Skyscanner home

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

Return selected
Return selected
origin
Enter the city you're flying from, or choose from the options below
Include nearby airports
    selected
    destination
    . Enter your destination, or choose from the options below
    Include nearby airports
      selected
      Travellers and cabin class, 1 Adult, Economy
      Southwest Airlines

      Compare Philadelphia International to Chicago Midway flight deals

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

      Book the best Chicago Midway fare with no extra fees

      Flight deals from Philadelphia International to Chicago Midway

      Looking for a cheap last-minute deal or the best return flight from Philadelphia International Airport to Chicago Midway Airport? If you want to travel next month, return fares start from $203. Find the lowest prices on one-way and return tickets right here.
      Chicago.$203 per passenger.Departing Wed, 16 Sep, returning Mon, 21 Sep.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Philadelphia International on Wed, 16 Sep, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 21 Sep, arriving in Philadelphia International.Price includes taxes and charges.From $203, select.
      Chicago.$203 per passenger.Departing Wed, 28 Oct, returning Wed, 4 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Philadelphia International on Wed, 28 Oct, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 4 Nov, arriving in Philadelphia International.Price includes taxes and charges.From $203, select.
      Chicago.$203 per passenger.Departing Tue, 29 Sep, returning Thu, 1 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Philadelphia International on Tue, 29 Sep, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Thu, 1 Oct, arriving in Philadelphia International.Price includes taxes and charges.From $203, select.
      Chicago.$221 per passenger.Departing Tue, 20 Oct, returning Sat, 31 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Philadelphia International on Tue, 20 Oct, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 31 Oct, arriving in Philadelphia International.Price includes taxes and charges.From $221, select.
      Chicago.$266 per passenger.Departing Wed, 28 Oct, returning Wed, 4 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Philadelphia International on Wed, 28 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 4 Nov, arriving in Philadelphia International.Price includes taxes and charges.From $266, select.
      Chicago.$266 per passenger.Departing Tue, 8 Sep, returning Wed, 16 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Philadelphia International on Tue, 8 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 16 Sep, arriving in Philadelphia International.Price includes taxes and charges.From $266, select.
      Chicago.$266 per passenger.Departing Wed, 28 Oct, returning Sat, 31 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Philadelphia International on Wed, 28 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 31 Oct, arriving in Philadelphia International.Price includes taxes and charges.From $266, select.
      Chicago.$268 per passenger.Departing Sat, 12 Dec, returning Tue, 15 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Philadelphia International on Sat, 12 Dec, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 15 Dec, arriving in Philadelphia International.Price includes taxes and charges.From $268, select.
      Chicago.$278 per passenger.Departing Mon, 28 Sep, returning Sat, 7 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Philadelphia International on Mon, 28 Sep, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 7 Nov, arriving in Philadelphia International.Price includes taxes and charges.From $278, select.
      Chicago.$278 per passenger.Departing Wed, 4 Nov, returning Thu, 5 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Philadelphia International on Wed, 4 Nov, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Thu, 5 Nov, arriving in Philadelphia International.Price includes taxes and charges.From $278, select.
      Chicago.$290 per passenger.Departing Tue, 29 Sep, returning Thu, 1 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Philadelphia International on Tue, 29 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 1 Oct, arriving in Philadelphia International.Price includes taxes and charges.From $290, select.
      Chicago.$290 per passenger.Departing Mon, 2 Nov, returning Tue, 10 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Philadelphia International on Mon, 2 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 10 Nov, arriving in Philadelphia International.Price includes taxes and charges.From $290, select.
      Chicago.$292 per passenger.Departing Thu, 3 Dec, returning Wed, 6 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Philadelphia International on Thu, 3 Dec, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 6 Jan, arriving in Philadelphia International.Price includes taxes and charges.From $292, select.
      Chicago.$294 per passenger.Departing Wed, 20 Jan, returning Wed, 27 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Philadelphia International on Wed, 20 Jan, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Wed, 27 Jan, arriving in Philadelphia International.Price includes taxes and charges.From $294, select.
      Chicago.$344 per passenger.Departing Wed, 25 Nov, returning Wed, 2 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Philadelphia International on Wed, 25 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 2 Dec, arriving in Philadelphia International.Price includes taxes and charges.From $344, select.
      Chicago.$389 per passenger.Departing Thu, 4 Feb, returning Mon, 8 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Philadelphia International on Thu, 4 Feb, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 8 Feb, arriving in Philadelphia International.Price includes taxes and charges.From $389, select.

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

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Philadelphia International to Chicago Midway flights are currently cheapest in September.
      Aug
      from $419
      Sep
      from $203
      Oct
      from $221
      Nov
      from $278
      Dec
      from $268
      Jan
      from $294
      Feb
      from $389
      Mar
      from $419
      Apr
      from $500
      May
      from $445
      Jun
      from $609
      Jul
      Find prices

      Direct flights from Philadelphia International to Chicago Midway

      Southwest Airlines

      Philadelphia International to Chicago Midway: Alternative routes

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

      Chicago Midway

      14km from central Chicago
      Closest
      from $205
      Search flights

      Chicago O'Hare International

      25km from central Chicago
      Cheapest
      from $128
      Search flights

      Chicago Rockford

      127km from central Chicago
      from $353
      Search flights

      Philadelphia to Chicago: Flight information

      The things to know before you go.
      Cheapest flight found$205
      Cheapest month to flySeptember
      Average flight time2 hrs, 11 mins
      Most popular airlineSouthwest Airlines
      Average flights per week32

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

      The best price we found for a return flight from Philadelphia International to Chicago Midway is $205. 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.
      2 hours and 11 minutes is the average flight time from Philadelphia International to Chicago Midway.
      Southwest Airlines flies direct from Philadelphia International to Chicago Midway.
      As of August 2026, there are 32 flights per week flying from Philadelphia International to Chicago Midway.
      The cheapest month to fly from Philadelphia International to Chicago Midway is usually September.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Philadelphia International Airport to Chicago Midway Airport on Wednesday, 16 September 2026.
      Yes – the average flight time is 2 hours and 11 minutes.
      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.

      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.

      Currently, Frontier Airlines and Southwest Airlines offer the cheapest flight tickets to Chicago Midway.

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

      • The average length of a direct flight from Philadelphia International Airport to Chicago Midway Airport is 2 hours 10 minutes.

      • Chicago's timezone is UTC-6, which makes Chicago one hour behind Philadelphia.

      • Flights from PHL to MDW start from 05:25 — the earliest with Southwest Airlines. The last departure is at 20:45 with Southwest Airlines. In total, you can choose from 19 weekly Philadelphia International Airport to Chicago Midway Airport flights.

      • Your PHL to MDW flight won't wait if you're late, so show up at the airport on time. Arrive up to one hour in advance for domestic flights and two hours ahead when you're flying internationally.

      • Be prepared for longer queues in popular months like August. Arriving up to four hours ahead of an international flight and two hours for domestic departures is a wise move.

      • Southwest Airlines is your ticket to exploring Chicago (and maybe even some other great corners of the United States!). Browse the direct flights from Philadelphia International Airport to Chicago Midway Airport offered by this carrier.

      • Southwest Airlines has the highest passenger demand on this route.

      • Frontier Airlines is the most punctual carrier operating PHL to MDW flights, with 77.78% of its services arriving as scheduled.

      • We make it easy to book a flight with a stopover. To see your options for tickets from Philadelphia International Airport to Chicago Midway Airport, deselect 'Direct flights only.' Then, pick a flight that has a stop long enough to tour the city of your choice. Stopovers between PHL and MDW include:

        • Detroit Wayne County Airport

        • Buffalo Niagara Airport

        • Grand Rapids Airport

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

      • The cheapest price we've seen for a one-way Philadelphia International Airport to Chicago Midway Airport flight is $102. A return plane ticket is currently $203. Depending on the availability and when you book, these fares can change.

      • Don't leave everything to the last minute. You're more likely to find cheap tickets from PHL to MDW if you book ahead. Airlines often have some fantastic early bird rates.

      • May is the cheapest month for flights from Philadelphia International Airport to Chicago Midway Airport. If you need to travel at a different time of year, the 'Whole month' tool will give you the lowest airfares for every month.

      • There's no need to check every day to find out if fares have dropped when you create a Price Alert. We'll send you an update the moment there's a better deal on cheap flights from PHL to MDW.

      • Select your ideal departure and arrival times, airlines and number of stops with the filters. Alternatively, sort your results by 'Cheapest' to see the best deals on flights from Philadelphia International Airport to Chicago Midway Airport.

      Handy information about Philadelphia International Airport (PHL)

      • The address for PHL is 8500 Essington Ave.

      • When it comes to Philadelphia International Airport's on-time performance, data shows 77% of flights meet their scheduled arrival time.

      • To reach Philadelphia International Airport from central Philadelphia, it takes around 20 minutes if you're planning to drive. Of course, this depends on traffic. It's approximately 18 kilometres from the airport to the city centre.

      • Expect a journey time of around 30 minutes when using public transport.

      • Get your holiday off to a hassle-free start by staying near PHL. Whether you're boarding an early flight from Philadelphia International Airport to Chicago Midway Airport or just don't want to be rushed, these hotels have you covered:

      Arriving at Chicago Midway Airport (MDW)

      • The last thing you want is a long journey to your hotel if you're arriving on a late Philadelphia International Airport to Chicago Midway Airport flight. Book one of these accommodation options near MDW instead:

      • Grab a Chicago Midway Airport rental car and discover Chicago and beyond with your own wheels. Dollar, Hertz and Budget are popular providers you can book with here.

      • Reserving your vehicle from Chicago Midway Airport around four weeks ahead gives you the best shot at securing a great deal.

      When to fly to Chicago Midway Airport (MDW)

      • July is the busiest month for flights from Philadelphia International Airport to Chicago Midway Airport. To escape the crowds, travel to Chicago in December.

      • Lock in your flight from Philadelphia International Airport to Chicago Midway Airport for July if you'd like to visit Chicago during its warmest month. You can expect temperatures of between 16ºC (61ºF) and 28ºC (82ºF).

      • Look for cheap tickets from PHL to MDW in January if you like travelling in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

      Explore more of the United States

      • Columbus is just one of the many cities in the United States waiting to be explored once you've taken in the sights of Chicago. Around 451 kilometres away to the south-east, popular attractions include Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

      • Indianapolis is another essential stop in the United States and is around 257 kilometres south-east of Chicago. No journey is complete without seeing Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

      Plan smart, explore more

      Where should Australians travel this year?

      What are the cheapest days and weeks to fly?

      5 best premium economy airlines worth paying for

      How to search for multi-city flights with Skyscanner

      Plan the rest of your trip from Philadelphia to Chicago

      Prices shown on this page are estimated lowest prices only. Found in the last 12 days.