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$88+ 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
PHX — MDW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Phoenix Sky Harbor Intl to Chicago Midway are usually found in September or October, booked 33 days in advance, depart on a Thursday or Tuesday and return on a Thursday

Cheap 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 September 11, 2025.

Round-trip from

$137
(Cheapflightsfares)

One-way from

$88
(Priceline)

Popular in

March

Cheapest in

September

Average price

$169

Good round-trip deal

$180 or less

Good one-way deal

$157 or less
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. 11% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Phoenix Sky Harbor Intl to Chicago Midway.
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Price to beat on a one-way flight from Phoenix Sky Harbor Intl to Chicago Midway.
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Find 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 September 11, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2810:00 amPHX - MDW
Nonstop3h 23mFrontier
Sun 12/76:00 amMDW - PHX
Nonstop4h 04mFrontier
Deal found 9/10$137
This Booking.com deal was found by Cheapflights users on 9/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1610:39 amPHX - MDW
Nonstop3h 26mFrontier
Sun 10/1910:30 amMDW - PHX
1 stop15h 24mFrontier
Deal found 9/11$140
This Booking.com deal was found by Cheapflights users on 9/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/64:41 pmPHX - MDW
1 stop18h 56mFrontier
Mon 11/108:30 amMDW - PHX
Nonstop3h 53mFrontier
Deal found 9/11$141
This Priceline deal was found by Cheapflights users on 9/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2210:59 pmPHX - MDW
1 stop8h 48mFrontier
Mon 10/2710:56 pmMDW - PHX
Nonstop3h 51mFrontier
Deal found 9/8$143
This Frontier deal was found by Cheapflights users on 9/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/610:53 pmPHX - MDW
1 stop11h 37mFrontier
Sun 11/99:00 amMDW - PHX
Nonstop3h 54mFrontier
Deal found 9/11$145
This Priceline deal was found by Cheapflights users on 9/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/315:05 amPHX - MDW
1 stop10h 10mFrontier
Mon 11/312:30 pmMDW - PHX
1 stop10h 14mFrontier
Deal found 9/10$148
This Flightnetwork deal was found by Cheapflights users on 9/10. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/239:59 pmPHX - MDW
1 stop11h 17mFrontier
Thu 10/3012:30 pmMDW - PHX
1 stop21h 20mFrontier
Deal found 9/10$149
This Booking.com deal was found by Cheapflights users on 9/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/197:25 amPHX - MDW
1 stop11h 21mFrontier
Sun 9/216:30 amMDW - PHX
1 stop9h 17mFrontier
Deal found 9/10$150
This CheapOair deal was found by Cheapflights users on 9/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/204:20 pmPHX - MDW
Nonstop3h 26mFrontier
Mon 10/2710:56 pmMDW - PHX
Nonstop3h 51mFrontier
Deal found 9/11$151
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1610:39 amPHX - MDW
Nonstop3h 26mFrontier
Mon 10/2010:56 pmMDW - PHX
Nonstop3h 51mFrontier
Deal found 9/11$152
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/13:30 pmPHX - MDW
1 stop5h 50mSouthwest
Sat 10/45:15 amMDW - PHX
1 stop5h 30mSouthwest
Deal found 9/10$153
This Priceline deal was found by Cheapflights users on 9/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1610:39 amPHX - MDW
Nonstop3h 26mFrontier
Sat 10/1810:00 amMDW - PHX
1 stop11h 41mFrontier
Deal found 9/10$154

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 September 11, 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

Fri 10/24

5:50 pm-11:05 pm

Nonstop3h 15m

Chicago Midway

Tue 10/28

6:25 am-8:10 am

Nonstop3h 45m

$165

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Wed 11/5

6:40 pm-10:55 pm

Nonstop3h 15m

Chicago Midway

Sun 11/9

5:30 am-8:25 am

Nonstop3h 55m

$169

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Mon 12/8

5:00 am-9:15 am

Nonstop3h 15m

Chicago Midway

Fri 12/12

3:30 pm-6:25 pm

Nonstop3h 55m

$186

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Tue 12/9

5:25 am-12:30 pm

2 stops6h 05m

Chicago Midway

Fri 12/12

9:50 pm-12:35 am

Nonstop3h 45m

$196

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Fri 11/7

1:20 pm-8:45 pm

1 stop6h 25m

Chicago Midway

Tue 11/11

1:55 pm-6:00 pm

1 stop5h 05m

$203

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Thu 10/16

5:50 pm-11:05 pm

Nonstop3h 15m

Chicago Midway

Sat 10/18

4:30 pm-9:25 pm

1 stop6h 55m

$206

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Fri 11/7

11:40 pm-8:40 am

1 stop8h 00m

Chicago Midway

Mon 11/10

1:14 pm-7:17 pm

1 stop7h 03m

$237

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Mon 11/24

12:59 am-9:01 am

1 stop7h 02m

Chicago Midway

Fri 11/28

7:02 pm-11:59 pm

1 stop5h 57m

$237

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Tue 10/28

12:40 am-8:55 am

1 stop6h 15m

Chicago Midway

Sat 11/1

4:23 pm-11:00 pm

1 stop8h 37m

$237

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Fri 10/24

5:00 am-10:15 am

Nonstop3h 15m

Chicago Midway

Sun 10/26

10:40 pm-12:30 am

Nonstop3h 50m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 21 results
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The best insider tips for Phoenix Sky Harbor Intl Airport to Chicago Midway Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
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

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 August 29, 2025.

Booking 33 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, April is the cheapest month in which you can book a flight from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport (average of $160). Flying from Phoenix Sky Harbor Intl Airport 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.

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 September 11, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 30% on flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport by exploring options for tickets in the evening.

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 September 7, 2025.

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

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 September 11, 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
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 3h 15m. Fly via Southwest to get the fastest option. The distance between Phoenix Sky Harbor Intl Airport and Chicago Midway Airport is about 1440 mi. Most flights are nonstop.

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

    Currently priced at $108, 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 $199, respectively. Frontier is currently priced 62% below the average price you’ll pay for this route.

  • 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 $236, our data indicates the cheapest price to be $86. The most popular route (Phoenix Sky Harbor Intl - Chicago Midway), is priced around $103.

  • 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, April is the cheapest month in which you can book a flight from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport (average of $160). Flying from Phoenix Sky Harbor Intl Airport 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.

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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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.
Sky Harbor Intl to O'Hare Intl flights
Phoenix-Mesa Gateway to Rockford flights
Sky Harbor Intl to Rockford flights

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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$219FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$149Average$217FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$199Average$339FlexibilityNo cancel feeOn-time63%

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