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$62+ Cheap flights from Portland (PWM) 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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MDW
jul.. 31 — ag. 71
From?
To?
dc. 7/31
dc. 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 (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 juliol 26, 2024.

Popular in

June

Cheapest in

January

Round-trip from

$117
(mytrip.com)

One-way from

$62
(mytrip.com)
High demand for flights, 38% potential price rise
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Best time to find cheap flights, 54% 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, 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 50% 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 45 days before your planned departure. Booking around this time can save you about 70% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $277 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $363.

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 $388 per person but you can even find prices for as low as $93. 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?

When flying from Portland, Maine to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 2,751,780 searches. Prices were last updated on juliol 26, 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.
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.
dv. 8/238:26 pmPWM - MDW
1 stop20h 55mFrontier
dl. 8/261:23 pmMDW - PWM
1 stop5h 13mFrontier
Deal found 7/25$117
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.
dl. 8/264:53 pmPWM - MDW
1 stop7h 26mFrontier
dj. 8/299:04 pmMDW - PWM
1 stop18h 20mFrontier
Deal found 7/25$128
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.
dj. 8/291:58 pmPWM - MDW
1 stop23h 47mFrontier
dg. 9/19:04 pmMDW - PWM
1 stop17h 59mFrontier
Deal found 7/25$132
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.
dv. 8/235:14 pmPWM - MDW
1 stop7h 24mFrontier
dj. 8/299:04 pmMDW - PWM
1 stop18h 20mFrontier
Deal found 7/24$140
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.
dv. 8/165:14 pmPWM - MDW
1 stop7h 24mFrontier
dl. 8/191:23 pmMDW - PWM
1 stop5h 13mFrontier
Deal found 7/25$142
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.
dv. 8/165:14 pmPWM - MDW
1 stop7h 24mFrontier
dl. 8/191:23 pmMDW - PWM
1 stop5h 13mFrontier
Deal found 7/25$143
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.
dj. 8/221:58 pmPWM - MDW
1 stop23h 47mFrontier
dl. 8/261:23 pmMDW - PWM
1 stop5h 13mFrontier
Deal found 7/25$144
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.
dv. 8/165:14 pmPWM - MDW
1 stop7h 24mFrontier
dl. 8/191:23 pmMDW - PWM
1 stop5h 13mFrontier
Deal found 7/25$152
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.
dt. 8/64:06 pmPWM - MDW
1 stop6h 19mFrontier
dj. 8/810:26 amMDW - PWM
1 stop8h 35mFrontier
Deal found 7/25$157

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 2,751,780 searches. Data last updated juliol 26, 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.
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.
dv. 8/238:26 pmPWM - MDW
1 stop20h 55mFrontier
dl. 8/261:23 pmMDW - PWM
1 stop5h 13mFrontier
Deal found 7/25$117
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.
dl. 8/264:53 pmPWM - MDW
1 stop7h 26mFrontier
dj. 8/299:04 pmMDW - PWM
1 stop18h 20mFrontier
Deal found 7/25$128
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.
dj. 8/291:58 pmPWM - MDW
1 stop23h 47mFrontier
dg. 9/19:04 pmMDW - PWM
1 stop17h 59mFrontier
Deal found 7/25$132
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.
dv. 8/235:14 pmPWM - MDW
1 stop7h 24mFrontier
dj. 8/299:04 pmMDW - PWM
1 stop18h 20mFrontier
Deal found 7/24$140
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.
dv. 8/165:14 pmPWM - MDW
1 stop7h 24mFrontier
dl. 8/191:23 pmMDW - PWM
1 stop5h 13mFrontier
Deal found 7/25$142
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.
dv. 8/165:14 pmPWM - MDW
1 stop7h 24mFrontier
dl. 8/191:23 pmMDW - PWM
1 stop5h 13mFrontier
Deal found 7/25$143
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.
dj. 8/221:58 pmPWM - MDW
1 stop23h 47mFrontier
dl. 8/261:23 pmMDW - PWM
1 stop5h 13mFrontier
Deal found 7/25$144
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.
dv. 8/165:14 pmPWM - MDW
1 stop7h 24mFrontier
dl. 8/191:23 pmMDW - PWM
1 stop5h 13mFrontier
Deal found 7/25$152
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.
dt. 8/64:06 pmPWM - MDW
1 stop6h 19mFrontier
dj. 8/810:26 amMDW - PWM
1 stop8h 35mFrontier
Deal found 7/25$157

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 2,751,780 searches. Data last updated juliol 26, 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.
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.
dj. 8/13:55 pmPWM - MDW
1 stop5h 14mFrontier
dg. 8/410:40 amMDW - PWM
1 stop8h 21mFrontier
Deal found 7/25$388
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.
dj. 8/12:23 pmPWM - MDW
1 stop27h 42mFrontier
dg. 8/410:40 amMDW - PWM
1 stop8h 21mFrontier
Deal found 7/26$428
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dv. 8/212:55 pmPWM - MDW
1 stop5h 08mDelta
dl. 8/59:32 amMDW - PWM
1 stop5h 41mDelta
Deal found 7/25$508
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dc. 7/315:03 amPWM - MDW
2 stops8h 42mDelta
dl. 8/59:32 amMDW - PWM
1 stop5h 41mDelta
Deal found 7/24$578
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dv. 8/212:55 pmPWM - MDW
1 stop5h 08mDelta
dl. 8/59:32 amMDW - PWM
1 stop5h 41mDelta
Deal found 7/26$598
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dv. 8/212:55 pmPWM - MDW
1 stop5h 08mDelta
dl. 8/56:11 amMDW - PWM
2 stops10h 46mDelta
Deal found 7/26$663
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dc. 7/315:03 amPWM - MDW
2 stops8h 42mDelta
dl. 8/56:11 amMDW - PWM
2 stops10h 46mDelta
Deal found 7/24$668
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dj. 8/112:55 pmPWM - MDW
2 stops9h 51mDelta
dg. 8/49:33 amMDW - PWM
1 stop5h 44mDelta
Deal found 7/26$723
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dc. 7/315:37 amPWM - MDW
1 stop4h 01mDelta
dl. 8/59:32 amMDW - PWM
1 stop5h 41mDelta
Deal found 7/24$743

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 2,751,780 searches. Data last updated juliol 26, 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.
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.
dl. 10/219:52 amPWM - MDW
1 stop13h 03mFrontier
Deal found 7/25$62
This mytrip.com 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dt. 8/64:06 pmPWM - MDW
1 stop6h 19mFrontier
Deal found 7/26$80
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.
dt. 8/64:06 pmPWM - MDW
1 stop6h 19mFrontier
Deal found 7/25$81
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dj. 8/13:55 pmPWM - MDW
1 stop5h 14mFrontier
Deal found 7/26$123
This mytrip.com 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 mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dg. 9/225:55 pmPWM - MDW
1 stop21h 51mFrontier
Deal found 7/26$137
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dt. 7/304:01 pmPWM - MDW
1 stop6h 24mFrontier
Deal found 7/26$154
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.
dj. 8/12:23 pmPWM - MDW
1 stop27h 42mFrontier
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.
dg. 8/43:55 pmPWM - MDW
1 stop5h 14mFrontier
Deal found 7/25$161
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dg. 8/43:55 pmPWM - MDW
1 stop5h 14mFrontier
Deal found 7/26$163

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 2,751,780 searches. Data last updated juliol 26, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$117 - $206

Route

Depart

Return

Price

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

dv. 8/23

1 stop20h 55m

Chicago Midway

dl. 8/26

1 stop5h 13m

$117

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

dl. 8/26

1 stop7h 26m

Chicago Midway

dj. 8/29

1 stop18h 20m

$128

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

dj. 8/29

1 stop23h 47m

Chicago Midway

dg. 9/1

1 stop17h 59m

$132

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

dv. 8/23

1 stop7h 24m

Chicago Midway

dj. 8/29

1 stop18h 20m

$140

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

dv. 8/16

1 stop7h 24m

Chicago Midway

dl. 8/19

1 stop5h 13m

$142

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

dv. 8/16

1 stop7h 24m

Chicago Midway

dl. 8/19

1 stop5h 13m

$143

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

dj. 8/22

1 stop23h 47m

Chicago Midway

dl. 8/26

1 stop5h 13m

$144

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

dj. 9/12

1 stop4h 22m

Chicago Midway

dt. 9/17

1 stop8h 06m

$201

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

dj. 9/12

1 stop4h 22m

Chicago Midway

dt. 9/17

2 stops8h 42m

$206

Flights are sorted by cheapest first

Deals found on 7/25

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 July 21, 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 juliol 26, 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
8.0
Very good
9,615 reviews

Boarding

8.2

Entertainment

8.0

Food

7.4

Overall

8.0

Comfort

7.9

Crew

8.6

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
9,615 reviews
Delta
8.0
Very good
9,615 reviews

Boarding

8.2

Entertainment

8.0

Food

7.4

Overall

8.0

Comfort

7.9

Crew

8.6

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
2,759 reviews
Delta
8.0
Very good
9,615 reviews

Boarding

8.2

Entertainment

8.0

Food

7.4

Overall

8.0

Comfort

7.9

Crew

8.6

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
9,615 reviews

Boarding

8.2

Entertainment

8.0

Food

7.4

Overall

8.0

Comfort

7.9

Crew

8.6

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?

    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 $117, but on average you can expect to pay $185.

  • Are there last-minute flights available from Portland, Maine to Chicago Midway Airport for under $400?

    There are currently 18+ open flights from Portland, Maine to Chicago Midway Airport within the next 7 days for less than $400.

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

    Frontier, at $117, 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 76% 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 $62 on Frontier. Other airlines that offer cheap prices include Delta from $189 and WestJet from $735 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 7/25.

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

    Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Chicago Midway Airport (average of $137). Flying from Portland, Maine 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 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 2,751,780 searches. Data last updated juliol 26, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$342Average$457FlexibilityNo cancel feeOn-timeN/A
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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 juliol 26, 2024.
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0%of flight departuresMorning6 am to noon
100%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
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