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Cheap flights from Portland (PWM) to Midway (MDW) from $77

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 7/11. 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
Jun 14 — Jun 211
From?
To?
Fri 6/14
Fri 6/21
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 June 9, 2024.

Popular in

August

Cheapest in

January

Average price

$671

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 June 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 $303 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 $401 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 47% on your journey compared to booking in April

What is the cheapest time of day to fly from PWM to 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 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 3,022,473 searches. Prices were last updated on June 9, 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.
Tue 6/183:23 pmPWM - MDW
1 stop6h 57mFrontier
Thu 7/45:20 amMDW - PWM
2 stops9h 05mFrontier
Deal found 6/8$229
Tue 6/189:59 amPWM - MDW
2 stops12h 21mFrontier
Thu 7/45:20 amMDW - PWM
2 stops9h 05mFrontier
Deal found 6/8$235
Thu 7/113:55 pmPWM - MDW
1 stop5h 14mFrontier
Sat 7/2011:51 amMDW - PWM
1 stop23h 06mFrontier
Deal found 6/8$244
Tue 7/23:23 pmPWM - MDW
1 stop6h 57mFrontier
Wed 7/171:05 pmMDW - PWM
1 stop23h 18mFrontier
Deal found 6/8$296
Tue 7/29:59 amPWM - MDW
2 stops12h 21mFrontier
Wed 7/171:05 pmMDW - PWM
1 stop23h 18mFrontier
Deal found 6/8$301
Tue 6/183:23 pmPWM - MDW
1 stop6h 57mFrontier
Thu 7/410:26 amMDW - PWM
1 stop8h 44mFrontier
Deal found 6/8$307
Thu 6/204:04 pmPWM - MDW
1 stop4h 52mFrontier
Sat 6/2911:51 amMDW - PWM
1 stop20h 15mFrontier
Deal found 6/8$337
Thu 6/131:57 pmPWM - MDW
1 stop28h 18mFrontier
Mon 6/1712:57 pmMDW - PWM
1 stop20h 52mFrontier
Deal found 6/8$378
Fri 6/145:37 amPWM - MDW
1 stop4h 11mDelta
Sat 6/155:45 pmMDW - PWM
1 stop4h 36mDelta
Deal found 6/8$388

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 3,022,473 searches. Data last updated June 9, 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 8/2211:46 amPWM - MDW
1 stop25h 37mFrontier
Mon 8/2612:15 pmMDW - PWM
1 stop21h 41mFrontier
Deal found 6/7$177
Tue 6/183:23 pmPWM - MDW
1 stop6h 57mFrontier
Thu 7/45:20 amMDW - PWM
2 stops9h 05mFrontier
Deal found 6/8$229
Wed 9/49:52 amPWM - MDW
1 stop13h 03mFrontier
Mon 9/911:38 amMDW - PWM
1 stop20h 24mFrontier
Deal found 6/7$231
Tue 6/189:59 amPWM - MDW
2 stops12h 21mFrontier
Thu 7/45:20 amMDW - PWM
2 stops9h 05mFrontier
Deal found 6/8$235
Thu 7/113:55 pmPWM - MDW
1 stop5h 14mFrontier
Sat 7/2011:51 amMDW - PWM
1 stop23h 06mFrontier
Deal found 6/8$244
Fri 8/239:52 amPWM - MDW
1 stop13h 03mFrontier
Fri 8/301:13 pmMDW - PWM
1 stop18h 49mFrontier
Deal found 6/8$246
Wed 9/1811:55 amPWM - MDW
1 stop7h 29mDelta
Mon 9/235:45 pmMDW - PWM
1 stop4h 41mDelta
Deal found 6/8$258
Sat 8/315:37 amPWM - MDW
1 stop4h 01mDelta
Wed 9/412:35 pmMDW - PWM
1 stop8h 25mDelta
Deal found 6/8$262
Wed 9/186:01 amPWM - MDW
2 stops9h 57mDelta
Mon 9/235:45 pmMDW - PWM
1 stop4h 41mDelta
Deal found 6/8$263

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 3,022,473 searches. Data last updated June 9, 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.
Tue 6/183:23 pmPWM - MDW
1 stop6h 57mFrontier
Thu 7/45:20 amMDW - PWM
2 stops9h 05mFrontier
Deal found 6/8$229
Tue 6/189:59 amPWM - MDW
2 stops12h 21mFrontier
Thu 7/45:20 amMDW - PWM
2 stops9h 05mFrontier
Deal found 6/8$235
Tue 6/183:23 pmPWM - MDW
1 stop6h 57mFrontier
Thu 7/410:26 amMDW - PWM
1 stop8h 44mFrontier
Deal found 6/8$307
Thu 6/131:57 pmPWM - MDW
1 stop28h 18mFrontier
Mon 6/1712:57 pmMDW - PWM
1 stop20h 52mFrontier
Deal found 6/8$378
Fri 6/145:37 amPWM - MDW
1 stop4h 11mDelta
Sat 6/155:45 pmMDW - PWM
1 stop4h 36mDelta
Deal found 6/8$388
Sat 6/155:37 amPWM - MDW
1 stop4h 11mDelta
Sun 6/166:00 amMDW - PWM
1 stop5h 33mDelta
Deal found 6/8$423
Fri 6/1411:57 amPWM - MDW
1 stop7h 39mDelta
Sat 6/1512:07 pmMDW - PWM
2 stops10h 14mDelta
Deal found 6/8$488
Sat 6/155:37 amPWM - MDW
1 stop4h 11mDelta
Sun 6/166:00 amMDW - PWM
2 stops9h 46mDelta
Deal found 6/8$503
Sat 6/155:37 amPWM - MDW
2 stops6h 50mDelta
Sun 6/166:00 amMDW - PWM
2 stops9h 46mDelta
Deal found 6/8$603

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 3,022,473 searches. Data last updated June 9, 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.
Thu 7/113:55 pmPWM - MDW
1 stop5h 14mFrontier
Deal found 6/7$77
Thu 7/113:55 pmPWM - MDW
1 stop5h 14mFrontier
Deal found 6/6$79
Fri 9/139:52 amPWM - MDW
1 stop13h 03mFrontier
Deal found 6/7$84
Tue 6/253:23 pmPWM - MDW
1 stop6h 57mFrontier
Deal found 6/7$87
Fri 9/139:52 amPWM - MDW
1 stop13h 03mFrontier
Deal found 6/6$111
Sat 8/176:15 amPWM - MDW
1 stop6h 29mDelta
Deal found 6/6$124
Sun 6/231:57 pmPWM - MDW
1 stop22h 13mFrontier
Deal found 6/8$130
Wed 6/195:37 amPWM - MDW
1 stop4h 11mDelta
Deal found 6/8$158
Sat 6/155:37 amPWM - MDW
1 stop4h 11mDelta
Deal found 6/8$164

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 3,022,473 searches. Data last updated June 9, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$177 - $501

Route

Depart

Return

Price

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Thu 8/22

1 stop25h 37m

Chicago Midway

Mon 8/26

1 stop21h 41m

$177

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Thu 8/29

1 stop4h 01m

Chicago Midway

Sat 9/7

1 stop8h 25m

$227

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Tue 6/18

1 stop6h 57m

Chicago Midway

Thu 7/4

2 stops9h 05m

$229

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Sun 6/23

1 stop22h 13m

Chicago Midway

Wed 6/26

1 stop23h 00m

$230

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Wed 9/4

1 stop13h 03m

Chicago Midway

Mon 9/9

1 stop20h 24m

$231

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Tue 6/18

2 stops12h 21m

Chicago Midway

Thu 7/4

2 stops9h 05m

$235

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Wed 9/18

1 stop7h 29m

Chicago Midway

Mon 9/23

1 stop4h 41m

$258

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Sat 8/31

1 stop4h 01m

Chicago Midway

Wed 9/4

1 stop8h 25m

$262

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Wed 6/26

1 stop5h 10m

Chicago Midway

Thu 6/27

2 stops13h 30m

$501

Flights are sorted by cheapest first

Deals found on 6/7

What is the cheapest day 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 June 2, 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. Friday 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 9, 2024.
To help decide which airline to fly from Portland to Chicago, see what other customers have to say about Frontier, Delta and Southwest. 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.
Southwest
8.2
Very good
5,905 reviews

Comfort

8.1

Overall

8.2

Food

7.3

Boarding

8.3

Entertainment

7.8

Crew

8.7

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Southwest
8.2
Very good
5,905 reviews
Southwest
8.2
Very good
5,905 reviews

Comfort

8.1

Overall

8.2

Food

7.3

Boarding

8.3

Entertainment

7.8

Crew

8.7

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Delta
8.0
Very good
10,310 reviews
Southwest
8.2
Very good
5,905 reviews

Comfort

8.1

Overall

8.2

Food

7.3

Boarding

8.3

Entertainment

7.8

Crew

8.7

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

WestJet
7.5
Good
2,850 reviews
Southwest
8.2
Very good
5,905 reviews

Comfort

8.1

Overall

8.2

Food

7.3

Boarding

8.3

Entertainment

7.8

Crew

8.7

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Frontier
6.2
Okay
3,975 reviews
Southwest
8.2
Very good
5,905 reviews

Comfort

8.1

Overall

8.2

Food

7.3

Boarding

8.3

Entertainment

7.8

Crew

8.7

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

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 Frontier for just $177, but on average you can expect to pay $268.

  • Are there nonstop flights from Portland, Maine to Chicago Midway Airport for under $700 on Cheapflights?

    Cheapflights has at least 1 direct flight from Portland, Maine to Chicago Midway Airport under $700. A good price for a nonstop flight from Portland, Maine to Chicago Midway Airport is less than $606.

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

    There are currently 13+ open flights from Portland, Maine to Chicago Midway Airport within the next 7 days for less than $300.

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

    Frontier, at $177, was found to be the cheapest airline from Portland, Maine to Chicago Midway Airport. An alternate airline flying to your destination would be Delta. These flights start at 64% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Portland, Maine to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $77 on Frontier. Other airlines that offer cheap prices include Delta from $124 and WestJet from $717 one-way.

  • 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 6/8.

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

    Currently, December is the cheapest month in which you can book a flight from Portland, Maine to Chicago Midway Airport (average of $141). Flying from Portland, Maine 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.

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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 3,022,473 searches. Data last updated June 9, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$347Average$493FlexibilityNo 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 9, 2024.
0%of flight departuresEarly morningMidnight to 6 am
0%of flight departuresMorning6 am to noon
100%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

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