Cheap Flight Tickets from Philadelphia (PHL) to Chicago (MDW), Starting at $270

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

$406

WN Southwest Airlines • nonstop • 3h 40m

Nov 24 – Nov 29

The cheapest round trip flight from Philadelphia to Chicago (PHL-MDW-PHL) is currently $406

🔍 Search Flights

Cheapest One way Flight

$343

WN Southwest Airlines • 2 stops • 30h 5m

Sep 17

The cheapest one way flight from Philadelphia to Chicago (PHL-MDW) is currently $343

🔍 Search Flights

Cheapest Direct Flight

$270

WN Southwest Airlines • nonstop • 3h 45m

Nov 24

The cheapest nonstop flight from Philadelphia to Chicago (PHL-MDW) is currently $270

🔍 Search Flights

Fastest Flight

3h 20m

The fastest nonstop flight from Philadelphia to Chicago (PHL-MDW) takes 3h 20m

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 24 - Nov 29, Economy
WN
Philadelphia → Chicago
3h 40m
7:05 PM - 8:25 PM • nonstop
WN
Philadelphia → Chicago
11h 40m
7:30 AM - 3:30 PM • 1 stop
$406
Southwest Airlines
Nov 24 - Nov 29, Economy
WN
Philadelphia → Chicago
25h 5m
6:15 AM - 8:20 PM • 2 stops
WN
Philadelphia → Chicago
3h 20m
6:20 AM - 9:20 AM • nonstop
$406
Southwest Airlines
Nov 24 - Nov 29, Economy
WN
Philadelphia → Chicago
15h 10m
1:45 PM - 9:55 PM • 1 stop
WN
Philadelphia → Chicago
18h 25m
8:00 AM - 8:05 PM • 2 stops
$473
Southwest Airlines
Nov 24 - Nov 29, Economy
WN
Philadelphia → Chicago
15h 55m
12:10 PM - 9:05 PM • 1 stop
WN
Philadelphia → Chicago
10h 15m
5:50 AM - 1:05 PM • 1 stop
$532
Southwest Airlines
Nov 24 - Nov 29, Economy
WN
Philadelphia → Chicago
26h 55m
5:50 AM - 9:05 PM • 1 stop
WN
Philadelphia → Chicago
3h 20m
6:20 AM - 9:20 AM • nonstop
$543
Southwest Airlines
Nov 24 - Nov 29, Economy
DL
Philadelphia → Chicago
6h 51m
9:40 AM - 12:51 PM • 1 stop
DL
Philadelphia → Chicago
6h 56m
11:19 AM - 4:35 PM • 1 stop
$630
Delta 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 5:50 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 DL : USD 762
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 7:05 pm

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

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

More Flight Options for Philadelphia (PHL) and Chicago (MDW)

Why Fareleaders for PHL to MDW Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on Philadelphia to Chicago flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on PHL to MDW flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of Philadelphia to Chicago flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the Philadelphia (PHL) to Chicago (MDW)
Terms and Conditions*