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Cheap flights from Midway (MDW) to Portland (PWM) from $68

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 5/15. 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.
MDW — PWM
May 5 — May 121
From?
To?
Sun 5/5
Sun 5/12
1 adult, Economy
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Cheap flight deals from Midway to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Portland (PWM). 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 30, 2024.

Round-trip from

$293

One-way from

$68
From Chicago Midway to Portland
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One-way flight from Chicago Midway to Portland
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What is the cheapest day to fly round-trip from Chicago Midway Airport to Portland, Maine?

Flying to your destination on a Thursday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Portland, Maine. Check prices with Cheapflights to find a great deal for your trip.

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

Users have found that booking a flight from Chicago Midway Airport to Portland, Maine at least 53 days early can save you up to 26% on average compared to booking a flight this week. If booking 53 days before your flight isn’t an option for you, users have found flights from Chicago Midway Airport to Portland, Maine for as little as $329 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $329 for flights departing within the next 3 days.

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

April is one of the best times of the year to fly to Portland, Maine from Chicago Midway Airport. Prices for April average $386 per person but you can even find prices for as low as $244. The most expensive prices can be found in the month of November. Opting for a April flight can save you 27% on your journey compared to booking in November

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

It’s typically best to fly out from Chicago Midway Airport to Portland, Maine at noon. Doing so could potentially save you 33% on the flight price compared to flying in the morning, which is usually more expensive.

Cheap Delta flights from Midway to Portland

Explore cheap flight options specifically provided by Delta for the route between Midway and Portland. 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 2,948,547 searches. Data last updated April 30, 2024.
Take a look at some of the lowest-priced Delta flights heading from Chicago to Portland. Be sure to come back soon if the deals available don't appeal to you at this time.
Tue 8/203:45 pmMDW - PWM
1 stop6h 54mDelta
Wed 8/2812:55 pmPWM - MDW
1 stop5h 08mDelta
Deal found 4/28$198
Tue 6/251:24 pmMDW - PWM
2 stops8h 36mDelta
Tue 7/25:37 amPWM - MDW
1 stop4h 12mDelta
Deal found 4/29$203
Tue 8/201:10 pmMDW - PWM
2 stops8h 57mDelta
Tue 8/276:05 amPWM - MDW
1 stop8h 01mDelta
Deal found 4/28$223
Tue 6/251:24 pmMDW - PWM
2 stops8h 36mDelta
Mon 7/15:37 amPWM - MDW
1 stop4h 12mDelta
Deal found 4/29$228
Wed 8/213:45 pmMDW - PWM
1 stop6h 54mDelta
Wed 8/2812:55 pmPWM - MDW
1 stop5h 08mDelta
Deal found 4/28$247
Mon 8/195:59 pmMDW - PWM
1 stop4h 07mDelta
Thu 8/2912:55 pmPWM - MDW
1 stop5h 08mDelta
Deal found 4/28$248
Sat 6/225:45 pmMDW - PWM
1 stop4h 36mDelta
Wed 6/265:37 amPWM - MDW
1 stop4h 11mDelta
Deal found 4/29$269
Wed 8/213:45 pmMDW - PWM
1 stop6h 54mDelta
Sat 8/245:40 amPWM - MDW
1 stop4h 04mDelta
Deal found 4/28$272
Fri 6/712:45 pmMDW - PWM
1 stop8h 13mDelta
Fri 6/145:37 amPWM - MDW
1 stop4h 11mDelta
Deal found 4/29$273

Cheap Frontier flights from Midway to Portland

Explore cheap flight options specifically provided by Frontier for the route between Midway and Portland. 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 2,948,547 searches. Data last updated April 30, 2024.
Have a look at some of the cheapest available Frontier flights departing from Chicago and landing in Portland. If these deals don't fit your criteria, make sure to check back soon as new deals are always added.
Wed 5/2212:09 pmMDW - PWM
1 stop21h 41mFrontier
Tue 5/2811:40 amPWM - MDW
1 stop20h 14mFrontier
Deal found 4/29$119
Wed 6/1212:57 pmMDW - PWM
1 stop20h 53mFrontier
Tue 6/183:23 pmPWM - MDW
1 stop6h 58mFrontier
Deal found 4/29$138
Sat 8/2410:08 amMDW - PWM
1 stop21h 54mFrontier
Sat 8/3111:46 amPWM - MDW
1 stop27h 13mFrontier
Deal found 4/29$141
Fri 9/131:13 pmMDW - PWM
1 stop18h 49mFrontier
Sun 9/1511:46 amPWM - MDW
1 stop24h 02mFrontier
Deal found 4/30$158
Mon 6/1012:57 pmMDW - PWM
1 stop20h 53mFrontier
Tue 6/183:23 pmPWM - MDW
1 stop6h 58mFrontier
Deal found 4/29$161
Sat 8/2410:08 amMDW - PWM
1 stop21h 54mFrontier
Sat 8/3111:46 amPWM - MDW
1 stop27h 13mFrontier
Deal found 4/29$167
Wed 6/512:57 pmMDW - PWM
1 stop20h 53mFrontier
Sun 6/911:40 amPWM - MDW
1 stop24h 31mFrontier
Deal found 4/28$199
Mon 5/206:30 pmMDW - PWM
1 stop13h 39mFrontier
Tue 5/2111:40 amPWM - MDW
1 stop20h 14mFrontier
Deal found 4/29$211
Wed 8/1412:15 pmMDW - PWM
1 stop21h 41mFrontier
Fri 8/239:52 amPWM - MDW
1 stop13h 03mFrontier
Deal found 4/29$220

Cheap Midway to Portland flights in April & May 2024

Find cheap flight options from Midway to Portland specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,948,547 searches. Prices were last updated on April 30, 2024.
These are some of the best deals we've found on flights to Portland in 2024 at this time. For more flight deals, be sure to check back very soon.
Wed 5/2212:09 pmMDW - PWM
1 stop21h 41mFrontier
Tue 5/2811:40 amPWM - MDW
1 stop20h 14mFrontier
Deal found 4/29$119
Mon 5/206:30 pmMDW - PWM
1 stop13h 39mFrontier
Tue 5/2111:40 amPWM - MDW
1 stop20h 14mFrontier
Deal found 4/29$211
Thu 5/25:56 pmMDW - PWM
1 stop17h 04mFrontier
Mon 5/69:11 amPWM - MDW
1 stop14h 25mFrontier
Deal found 4/29$227
Sat 5/189:08 pmMDW - PWM
1 stop11h 01mFrontier
Thu 5/231:11 pmPWM - MDW
2 stops8h 06mFrontier
Deal found 4/29$257
Sat 5/189:08 pmMDW - PWM
1 stop11h 01mFrontier
Tue 5/2111:40 amPWM - MDW
1 stop20h 14mFrontier
Deal found 4/29$261
Mon 5/206:30 pmMDW - PWM
1 stop13h 39mFrontier
Thu 5/231:11 pmPWM - MDW
1 stop7h 29mFrontier
Deal found 4/29$298
Sat 5/189:08 pmMDW - PWM
1 stop11h 01mFrontier
Thu 5/231:11 pmPWM - MDW
1 stop7h 29mFrontier
Deal found 4/29$328
Sun 5/125:47 pmMDW - PWM
1 stop4h 57mDelta
Wed 5/225:00 amPWM - MDW
1 stop5h 06mDelta
Deal found 4/29$343
Tue 5/211:21 pmMDW - PWM
2 stops8h 29mDelta
Fri 5/245:00 amPWM - MDW
1 stop5h 06mDelta
Deal found 4/29$394

Midway to Portland 2024 flight deals

Discover exclusive flight deals for travel between Midway and Portland in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,948,547 searches. Data last updated April 30, 2024.
These are some of the best deals we've found on flights to Portland in 2024 at this time. For more flight deals, be sure to check back very soon.
Wed 5/2212:09 pmMDW - PWM
1 stop21h 41mFrontier
Tue 5/2811:40 amPWM - MDW
1 stop20h 14mFrontier
Deal found 4/29$119
Wed 6/1212:57 pmMDW - PWM
1 stop20h 53mFrontier
Tue 6/183:23 pmPWM - MDW
1 stop6h 58mFrontier
Deal found 4/29$138
Sat 8/2410:08 amMDW - PWM
1 stop21h 54mFrontier
Sat 8/3111:46 amPWM - MDW
1 stop27h 13mFrontier
Deal found 4/29$141
Fri 9/131:13 pmMDW - PWM
1 stop18h 49mFrontier
Sun 9/1511:46 amPWM - MDW
1 stop24h 02mFrontier
Deal found 4/30$158
Mon 6/1012:57 pmMDW - PWM
1 stop20h 53mFrontier
Tue 6/183:23 pmPWM - MDW
1 stop6h 58mFrontier
Deal found 4/29$161
Sat 8/2410:08 amMDW - PWM
1 stop21h 54mFrontier
Sat 8/3111:46 amPWM - MDW
1 stop27h 13mFrontier
Deal found 4/29$167
Tue 8/203:45 pmMDW - PWM
1 stop6h 54mDelta
Tue 8/2712:55 pmPWM - MDW
1 stop5h 08mDelta
Deal found 4/28$198
Wed 6/512:57 pmMDW - PWM
1 stop20h 53mFrontier
Sun 6/911:40 amPWM - MDW
1 stop24h 31mFrontier
Deal found 4/28$199
Tue 6/251:24 pmMDW - PWM
2 stops8h 36mDelta
Tue 7/25:37 amPWM - MDW
1 stop4h 12mDelta
Deal found 4/29$203

Midway to Portland flights leaving soon

Find last-minute flight options from Midway to Portland 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 2,948,547 searches. Data last updated April 30, 2024.
Have a look at some of the last-minute flights available departing from Chicago to Portland. Users should examine the flight details to ensure there are no surprises.
Fri 5/105:47 pmMDW - PWM
1 stop4h 57mDelta
Tue 5/145:00 amPWM - MDW
1 stop5h 06mDelta
Deal found 4/29$468
Fri 5/105:47 pmMDW - PWM
1 stop4h 57mDelta
Tue 5/145:00 amPWM - MDW
2 stops9h 35mDelta
Deal found 4/29$536
Fri 5/101:21 pmMDW - PWM
2 stops7h 38mDelta
Tue 5/145:00 amPWM - MDW
2 stops9h 35mDelta
Deal found 4/29$701

One-way flights to Portland from Midway

Search for one-way flight options from Midway to Portland. 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 2,948,547 searches. Data last updated April 30, 2024.
If you're seeking multiple options on one-way flights from Chicago to Portland, be sure to check out these deals, which are updated often. Those seeking round-trip flights from Chicago to Portland should utilize the search form at the the top of the page.
Wed 5/154:56 pmMDW - PWM
1 stop16h 54mFrontier
Deal found 4/29$68
Wed 5/2212:09 pmMDW - PWM
1 stop21h 41mFrontier
Deal found 4/29$69
Mon 5/2012:14 pmMDW - PWM
1 stop21h 36mFrontier
Deal found 4/29$84
Mon 5/276:30 pmMDW - PWM
1 stop13h 39mFrontier
Deal found 4/29$92
Wed 6/512:57 pmMDW - PWM
1 stop20h 53mFrontier
Deal found 4/28$93
Mon 5/276:30 pmMDW - PWM
1 stop13h 39mFrontier
Deal found 4/28$94
Tue 6/115:45 pmMDW - PWM
1 stop4h 36mDelta
Deal found 4/29$99
Sat 5/118:17 pmMDW - PWM
1 stop11h 19mFrontier
Deal found 4/29$104
Tue 6/111:24 pmMDW - PWM
2 stops8h 36mDelta
Deal found 4/30$109

Find flights from Midway to Portland within your budget

Customize your flight search to find flights from Midway to Portland 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 2,948,547 searches. Data last updated April 30, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$119 - $223

Route

Depart

Return

Price

Chicago MidwayPortland

MDW - PWM

MDWPWM

Chicago Midway

Wed 5/22

1 stop21h 41m

Portland

Tue 5/28

1 stop20h 14m

$119

Chicago MidwayPortland

MDW - PWM

MDWPWM

Chicago Midway

Wed 6/12

1 stop20h 53m

Portland

Tue 6/18

1 stop6h 58m

$138

Chicago MidwayPortland

MDW - PWM

MDWPWM

Chicago Midway

Sat 8/24

1 stop21h 54m

Portland

Sat 8/31

1 stop27h 13m

$141

Chicago MidwayPortland

MDW - PWM

MDWPWM

Chicago Midway

Fri 9/13

1 stop18h 49m

Portland

Sun 9/15

1 stop24h 02m

$158

Chicago MidwayPortland

MDW - PWM

MDWPWM

Chicago Midway

Mon 6/10

1 stop20h 53m

Portland

Tue 6/18

1 stop6h 58m

$161

Chicago MidwayPortland

MDW - PWM

MDWPWM

Chicago Midway

Sat 8/24

1 stop21h 54m

Portland

Sat 8/31

1 stop27h 13m

$167

Chicago MidwayPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 8/20

1 stop6h 54m

Portland

Wed 8/28

1 stop5h 08m

$198

Chicago MidwayPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 6/25

2 stops8h 36m

Portland

Tue 7/2

1 stop4h 12m

$203

Chicago MidwayPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 8/20

2 stops8h 57m

Portland

Tue 8/27

1 stop8h 01m

$223

Flights are sorted by cheapest first

Deals found on 4/29

When is the cheapest time to fly from Chicago Midway Airport to Portland, Maine?

Use this chart to determine the cheapest time to fly round-trip from Midway to Portland. Price data was last updated on April 28, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Chicago Midway Airport to Portland, Maine flight should consider departing on Sunday afternoons when fares are most often at their lowest. Sunday afternoons 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 Portland by month

Plan your trip from Midway to Portland by taking into account the cheapest months to travel. The average price of a one-way flight from Midway to Portland is currently $90 while a round-trip flight costs $168. Price data was last updated on April 21, 2024.

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Portland, Maine (average of $293). Flying from Chicago Midway Airport to Portland, Maine in April is currently the most expensive (average of $497). 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

$293

February

$332

March

$414

April

$497

May

$431

June

$413

July

$448

August

$360

September

$340

October

$323

November

$333

December

$333

Temperature and rainfall in Portland by month

Plan your trip to Portland by taking into account the average temperature and rainfall totals by month.

PWM

Temperature

23 - 68 °F

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated April 30, 2024.
Read reviews from past customers who have flown Delta and Frontier from Chicago to Portland. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.1
Very good
10,913 reviews
Check prices

Crew

8.6

Food

7.4

Entertainment

8.0

Comfort

7.9

Overall

8.1

Boarding

8.2

Reviews

1 / 10

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

Delta
8.1
Very good
10,913 reviews
Delta
8.1
Very good
10,913 reviews
Check prices

Crew

8.6

Food

7.4

Entertainment

8.0

Comfort

7.9

Overall

8.1

Boarding

8.2

Reviews

1 / 10

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

WestJet
7.6
Good
2,971 reviews
Delta
8.1
Very good
10,913 reviews
Check prices

Crew

8.6

Food

7.4

Entertainment

8.0

Comfort

7.9

Overall

8.1

Boarding

8.2

Reviews

1 / 10

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

Frontier
6.3
Okay
4,123 reviews
Delta
8.1
Very good
10,913 reviews
Check prices

Crew

8.6

Food

7.4

Entertainment

8.0

Comfort

7.9

Overall

8.1

Boarding

8.2

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 Midway to Portland. 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 into for flights to Portland from Chicago Midway?

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

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

    Yes, there are multiple flights from Chicago Midway Airport to Portland, Maine for under $200. The cheapest flight booked recently is on Frontier for just $119, but on average you can expect to pay $207.

  • Are there last-minute flights available from Chicago Midway Airport to Portland, Maine for under $500?

    There are currently 3+ open flights from Chicago Midway Airport to Portland, Maine within the next 7 days for less than $500.

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

    Flying on Frontier is currently your cheapest option to Portland, Maine, with prices starting at $119. Another option worth looking into is Delta, starting at $198 round trip.

  • What does MDW to PWM mean?

    These are just IATA (International Air Transport Association) codes. They are used in aviation to identify and differentiate airports. That’s why a Chicago Midway Airport to Portland Airport flight would often be abbreviated as a MDW to PWM flight.

  • Can I find deals for flights from Midway to Portland that include extra baggage allowance?

    The amount of baggage you can bring on your Midway to Portland 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 Midway to Portland with specific airlines?

    Yes, Cheapflights allows you to browse and filter Midway to Portland 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 Midway to Portland that include hotel bookings?

    Yes. In addition to deals on Midway to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Portland.

  • Can I find deals for business class flights from Midway to Portland?

    Yes. Cheapflights offers flight deals from Midway to Portland 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 Midway to Portland that allow pets onboard?

    Many airlines flying from Midway to Portland 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 Midway to Portland?

    Yes, you can often find last-minute deals on Midway to Portland 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 Chicago Midway Airport to Portland, Maine flight deals updated?

    The Chicago Midway Airport to Portland, Maine flight deals you see on this page were last updated on 4/30.

See more FAQs

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

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Top airline flying from Midway to Portland

Discover the top airline that operate flights from Midway to Portland. 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 2,948,547 searches. Data last updated April 30, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$272Average$393FlexibilityNo cancel feeOn-timeN/A
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Search flights from Midway to Portland by cabin class

Find flights from Midway to Portland, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

Weekly flight availability from Midway to Portland

Explore weekly flight availability from Midway to Portland. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 30, 2024.
Sunday0daily flights
Monday1daily flight
Tuesday1daily flight
Wednesday1daily flight
Thursday1daily flight
Friday1daily flight
Saturday0daily flights

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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 Midway to Portland?

Cheapflights helps you search for flights from Midway to Portland via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from Midway to Portland?

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 Portland from Midway.

Can Cheapflights find flights from Midway to Portland with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Midway to Portland, users can toggle the no change fees filter when performing a flight search.

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

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

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