Is Southwest the cheapest airline to fly with from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?

With an average price of $344 return, Southwest is not the cheapest airline to fly from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport with. Instead, for the lowest price, our data suggests flying with Frontier, where a return flight costs $217 on average.

Does Southwest fly direct to Chicago Midway Airport from Phoenix Sky Harbor Intl Airport?

Yes, Southwest does offer direct flights for the route, with around 15 flights per week.

What’s the cheapest day of the week to fly from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport with Southwest?

On average, the cheapest day of the week to fly from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport with Southwest is Tuesday, when prices are around $99. The most expensive day is generally Sunday, where the average price is around $182.

$89 Cheap Southwest Flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport

PHX - MDW

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Cheap Southwest Flight Deals from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport

Here are some of the best deals found on KAYAK recently from Southwest for round-trip flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip Southwest flight deals from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport

sáb, fev 14 - sáb, fev 21

4:10 pm - 8:20 pmPHX-MDW

3h 10mnonstop

5:45 pm - 8:40 pmMDW-PHX

3h 55mnonstop

$177Southwest

Find Deal

ter, fev 24 - sex, fev 27

5:00 am - 9:15 amPHX-MDW

3h 15mnonstop

10:15 pm - 1:10 amMDW-PHX

3h 55mnonstop

$189Southwest

Find Deal

qua, dez 10 - dom, dez 14

5:00 am - 9:15 amPHX-MDW

3h 15mnonstop

5:30 am - 8:25 amMDW-PHX

3h 55mnonstop

$208Southwest

Find Deal

sáb, jan 17 - seg, jan 26

10:20 pm - 5:05 amPHX-MDW

5h 45m1 stop

5:05 am - 8:15 amMDW-PHX

4h 10mnonstop

$211Southwest

Find Deal

qui, dez 4 - qui, dez 11

5:00 am - 9:15 amPHX-MDW

3h 15mnonstop

5:25 am - 8:15 amMDW-PHX

3h 50mnonstop

$217Southwest

Find Deal

ter, dez 2 - qua, dez 3

5:00 am - 9:15 amPHX-MDW

3h 15mnonstop

3:15 pm - 6:05 pmMDW-PHX

3h 50mnonstop

$218Southwest

Find Deal

ter, dez 2 - qua, dez 3

5:00 am - 9:15 amPHX-MDW

3h 15mnonstop

1:55 pm - 6:00 pmMDW-PHX

5h 05m1 stop

$224Southwest

Find Deal

qui, dez 11 - qui, dez 18

5:00 am - 9:15 amPHX-MDW

3h 15mnonstop

5:30 am - 8:25 amMDW-PHX

3h 55mnonstop

$227Southwest

Find Deal

ter, dez 16 - qui, dez 18

5:00 am - 9:15 amPHX-MDW

3h 15mnonstop

5:40 am - 10:30 amMDW-PHX

5h 50m1 stop

$228Southwest

Find Deal

ter, fev 24 - sex, fev 27

12:10 pm - 6:45 pmPHX-MDW

5h 35m1 stop

5:00 am - 8:10 amMDW-PHX

4h 10mnonstop

$229Southwest

Find Deal

Useful Info

Low season	February
High season	October
Cheapest flight	$89
Average price round-trip	$229

Best time to beat the crowds with an average 17% drop in price.

Most popular time to fly and prices are also 21% lower on average.

Flight from Phoenix to Chicago Midway Airport

(price for this month)

When to Book Flights with Southwest from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport

Average price per month

Flight prices as travel date approaches

Is Southwest the cheapest airline to fly with from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?
With an average price of $344 return, Southwest is not the cheapest airline to fly from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport with. Instead, for the lowest price, our data suggests flying with Frontier, where a return flight costs $217 on average.
What is the cheapest Southwest flight from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?
In the last 3 days, the lowest price for a flight with Southwest from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport was $123 for a return flight and $98 for a one-way flight.
Does Southwest fly direct to Chicago Midway Airport from Phoenix Sky Harbor Intl Airport?
Yes, Southwest does offer direct flights for the route, with around 15 flights per week.
What’s the cheapest day of the week to fly from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport with Southwest?
On average, the cheapest day of the week to fly from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport with Southwest is Tuesday, when prices are around $99. The most expensive day is generally Sunday, where the average price is around $182.
What’s the cheapest month to fly from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport with Southwest?
The cheapest month for Southwest flights to Chicago Midway Airport from Phoenix Sky Harbor Intl Airport is generally May, where plane tickets cost $148 on average. If possible, try to avoid the most expensive months of October and January, where tickets cost $268 and $284 respectively.

8.0

Very good4,243 verified ratings

8.1Boarding

8.6Crew

7.0Food

8.0Comfort

7.5Entertainment

Pros +

Cons -

Show reviews that mention

10.0 Wonderful

James, Oct 2025

TUS-LAS

Very good

8.0 Very good

Greg, Oct 2025

OAK-BUR

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 Very good

Margaret, Oct 2025

SAV-HOU

Full cans of soda would be nice. A choice between two snacks would be appreciated.

8.0 Very good

TODD, Oct 2025

CMH-HOU

Tried watching free movie and it kept freezing so I couldn’t finish.

10.0 Wonderful

Antonio, Oct 2025

PVD-MCO

Always reliable

10.0 Wonderful

Verified traveler, Oct 2025

MDW-BWI

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

4.0 Mediocre

Mike, Oct 2025

GRR-MDW

Staff/crew very good. 4 hour delay not good.

10.0 Wonderful

Stacy, Oct 2025

SMF-DEN

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

2.0 Poor

Verified traveler, Oct 2025

DAL-LIT

Delayed 5.5 hours

10.0 Wonderful

Verified traveler, Oct 2025

BOS-BWI

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

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

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Cabin class types available on flights to Chicago Midway Airport

First Class flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport

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PHX - MDW

$89 Find Cheap Southwest Flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport

Search hundreds of travel sites at once for deals on Southwest flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport

Cheap Southwest Flight Deals from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport

Recent round-trip Southwest flight deals from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport

Recent one-way Southwest flight deals from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport

Recent last minute Southwest flight deals from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport

Recent direct Southwest flight deals from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport

Good to know

When to Book Flights with Southwest from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport

FAQs for flying to Chicago Midway Airport with Southwest

Is Southwest the cheapest airline to fly with from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?

What is the cheapest Southwest flight from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?

Does Southwest fly direct to Chicago Midway Airport from Phoenix Sky Harbor Intl Airport?

What’s the cheapest day of the week to fly from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport with Southwest?

What’s the cheapest month to fly from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport with Southwest?

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

Cabin class types available on flights to Chicago Midway Airport

Cabin classes available on flights to Phoenix Sky Harbor Intl Airport. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

Complete your trip to Chicago Midway Airport with a hotel stay or car rental

Flights to other popular destinations

The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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Top Southwest flights

The most popular destinations for flights with Southwest according to clicks from KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.