Cheap Flight Tickets from Philadelphia (PHL) to Chicago (MDW), Starting at $105

Good to Know: Cheapest and Fastest PHL - MDW Flights

Useful information for finding best airline tickets from Philadelphia International to Chicago Midway International on your next trip.

Cheapest Round Trip Flight

$347

WN Southwest Airlines • nonstop • 3h 30m

Nov 22 – Nov 29

The cheapest round trip flight from Philadelphia to Chicago (PHL-MDW-PHL) is currently $347

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Cheapest One way Flight

$105

WN Southwest Airlines • 3 stops • 22h 10m

Oct 20

The cheapest one way flight from Philadelphia to Chicago (PHL-MDW) is currently $105

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Cheapest Direct Flight

$347

WN Southwest Airlines • nonstop • 3h 30m

Nov 22

The cheapest nonstop flight from Philadelphia to Chicago (PHL-MDW) is currently $347

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Fastest Flight

3h 30m

The fastest nonstop flight from Philadelphia to Chicago (PHL-MDW) takes 3h 30m

Top Airlines Flying from Philadelphia to Chicago

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

American Airlines, AA

American Airlines

Latest Flight Deals from Philadelphia (PHL) to Chicago (MDW)

Compare and book low fare round-trip air tickets from Philadelphia to Chicago. Ideal for travelers with confirmed return itineraries.

Nov 22 - Nov 29, Economy
WN
Philadelphia → Chicago
3h 30m
11:40 AM - 12:50 PM • nonstop
WN
Philadelphia → Chicago
3h 20m
6:20 AM - 9:20 AM • nonstop
$347
Southwest Airlines
Nov 22 - Nov 29, Economy
WN
Philadelphia → Chicago
7h 35m
8:15 PM - 12:10 AM • 1 stop
WN
Philadelphia → Chicago
3h 20m
6:20 AM - 9:20 AM • nonstop
$353
Southwest Airlines
Nov 22 - Nov 29, Economy
WN
Philadelphia → Chicago
13h 20m
5:00 AM - 12:00 PM • 1 stop
WN
Philadelphia → Chicago
2h 35m
8:30 PM - 11:25 PM • nonstop
$354
Southwest Airlines
Nov 22 - Nov 29, Economy
WN
Philadelphia → Chicago
7h
7:25 PM - 10:45 PM • 1 stop
WN
Philadelphia → Chicago
3h 20m
6:20 AM - 9:20 AM • nonstop
$377
Southwest Airlines
Nov 22 - Nov 29, Economy
WN
Philadelphia → Chicago
7h
7:25 PM - 10:45 PM • 1 stop
WN
Philadelphia → Chicago
10h 10m
5:10 AM - 12:20 PM • 1 stop
$441
Southwest Airlines
Nov 22 - Nov 29, Economy
WN
Philadelphia → Chicago
3h 35m
1:50 PM - 3:05 PM • nonstop
WN
Philadelphia → Chicago
10h 10m
5:10 AM - 12:20 PM • 1 stop
$443
Southwest Airlines

Fly from Philadelphia to Chicago with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Philadelphia to Chicago? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Philadelphia to Chicago Flights

What are the airports in Philadelphia?
PHL
What’s the most popular airline flying from PHL to MDW?
The most popular airline flying from Philadelphia to Chicago are
Can I fly from PHL to MDW non-stop?
Yes, you can fly PHL to MDW non-stop on
Which airlines fly nonstop between Philadelphia and Chicago?
The non-stop flights between Philadelphia and Chicago are .
What’s the earliest departure time from PHL to MDW Airport?
The earliest flight leaves PHL at 5:00 am and lands in MDW - Chicago Midway International
What are the airports in Chicago?
ORD,MDW
Can I make changes to my Philadelphia to Chicago flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from PHL to MDW?
Read the fare rules of the Philadelphia to Chicago air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Philadelphia and Chicago?
operate flights between Philadelphia and Chicago
How long does a flight from Philadelphia to Chicago take?
It takes approximately 2 hour to fly non-stop from PHL to MDW, which is 668.29 miles by air.
Which airlines provide the cheapest flights from Philadelphia (PHL) to Chicago (MDW) ?
In the past couple of days, the cheapest tickets to MDW from PHL were found on WN : USD 105
Do I need a passport to fly between PHL and MDW?
No
What’s the latest departure time from PHL to MDW ?
The last flight leaves PHL at 3:4600 pm

Philadelphia (PHL) to Chicago (MDW): Airport Information

Origin Airport Philadelphia International , Philadelphia, US
Destination Airport Chicago Midway International , Chicago, US
Distance 668 miles

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