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CA $194 Cheap Flights from Philadelphia (PHL) to Chicago (MDW)

View CA $194 flight on Sat, Jul 25, 2026Opens in a new window

Popular airlines from Philadelphia International Airport (PHL) to Chicago Midway Airport (MDW)

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

Prices were available within the past 7 days and start at CA $194 for one-way flights and CA $471 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Jul 28 - Fri, Jul 31
PHL
Philadelphia
MDW
Chicago
CA $471 Roundtrip, just found
CA $471
Roundtrip
just found
Select Delta flight, departing Tue, Jul 28 from Philadelphia to Chicago, returning Fri, Jul 31, priced at CA $471 just found
Delta
Fri, Sep 11 - Mon, Sep 14
PHL
Philadelphia
MDW
Chicago
CA $476 Roundtrip, found 6 days ago
CA $476
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Sep 11 from Philadelphia to Chicago, returning Mon, Sep 14, priced at CA $476 found 6 days ago
Delta
Sat, Sep 19 - Sun, Sep 20
PHL
Philadelphia
MDW
Chicago
CA $512 Roundtrip, found 2 days ago
CA $512
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Sep 19 from Philadelphia to Chicago, returning Sun, Sep 20, priced at CA $512 found 2 days ago
Delta
Fri, Sep 11 - Mon, Sep 14
PHL
Philadelphia
MDW
Chicago
CA $514 Roundtrip, found 6 days ago
CA $514
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Sep 11 from Philadelphia to Chicago, returning Mon, Sep 14, priced at CA $514 found 6 days ago
Delta
Thu, Aug 6 - Mon, Aug 10
PHL
Philadelphia
MDW
Chicago
CA $515 Roundtrip, found 3 days ago
CA $515
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Aug 6 from Philadelphia to Chicago, returning Mon, Aug 10, priced at CA $515 found 3 days ago
Delta
Fri, Sep 11 - Mon, Sep 14
PHL
Philadelphia
MDW
Chicago
CA $526 Roundtrip, found 6 days ago
CA $526
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Sep 11 from Philadelphia to Chicago, returning Mon, Sep 14, priced at CA $526 found 6 days ago
Delta
Tue, Jul 28 - Fri, Jul 31
PHL
Philadelphia
MDW
Chicago
CA $532 Roundtrip, just found
CA $532
Roundtrip
just found
Select Delta flight, departing Tue, Jul 28 from Philadelphia to Chicago, returning Fri, Jul 31, priced at CA $532 just found
Delta
Thu, Sep 17 - Sun, Sep 20
PHL
Philadelphia
MDW
Chicago
CA $549 Roundtrip, found 6 days ago
CA $549
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Sep 17 from Philadelphia to Chicago, returning Sun, Sep 20, priced at CA $549 found 6 days ago
Delta
Thu, Sep 17 - Sun, Sep 20
PHL
Philadelphia
MDW
Chicago
CA $552 Roundtrip, found 16 hours ago
CA $552
Roundtrip
found 16 hours ago
Select Delta flight, departing Thu, Sep 17 from Philadelphia to Chicago, returning Sun, Sep 20, priced at CA $552 found 16 hours ago
Delta
Thu, Aug 6 - Mon, Aug 10
PHL
Philadelphia
MDW
Chicago
CA $554 Roundtrip, found 3 days ago
CA $554
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Aug 6 from Philadelphia to Chicago, returning Mon, Aug 10, priced at CA $554 found 3 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city centre is 23 minutes. Flights from CA $439
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from CA $439

Frequently asked questions

How much does a flight from Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find one-way and return flights from PHL to MDW with Expedia. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see our cheapest fares first, and use the Price Tracking tool to receive alerts when PHL to MDW ticket fares go up or down.
What is the cheapest month to fly from Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.)?
The cheapest months to fly from PHL to MDW are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.)?
Only one airline offers direct flights from Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.). Southwest Airlines operates 33 direct flights from PHL to MDW every week.
What is the cheapest airline that flies from Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.)?
Southwest Airlines also offers one of the cheapest connecting return flights on this route, with a layover in Nashville Intl. (BNA), starting from around CA$149. Southwest Airlines is one of the cheapest airlines offering nonstop return flights from Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.), with tickets starting from around CA$192 for flights that can be booked for departure within the next year. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.
How do I find cheap flights from Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.)?
The best airline to fly with from Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.) will differ from traveler to traveler. If you like to fly early, Southwest Airlines offers early morning flights. If price is the most important factor, Southwest Airlines typically offers the lowest fares. Southwest Airlines offers the most daily flights from Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.), which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.)?
You'll find around 5 nonstop flights per day from Philadelphia International Airport (PHL) to Chicago Midway International Airport (MDW). For even more choices, look at flights that include layovers, as there are approximately 37 connecting flights per day. Some common connection points include Nashville International (BNA), Lambert-St. Louis International (STL), and Hartsfield-Jackson Atlanta International (ATL).
What is the earliest flight from Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.) typically departs around 5:00 AM. This service is operated by Frontier Airlines and is a seasonal service active in March. An early departure like this can help you make the most of your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.)?
You'll find the most flights from Philadelphia International Airport (PHL) to Midway International Airport (MDW) on a Friday, with around 30 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include Southwest Airlines, Delta, and Frontier Airlines. Fridays offer notably more flight options compared to other days of the week, making it a popular choice for travellers.
What are the most popular departure times for flights from Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Philadelphia Intl. (PHL) to Midway Intl. (MDW) are in the early morning, from 6am to 9am. Many major carriers, including Southwest Airlines, Delta and Frontier Airlines, offer flights during this window. Many travellers prefer this time as it allows you to arrive at your destination early, giving you a full day for business or exploring.
How long does it take to fly from Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.)?
When flying from Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.), you have a few options. A nonstop flight typically takes around 2 hours 18 minutes, covering a distance of approximately 1,072 kilometres. If you opt for a one-stop flight, your travel time will be longer, usually around 6 hours 30 minutes. Flights with two or more stops will take even more time, averaging about 11 hours 30 minutes. Keep in mind that actual flight times can vary due to factors like wind patterns and air traffic, so it's always a good idea to allow for some flexibility in your travel plans.
Can you fly business or first class from Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.)?
Yes, you can fly business class or first class between PHL and MDW. You can fly business class with Frontier Airlines and Delta.First class cabins are available on Delta and United.
How do I earn miles on a Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago, IL (MDW) from Philadelphia, PA (PHL)?
If you're planning to travel to Chicago from Philadelphia Intl. (PHL), you can fly directly into Midway Intl. (MDW). Some flights may connect through major hubs like Nashville Intl. (BNA), Lambert-St. Louis Intl. (STL), or Orlando Intl. (MCO) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Philadelphia, PA (PHL-Philadelphia Intl.) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Philadelphia Intl.
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
CA $470
Distance
1065 km
Average flight time
1 hour 6 mins

Book with confidence

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 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 $471 rising to CA $554.  

Here are more money-saving tips: 

  • Fly in July 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.

Philadelphia to Chicago Flights

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*Available to Expedia members.