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 Southwest. According to our data, you can fly for as low as $99. Users have also found prices from $102 and $119 on Frontier and Delta, respectively.

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.

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).

What are the most popular airlines that fly from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?

When booking a flight from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport, you may want to consider flying on Frontier, United Airlines or Southwest as they are the most popular for this route.

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

It’s generally more expensive to depart on a Friday, if you have to leave on this day you can still search on Cheapflights to find great options that meet your needs.

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

Flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport lean towards being more expensive in December. Prices are generally better when you fly from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport in September, with the cheapest ticket starting at $70.

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.

$99+ Flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

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 33 days in advance, depart on a Saturday or Thursday and return on a Thursday

Cheap flight deals from Sky Harbor Intl to Midway

Round-trip from	$180 (Cheapflightsfares)
One-way from	$99 (Southwest)
Popular in	March
Cheapest in	September
Average price	$291
Good round-trip deal	$203 or less
Good one-way deal	$151 or less

From Phoenix Sky Harbor Intl to Chicago Midway

Search Deals

One-way flight from Phoenix Sky Harbor Intl to Chicago Midway

Search Deals

Highest demand for flights based on searches. 11% potential increase in price ($38 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 5% potential price decrease ($14 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in July 2025

Search Deals

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.

Search Deals

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 July 28, 2025.

Thu 8/281:35 pmPHX - MDW

Nonstop3h 27mFrontier

Sun 8/314:41 pmMDW - PHX

Nonstop3h 40mFrontier

Deal found 7/28

$180

Sat 8/236:05 pmPHX - MDW

Nonstop3h 20mSouthwest

Sat 8/302:40 pmMDW - PHX

Nonstop3h 40mSouthwest

Deal found 7/26

$188

Fri 8/2211:59 pmPHX - MDW

1 stop7h 37mDelta

Mon 8/254:25 pmMDW - PHX

1 stop8h 24mDelta

Deal found 7/28

$237

Best flights from Sky Harbor Intl to Midway
Discover carefully curated flight deals from Sky Harbor Intl to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 28, 2025.

Thu 8/281:35 pmPHX - MDW

Nonstop3h 27mFrontier

Sun 8/314:41 pmMDW - PHX

Nonstop3h 40mFrontier

Deal found 7/28

$180

Sat 8/236:05 pmPHX - MDW

Nonstop3h 20mSouthwest

Sat 8/302:40 pmMDW - PHX

Nonstop3h 40mSouthwest

Deal found 7/26

$188

Fri 8/2211:59 pmPHX - MDW

1 stop7h 37mDelta

Mon 8/254:25 pmMDW - PHX

1 stop8h 24mDelta

Deal found 7/28

$237

Last-minute flights from Sky Harbor Intl to Midway
Discover last-minute flight deals from Sky Harbor Intl to Midway. Data last updated July 28, 2025 and is based on user searches.

Wed 8/61:40 pmPHX - MDW

1 stop5h 50mSouthwest

Wed 8/205:10 pmMDW - PHX

Nonstop3h 45mSouthwest

Deal found 7/27

$357

Thu 8/72:11 pmPHX - MDW

Nonstop3h 30mFrontier

Thu 8/148:38 pmMDW - PHX

Nonstop3h 42mFrontier

Deal found 7/27

$196

Thu 8/710:50 amPHX - MDW

1 stop5h 50mDelta

Tue 8/126:04 amMDW - PHX

1 stop8h 23mDelta

Deal found 7/28

$358

Fri 8/2211:59 pmPHX - MDW

1 stop7h 37mDelta

Mon 8/254:25 pmMDW - PHX

1 stop8h 24mDelta

Deal found 7/28

$237

Sat 8/236:05 pmPHX - MDW

Nonstop3h 20mSouthwest

Sat 8/302:40 pmMDW - PHX

Nonstop3h 40mSouthwest

Deal found 7/26

$188

Thu 8/281:35 pmPHX - MDW

Nonstop3h 27mFrontier

Sun 8/314:41 pmMDW - PHX

Nonstop3h 40mFrontier

Deal found 7/28

$180

One-way flights from Sky Harbor Intl to Midway
Search for one-way flight options from Sky Harbor Intl to Midway. Find affordable one-way fares based on user searches. Data last updated July 28, 2025.

Tue 9/25:40 pmPHX - MDW

Nonstop3h 20mSouthwest

Deal found 7/28

$99

Sat 10/252:51 pmPHX - MDW

1 stop7h 20mFrontier

Deal found 7/27

$102

Mon 9/1511:44 pmPHX - MDW

1 stop7h 56mDelta

Deal found 7/28

$119

Thu 10/25:59 pmPHX - MDW

2 stops20h 35mMultiple Airlines

Deal found 7/26

$169

Cheapflights Fare Finder

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

Fly to

Route

Depart

Return

Price

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Thu 8/28

1:35 pm-7:02 pm

Nonstop3h 27m

Chicago Midway

Sun 8/31

4:41 pm-6:21 pm

Nonstop3h 40m

$180

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Sat 8/23

6:05 pm-11:25 pm

Nonstop3h 20m

Chicago Midway

Sat 8/30

2:40 pm-4:20 pm

Nonstop3h 40m

$188

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Fri 8/22

11:59 pm-9:36 am

1 stop7h 37m

Chicago Midway

Mon 8/25

4:25 pm-10:49 pm

1 stop8h 24m

$237

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Tue 9/2

5:40 pm-11:00 pm

Nonstop3h 20m

$99

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Sat 10/25

2:51 pm-12:11 am

1 stop7h 20m

$102

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Mon 9/15

11:10 pm-8:40 am

1 stop7h 30m

$119

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Thu 9/18

6:02 pm-4:43 pm

2 stops20h 41m

$169

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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

Cheapflights partnered with top experts to bring you the best recommendations for your Phoenix Sky Harbor Intl Airport to Chicago Midway Airport trip

Airlines

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

Southwest

Southwest offers two free checked bags, including oversized items like skis or golf clubs.

Southwest's Early Bird check-in ensures priority boarding, available with Anytime fares.

Read more about Southwestby Marisa Garcia

Airports

PHX

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

MDW

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

Our travel experts

Marisa Garcia

Expert on Frontier and Southwest

Brandon Schultz

Expert on PHX

Ramsey Qubein

Expert on MDW

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?

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?

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?

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. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

What’s the top layover airport for flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?

Denver (DEN) – chosen by Cheapflights users on 50% of 1-stop itineraries from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport on Cheapflights.

What’s the cheapest layover airport for flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?

Las Vegas (LAS) is the most affordable 1-stop option, with an average round-trip price of $128.

What’s the fastest layover option from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?

Flights via Denver (DEN) have the shortest average one-way travel time for 1-stop routes: 3h 20m.

Which airport typically offers the quickest layover for flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?

Flights via Denver (DEN) offer the fastest connection on this route, with an average layover time of 0h 53m.

Reviews of airlines servicing Midway

Read reviews from past customers who have flown Southwest, Delta, 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

4,238 reviews

Reviews

1 / 20

8.0

Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Southwest

8.0

Very good

4,238 reviews

Southwest

8.0

Very good

4,238 reviews

Reviews

1 / 20

8.0

Excellent

Gina,Jul 2025

LAS - DEN

Delta

8.0

Very good

7,975 reviews

Southwest

8.0

Very good

4,238 reviews

Reviews

1 / 20

8.0

Excellent

Gina,Jul 2025

LAS - DEN

Frontier

5.9

Fair

3,238 reviews

Southwest

8.0

Very good

4,238 reviews

Reviews

1 / 20

8.0

Excellent

Gina,Jul 2025

LAS - DEN

Related info for your journey

What are the cheapest airlines flying from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport round-trip?
Currently priced at $180, 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 Southwest and Delta - these airlines can fly you to your destination from $188 and $237, respectively. Frontier is currently priced 37% 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 Southwest. According to our data, you can fly for as low as $99. Users have also found prices from $102 and $119 on Frontier 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 $232, our data indicates the cheapest price to be $99. The most popular route (Phoenix Sky Harbor Intl - Chicago Midway), is priced around $182.
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

Merrillville

Lansing

Hammond

Benton Harbor

Porter

Valparaiso

Chesterton

Browse thousands of different options on Cheapflights for your next trip

Top 3 airlines flying from Sky Harbor Intl to Midway

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$89	Average$220	FlexibilityNo cancel fee	On-time62%
United Airlines	Cheapest$149	Average$217	FlexibilityNo cancel fee	On-time69%
Southwest	Cheapest$199	Average$335	FlexibilityNo cancel fee	On-time63%

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.

$99+ 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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Sky Harbor Intl to Midway with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

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 Saturday or Thursday and return on a Thursday

Cheap flight deals from Sky Harbor Intl to Midway

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Sky Harbor Intl to Midway

Cheapest flights from Sky Harbor Intl to MidwayExplore 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 July 28, 2025.

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 July 28, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport that are best for you.

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

Cheapflights partnered with top experts to bring you the best recommendations for your Phoenix Sky Harbor Intl Airport to Chicago Midway Airport trip

Airlines

Frontier

Southwest

Airports

PHX

MDW

Our travel experts

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.

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 July 25, 2025.

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

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 July 28, 2025.

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 July 27, 2025.

What’s the top layover airport for flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?

Share of 1-stop round-trip flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport chosen by Cheapflights users in the past 12 months, using the same layover each way.

What’s the cheapest layover airport for flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?

Average round-trip fare for 1-stop flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport, chosen by Cheapflights users in the past 12 months, with the same layover each way.

What’s the fastest layover option from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?

Shortest average travel time for 1-stop one-way flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Which airport typically offers the quickest layover for flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?

Average layover duration for 1-stop one-way flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

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 July 28, 2025.

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.

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

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

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

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

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

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

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

Traveling to a place near Chicago Midway Airport?

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 Sky Harbor Intl to Midway

See prices for flight routes from nearby airports that may be better suited for you.

Top 3 airlines flying from Sky Harbor Intl to Midway

100% Free

Book with Flexibility

Travel Smart

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 July 28, 2025.