HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news

Cheap flights from Portland (PWM) to Midway (MDW) from $80

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 6/25. 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. 2 — jun. 91
From?
To?
dom. 6/2
dom. 6/9
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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 mayo 28, 2024.

Popular in

August

Cheapest in

January

Average price

$611

Round-trip from

$222
High demand for flights, 34% potential price rise
Search Deals
Best time to find cheap flights, 53% potential price drop
Search Deals
Average for round-trip flights in May 2024
Search Deals
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 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 $402 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 46% 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 2,740,132 searches. Data last updated mayo 28, 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.
mar. 7/3011:59 amPWM - MDW
1 stop7h 40mDelta
mar. 8/65:45 pmMDW - PWM
1 stop4h 41mDelta
Deal found 5/27$257
mié. 9/1812:55 pmPWM - MDW
1 stop5h 08mDelta
lun. 9/235:59 pmMDW - PWM
1 stop4h 07mDelta
Deal found 5/27$258
mar. 7/3011:59 amPWM - MDW
1 stop7h 40mDelta
mar. 8/69:33 amMDW - PWM
2 stops11h 27mDelta
Deal found 5/27$262
mié. 7/31:02 pmPWM - MDW
1 stop5h 03mDelta
jue. 7/412:45 pmMDW - PWM
1 stop7h 55mDelta
Deal found 5/27$283
mié. 7/31:02 pmPWM - MDW
1 stop5h 03mDelta
jue. 7/410:41 amMDW - PWM
2 stops11h 19mDelta
Deal found 5/27$288
jue. 9/1912:55 pmPWM - MDW
1 stop5h 08mDelta
mar. 9/249:35 amMDW - PWM
1 stop5h 32mDelta
Deal found 5/27$293
mié. 9/185:30 amPWM - MDW
2 stops8h 32mDelta
lun. 9/235:59 pmMDW - PWM
1 stop4h 07mDelta
Deal found 5/27$298
mié. 10/25:30 amPWM - MDW
2 stops10h 26mDelta
sáb. 10/59:35 amMDW - PWM
2 stops8h 12mDelta
Deal found 5/26$303
jue. 7/411:49 amPWM - MDW
1 stop7h 42mDelta
dom. 7/75:45 pmMDW - PWM
1 stop4h 36mDelta
Deal found 5/27$323

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 2,740,132 searches. Data last updated mayo 28, 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.
mar. 6/113:23 pmPWM - MDW
1 stop6h 57mFrontier
lun. 6/1712:57 pmMDW - PWM
1 stop20h 52mFrontier
Deal found 5/27$158
jue. 6/134:04 pmPWM - MDW
1 stop4h 52mFrontier
lun. 6/1712:57 pmMDW - PWM
1 stop20h 52mFrontier
Deal found 5/27$159
mar. 7/234:01 pmPWM - MDW
1 stop6h 24mFrontier
jue. 8/810:26 amMDW - PWM
1 stop8h 35mFrontier
Deal found 5/27$168
dom. 6/91:57 pmPWM - MDW
1 stop22h 13mFrontier
mié. 6/1212:57 pmMDW - PWM
1 stop23h 00mFrontier
Deal found 5/27$180
vie. 9/69:52 amPWM - MDW
1 stop13h 03mFrontier
lun. 9/911:38 amMDW - PWM
1 stop20h 24mFrontier
Deal found 5/28$213
mié. 10/29:52 amPWM - MDW
1 stop13h 03mFrontier
sáb. 10/510:08 amMDW - PWM
1 stop21h 54mFrontier
Deal found 5/26$238
jue. 6/131:57 pmPWM - MDW
1 stop28h 18mFrontier
lun. 6/1712:57 pmMDW - PWM
1 stop20h 52mFrontier
Deal found 5/27$239
jue. 7/113:55 pmPWM - MDW
1 stop5h 14mFrontier
sáb. 7/2011:51 amMDW - PWM
1 stop23h 06mFrontier
Deal found 5/26$254
jue. 6/204:04 pmPWM - MDW
1 stop4h 52mFrontier
sáb. 6/2211:51 amMDW - PWM
1 stop20h 15mFrontier
Deal found 5/27$272

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 2,740,132 searches. Prices were last updated on mayo 28, 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.
mar. 6/113:23 pmPWM - MDW
1 stop6h 57mFrontier
lun. 6/1712:57 pmMDW - PWM
1 stop20h 52mFrontier
Deal found 5/27$158
jue. 6/134:04 pmPWM - MDW
1 stop4h 52mFrontier
lun. 6/1712:57 pmMDW - PWM
1 stop20h 52mFrontier
Deal found 5/27$159
dom. 6/91:57 pmPWM - MDW
1 stop22h 13mFrontier
mié. 6/1212:57 pmMDW - PWM
1 stop23h 00mFrontier
Deal found 5/27$180
jue. 6/131:57 pmPWM - MDW
1 stop28h 18mFrontier
lun. 6/1712:57 pmMDW - PWM
1 stop20h 52mFrontier
Deal found 5/27$239
jue. 6/204:04 pmPWM - MDW
1 stop4h 52mFrontier
sáb. 6/2211:51 amMDW - PWM
1 stop20h 15mFrontier
Deal found 5/27$272
mié. 6/125:37 amPWM - MDW
1 stop4h 11mDelta
lun. 6/175:45 pmMDW - PWM
1 stop4h 36mDelta
Deal found 5/27$363
jue. 6/134:04 pmPWM - MDW
1 stop4h 52mFrontier
dom. 6/1610:28 amMDW - PWM
1 stop8h 34mFrontier
Deal found 5/27$369
sáb. 6/15:00 amPWM - MDW
1 stop4h 51mDelta
sáb. 6/85:45 pmMDW - PWM
1 stop4h 36mDelta
Deal found 5/27$388
sáb. 6/16:05 amPWM - MDW
2 stops11h 08mDelta
sáb. 6/85:45 pmMDW - PWM
1 stop4h 36mDelta
Deal found 5/27$393

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 2,740,132 searches. Data last updated mayo 28, 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.
mar. 6/113:23 pmPWM - MDW
1 stop6h 57mFrontier
lun. 6/1712:57 pmMDW - PWM
1 stop20h 52mFrontier
Deal found 5/27$158
jue. 6/134:04 pmPWM - MDW
1 stop4h 52mFrontier
lun. 6/1712:57 pmMDW - PWM
1 stop20h 52mFrontier
Deal found 5/27$159
mar. 7/234:01 pmPWM - MDW
1 stop6h 24mFrontier
jue. 8/810:26 amMDW - PWM
1 stop8h 35mFrontier
Deal found 5/27$168
dom. 6/91:57 pmPWM - MDW
1 stop22h 13mFrontier
mié. 6/1212:57 pmMDW - PWM
1 stop23h 00mFrontier
Deal found 5/27$180
vie. 9/69:52 amPWM - MDW
1 stop13h 03mFrontier
lun. 9/911:38 amMDW - PWM
1 stop20h 24mFrontier
Deal found 5/28$213
mié. 10/29:52 amPWM - MDW
1 stop13h 03mFrontier
sáb. 10/510:08 amMDW - PWM
1 stop21h 54mFrontier
Deal found 5/26$238
jue. 6/131:57 pmPWM - MDW
1 stop28h 18mFrontier
lun. 6/1712:57 pmMDW - PWM
1 stop20h 52mFrontier
Deal found 5/27$239
jue. 7/113:55 pmPWM - MDW
1 stop5h 14mFrontier
sáb. 7/2011:51 amMDW - PWM
1 stop23h 06mFrontier
Deal found 5/26$254
mar. 7/3011:59 amPWM - MDW
1 stop7h 40mDelta
mar. 8/65:45 pmMDW - PWM
1 stop4h 41mDelta
Deal found 5/27$257

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 2,740,132 searches. Data last updated mayo 28, 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.
mar. 6/253:23 pmPWM - MDW
1 stop6h 57mFrontier
Deal found 5/27$80
jue. 9/1211:46 amPWM - MDW
1 stop25h 37mFrontier
Deal found 5/27$88
mar. 6/259:59 amPWM - MDW
2 stops12h 21mFrontier
Deal found 5/27$91
mar. 7/169:52 amPWM - MDW
1 stop12h 33mFrontier
Deal found 5/27$95
mar. 6/45:00 amPWM - MDW
2 stops9h 35mDelta
Deal found 5/27$169
dom. 7/77:37 pmPWM - MDW
1 stop16h 28mFrontier
Deal found 5/27$173
dom. 6/231:57 pmPWM - MDW
1 stop22h 13mFrontier
Deal found 5/27$210
jue. 7/183:55 pmPWM - MDW
1 stop5h 14mFrontier
Deal found 5/27$213
mié. 6/195:37 amPWM - MDW
1 stop4h 11mDelta
Deal found 5/27$235

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 2,740,132 searches. Data last updated mayo 28, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$158 - $283

Route

Depart

Return

Price

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

mar. 6/11

1 stop6h 57m

Chicago Midway

lun. 6/17

1 stop20h 52m

$158

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

jue. 6/13

1 stop4h 52m

Chicago Midway

lun. 6/17

1 stop20h 52m

$159

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

mar. 7/23

1 stop6h 24m

Chicago Midway

jue. 8/8

1 stop8h 35m

$168

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

dom. 6/9

1 stop22h 13m

Chicago Midway

mié. 6/12

1 stop23h 00m

$180

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

vie. 9/6

1 stop13h 03m

Chicago Midway

lun. 9/9

1 stop20h 24m

$213

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

mar. 7/30

1 stop7h 40m

Chicago Midway

mar. 8/6

1 stop4h 41m

$257

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

mié. 9/18

1 stop5h 08m

Chicago Midway

lun. 9/23

1 stop4h 07m

$258

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

mar. 7/30

1 stop7h 40m

Chicago Midway

mar. 8/6

2 stops11h 27m

$262

PortlandChicago Midway

PWM - MDW

PWMMDW

Portland

mié. 7/3

1 stop5h 03m

Chicago Midway

jue. 7/4

1 stop7h 55m

$283

Flights are sorted by cheapest first

Deals found on 5/27

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 26, 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

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 mayo 28, 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
10,476 reviews
Check prices

Comfort

7.9

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

8.0

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
8.0
Very good
10,476 reviews
Delta
8.0
Very good
10,476 reviews
Check prices

Comfort

7.9

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

8.0

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
4,016 reviews
Delta
8.0
Very good
10,476 reviews
Check prices

Comfort

7.9

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

8.0

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 Frontier for just $158, but on average you can expect to pay $248.

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

    Frontier, at $158, 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 68% 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 5/28.

  • When is the best time 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 $248). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Midway
See prices for flight routes from nearby airports that may be better suited for you.

Boston to O'Hare Intl flights
Boston to Midway flights
Portland to O'Hare Intl flights
Bangor to O'Hare Intl flights
Boston to Rockford flights
Bangor to Midway flights
Augusta to O'Hare Intl flights
Bar Harbor 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 2,740,132 searches. Data last updated mayo 28, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$345Average$457FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
New York to Hong Kong flights
San Francisco to Maui flights
Chicago to Dubai flights
Chicago to Miami flights
St. Louis to Miami flights
Phoenix to Seattle flights
Aruba to Curaçao flights
Fresno to Las Vegas flights
Los Angeles to Sydney flights
Chicago to Dallas flights
Austin to Denver flights
Portland, Maine to Memphis flights

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

Book a flight to one of these trending destinations

User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
Flights to Laayoune Hassan I
Flights to Virac
Flights to Figari-Sud Corse
Flights to Edremit/Korfez
Flights to Rhinelander Oneida County
Flights to Girona Costa Brava
Flights to Brainerd Crow Wing County
Flights to Parikia Paros
Flights to Cortez Montezuma County
Flights to Miyakojima Hirara
Flights to Zadar
Flights to Trapani Birgi
Flights to Provincetown
Flights to Oran Es Senia
Flights to Constanţa Mihail Kogalniceanu
Flights to Vava'u Lupepau'U
Flights to Urumqi
Flights to Hakodate
Flights to Naxos
Flights to Dalaman
Flights to Hyannis Barnstable
Flights to Devils Lake
Flights to Bastia Poretta
Flights to Karpathos

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.

100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
View all available airlines