Popular airlines from Philadelphia International Airport (PHL) to Chicago Midway Airport (MDW)
Frontier AirlinesFrontier Airlines
Southwest AirlinesSouthwest Airlines
DeltaDelta
- Plan, book, fly with confidence
- Be in the knowGet alerts if flight prices drop or rise*
- Book smarterSave up to 30% on select hotels after you book a flight*
Cheap flights from Philadelphia (PHL) to Chicago (MDW)
Prices were available within the past 7 days and start at CA $136 for one-way flights and CA $300 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Find the cheapest month to fly from Philadelphia (PHL) to Chicago (MDW)
September is typically the cheapest month to fly
Graph displaying average flight prices per month
Origin airport | Philadelphia Intl. |
Destination airport | Midway Intl. |
Roundtrip price | CA $299 |
Distance | 1065 km |
Average flight time | 1 hour 6 mins |
Philadelphia to Chicago Flights
The easy way to book your flights from Philadelphia to Chicago
With Expedia, it’s simple to find and book flights to Chicago from Philadelphia whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are Southwest Airlines nonstop flights to Midway Intl., too.
Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Philadelphia to Chicago today, tomorrow, or this week.
Save dollars with cheap flights from Philadelphia Intl., PHL to Midway Intl., MDW
Sort your search results by price to find great deals on your flight from Philadelphia to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Philadelphia currently is just CA $300 rising to CA $439.
Here are more money-saving tips:
- Fly in September when flight prices are normally at their lowest
- Book about a month to 6 weeks before you travel for the best prices to Chicago
- Avoid peak season and weekends when flights can cost more
- Early morning and late-night flights are sometimes cheaper, so try varying your travel times
- One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free!
Reasons to choose Expedia for your flight to Chicago from Philadelphia
Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today.
Frequently asked questions
Explore a world of travel with Expedia
- Trending Routes
- Trending Flights
- Top Flights Destinations
- Other Airlines
- Main Airports for Flights
- Cheap Flights from Other Airports
- Expedia's Latest Trends
Top Routes from Philadelphia
- Philadelphia to Mumbai (PHL - BOM)
- Philadelphia to Los Angeles (PHL - LAX)
- Philadelphia to Detroit (PHL - DTW)
- Philadelphia to Winnipeg (PHL - YWG)
- Philadelphia to Halifax (PHL - YHZ)
- Philadelphia to St. Louis (PHL - STL)
- Philadelphia to Seattle (PHL - SEA)
- Philadelphia to Montreal (PHL - YUL)
- Philadelphia to Houston (PHL - IAH)
- Philadelphia to Buffalo (PHL - BUF)
- Philadelphia to Vancouver (PHL - YVR)
- Philadelphia to Kitchener (PHL - YKF)
Top Routes to Chicago
- Ottawa to Chicago (YOW - MDW)
- Calgary to Chicago (YYC - MDW)
- Detroit to Chicago (DTW - MDW)
- Winnipeg to Chicago (YWG - MDW)
- Halifax to Chicago (YHZ - MDW)
- Québec to Chicago (YQB - MDW)
- Montreal to Chicago (YUL - MDW)
- Buffalo to Chicago (BUF - MDW)
- Vancouver to Chicago (YVR - MDW)
- Moncton to Chicago (YQM - MDW)
- Edmonton to Chicago (YEG - MDW)
- Toronto to Chicago (YYZ - MDW)
Top Routes from Philadelphia
Top Routes to Chicago
Top Flight Destinations
- Flights to Las Vegas
- Flights to New York
- Flights to Orlando
- Flights to Chicago
- Flights to San Diego
- Flights to Myrtle Beach
- Flights to Los Angeles
- Flights to Ocean City
- Flights to San Francisco
- Flights to Miami
- Flights to Destin
- Flights to Nashville
- Flights to Panama City Beach
- Flights to Atlantic City
- Flights to Pigeon Forge
- Flights to Honolulu
- Flights to Houston
- Flights to Atlanta
- Flights to Seattle
- Flights to Virginia Beach
Chicago
Main Airports for Flights
Expedia's Latest Trends
- Flights from Ottawa to Las Vegas
- Flights from Vancouver to San Diego
- Flights from Vancouver to Las Vegas
- Flights from Hamilton to Las Vegas
- Flights from Abbotsford to Las Vegas
- Flights from Toronto to Seattle
- Flights from Toronto to San Diego
- Flights from Toronto to Myrtle Beach
- Flights from Toronto to New York
- Flights from Montreal to Las Vegas
- Flights from Detroit to Las Vegas
- Flights from Vancouver to Seattle
- Flights from Montreal to Fort Lauderdale
- Flights from Kelowna to Las Vegas
- Flights from Fort Lauderdale to Toronto
- Flights from Vancouver to Boston
- Flights from Winnipeg to Las Vegas
- Flights from Calgary to Dallas
- Flights from Calgary to Seattle
- Flights from Buffalo to Fort Lauderdale
- Flights from Toronto to Fort Lauderdale
- Flights from Bellingham to Las Vegas
- Flights from Seattle to Delhi
- Flights from Vancouver to Palm Springs
- Flights from Vancouver to Dallas
- Flights from Toronto to Las Vegas
- Flights from Buffalo to Las Vegas
- Flights from Las Vegas to Toronto
- Flights from Edmonton to Seattle
- Flights from Victoria to Las Vegas