Midway

$62+ Cheap flights from Maine 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MDW
feb. 18 — feb. 251
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Cheap flight deals from Maine to Midway

Keep the following information in mind while searching for Maine to Midway flight deals. Data was last updated febrero 13, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$150
(Frontier)

One-way from

$62
(Mytrip)

Popular in

April

Cheapest in

September

Average price

$334

Good round-trip deal

$496 or less
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Portland-Chicago (CHI) flights.
From Maine to Chicago Midway
One-way flight from Maine to Chicago Midway
Highest demand for flights based on searches. 16% potential increase in price ($75 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Average for round-trip flights in February 2025
Price to beat on a round-trip flight from Maine to Chicago Midway.

Find flight deals from Maine to Midway

Cheapest flights from Maine to Midway
Explore the most affordable flight options available from Maine to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on febrero 13, 2025.

This Frontier deal was found by Cheapflights users on 2/12. 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.
vie. 2/2812:45 pmBOS - MDW
1 stop7h 34mFrontier
dom. 3/24:08 pmMDW - BOS
1 stop7h 28mFrontier
Deal found 2/12$150
This Southwest deal was found by Cheapflights users on 2/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/66:30 amBOS - MDW
Nonstop2h 45mSouthwest
mar. 3/1110:05 amMDW - BOS
Nonstop2h 10mSouthwest
Deal found 2/13$157
This Kissandfly.com deal was found by Cheapflights users on 2/12. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/276:05 amBOS - MDW
2 stops16h 24mMultiple Airlines
dom. 3/24:08 pmMDW - BOS
1 stop7h 28mMultiple Airlines
Deal found 2/12$229
This Delta deal was found by Cheapflights users on 2/12. 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.
jue. 3/66:00 amPWM - MDW
2 stops8h 05mDelta
lun. 3/1012:51 pmMDW - PWM
2 stops9h 01mDelta
Deal found 2/12$243
This Southwest deal was found by Cheapflights users on 2/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/121:30 pmPWM - MDW
1 stop5h 30mSouthwest
mié. 3/194:05 pmMDW - PWM
2 stops5h 55mSouthwest
Deal found 2/12$257
This Delta deal was found by Cheapflights users on 2/13. 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.
mié. 4/165:30 amBOS - MDW
1 stop8h 05mDelta
mar. 4/223:02 pmMDW - BOS
1 stop7h 47mDelta
Deal found 2/13$263
This Booking.com deal was found by Cheapflights users on 2/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/196:48 pmPWM - MDW
1 stop28h 58mFrontier
vie. 2/2112:33 pmMDW - PWM
1 stop19h 50mFrontier
Deal found 2/13$300
This Delta deal was found by Cheapflights users on 2/13. 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.
sáb. 3/226:00 amBGR - MDW
2 stops7h 32mDelta
mar. 3/2510:25 amMDW - BGR
2 stops12h 00mDelta
Deal found 2/13$379
This Mytrip deal was found by Cheapflights users on 2/13. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 6/17:50 pmBGR - MDW
2 stops23h 20mMultiple Airlines
lun. 6/302:53 pmMDW - BGR
2 stops18h 25mMultiple Airlines
Deal found 2/13$432

Find flights from Maine to Midway within your budget

Customize your flight search to find flights from Maine 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 2,558,603 searches. Data last updated febrero 13, 2025.

Fly from

Maine

Fly to

Midway

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

vie. 2/28

12:45 pm-7:19 pm

1 stop7h 34m

Chicago Midway

dom. 3/2

4:08 pm-12:36 am

1 stop7h 28m

$150

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

jue. 3/6

6:30 am-8:15 am

Nonstop2h 45m

Chicago Midway

mar. 3/11

10:05 am-1:15 pm

Nonstop2h 10m

$157

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

jue. 2/27

6:05 am-9:29 pm

2 stops16h 24m

Chicago Midway

dom. 3/2

4:08 pm-12:36 am

1 stop7h 28m

$229

PortlandChicago

PWM - MDW

PWMMDW

Portland

jue. 3/6

6:00 am-1:05 pm

2 stops8h 05m

Chicago Midway

lun. 3/10

12:51 pm-10:52 pm

2 stops9h 01m

$243

PortlandChicago

PWM - MDW

PWMMDW

Portland

mié. 3/12

1:30 pm-6:00 pm

1 stop5h 30m

Chicago Midway

mié. 3/19

4:05 pm-11:00 pm

2 stops5h 55m

$257

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

mié. 4/16

5:30 am-12:35 pm

1 stop8h 05m

Chicago Midway

mar. 4/22

3:02 pm-11:49 pm

1 stop7h 47m

$263

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

jue. 5/22

11:31 am-12:25 pm

1 stop25h 54m

Chicago Midway

lun. 5/26

2:54 pm-9:14 am

1 stop17h 20m

$346

BangorChicago

BGR - MDW

BGRMDW

Bangor

sáb. 3/22

6:00 am-12:32 pm

2 stops7h 32m

Chicago Midway

mar. 3/25

10:25 am-11:25 pm

2 stops12h 00m

$379

BangorChicago

BGR - MDW

BGRMDW

Bangor

dom. 6/1

7:50 pm-6:10 pm

2 stops23h 20m

Chicago Midway

lun. 6/30

2:53 pm-10:18 am

2 stops18h 25m

$432

PortlandChicago

PWM - MDW

PWMMDW

Portland

jue. 5/1

9:29 pm-12:24 pm

1 stop15h 55m

$62

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/13

Showing 1-10 of 18 results
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Best time to book a flight from Maine to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Maine 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.

Travel insights for flights from Maine to Midway

Get recent, data-driven insights about flights from Maine to Midway including ideal travel times, pricing trends, and more.

What is the cheapest time of day to fly from ME to MDW?

Find hourly flight availability from Maine 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 febrero 13, 2025.

When flying from 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.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

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 febrero 13, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and Allegiant Air from Maine to Chicago to help guide your decision. 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.

Entertainment

7.6

Food

7.1

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

Entertainment

7.6

Food

7.1

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

8.0
Very good

Entertainment

7.6

Food

7.1

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

Entertainment

7.6

Food

7.1

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

Entertainment

7.6

Food

7.1

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

Related info for your journey

Find useful and relevant information for your journey from Maine to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • What are the cheapest airlines to fly from 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 Southwest from $79 and Delta from $109 one-way.

  • What are the most popular routes from Maine to Chicago Midway Airport?

  • What are the cheapest flights from Maine to Chicago Midway Airport?

    While on average a flight from Maine to Chicago Midway Airport is generally $506, our data shows the cheapest flight currently is $401. When looking at the most popular route, (Boston Logan Intl - Chicago Midway), you can expect to pay $130 for that flight.

  • Can I find deals for flights from Maine to Midway that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Maine 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.

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

    Currently, April is the cheapest month in which you can book a flight from Maine to Chicago Midway Airport (average of $160). Flying from Maine to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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