CA $137 Cheap Flights from Philadelphia (PHL) to Chicago (MDW)

View CA $137 flight on Tue, Jul. 29, 2025Opens in a new window

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Cheap flights from Philadelphia (PHL) to Chicago (MDW)

Prices were available within the past 7 days and start at CA $137 for one-way flights and CA $273 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue., Jul. 8 - Wed., Jul. 9
PHL
Philadelphia
MDW
Chicago
CA $273 Roundtrip, found 3 days ago
CA $273
Roundtrip
found 3 days ago
Select Delta flight, departing Tue., Jul. 8 from Philadelphia to Chicago, returning Wed., Jul. 9, priced at CA $273 found 3 days ago
Delta
Tue., May 20 - Tue., Jun. 3
PHL
Philadelphia
MDW
Chicago
CA $274 Roundtrip, found 3 days ago
CA $274
Roundtrip
found 3 days ago
Select Delta flight, departing Tue., May 20 from Philadelphia to Chicago, returning Tue., Jun. 3, priced at CA $274 found 3 days ago
Delta
Tue., May 13 - Sat., May 24
PHL
Philadelphia
MDW
Chicago
CA $288 Roundtrip, found 3 days ago
CA $288
Roundtrip
found 3 days ago
Select Delta flight, departing Tue., May 13 from Philadelphia to Chicago, returning Sat., May 24, priced at CA $288 found 3 days ago
Delta
Tue., Jul. 8 - Thu., Jul. 17
PHL
Philadelphia
MDW
Chicago
CA $301 Roundtrip, found 3 days ago
CA $301
Roundtrip
found 3 days ago
Select Delta flight, departing Tue., Jul. 8 from Philadelphia to Chicago, returning Thu., Jul. 17, priced at CA $301 found 3 days ago
Delta
Wed., Jul. 23 - Thu., Jul. 31
PHL
Philadelphia
MDW
Chicago
CA $301 Roundtrip, found 5 days ago
CA $301
Roundtrip
found 5 days ago
Select Delta flight, departing Wed., Jul. 23 from Philadelphia to Chicago, returning Thu., Jul. 31, priced at CA $301 found 5 days ago
Delta
Tue., May 13 - Thu., May 29
PHL
Philadelphia
MDW
Chicago
CA $316 Roundtrip, found 3 days ago
CA $316
Roundtrip
found 3 days ago
Select Delta flight, departing Tue., May 13 from Philadelphia to Chicago, returning Thu., May 29, priced at CA $316 found 3 days ago
Delta
Sat., May 10 - Sat., May 24
PHL
Philadelphia
MDW
Chicago
CA $322 Roundtrip, found 3 days ago
CA $322
Roundtrip
found 3 days ago
Select Delta flight, departing Sat., May 10 from Philadelphia to Chicago, returning Sat., May 24, priced at CA $322 found 3 days ago
Delta
Sat., May 3 - Sat., May 10
PHL
Philadelphia
MDW
Chicago
CA $324 Roundtrip, found 5 days ago
CA $324
Roundtrip
found 5 days ago
Select Delta flight, departing Sat., May 3 from Philadelphia to Chicago, returning Sat., May 10, priced at CA $324 found 5 days ago
Delta
Wed., May 7 - Tue., May 20
PHL
Philadelphia
MDW
Chicago
CA $324 Roundtrip, found 3 days ago
CA $324
Roundtrip
found 3 days ago
Select Delta flight, departing Wed., May 7 from Philadelphia to Chicago, returning Tue., May 20, priced at CA $324 found 3 days ago
Delta
Thu., May 22 - Sat., Jun. 7
PHL
Philadelphia
MDW
Chicago
CA $328 Roundtrip, found 3 days ago
CA $328
Roundtrip
found 3 days ago
Select Delta flight, departing Thu., May 22 from Philadelphia to Chicago, returning Sat., Jun. 7, priced at CA $328 found 3 days ago
Flight from Philadelphia to Chicago (PHL - MDW) route information
Origin airport
Philadelphia Intl.
Destination airport
Midway Intl.
Roundtrip price
CA $265
Distance
1065 km

Philadelphia to Chicago Flights

Ready for an adventure? Thought so! Prepare to see the sights when you book your trip from Philadelphia to Chicago with Expedia.ca. Whether you’re visiting for business or pleasure, we know how important it is to bring home travel stories. Maybe your tales will include the best dinner of your life, or the weirdest street art you saw in the city, or the concert that turned you into a fan of a new band. Whatever it is, your new favourite anecdote is right around the corner. Book your trip from PHL to MDW and begin your journey!

Getting a cheap deal on your trip sets the tone for the perfect holiday. And with Expedia.ca, you know you can travel from Philadelphia to Chicago on the cheap, with enough money left over for a stellar time in the city. That could mean more tours with the kids, more concerts with the spouse, more dessert amongst co-workers, or even front row seats to a sports game if you’re travelling solo. It’s your holiday! Make it great.

Travelling shouldn’t cost an arm and a leg before you even get to relax on the plane’s armrests. Count on Expedia.ca to get you the best discounts on flights from PHL to MDW. And remember this: You can also save big when you bundle. Add a hotel or car rental deal to your flight and witness those savings add up. Hey, more money for more souvenirs, right? Right! Pack your bags and we’ll see you on the route.

Combine your Chicago flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights from with Expedia Canada. Use us as your top travel destination and have the confidence that you’re getting a bargain!

Frequently asked questions

How much is a flight from Philadelphia Intl. Airport (PHL) to Chicago Airport?
The lowest price advertised for a round-trip journey from PHL to MDW is CA $273. But you better move fast. This price is based on fares listed within the last 7 days on Expedia for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Philadelphia Airport to Midway Intl. Airport (MDW)?
Each air carrier has its own set of terms and conditions. If you do decide to cancel, follow the simple instructions on our Customer Service Portal.
How do I find cheap flights from Philadelphia Intl. Airport (PHL) to Midway Intl. Airport (MDW) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you’re searching for Philadelphia Airport to Chicago Airport flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from Philadelphia Airport to MDW?
You can forget about a movie marathon on this flight — it’s only 1,050 kilometers from Philadelphia to Chicago. Sit down, order a snack and you’ll be there in next to no time.
Which airlines fly direct from Philadelphia Intl. Airport (PHL) to Midway Intl. Airport (MDW)?
With 117 flights a month operating from Philadelphia Intl. Airport (PHL) to Chicago Airport, Southwest Airlines (WN) is a popular choice. Like some more options? Check out the ticket prices from Frontier Airlines (F9). This carrier offers 30 flights a month between these airports.
Are PHL to Midway Intl. Airport (MDW) flight tickets cheaper when they're purchased at the last minute?
It is possible to nab an amazing last-minute deal from Philadelphia Intl. Airport (PHL) to Midway Airport, but there’s no guarantee. As many airlines release prices up to 12 months in advance, it’s worthwhile keeping an eye on fares early and being ready to pounce when you see a bargain. Expedia compares air carrier prices and updates flight deals frequently, so you can rest easy knowing you’re always seeing the latest offers.

Explore a world of travel with Expedia

Chicago nearby Airports

Chicago

Philadelphia to O'Hare Intl.
CA $272.40
*Available to Expedia members.