of the year to fly to Chicago Midway Airport from Portland, Maine. Prices for September average $411 per person but you can even find prices for as low as $158. The most expensive prices can be found in the month of April. Opting for a September flight can save you 43% on your journey compared to booking in April

When is the cheapest time to fly from Portland, Maine to Chicago Midway Airport (PWM - MDW)?

One of the essential ways to save on airfare from Portland, Maine to Chicago Midway Airport is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 17% on airfare.

Cheap Delta flights from Portland to Midway

Explore cheap flight options specifically provided by Delta for the route between Portland and Midway. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,749,864 searches. Data last updated May 8, 2024.
Check out some of the cheapest Delta flights we've come across from Portland to Chicago. Make sure to check back often as deals are often changing.
Tue 7/25:37 amPWM - MDW
1 stop4h 12mDelta
Tue 7/95:45 pmMDW - PWM
1 stop4h 39mDelta
Deal found 5/7$196
Wed 6/265:37 amPWM - MDW
1 stop4h 11mDelta
Sat 6/295:45 pmMDW - PWM
1 stop4h 36mDelta
Deal found 5/7$233
Thu 6/65:00 amPWM - MDW
1 stop5h 06mDelta
Thu 6/133:45 pmMDW - PWM
1 stop5h 13mDelta
Deal found 5/7$238
Tue 7/25:37 amPWM - MDW
2 stops6h 51mDelta
Tue 7/95:45 pmMDW - PWM
1 stop4h 39mDelta
Deal found 5/7$241
Thu 6/66:27 amPWM - MDW
2 stops7h 13mDelta
Thu 6/133:45 pmMDW - PWM
1 stop5h 13mDelta
Deal found 5/7$243
Thu 6/65:00 amPWM - MDW
1 stop5h 06mDelta
Sat 6/85:45 pmMDW - PWM
1 stop4h 36mDelta
Deal found 5/6$248
Thu 6/66:27 amPWM - MDW
2 stops7h 13mDelta
Sat 6/85:45 pmMDW - PWM
1 stop4h 36mDelta
Deal found 5/6$253
Fri 7/195:37 amPWM - MDW
1 stop4h 03mDelta
Mon 7/225:45 pmMDW - PWM
1 stop4h 39mDelta
Deal found 5/7$258
Mon 7/85:37 amPWM - MDW
1 stop4h 03mDelta
Wed 7/101:24 pmMDW - PWM
2 stops8h 32mDelta
Deal found 5/7$263

Cheap Frontier flights from Portland to Midway

Explore cheap flight options specifically provided by Frontier for the route between Portland and Midway. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,749,864 searches. Data last updated May 8, 2024.
To aid your search, here are some of the cheapest Frontier flights we've found from Portland to Chicago. Deals are refreshing constantly so come back soon for more options.
Thu 5/161:11 pmPWM - MDW
1 stop7h 29mFrontier
Mon 5/206:30 pmMDW - PWM
1 stop13h 39mFrontier
Deal found 5/6$150
Thu 5/161:11 pmPWM - MDW
2 stops8h 06mFrontier
Mon 5/206:30 pmMDW - PWM
1 stop13h 39mFrontier
Deal found 5/6$155
Sun 6/94:04 pmPWM - MDW
1 stop4h 52mFrontier
Wed 6/1212:57 pmMDW - PWM
1 stop23h 00mFrontier
Deal found 5/7$217
Thu 6/274:04 pmPWM - MDW
1 stop4h 52mFrontier
Wed 7/312:57 pmMDW - PWM
1 stop23h 00mFrontier
Deal found 5/7$347
Thu 6/204:04 pmPWM - MDW
1 stop4h 52mFrontier
Sun 6/2310:28 amMDW - PWM
1 stop8h 34mFrontier
Deal found 5/7$375
Thu 10/1011:46 amPWM - MDW
1 stop25h 37mFrontier
Mon 10/1411:38 amMDW - PWM
1 stop20h 24mFrontier
Deal found 5/7$438
Fri 10/119:52 amPWM - MDW
1 stop13h 03mFrontier
Mon 10/1411:38 amMDW - PWM
1 stop20h 24mFrontier
Deal found 5/7$558

Cheap Portland to Midway flights in May & June 2024

Find cheap flight options from Portland to Midway specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,749,864 searches. Prices were last updated on May 8, 2024.
Scroll through some of the best deals on flights from Portland to Chicago in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Thu 5/161:11 pmPWM - MDW
1 stop7h 29mFrontier
Mon 5/206:30 pmMDW - PWM
1 stop13h 39mFrontier
Deal found 5/6$150
Thu 5/161:11 pmPWM - MDW
2 stops8h 06mFrontier
Mon 5/206:30 pmMDW - PWM
1 stop13h 39mFrontier
Deal found 5/6$155
Sun 6/94:04 pmPWM - MDW
1 stop4h 52mFrontier
Wed 6/1212:57 pmMDW - PWM
1 stop23h 00mFrontier
Deal found 5/7$217
Wed 6/265:37 amPWM - MDW
1 stop4h 11mDelta
Sat 6/295:45 pmMDW - PWM
1 stop4h 36mDelta
Deal found 5/7$233
Thu 6/65:00 amPWM - MDW
1 stop5h 06mDelta
Thu 6/133:45 pmMDW - PWM
1 stop5h 13mDelta
Deal found 5/7$238
Thu 6/66:27 amPWM - MDW
2 stops7h 13mDelta
Thu 6/133:45 pmMDW - PWM
1 stop5h 13mDelta
Deal found 5/7$243
Thu 6/65:00 amPWM - MDW
1 stop5h 06mDelta
Sat 6/85:45 pmMDW - PWM
1 stop4h 36mDelta
Deal found 5/6$248
Thu 6/66:27 amPWM - MDW
2 stops7h 13mDelta
Sat 6/85:45 pmMDW - PWM
1 stop4h 36mDelta
Deal found 5/6$253
Sun 6/95:37 amPWM - MDW
1 stop4h 11mDelta
Wed 6/121:24 pmMDW - PWM
2 stops8h 36mDelta
Deal found 5/7$288

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 2,749,864 searches. Data last updated May 8, 2024.
Scroll through some of the best deals on flights from Portland to Chicago in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Thu 5/161:11 pmPWM - MDW
1 stop7h 29mFrontier
Mon 5/206:30 pmMDW - PWM
1 stop13h 39mFrontier
Deal found 5/6$150
Thu 5/161:11 pmPWM - MDW
2 stops8h 06mFrontier
Mon 5/206:30 pmMDW - PWM
1 stop13h 39mFrontier
Deal found 5/6$155
Tue 7/25:37 amPWM - MDW
1 stop4h 12mDelta
Tue 7/95:45 pmMDW - PWM
1 stop4h 39mDelta
Deal found 5/7$196
Sun 6/94:04 pmPWM - MDW
1 stop4h 52mFrontier
Wed 6/1212:57 pmMDW - PWM
1 stop23h 00mFrontier
Deal found 5/7$217
Wed 6/265:37 amPWM - MDW
1 stop4h 11mDelta
Sat 6/295:45 pmMDW - PWM
1 stop4h 36mDelta
Deal found 5/7$233
Thu 6/65:00 amPWM - MDW
1 stop5h 06mDelta
Thu 6/133:45 pmMDW - PWM
1 stop5h 13mDelta
Deal found 5/7$238
Tue 7/25:37 amPWM - MDW
2 stops6h 51mDelta
Tue 7/95:45 pmMDW - PWM
1 stop4h 39mDelta
Deal found 5/7$241
Thu 6/66:27 amPWM - MDW
2 stops7h 13mDelta
Thu 6/133:45 pmMDW - PWM
1 stop5h 13mDelta
Deal found 5/7$243
Thu 6/65:00 amPWM - MDW
1 stop5h 06mDelta
Sat 6/85:45 pmMDW - PWM
1 stop4h 36mDelta
Deal found 5/6$248

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 2,749,864 searches. Data last updated May 8, 2024.
Have a look at some of the flights available from Portland to Chicago departing last-minute. To prevent any unwanted surprises, users should verify their flight info before booking.
Thu 5/161:11 pmPWM - MDW
1 stop7h 29mFrontier
Mon 5/206:30 pmMDW - PWM
1 stop13h 39mFrontier
Deal found 5/6$150
Thu 5/161:11 pmPWM - MDW
2 stops8h 06mFrontier
Mon 5/206:30 pmMDW - PWM
1 stop13h 39mFrontier
Deal found 5/6$155
Sat 5/185:00 amPWM - MDW
1 stop4h 51mDelta
Sat 5/255:47 pmMDW - PWM
1 stop4h 57mDelta
Deal found 5/7$574
Sat 5/185:00 amPWM - MDW
2 stops10h 55mDelta
Sat 5/255:47 pmMDW - PWM
1 stop4h 57mDelta
Deal found 5/7$579
Wed 5/155:00 amPWM - MDW
2 stops9h 35mDelta
Thu 5/1612:42 pmMDW - PWM
1 stop8h 17mDelta
Deal found 5/7$634
Sat 5/185:00 amPWM - MDW
2 stops10h 55mDelta
Sat 5/2511:59 amMDW - PWM
2 stops10h 45mDelta
Deal found 5/7$638
Wed 5/155:00 amPWM - MDW
2 stops9h 35mDelta
Fri 5/171:21 pmMDW - PWM
2 stops8h 29mDelta
Deal found 5/7$644
Fri 5/175:00 amPWM - MDW
1 stop5h 06mDelta
Tue 5/211:21 pmMDW - PWM
2 stops8h 29mDelta
Deal found 5/7$669
Fri 5/175:00 amPWM - MDW
1 stop5h 06mDelta
Mon 5/205:47 pmMDW - PWM
1 stop4h 57mDelta
Deal found 5/7$670

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 2,749,864 searches. Data last updated May 8, 2024.
Take a look at some of the one-way flights we've detected from Portland to Chicago. For those needing a return trip from Portland, there is a search form available above.
Tue 5/2111:40 amPWM - MDW
1 stop20h 14mFrontier
Deal found 5/7$52
Tue 5/2811:40 amPWM - MDW
1 stop20h 14mFrontier
Deal found 5/7$66
Tue 6/253:23 pmPWM - MDW
1 stop6h 57mFrontier
Deal found 5/7$80
Mon 5/139:11 amPWM - MDW
1 stop14h 25mFrontier
Deal found 5/7$84
Mon 5/139:11 amPWM - MDW
1 stop14h 25mFrontier
Deal found 5/7$87
Thu 5/301:11 pmPWM - MDW
2 stops8h 06mFrontier
Deal found 5/7$92
Thu 7/2511:46 amPWM - MDW
1 stop25h 37mFrontier
Deal found 5/7$113
Sun 6/95:37 amPWM - MDW
1 stop4h 11mDelta
Deal found 5/7$119
Thu 6/135:37 amPWM - MDW
2 stops7h 18mDelta
Deal found 5/7$124

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 2,749,864 searches. Data last updated May 8, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$196 - $347

Route

Depart

Return

Price

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Tue 7/2

1 stop4h 12m

Chicago Midway

Tue 7/9

1 stop4h 39m

$196

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Sun 6/9

1 stop4h 52m

Chicago Midway

Wed 6/12

1 stop23h 00m

$217

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Wed 6/26

1 stop4h 11m

Chicago Midway

Sat 6/29

1 stop4h 36m

$233

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Thu 6/6

1 stop5h 06m

Chicago Midway

Thu 6/13

1 stop5h 13m

$238

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Tue 7/2

2 stops6h 51m

Chicago Midway

Tue 7/9

1 stop4h 39m

$241

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Thu 6/6

2 stops7h 13m

Chicago Midway

Thu 6/13

1 stop5h 13m

$243

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Thu 6/6

1 stop5h 06m

Chicago Midway

Sat 6/8

1 stop4h 36m

$248

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Thu 6/6

2 stops7h 13m

Chicago Midway

Sat 6/8

1 stop4h 36m

$253

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Thu 6/27

1 stop4h 52m

Chicago Midway

Wed 7/3

1 stop23h 00m

$347

Flights are sorted by cheapest first

Deals found on 5/7

When is the cheapest time to fly from Portland, Maine 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 May 5, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Portland, Maine to Chicago Midway Airport flight should consider departing on Sunday mornings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Average price of flights to Midway by month

Plan your trip from Portland to Midway by taking into account the cheapest months to travel. The average price of a one-way flight from Portland to Midway is currently $91 while a round-trip flight costs $246. Price data was last updated on May 5, 2024.

Currently, December is the cheapest month in which you can book a flight from Portland, Maine to Chicago Midway Airport (average of $140). Flying from Portland, Maine to Chicago Midway Airport in July is currently the most expensive (average of $252). 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.

January

$194

February

$190

March

$219

April

$159

May

$188

June

$230

July

$252

August

$196

September

$158

October

$143

November

$166

December

$140

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

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 May 8, 2024.
To help decide which airline to fly from Portland to Chicago, see what other customers have to say about Delta and Frontier. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.1
Very good
10,810 reviews
Check prices

Comfort

7.9

Boarding

8.2

Crew

8.6

Entertainment

8.0

Overall

8.1

Food

7.4

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
8.1
Very good
10,810 reviews
Delta
8.1
Very good
10,810 reviews
Check prices

Comfort

7.9

Boarding

8.2

Crew

8.6

Entertainment

8.0

Overall

8.1

Food

7.4

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
7.6
Good
2,945 reviews
Delta
8.1
Very good
10,810 reviews
Check prices

Comfort

7.9

Boarding

8.2

Crew

8.6

Entertainment

8.0

Overall

8.1

Food

7.4

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
6.3
Okay
4,088 reviews
Delta
8.1
Very good
10,810 reviews
Check prices

Comfort

7.9

Boarding

8.2

Crew

8.6

Entertainment

8.0

Overall

8.1

Food

7.4

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?

    For a flight from Portland to Chicago Midway, you will be flying from Portland. Portland (PWM) is just 2.9 mi from the center of the city. Portland is the only Portland airport and it handles 0 outbound flights to Chicago Midway per day. 1 airline has flights to Chicago Midway from Portland on a regular basis.

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

    Yes, there are multiple flights from Portland, Maine to Chicago Midway Airport for under $200. The cheapest flight booked recently is on Delta for just $196, but on average you can expect to pay $266.

  • Are there last-minute flights available from Portland, Maine to Chicago Midway Airport for under $200?

    There are currently 20+ open flights from Portland, Maine to Chicago Midway Airport within the next 7 days for less than $200.

  • What are the cheapest airlines flying from Portland, Maine to Chicago Midway Airport round-trip?

    Delta, at $196, was found to be the cheapest airline from Portland, Maine to Chicago Midway Airport. An alternate airline flying to your destination would be Frontier. These flights start at 60% lower than the current average price 3 months from now.

  • What does PWM to MDW mean?

    PWM stands for Portland Airport, while MDW stands for Chicago Midway Airport. These codes are often called IATA codes, a set of identifiers established by IATA (International Air Transport Association) that is widely used by airlines and the aviation industry.

  • 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, Maine to Chicago Midway Airport flight deals updated?

    The Portland, Maine to Chicago Midway Airport flight deals you see on this page were last updated on 5/7.

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
Bangor to O'Hare Intl flights
Bangor to Midway flights
Bar Harbor to O'Hare Intl flights
Augusta to O'Hare Intl flights
Rockland to O'Hare Intl flights

Top airline flying from Portland to Midway

Discover the top airline 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 2,749,864 searches. Data last updated May 8, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$337Average$457FlexibilityNo 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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Business Class
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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?

Yes! Cheapflights helps users easily find flights from Portland to Midway with no change fees.

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Not ready to book yet? You can track prices for flights from Portland to Midway on Cheapflights with our Price Alert feature and get notified when better prices are available.

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