Cheap Flights from Philadelphia to Chicago

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Flight deals from Philadelphia to Chicago

Looking for a cheap last-minute deal or the best return flight from Philadelphia to Chicago? Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Philadelphia to Chicago

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

Direct flights from Philadelphia to Chicago

Alternative Philadelphia to Chicago routes

Looking for the cheapest, fastest or easiest route from Philadelphia to Chicago? You could fly into the following airports instead.

Philadelphia to Chicago: Flight information

The things to know before you go.
Cheapest flight found99 €
Cheapest month to flyAugust
Average flight time2 hrs, 19 mins
Most popular airlineAmerican Airlines
Average flights per week5,504

Finding cheap flights from Philadelphia to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Philadelphia to Chicago is 99 €. 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 18 minutes is the average flight time from Philadelphia to Chicago.
American Airlines, Alaska Airlines and Southwest Airlines fly direct from Philadelphia to Chicago.
As of June 2025, there are 344 flights per week flying from Philadelphia to Chicago.
The cheapest month to fly from Philadelphia to Chicago is usually June 2025.
If you're flying from Philadelphia, the cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the centre of Chicago. We've found flights into this airport from 99 €.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Philadelphia to Chicago on Monday, 11 August 2025.
Yes – the average flight time is 2 hours and 18 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 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.
In June, the average temperature is usually around 19°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
The cheapest airline that flies to Chicago is Frontier Airlines .

Flying from Philadelphia to Chicago: what you need to know

  • Begin your trip planning by checking out the departure points for your flight from Philadelphia to Chicago. Explore your options for setting off from Philadelphia International Airport (PHL) or Trenton-Mercer Airport (TTN), two of the city's main airports.

  • When it comes to arriving in Chicago, O'Hare International Airport (ORD) is a major gateway. Chicago Midway International Airport (MDW) is another.

  • Around 2 hours 15 minutes is how long you'll be in transit on a direct Philadelphia to Chicago flight.

  • The timezone in Chicago is UTC-5, which is one hour behind Philadelphia.

  • With 86 weekly flights between the two airports, Philadelphia International Airport (PHL) to O'Hare International Airport (ORD) is the most popular route. Board the first flight from Philadelphia to Chicago with American Airlines at 05:00. If you prefer to get more out of your day before leaving, the last flight from PHL to ORD is with Frontier Airlines at 22:42.

  • To ensure you catch your Philadelphia to Chicago flight, allow plenty of time for things like baggage drop and finding your gate. Turning up two hours before international departures and one hour before domestic flights is the standard rule.

  • Popular months like August or high seasons such as Thanksgiving and Christmas will mean longer queues at security and check-in. Be on the safe side and head to the airport even earlier. Arriving two hours before a domestic flight and four hours ahead of an international departure is a wise move.

How to find the cheapest flights from Philadelphia to Chicago

  • The cheapest price we've found for a one-way ticket from Philadelphia to Chicago is 50 €. For a return flight on this route, the best price is 99 €. Depending on when you book and the availability, these fares could change.

  • To snag cheap Philadelphia to Chicago flights, book your journey two months ahead of your planned departure.

  • Schedule your trip for May. That's the best month for landing cheap plane tickets from Philadelphia to Chicago. If you have flexibility with your dates, use the 'Whole month' tool to see the lowest price across each month.

  • Finding a cheap flight from Philadelphia to Chicago is easy with Price Alerts. All you need to do is set up one of these automatic alerts and we'll get in touch when there's a better deal.

  • Save money on your Philadelphia to Chicago flight with the help of our filters. Choose your ideal times, airlines and number of stops, then sort the results by 'Cheapest' to see the best deals.

Flying from Philadelphia

Philadelphia International Airport (PHL)

  • Take off from Philadelphia International Airport (PHL) and fly right through to O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW). If you're looking for a direct flight from Philadelphia to Chicago out of PHL, those are your landing points.

  • Choose from a variety of airlines that offer direct Philadelphia to Chicago plane tickets out of PHL. Get on board with any of these:

  • PHL is about 11 kilometres from central Philadelphia. If you're catching a cab, ride-sharing or driving from the centre, it'll take 15 minutes or so to get there, depending on the traffic. If you're taking public transport, expect the trip time to be around 45 minutes.

  • Searching for a handy hotel close to Philadelphia International Airport? If you're catching an early flight from Philadelphia to Chicago, these stays will put you nice and close to your departure gate:

  • When it comes to the on-time performance of Philadelphia International Airport, 78.93% of flights stick to their scheduled arrival time.

  • PHL is located at 8500 Essington Ave.

Arriving in Chicago

O'Hare International Airport (ORD)

  • The distance from O'Hare International Airport (ORD) to central Chicago is approximately 26 kilometres. It'll take you about 35 minutes to get to the centre driving.

  • It usually takes 55 minutes to get there on public transport.

  • If you're coming in on a late flight from Philadelphia to Chicago, nothing beats the convenience of staying near the terminal. Grab your bags from the carousel and then be showered and snoozing soon after at one of these hotels near ORD:

  • Pick up an O'Hare International Airport rental car and explore Chicago and beyond with your own set of wheels. Routes Car Rentals, Dollar and Budget are well-known companies to choose from here.

  • Reserving your vehicle from O'Hare International Airport about four weeks ahead increases your chances of getting a good deal.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • After your flight from Philadelphia to Chicago has hit the tarmac, you can reach the city centre in around 20 minutes by car. Central Chicago is approximately 14 kilometres from Chicago Midway International Airport (MDW).

  • Travelling by public transport will take around 45 minutes.

  • There are some comfortable places to call home for the night near MDW. Kick back after your Philadelphia to Chicago flight at one of these well-located options:

  • Forget about inconvenient public transport schedules or slow-moving cab lines. Grab a Chicago Midway International Airport rental car and let the journey unfold your way. Check out the rates and availability from Dollar, Hertz and Budget.

  • Snap up a deal by securing your ride from MDW four weeks in advance. You can also expect to have a bigger selection of vehicles.

  • The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Hop off your flight from Philadelphia to Chicago and go directly to your hotel or start sightseeing right away. Central Chicago is around 129 kilometres from Chicago Rockford International Airport (RFD) and typically takes 1 hour 25 minutes to drive there.

  • The journey will take you roughly 4 hours 15 minutes when travelling by public transport.

  • Whether you're looking for an economy just for you or a spacious SUV to fit the whole crew comfortably, you'll find the right Chicago Rockford International Airport rental car for your needs. Explore wheels available here from providers such as Budget, Alamo and National.

  • Rental providers sometimes offer promotions on early bookings, so secure your ride from RFD ahead of your flight from Philadelphia to Chicago. A little prep work can make a big difference in cost.

  • Chicago Rockford International Airport's official address is 2 Airport Cir.

Best time to go to Chicago

  • January is the quietest month for flights from Philadelphia to Chicago, while August is the most popular. Pick the ideal time to go to Chicago based on whether you like a laid-back vibe or a lively atmosphere.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC (59ºF) and 29ºC (84ºF). Book your Philadelphia to Chicago ticket then if that's your idea of comfortable weather.

  • Search for cheap flights from Philadelphia to Chicago in January if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

Explore more of United States

  • Chicago will leave a lasting impression, but there are so many other corners of United States just waiting to be explored. About 451 kilometres south-east of Chicago, a trip to Columbus will keep you busy. Start with leading sights like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Indianapolis is another favourite destination in United States and is around 257 kilometres south-east of Chicago. No trip is complete without experiencing The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.