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$64+ Cheap flights from Sky Harbor Intl (PHX) 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
PHX — MDW
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Find cheap flights from Sky Harbor Intl to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Phoenix Sky Harbor Intl to Chicago Midway are usually found in September or October, booked 59 days in advance, depart on a Thursday or Tuesday and return on a Thursday

Cheap flight deals from Sky Harbor Intl to Midway

Cheapest flights from Sky Harbor Intl to Midway
Explore the most affordable flight options available from Sky Harbor Intl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This Expedia deal was found by Cheapflights users on 12/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2910:31 pmPHX - MDW
1 stop20h 24mFrontier
Fri 1/306:20 amMDW - PHX
1 stop10h 02mFrontier
Deal found 12/10$176
This Kiwi.com deal was found by Cheapflights users on 12/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/286:05 amPHX - MDW
1 stop6h 54mFrontier
Wed 12/312:16 pmMDW - PHX
1 stop11h 19mFrontier
Deal found 12/9$191
This Booking.com deal was found by Cheapflights users on 12/9. 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.
Tue 12/309:31 amPHX - MDW
1 stop9h 24mFrontier
Mon 1/52:16 pmMDW - PHX
1 stop11h 12mFrontier
Deal found 12/9$194
This CheapOair deal was found by Cheapflights users on 12/10. 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.
Thu 12/1110:26 pmPHX - MDW
1 stop11h 42mFrontier
Tue 1/62:03 pmMDW - PHX
Nonstop3h 59mFrontier
Deal found 12/10$203
This CheapOair deal was found by Cheapflights users on 12/9. 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.
Mon 12/2910:31 pmPHX - MDW
1 stop20h 24mFrontier
Mon 1/52:16 pmMDW - PHX
1 stop11h 12mFrontier
Deal found 12/9$204
This Frontier deal was found by Cheapflights users on 12/9. 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.
Tue 12/309:31 amPHX - MDW
1 stop9h 24mFrontier
Fri 1/28:00 amMDW - PHX
1 stop9h 48mFrontier
Deal found 12/9$207
This Kiwi.com deal was found by Cheapflights users on 12/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/286:05 amPHX - MDW
1 stop6h 54mFrontier
Fri 1/28:00 amMDW - PHX
1 stop9h 48mFrontier
Deal found 12/9$215
This Delta deal was found by Cheapflights users on 12/9. 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.
Thu 12/252:00 pmPHX - MDW
1 stop7h 22mDelta
Thu 1/15:59 pmMDW - PHX
1 stop7h 04mDelta
Deal found 12/9$217
This Frontier deal was found by Cheapflights users on 12/9. 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.
Tue 12/309:31 amPHX - MDW
1 stop9h 24mFrontier
Sun 1/43:01 pmMDW - PHX
Nonstop4h 00mFrontier
Deal found 12/9$220
This Southwest deal was found by Cheapflights users on 12/11. 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.
Wed 12/243:45 pmPHX - MDW
1 stop5h 25mSouthwest
Thu 1/157:55 amMDW - PHX
1 stop6h 35mSouthwest
Deal found 12/11$227

Find flight deals from Sky Harbor Intl to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Sky Harbor Intl (PHX) 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 December 12, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$103
(Expedia)

One-way from

$64
(Priceline)

Popular in

March

Cheapest in

September

Average price

$331

Good round-trip deal

$250 or less

Good one-way deal

$143 or less
Provider with most accurate pricing for Phoenix Sky Harbor Intl-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Phoenix Sky Harbor Intl-Chicago Midway flights.
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From Phoenix Sky Harbor Intl to Chicago Midway
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One-way flight from Phoenix Sky Harbor Intl to Chicago Midway
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Highest demand for flights based on searches. 6% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Price to beat on a round-trip flight from Phoenix Sky Harbor Intl to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Phoenix Sky Harbor Intl to Chicago Midway.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Sky Harbor Intl 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 December 12, 2025.
Use the filters below to find and compare flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport that are best for you.

Fly from

Sky Harbor Intl

Fly to

Midway

Route

Depart

Return

Price

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Tue 1/6

12:10 pm-6:45 pm

1 stop5h 35m

Chicago Midway

Sat 1/10

7:00 am-10:10 am

Nonstop4h 10m

$197

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Wed 1/7

11:55 am-10:07 pm

1 stop9h 12m

Chicago Midway

Wed 1/14

11:21 am-7:13 pm

1 stop8h 52m

$217

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Tue 2/24

1:55 pm-10:44 pm

1 stop7h 49m

Chicago Midway

Sat 2/28

1:28 pm-7:38 pm

1 stop7h 10m

$217

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Wed 1/7

1:55 pm-10:07 pm

1 stop7h 12m

Chicago Midway

Sat 1/10

1:28 pm-7:05 pm

1 stop6h 37m

$217

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Sat 1/17

7:30 am-4:29 pm

1 stop7h 59m

Chicago Midway

Sat 1/24

1:26 pm-8:11 pm

1 stop7h 45m

$217

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Mon 2/23

11:59 pm-8:53 am

1 stop7h 54m

Chicago Midway

Sat 2/28

6:00 am-12:24 pm

1 stop7h 24m

$227

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Wed 1/28

1:55 pm-10:22 pm

1 stop7h 27m

Chicago Midway

Sun 2/1

7:16 pm-12:11 am

1 stop5h 55m

$227

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Wed 12/24

4:40 pm-8:55 pm

Nonstop3h 15m

Chicago Midway

Mon 1/5

4:40 pm-8:50 pm

1 stop5h 10m

$252

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Thu 1/8

5:05 pm-9:15 pm

Nonstop3h 10m

Chicago Midway

Thu 1/15

12:30 pm-4:35 pm

1 stop5h 05m

$256

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Sat 1/17

9:00 am-4:45 pm

2 stops6h 45m

Chicago Midway

Sat 1/24

9:45 am-4:40 pm

2 stops7h 55m

$267

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 20 results
1
2

Compare providers for flights from Sky Harbor Intl to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Sky Harbor Intl to Midway in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
MytripPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
Trip.comPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Phoenix Sky Harbor Intl Airport-Chicago Midway Airport flights, users find the pricing of CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Phoenix Sky Harbor Intl Airport-Chicago Midway Airport flight deals on Cheapflights vs. CheapOair >95% of the time. Price accuracy is based on data collected from Phoenix Sky Harbor Intl Airport-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Phoenix Sky Harbor Intl Airport-Chicago Midway Airport flights, Cheapflights users trust CheapOair the most. CheapOair has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Phoenix Sky Harbor Intl Airport-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Sky Harbor Intl to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Sky Harbor Intl 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.

Cheapflights Insights

Everything you need to know about your flight from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport

How far ahead should I book a flight from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?

Use this chart to determine the optimal time to book a round-trip flight from Sky Harbor Intl to Midway. Price data was last updated on December 5, 2025.

Booking 59 days in advance of your planned departure date is, on average, the best time to get cheap flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?

Currently, December is the cheapest month in which you can book a flight from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport (average of $62). Flying from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport in March is currently the most expensive (average of $206). 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.

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

Find hourly flight availability from Sky Harbor Intl 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 December 12, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 22% on flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport by exploring options for tickets at noon.

What is the cheapest day to fly from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Sky Harbor Intl to Midway. Price data was last updated on December 6, 2025.

Travelers seeking maximum savings on their Phoenix Sky Harbor Intl Airport to Chicago Midway Airport flight should consider departing on Monday evenings when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

The best insider tips for Phoenix Sky Harbor Intl Airport to Chicago Midway Airport flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Phoenix Sky Harbor Intl Airport to Chicago Midway Airport trip
Airlines
Southwest

Southwest's Early Bird check-in gives priority boarding 36 hours before departure.


Southwest offers free messaging and in-flight entertainment streamed to your device.

Read more about SouthwestBy Marisa Garcia
Frontier

Frontier offers extra comfort seats with 32” separation for a fee, enhancing travel comfort.


Frontier's Board First option is available for carry-on purchasers and elite members, ensuring early boarding.

Read more about FrontierBy Marisa Garcia
Airports
PHX

PHX offers short security lines, often under 10 minutes, with live wait times displayed online for Terminal 4's checkpoints.

Read more about PHXBy Brandon Schultz
MDW

The Orange Line train connects MDW to downtown Chicago in under 30 minutes, offering a cheap and convenient travel option.

Read more about MDWBy Ramsey Qubein
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Southwest and Frontier

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Brandon Schultz

Brandon Schultz

Expert on PHX

Brandon Schultz

Brandon Schultz

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

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 December 12, 2025.
Read reviews from past customers who have flown Southwest, United Airlines, and Frontier from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport. 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.
Southwest
7.9
Good
4,252 reviews

Entertainment

7.5

Overall

7.9

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,252 reviews
Southwest
7.9
Good
4,252 reviews

Entertainment

7.5

Overall

7.9

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,095 reviews
Southwest
7.9
Good
4,252 reviews

Entertainment

7.5

Overall

7.9

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,084 reviews
Southwest
7.9
Good
4,252 reviews

Entertainment

7.5

Overall

7.9

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Sky Harbor Intl to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?

    There are many flights that can get you from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport in 5h 35m. Fly via Southwest or Delta to get the fastest option. The distance between Phoenix Sky Harbor Intl Airport and Chicago Midway Airport is about 1440 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport round-trip?

    Currently priced at $107, Frontier will fly you from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from United Airlines and Southwest - these airlines can fly you to your destination from $149 and $206, respectively. Frontier is currently priced 63% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $69. Users have also found prices from $99 and $124 on Southwest and Delta, respectively.

  • What are the cheapest flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?

    Looking for the cheapest flight from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport? While on average our users pay $284, our data indicates the cheapest price to be $68. The most popular route (Phoenix Sky Harbor Intl - Chicago Midway), is priced around $83.

  • Can I find deals for flights from Sky Harbor Intl to Midway that include hotel bookings?

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

  • How can I find direct flights from Sky Harbor Intl to Midway?

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

  • Can I find deals for business class flights from Sky Harbor Intl to Midway?

    Yes. Cheapflights offers flight deals from Sky Harbor Intl 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 Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?

    Currently, December is the cheapest month in which you can book a flight from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport (average of $62). Flying from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport in March is currently the most expensive (average of $206). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Sky Harbor Intl to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Sky Harbor Intl to Midway

Discover the top 3 airlines that operate flights from Sky Harbor Intl 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 2,558,603 searches. Data last updated December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$110Average$215FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$149Average$272FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$206Average$346FlexibilityNo cancel feeOn-time63%

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