Cheap Flights from Philadelphia to Chicago Midway

Compare Philadelphia to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from Philadelphia to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Philadelphia to Chicago Midway Airport? If you want to travel next month, return fares start from $237. Find the lowest prices on one-way and return tickets right here.

Chicago.$237 per passenger.Departing Sat, 9 May, returning Mon, 11 May.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Philadelphia International on Sat, 9 May, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 11 May, arriving in Philadelphia International.Price includes taxes and charges.From $237, select.

Chicago.$242 per passenger.Departing Wed, 29 Apr, returning Thu, 30 Apr.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Philadelphia International on Wed, 29 Apr, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Thu, 30 Apr, arriving in Philadelphia International.Price includes taxes and charges.From $242, select.

Chicago.$271 per passenger.Departing Thu, 30 Apr, returning Tue, 5 May.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Philadelphia International on Thu, 30 Apr, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 5 May, arriving in Philadelphia International.Price includes taxes and charges.From $271, select.

Chicago.$282 per passenger.Departing Fri, 14 Aug, returning Mon, 17 Aug.Return flight with Delta.Outbound indirect flight with Delta, departs from Philadelphia International on Fri, 14 Aug, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Mon, 17 Aug, arriving in Philadelphia International.Price includes taxes and charges.From $282, select.

Chicago.$282 per passenger.Departing Fri, 5 Jun, returning Tue, 9 Jun.Return flight with Delta.Outbound indirect flight with Delta, departs from Philadelphia International on Fri, 5 Jun, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 9 Jun, arriving in Philadelphia International.Price includes taxes and charges.From $282, select.

Chicago.$282 per passenger.Departing Fri, 3 Jul, returning Tue, 7 Jul.Return flight with Delta.Outbound indirect flight with Delta, departs from Philadelphia International on Fri, 3 Jul, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 7 Jul, arriving in Philadelphia International.Price includes taxes and charges.From $282, select.

Chicago.$282 per passenger.Departing Fri, 29 May, returning Mon, 1 Jun.Return flight with Delta.Outbound indirect flight with Delta, departs from Philadelphia International on Fri, 29 May, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Mon, 1 Jun, arriving in Philadelphia International.Price includes taxes and charges.From $282, select.

Chicago.$315 per passenger.Departing Wed, 29 Jul, returning Sat, 1 Aug.Return flight with Delta.Outbound indirect flight with Delta, departs from Philadelphia International on Wed, 29 Jul, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sat, 1 Aug, arriving in Philadelphia International.Price includes taxes and charges.From $315, select.

Chicago.$315 per passenger.Departing Tue, 30 Jun, returning Tue, 7 Jul.Return flight with Delta.Outbound indirect flight with Delta, departs from Philadelphia International on Tue, 30 Jun, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 7 Jul, arriving in Philadelphia International.Price includes taxes and charges.From $315, select.

Chicago.$349 per passenger.Departing Sat, 25 Apr, returning Sat, 1 Aug.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Philadelphia International on Sat, 25 Apr, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 1 Aug, arriving in Philadelphia International.Price includes taxes and charges.From $349, select.

Chicago.$362 per passenger.Departing Thu, 25 Jun, returning Wed, 19 Aug.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Philadelphia International on Thu, 25 Jun, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 19 Aug, arriving in Philadelphia International.Price includes taxes and charges.From $362, select.

Chicago.$404 per passenger.Departing Sat, 16 May, returning Wed, 20 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Philadelphia International on Sat, 16 May, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 20 May, arriving in Philadelphia International.Price includes taxes and charges.From $404, select.

Chicago.$418 per passenger.Departing Sat, 30 May, returning Sat, 6 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Philadelphia International on Sat, 30 May, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 6 Jun, arriving in Philadelphia International.Price includes taxes and charges.From $418, select.

Chicago.$418 per passenger.Departing Fri, 3 Jul, returning Tue, 7 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Philadelphia International on Fri, 3 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 7 Jul, arriving in Philadelphia International.Price includes taxes and charges.From $418, select.

Chicago.$418 per passenger.Departing Wed, 19 Aug, returning Sat, 22 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Philadelphia International on Wed, 19 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 22 Aug, arriving in Philadelphia International.Price includes taxes and charges.From $418, select.

Chicago.$418 per passenger.Departing Sat, 6 Jun, returning Tue, 9 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Philadelphia International on Sat, 6 Jun, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 9 Jun, arriving in Philadelphia International.Price includes taxes and charges.From $418, select.

Find the cheapest month to fly from Philadelphia to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Philadelphia to Chicago Midway flights are currently cheapest in May.

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Direct flights from Philadelphia to Chicago Midway

Philadelphia to Chicago Midway: Alternative routes

Compare routes from Philadelphia to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Philadelphia to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$237
Cheapest month to fly	May
Average flight time	2 hrs, 9 mins
Most popular airline	Southwest Airlines
Average flights per week	33

Finding cheap flights from Philadelphia to Chicago Midway: Frequently asked questions

How much are return flights from Philadelphia to Chicago Midway?

The best price we found for a return flight from Philadelphia to Chicago Midway is $237. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

How long does it take to fly from Philadelphia to Chicago Midway?

2 hours and 9 minutes is the average flight time from Philadelphia to Chicago Midway.

Which airlines fly direct from Philadelphia to Chicago Midway?

Southwest Airlines flies direct from Philadelphia to Chicago Midway.

How many flights are there a week from Philadelphia to Chicago Midway?

As of April 2026, there are 99 flights per week flying from Philadelphia to Chicago Midway.

When is the cheapest time to fly from Philadelphia to Chicago Midway?

The cheapest month to fly from Philadelphia to Chicago Midway is usually May.

Which upcoming date is cheapest to fly from Philadelphia to Chicago Midway Airport on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Philadelphia to Chicago Midway Airport on Saturday, 9 May 2026.

Can I get a direct flight from Philadelphia to Chicago Midway Airport?

Yes – the average flight time is 2 hours and 9 minutes.

How can I find the best flight deal to Chicago Midway?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Chicago?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

Flying from Philadelphia to Chicago Midway International Airport (MDW): What you need to know

Start planning your trip by checking out the most convenient departure point for your flight from Philadelphia to Chicago Midway International Airport (MDW). Explore the options for taking off from Philadelphia International Airport (PHL) or Trenton-Mercer Airport (TTN), the city's main airports.
2 hours 10 minutes is the average journey time for a direct Philadelphia to Chicago Midway International Airport flight.
The timezone in Chicago is UTC-5, which is one hour behind Philadelphia. Chicago Midway International Airport is located in Chicago.
With 19 direct weekly flights between the two airports, Philadelphia International Airport (PHL) to Chicago Midway International Airport (MDW) is the busiest route. Southwest Airlines operates the earliest flight at 5:25am. If you'd like to get more out of your day before leaving, the last departure from PHL to MDW is with Southwest Airlines at 8:45pm.
Leave enough time to make your flight from Philadelphia to MDW. As a rule of thumb, arrive two hours before international departures and an hour ahead for domestic flights.
Heading away during a peak period like public or school holidays? Expect longer lines at check-in and security. To give yourself peace of mind, arrive up to four hours before international flights and two hours before domestic departures.

Airports in Philadelphia

Philadelphia International Airport (PHL)

Fly without interruptions from Philadelphia International Airport (PHL). Direct flights from Philadelphia to Chicago Midway International Airport (MDW) operate from here.
When leaving from PHL, you can catch a direct flight from Philadelphia to Chicago Midway International Airport with Southwest Airlines.
Most passengers choose to book seats with Southwest Airlines from PHL to MDW.
Frontier Airlines is the most punctual carrier operating on this route, with 77.78% of its services arriving as planned.
The journey from central Philadelphia to PHL takes around 45 minutes on public transport. If you ride-share, drive or get a cab, you'll cover the 19 kilometres in 15 minutes or so, depending on traffic conditions.
Looking for a comfortable hotel close to Philadelphia International Airport? If you've booked an early flight from Philadelphia to Chicago Midway International Airport, these accommodation options will put you moments from your check-in counter:
When it comes to Philadelphia International Airport's on-time performance, 78.93% of flights complete their journey on time.
PHL is located at 8500 Essington Ave.

Trenton-Mercer Airport (TTN)

On public transport, you can travel from central Philadelphia to TTN in about 1 hour 45 minutes. The airport is roughly 56 kilometres away, and getting there by car takes approximately 40 minutes.
Want to treat yourself to an extra night away before catching your Philadelphia to MDW flight? Unwind in a hotel near Trenton-Mercer Airport before your trip officially begins. These stays have your key waiting:
Flights from Trenton-Mercer Airport have a track record for punctuality, with 82.45% of them arriving as planned.
The address for TTN is Scotch Road, Terminal Building.

About Chicago Midway International Airport (MDW)

The last thing you need is a lengthy journey to your hotel if you're arriving on a late flight from Philadelphia to Chicago Midway International Airport. Book one of these accommodation options near MDW instead:
Follow your own route with a Chicago Midway International Airport rental car. Pick up your wheels from Dollar, Hertz or Budget and discover more of Chicago and beyond.
To get the best deal, reserve your ride around four weeks in advance of your Philadelphia to Chicago Midway International Airport flight.
The address for MDW is 5700 South Cicero.

Getting from Chicago Midway International Airport (MDW) to central Chicago

Chicago Midway International Airport to central Chicago is roughly 14 kilometres. If you're renting a car or taking a cab, do a little research to make your trip as easy as possible. Journey times will vary depending on traffic and the time of day.
If you're taking public transport, expect a journey of roughly 45 minutes.

How to find the cheapest flights from Philadelphia to Chicago Midway International Airport (MDW)

The cheapest price we've found for a one-way ticket from Philadelphia to Chicago Midway International Airport is $118. For a return flight on this route, the best price is $237. Depending on the availability when you book, these fares may change.
To pick up cheap flights from Philadelphia to MDW, book in advance. Airlines usually offer lower prices when flights are first released.
The 'Whole month' search tool will show you the cheapest Philadelphia to Chicago Midway International Airport tickets throughout the month. It's a great way to snap up a bargain if your trip dates aren't set in stone.
Stay on top of deals for flight tickets from Philadelphia to MDW by creating a Price Alert. We'll send you an email or push notification on the app when a lower fare pops up.
Tailor your trip using filters. Choose your ideal departure and arrival times, airlines and total journey duration. You can also sort the results by 'Cheapest,' 'Best' or 'Fastest' flights from Philadelphia to Chicago Midway International Airport.

The best time to fly from Philadelphia to Chicago Midway International Airport (MDW)

July is the busiest month for flights from Philadelphia to Chicago Midway International Airport (MDW). Plan your visit to Chicago in May for a more low-key escape.
The warmest month in Chicago is July, with temperatures ranging between 15ºC and 29ºC. Lock in your Philadelphia to MDW flight ticket then if you enjoy this type of weather.
If you want cooler conditions, look for a cheap ticket from Philadelphia to Chicago Midway International Airport in January when temperatures are between -12ºC and 3ºC.

More about Chicago

After booking your flight from Philadelphia to Chicago Midway International Airport, find a hotel that puts you in a great location. Make one of these accommodation options your base for exploring Chicago:
Your Chicago visit wouldn't be complete without a bit of sightseeing. Highlights worth exploring include Millennium Park, Lollapalooza and Art Institute of Chicago.

Explore more of the United States

Chicago has its own special appeal, but there are so many other corners of the United States you'll want to see. Around 257 kilometres south-east of Chicago, a trip to Indianapolis will keep you busy. Start with popular sights like 9-11 Memorial, Lucas Oil Stadium and Eiteljorg Museum.
If you're looking to explore another well-known destination in the United States, consider Milwaukee, roughly 137 kilometres north of Chicago. Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo are among its highlights.