Cheap Flights from Chicago Midway to Philadelphia International

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Compare Chicago Midway to Philadelphia International flight deals

Find the cheapest month or even day of the year to fly to Philadelphia International

Book the best Philadelphia International fare with no extra fees

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Flight deals from Chicago Midway to Philadelphia International

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Philadelphia International Airport? If you want to travel next month, return fares start from $269. Find the lowest prices on one-way and return tickets right here.

Philadelphia.$269 per passenger.Departing Wed, 21 Oct, returning Tue, 27 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 21 Oct, arriving in Philadelphia International.Inbound indirect flight with Frontier Airlines, departs from Philadelphia International on Tue, 27 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $269, select.

Philadelphia.$269 per passenger.Departing Sat, 31 Oct, returning Sat, 7 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 31 Oct, arriving in Philadelphia International.Inbound indirect flight with Frontier Airlines, departs from Philadelphia International on Sat, 7 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $269, select.

Philadelphia.$293 per passenger.Departing Wed, 4 Nov, returning Fri, 13 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 4 Nov, arriving in Philadelphia International.Inbound indirect flight with Frontier Airlines, departs from Philadelphia International on Fri, 13 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $293, select.

Philadelphia.$299 per passenger.Departing Fri, 11 Dec, returning Sun, 13 Dec.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Fri, 11 Dec, arriving in Philadelphia International.Inbound indirect flight with Frontier Airlines, departs from Philadelphia International on Sun, 13 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $299, select.

Philadelphia.$321 per passenger.Departing Sat, 31 Oct, returning Sat, 7 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 31 Oct, arriving in Philadelphia International.Inbound direct flight with Southwest Airlines departs from Philadelphia International on Sat, 7 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $321, select.

Philadelphia.$321 per passenger.Departing Sat, 9 Jan, returning Mon, 11 Jan.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 9 Jan, arriving in Philadelphia International.Inbound indirect flight with Frontier Airlines, departs from Philadelphia International on Mon, 11 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $321, select.

Philadelphia.$321 per passenger.Departing Sat, 17 Oct, returning Sat, 24 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 17 Oct, arriving in Philadelphia International.Inbound direct flight with Southwest Airlines departs from Philadelphia International on Sat, 24 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $321, select.

Philadelphia.$323 per passenger.Departing Tue, 3 Nov, returning Sat, 7 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 3 Nov, arriving in Philadelphia International.Inbound direct flight with Southwest Airlines departs from Philadelphia International on Sat, 7 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $323, select.

Philadelphia.$344 per passenger.Departing Sat, 9 Jan, returning Mon, 11 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 9 Jan, arriving in Philadelphia International.Inbound direct flight with Southwest Airlines departs from Philadelphia International on Mon, 11 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $344, select.

Philadelphia.$350 per passenger.Departing Thu, 29 Oct, returning Tue, 1 Dec.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Thu, 29 Oct, arriving in Philadelphia International.Inbound indirect flight with Frontier Airlines, departs from Philadelphia International on Tue, 1 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $350, select.

Philadelphia.$382 per passenger.Departing Fri, 20 Nov, returning Tue, 1 Dec.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Fri, 20 Nov, arriving in Philadelphia International.Inbound indirect flight with Frontier Airlines, departs from Philadelphia International on Tue, 1 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $382, select.

Philadelphia.$389 per passenger.Departing Mon, 14 Dec, returning Tue, 15 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 14 Dec, arriving in Philadelphia International.Inbound direct flight with Southwest Airlines departs from Philadelphia International on Tue, 15 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $389, select.

Philadelphia.$390 per passenger.Departing Thu, 11 Feb, returning Tue, 16 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 11 Feb, arriving in Philadelphia International.Inbound direct flight with Southwest Airlines departs from Philadelphia International on Tue, 16 Feb, arriving in Chicago Midway.Price includes taxes and charges.From $390, select.

Philadelphia.$410 per passenger.Departing Wed, 30 Dec, returning Tue, 5 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 30 Dec, arriving in Philadelphia International.Inbound direct flight with Southwest Airlines departs from Philadelphia International on Tue, 5 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $410, select.

Philadelphia.$449 per passenger.Departing Wed, 30 Sep, returning Mon, 26 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 30 Sep, arriving in Philadelphia International.Inbound indirect flight with Frontier Airlines, departs from Philadelphia International on Mon, 26 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $449, select.

Philadelphia.$450 per passenger.Departing Thu, 29 Oct, returning Tue, 1 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 29 Oct, arriving in Philadelphia International.Inbound direct flight with Southwest Airlines departs from Philadelphia International on Tue, 1 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $450, select.

Find the cheapest month to fly from Chicago Midway to Philadelphia International

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

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Direct flights from Chicago Midway to Philadelphia International

Chicago Midway to Philadelphia International: Alternative routes

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

Chicago to Philadelphia: Flight information

The things to know before you go.

Cheapest flight found	$269
Cheapest month to fly	October
Average flight time	1 hr, 57 mins
Most popular airline	Southwest Airlines
Average flights per week	33

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

How much are return flights from Chicago Midway to Philadelphia International?

The best price we found for a return flight from Chicago Midway to Philadelphia International is $269. 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 Chicago Midway to Philadelphia International?

1 hour and 57 minutes is the average flight time from Chicago Midway to Philadelphia International.

Which airlines fly direct from Chicago Midway to Philadelphia International?

Southwest Airlines flies direct from Chicago Midway to Philadelphia International.

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

As of September 2026, there are 33 flights per week flying from Chicago Midway to Philadelphia International.

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

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

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

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Philadelphia International Airport on Wednesday, 21 October 2026.

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

Yes – the average flight time is 1 hour and 57 minutes.

How can I find the best flight deal to Philadelphia International?

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 Philadelphia International 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 Philadelphia?

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

Which is the cheapest airline to fly from Chicago Midway Airport to Philadelphia International with?

Currently, Frontier Airlines and Southwest Airlines offer the cheapest flight tickets to Philadelphia International.

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

The average duration of a direct flight from Chicago Midway Airport to Philadelphia International Airport is 2 hours.
Philadelphia is one hour ahead of Chicago and follows the UTC-5 timezone.
Take your pick of 19 weekly Chicago Midway Airport to Philadelphia International Airport flights. The 05:50 departure with Southwest Airlines is the earliest you can take. Southwest Airlines operates the last service of the day at 21:55.
Leave plenty of time to catch your MDW to PHL flight. As a general rule, turn up two hours before international departures and an hour ahead for domestic flights.
During popular months like July, you'll want to get to the airport earlier than usual. Arrive two hours before domestic departures and four hours ahead of international flights whenever you're travelling during peak periods in general.
Southwest Airlines is your ticket to exploring Philadelphia (and maybe even some other great corners of the United States!). Browse the direct flights from Chicago Midway Airport to Philadelphia International Airport offered by this popular airline.
Most travellers choose to fly with Southwest Airlines on this route.
With 76.18% of its services arriving as scheduled, Southwest Airlines is the most punctual carrier offering MDW to PHL flights.
If you want to explore another city along the way, simply deselect 'Direct flights only' when searching for your ticket from Chicago Midway Airport to Philadelphia International Airport. These are the most popular stopovers between MDW and PHL:
- Detroit Wayne County Airport
- Pittsburgh International Airport
- Cleveland Hopkins International Airport

Handy information about Chicago Midway Airport (MDW)

MDW is located at 5700 South Cicero.
When it comes to Chicago Midway Airport's on-time performance, data shows 76% of flights meet their scheduled arrival time.
Chicago Midway Airport is around 16 kilometres from central Chicago. If you're catching a taxi, ride-sharing or driving from the centre, it'll take 25 minutes or so to get there, depending on the traffic.
You can expect a journey time of roughly 30 minutes on public transport.
Need a handy hotel near MDW? If you're boarding an early flight from Chicago Midway Airport to Philadelphia International Airport, these accommodation options will put you moments from check-in:

Arriving at Philadelphia International Airport (PHL)

The last thing you need is a lengthy trip to your hotel if you're landing late on a Chicago Midway Airport to Philadelphia International Airport flight. Stay at one of these accommodation options near PHL instead:
Travel at your own pace with a Philadelphia International Airport rental car. Pick up your wheels from Dollar, Thrifty or Budget and see more of Philadelphia and beyond.
Reserving your vehicle from Philadelphia International Airport around three weeks ahead increases your chances of getting a good deal.

When to fly to Philadelphia International Airport (PHL)

It's time to work out your trip dates for your flight from Chicago Midway Airport to Philadelphia International Airport. August is the most popular month to head to Philadelphia. If you prefer a quieter vibe, go in March.
Book your flight from Chicago Midway Airport to Philadelphia International Airport for July if you'd like to explore Philadelphia during its warmest month. Expect temperatures of between 18ºC and 32ºC.
If you want cooler conditions, look for a cheap ticket from MDW to PHL in January. Temperatures average between -7ºC and 9ºC then.

Explore more of the United States

Philadelphia has its own special appeal, but there are so many other corners of the United States you should also see. Around 129 kilometres north-east of Philadelphia, a trip to New York will keep you on the go. Don't miss top attractions like Central Park, Statue of Liberty and Metropolitan Museum of Art.
Around 434 kilometres north-east of Philadelphia, Boston is another essential stop in the United States. Get a taste of what this destination has to offer at Museum of Fine Arts Boston, Freedom Trail and USS Constitution Museum.