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Cheap flights from Portland (PWM) to Midway (MDW) from $59

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 2 — May 91
From?
To?
Thu 5/2
Thu 5/9
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 April 27, 2024.

Round-trip from

$222
From Portland to Chicago Midway
Search Deals

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 43 days before your planned departure. Booking around this time can save you about 92% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $478 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 $384 per person but you can even find prices for as low as $166. The most expensive prices can be found in the month of April. Opting for a September flight can save you 40% 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 2,991,349 searches. Data last updated April 27, 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.
Thu 6/135:37 amPWM - MDW
1 stop4h 11mDelta
Mon 6/175:45 pmMDW - PWM
1 stop4h 36mDelta
Deal found 4/26$243
Thu 6/135:37 amPWM - MDW
1 stop4h 11mDelta
Mon 6/172:24 pmMDW - PWM
2 stops7h 57mDelta
Deal found 4/26$248
Thu 8/295:40 amPWM - MDW
1 stop4h 04mDelta
Sun 9/16:00 amMDW - PWM
2 stops7h 25mDelta
Deal found 4/26$253
Thu 10/245:30 amPWM - MDW
2 stops10h 26mDelta
Tue 10/299:35 amMDW - PWM
1 stop5h 32mDelta
Deal found 4/26$277
Thu 10/245:30 amPWM - MDW
2 stops10h 26mDelta
Tue 10/291:05 pmMDW - PWM
2 stops9h 02mDelta
Deal found 4/26$282
Thu 6/135:37 amPWM - MDW
1 stop4h 11mDelta
Sat 6/153:45 pmMDW - PWM
1 stop5h 14mDelta
Deal found 4/27$289
Sat 7/205:37 amPWM - MDW
1 stop4h 03mDelta
Tue 7/235:45 pmMDW - PWM
1 stop4h 39mDelta
Deal found 4/27$329
Thu 8/295:40 amPWM - MDW
1 stop4h 04mDelta
Sun 9/16:00 amMDW - PWM
1 stop6h 39mDelta
Deal found 4/26$334
Thu 6/135:05 amPWM - MDW
2 stops8h 38mDelta
Mon 6/172:24 pmMDW - PWM
2 stops7h 57mDelta
Deal found 4/26$344

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 2,991,349 searches. Data last updated April 27, 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 7/1111:46 amPWM - MDW
1 stop25h 37mFrontier
Sat 7/2010:08 amMDW - PWM
1 stop21h 54mFrontier
Deal found 4/26$306
Fri 5/1012:56 pmPWM - MDW
1 stop10h 35mFrontier
Mon 5/133:44 pmMDW - PWM
1 stop19h 26mFrontier
Deal found 4/27$370
Thu 7/2511:46 amPWM - MDW
1 stop25h 37mFrontier
Mon 10/2811:38 amMDW - PWM
1 stop20h 24mFrontier
Deal found 4/26$466
Fri 10/119:52 amPWM - MDW
1 stop13h 03mFrontier
Mon 10/1411:38 amMDW - PWM
1 stop20h 24mFrontier
Deal found 4/26$636
Fri 10/119:52 amPWM - MDW
1 stop13h 03mFrontier
Mon 10/1411:38 amMDW - PWM
1 stop20h 24mFrontier
Deal found 4/26$638
Sun 6/3011:40 amPWM - MDW
1 stop24h 08mFrontier
Sat 7/610:08 amMDW - PWM
1 stop21h 54mFrontier
Deal found 4/26$706
Thu 7/1811:46 amPWM - MDW
1 stop25h 37mFrontier
Wed 7/2412:15 pmMDW - PWM
1 stop21h 41mFrontier
Deal found 4/27$770

Cheap Portland to Midway flights in April & May 2024

Find cheap flight options from Portland to Midway specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,991,349 searches. Prices were last updated on April 27, 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.
Fri 5/1012:56 pmPWM - MDW
1 stop10h 35mFrontier
Mon 5/133:44 pmMDW - PWM
1 stop19h 26mFrontier
Deal found 4/27$370
Sat 5/115:00 amPWM - MDW
1 stop4h 51mDelta
Sun 5/125:47 pmMDW - PWM
1 stop4h 57mDelta
Deal found 4/26$374
Wed 5/155:00 amPWM - MDW
2 stops9h 35mDelta
Fri 5/175:47 pmMDW - PWM
1 stop4h 57mDelta
Deal found 4/26$379
Thu 5/95:00 amPWM - MDW
1 stop5h 06mDelta
Mon 5/135:47 pmMDW - PWM
1 stop4h 57mDelta
Deal found 4/26$399
Thu 5/305:00 amPWM - MDW
1 stop5h 06mDelta
Sun 6/25:47 pmMDW - PWM
1 stop4h 57mDelta
Deal found 4/27$420
Sat 5/115:00 amPWM - MDW
2 stops10h 55mDelta
Sun 5/125:47 pmMDW - PWM
1 stop4h 57mDelta
Deal found 4/26$442
Mon 4/295:00 amPWM - MDW
1 stop4h 50mDelta
Tue 4/301:25 pmMDW - PWM
2 stops9h 30mDelta
Deal found 4/26$443
Mon 4/292:55 pmPWM - MDW
2 stops8h 19mDelta
Tue 4/301:25 pmMDW - PWM
2 stops9h 30mDelta
Deal found 4/26$448
Thu 5/305:00 amPWM - MDW
1 stop5h 06mDelta
Sun 6/25:47 pmMDW - PWM
1 stop4h 57mDelta
Deal found 4/26$450

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 2,991,349 searches. Data last updated April 27, 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 6/135:37 amPWM - MDW
1 stop4h 11mDelta
Mon 6/175:45 pmMDW - PWM
1 stop4h 36mDelta
Deal found 4/26$243
Thu 6/135:37 amPWM - MDW
1 stop4h 11mDelta
Mon 6/172:24 pmMDW - PWM
2 stops7h 57mDelta
Deal found 4/26$248
Thu 8/295:40 amPWM - MDW
1 stop4h 04mDelta
Sun 9/16:00 amMDW - PWM
2 stops7h 25mDelta
Deal found 4/26$253
Thu 10/245:30 amPWM - MDW
2 stops10h 26mDelta
Tue 10/299:35 amMDW - PWM
1 stop5h 32mDelta
Deal found 4/26$277
Thu 10/245:30 amPWM - MDW
2 stops10h 26mDelta
Tue 10/291:05 pmMDW - PWM
2 stops9h 02mDelta
Deal found 4/26$282
Thu 6/135:37 amPWM - MDW
1 stop4h 11mDelta
Sat 6/153:45 pmMDW - PWM
1 stop5h 14mDelta
Deal found 4/27$289
Thu 7/1111:46 amPWM - MDW
1 stop25h 37mFrontier
Sat 7/2010:08 amMDW - PWM
1 stop21h 54mFrontier
Deal found 4/26$306
Wed 11/611:25 amPWM - MDW
2 stops7h 34mDelta
Mon 11/111:10 pmMDW - PWM
2 stops8h 57mDelta
Deal found 4/26$328
Sat 7/205:37 amPWM - MDW
1 stop4h 03mDelta
Tue 7/235:45 pmMDW - PWM
1 stop4h 39mDelta
Deal found 4/27$329

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 2,991,349 searches. Data last updated April 27, 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 4/25$59
Tue 5/2111:40 amPWM - MDW
1 stop20h 14mFrontier
Deal found 4/27$70
Sun 5/59:40 amPWM - MDW
1 stop9h 00mFrontier
Deal found 4/26$99
Fri 6/145:37 amPWM - MDW
1 stop4h 11mDelta
Deal found 4/27$124
Sun 5/59:40 amPWM - MDW
1 stop9h 00mFrontier
Deal found 4/27$129
Sat 9/1411:46 amPWM - MDW
1 stop27h 13mFrontier
Deal found 4/26$130
Sat 9/1411:46 amPWM - MDW
1 stop27h 13mFrontier
Deal found 4/26$160
Thu 7/1811:46 amPWM - MDW
1 stop25h 37mFrontier
Deal found 4/26$199
Sat 7/205:37 amPWM - MDW
1 stop4h 03mDelta
Deal found 4/26$210

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 2,991,349 searches. Data last updated April 27, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$243 - $466

Route

Depart

Return

Price

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Thu 6/13

1 stop4h 11m

Chicago Midway

Mon 6/17

1 stop4h 36m

$243

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Thu 6/13

1 stop4h 11m

Chicago Midway

Mon 6/17

2 stops7h 57m

$248

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Thu 8/29

1 stop4h 04m

Chicago Midway

Sun 9/1

2 stops7h 25m

$253

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Thu 10/24

2 stops10h 26m

Chicago Midway

Tue 10/29

1 stop5h 32m

$277

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Thu 10/24

2 stops10h 26m

Chicago Midway

Tue 10/29

2 stops9h 02m

$282

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Thu 6/13

1 stop4h 11m

Chicago Midway

Sat 6/15

1 stop5h 14m

$289

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Thu 7/11

1 stop25h 37m

Chicago Midway

Sat 7/20

1 stop21h 54m

$306

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Fri 5/10

1 stop10h 35m

Chicago Midway

Mon 5/13

1 stop19h 26m

$370

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

Thu 7/25

1 stop25h 37m

Chicago Midway

Mon 10/28

1 stop20h 24m

$466

Flights are sorted by cheapest first

Deals found on 4/26

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 April 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. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
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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 $131 while a round-trip flight costs $304. Price data was last updated on April 21, 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 $254). 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

$185

June

$235

July

$254

August

$196

September

$157

October

$143

November

$165

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 April 27, 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
10,951 reviews
Check prices

Crew

8.6

Comfort

7.9

Boarding

8.2

Food

7.4

Entertainment

8.0

Overall

8.1

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

Delta
8.1
Very good
10,951 reviews
Delta
8.1
Very good
10,951 reviews
Check prices

Crew

8.6

Comfort

7.9

Boarding

8.2

Food

7.4

Entertainment

8.0

Overall

8.1

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

Frontier
6.3
Okay
4,132 reviews
Delta
8.1
Very good
10,951 reviews
Check prices

Crew

8.6

Comfort

7.9

Boarding

8.2

Food

7.4

Entertainment

8.0

Overall

8.1

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

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 $300 on Cheapflights?

    Yes, there are multiple flights from Portland, Maine to Chicago Midway Airport for under $300. The cheapest flight booked recently is on Delta for just $243, but on average you can expect to pay $338.

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

    Delta, at $243, was found to be the cheapest airline from Portland, Maine to Chicago Midway Airport. An alternate airline flying to your destination would be Frontier.

  • 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 4/27.

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
Augusta to O'Hare Intl flights
Rockland to O'Hare Intl flights
Bar Harbor 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 2,991,349 searches. Data last updated April 27, 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.
First Class
Business Class
Prem Econ Class
Economy 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.

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

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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