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195 € 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

Book the best Chicago Midway fare with no extra fees

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 202 €. Find the lowest prices on one-way and return tickets right here.
Chicago.195 € per passenger.Departing Wed, 23 Sep, returning Tue, 29 Sep.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Philadelphia International on Wed, 23 Sep, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 29 Sep, arriving in Philadelphia International.Price includes taxes and charges.From 195 €, select.
Chicago.202 € per passenger.Departing Tue, 11 Aug, returning Sat, 15 Aug.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Philadelphia International on Tue, 11 Aug, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 15 Aug, arriving in Philadelphia International.Price includes taxes and charges.From 202 €, select.
Chicago.202 € per passenger.Departing Sat, 29 Aug, returning Tue, 1 Sep.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Philadelphia International on Sat, 29 Aug, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 1 Sep, arriving in Philadelphia International.Price includes taxes and charges.From 202 €, select.
Chicago.202 € per passenger.Departing Wed, 22 Jul, returning Tue, 28 Jul.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Philadelphia International on Wed, 22 Jul, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 28 Jul, arriving in Philadelphia International.Price includes taxes and charges.From 202 €, select.
Chicago.209 € per passenger.Departing Sat, 1 Aug, returning Tue, 20 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Philadelphia International on Sat, 1 Aug, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 20 Oct, arriving in Philadelphia International.Price includes taxes and charges.From 209 €, select.
Chicago.210 € per passenger.Departing Wed, 7 Oct, returning Sat, 10 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Philadelphia International on Wed, 7 Oct, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 10 Oct, arriving in Philadelphia International.Price includes taxes and charges.From 210 €, select.
Chicago.211 € per passenger.Departing Wed, 30 Sep, returning Mon, 5 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Philadelphia International on Wed, 30 Sep, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 5 Oct, arriving in Philadelphia International.Price includes taxes and charges.From 211 €, select.
Chicago.211 € per passenger.Departing Sat, 31 Oct, returning Tue, 3 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Philadelphia International on Sat, 31 Oct, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 3 Nov, arriving in Philadelphia International.Price includes taxes and charges.From 211 €, select.
Chicago.211 € per passenger.Departing Sat, 25 Jul, returning Sat, 1 Aug.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Philadelphia International on Sat, 25 Jul, 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 211 €, select.
Chicago.214 € per passenger.Departing Wed, 14 Oct, returning Sat, 17 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Philadelphia International on Wed, 14 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 17 Oct, arriving in Philadelphia International.Price includes taxes and charges.From 214 €, select.
Chicago.214 € per passenger.Departing Sat, 5 Sep, returning Tue, 8 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Philadelphia International on Sat, 5 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 8 Sep, arriving in Philadelphia International.Price includes taxes and charges.From 214 €, select.
Chicago.215 € per passenger.Departing Mon, 26 Oct, returning Mon, 2 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Philadelphia International on Mon, 26 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 2 Nov, arriving in Philadelphia International.Price includes taxes and charges.From 215 €, select.
Chicago.215 € per passenger.Departing Thu, 5 Nov, returning Sat, 7 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Philadelphia International on Thu, 5 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 7 Nov, arriving in Philadelphia International.Price includes taxes and charges.From 215 €, select.
Chicago.215 € per passenger.Departing Tue, 11 Aug, returning Wed, 12 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Philadelphia International on Tue, 11 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 12 Aug, arriving in Philadelphia International.Price includes taxes and charges.From 215 €, select.
Chicago.221 € per passenger.Departing Sat, 29 Aug, returning Tue, 1 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Philadelphia International on Sat, 29 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 1 Sep, arriving in Philadelphia International.Price includes taxes and charges.From 221 €, select.
Chicago.225 € per passenger.Departing Sat, 5 Dec, returning Mon, 7 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Philadelphia International on Sat, 5 Dec, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 7 Dec, arriving in Philadelphia International.Price includes taxes and charges.From 225 €, 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 September.
Jul
from 202 €
Aug
from 202 €
Sep
from 195 €
Oct
from 210 €
Nov
from 215 €
Dec
from 225 €
Jan
from 251 €
Feb
from 276 €
Mar
from 348 €
Apr
from 387 €
May
Find prices
Jun
Find prices

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.

Chicago Midway

14km from central Chicago
Closest
from 195 €
Search flights

Chicago O'Hare International

25km from central Chicago
Cheapest
from 100 €
Search flights

Chicago Rockford

127km from central Chicago
from 203 €
Search flights

Philadelphia to Chicago: Flight information

The things to know before you go.
Cheapest flight found195 €
Cheapest month to flySeptember
Average flight time2 hrs, 10 mins
Most popular airlineSouthwest Airlines
Average flights per week78

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

The best price we found for a return flight from Philadelphia to Chicago Midway is 195 €. 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 10 minutes is the average flight time from Philadelphia to Chicago Midway.
Southwest Airlines flies direct from Philadelphia to Chicago Midway.
As of July 2026, there are 78 flights per week flying from Philadelphia to Chicago Midway.
The cheapest month to fly from Philadelphia to Chicago Midway is usually September.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Philadelphia to Chicago Midway Airport on Wednesday, 23 September 2026.
Yes – the average flight time is 2 hours and 10 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.

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

  • Your travels get underway at Philadelphia's main airport, Philadelphia International Airport (PHL). Check out your options for reserving a flight from Philadelphia to Chicago Midway International Airport (MDW) leaving from this terminal.

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

  • The timezone in Chicago is UTC-6, which is one hour behind Philadelphia. Chicago Midway International Airport is located in Chicago.

  • With 22 direct flights a week 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 prefer to make the most of your day before you fly, the latest departure from PHL to MDW is with Southwest Airlines at 8:45pm.

  • Give yourself 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.

  • Hopping on a plane during a peak month like July? Popular periods (like Thanksgiving, Christmas/New Year and spring break) can easily add another hour at security. Play things extra safe and arrive up to four hours ahead of an international flight and two hours before domestic departures.

Airports in Philadelphia

Philadelphia International Airport (PHL)

  • Philadelphia International Airport (PHL) is a convenient option for travelling directly to your destination. Nonstop flights from Philadelphia to Chicago Midway International Airport (MDW) depart from this terminal.

  • You can book a direct flight from Philadelphia to Chicago Midway International Airport with Southwest Airlines. This top airline operates departures from PHL.

  • The airline most travellers choose when flying between PHL and MDW is Southwest Airlines.

  • Frontier Airlines is the most punctual carrier operating on this route, with 77.78% of its services landing on time.

  • PHL is about 18 kilometres from central Philadelphia. If you're ride-sharing, catching a taxi or driving from the centre, it'll take 20 minutes or so to get there, depending on the traffic. If you're using public transport, expect the journey time to be around 30 minutes.

  • Want a relaxed start to your journey? Stay near Philadelphia International Airport. Whether you're boarding an early flight from Philadelphia to Chicago Midway International Airport or just don't like being rushed, these hotels have you covered:

  • When it comes to Philadelphia International Airport's on-time performance, data shows 77% of flights arrive within the expected time frame.

  • PHL is located at 8500 Essington Ave.

Trenton-Mercer Airport (TTN)

  • You can get to TTN from the centre of Philadelphia in about 40 minutes by car, depending on traffic. The ride on public transport takes roughly 1 hour 35 minutes to travel the 48 kilometres or so.

  • Want to enjoy an extra night away before your Philadelphia to MDW flight? Relax in a hotel near Trenton-Mercer Airport before your adventure officially begins. Here's where you can stay:

  • 76% of all departures from Trenton-Mercer Airport make it to their destination as expected.

  • The address for TTN is Scotch Road, Terminal Building.

About Chicago Midway International Airport (MDW)

  • Have a late flight from Philadelphia to Chicago Midway International Airport? Don't let it leave you bleary-eyed. Stay at one of these hotels near MDW and give yourself a well-earned lights-out:

  • Lock in the best possible rate by reserving your ride around four weeks ahead of your Philadelphia to Chicago Midway International Airport flight.

  • MDW is located at 5700 South Cicero.

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

  • From Chicago Midway International Airport, central Chicago is around 16 kilometres away. It takes about 25 minutes to reach the city centre by car.

  • It typically takes 30 minutes to get there using public transport.

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

  • 75 € is currently the best price for a one-way ticket from Philadelphia to Chicago Midway International Airport. A return flight starts at 195 €. These fares can change based on demand.

  • Booking in advance is often the key to finding a cheap flight from Philadelphia to MDW. Fares tend to rise as seats fill up, so the closer your departure date, the more you'll likely spend.

  • Affordable Philadelphia to Chicago Midway International Airport tickets are easier to find when you have flexibility in your schedule. Try using the 'Whole month' search tool to compare fares across the month and then choose the cheapest day.

  • Locking in a cheap plane ticket from Philadelphia to MDW is easy with Price Alerts. Simply create one of these automatic alerts and we'll get in touch as soon as prices go down.

  • Save on your flight from Philadelphia to Chicago Midway International Airport by using filters. Choose your preferred duration, departure time and airlines, then sort the results by 'Cheapest' for the best deals.

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

  • Think about the kind of holiday you want when deciding your trip dates. November is the quietest month to go to Chicago. July is when most people book flights from Philadelphia to Chicago Midway International Airport (MDW), which may be perfect if you enjoy travelling when it's busier.

  • Lock in a Philadelphia to MDW plane ticket departing in July if you want to explore the city during its warmest month. Expect temperatures in Chicago to range from 16ºC (61ºF) to 28ºC (82ºF).

  • January sees temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Search for cheap tickets from Philadelphia to Chicago Midway International Airport around that time if you'd rather travel in cooler conditions.

More about Chicago

Explore more of the United States

  • Indianapolis is just one of the many cities in the United States waiting to be explored after you've experienced Chicago. Around 257 kilometres away to the southeast, its best attractions include Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

  • Milwaukee is another favourite destination in the United States and is around 137 kilometres north of Chicago. No journey is complete without experiencing Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo.

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.