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? If you want to travel next month, return fares start from R 2,045. Find the lowest prices on one-way and return tickets right here.

Chicago.R 1,043 per passenger.Departing Fri, 30 Oct.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Philadelphia International on Fri, 30 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 1,043, select.

Chicago.R 1,043 per passenger.Departing Sun, 6 Sep.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Philadelphia International on Sun, 6 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 1,043, select.

Chicago.R 1,047 per passenger.Departing Thu, 5 Nov.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Philadelphia International on Thu, 5 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 1,047, select.

Chicago.R 1,223 per passenger.Departing Mon, 31 Aug.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Philadelphia International on Mon, 31 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 1,223, select.

Chicago.R 1,451 per passenger.Departing Thu, 3 Dec.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Philadelphia International on Thu, 3 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 1,451, select.

Chicago.R 2,273 per passenger.Departing Thu, 28 Jan.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Philadelphia International on Thu, 28 Jan, arriving in Chicago Midway.Price includes taxes and charges.From R 2,273, select.

Chicago.R 2,425 per passenger.Departing Wed, 30 Jun.One-way flight with United.Outbound direct flight with United departs from Philadelphia International on Wed, 30 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,425, select.

Chicago.R 2,587 per passenger.Departing Tue, 6 Apr.One-way flight with Delta.Outbound indirect flight with Delta, departs from Philadelphia International on Tue, 6 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,587, select.

Chicago.R 2,884 per passenger.Departing Mon, 19 Apr.One-way flight with United.Outbound direct flight with United departs from Philadelphia International on Mon, 19 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,884, select.

Chicago.R 3,250 per passenger.Departing Fri, 26 Mar.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Philadelphia International on Fri, 26 Mar, arriving in Chicago Midway.Price includes taxes and charges.From R 3,250, select.

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 September.

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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 found	R 1,043
Cheapest month to fly	September
Average flight time	2 hrs, 24 mins
Most popular airline	American Airlines
Average flights per week	4,203

Finding cheap flights from Philadelphia to Chicago: Frequently asked questions

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.

How much are return flights from Philadelphia to Chicago?

The best price we found for a return flight from Philadelphia to Chicago is R 1,636. 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?

2 hours and 24 minutes is the average flight time from Philadelphia to Chicago.

Which airlines fly direct from Philadelphia to Chicago?

American Airlines, Southwest Airlines and United fly direct from Philadelphia to Chicago.

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

As of August 2026, there are 467 flights per week flying from Philadelphia to Chicago.

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

The cheapest month to fly from Philadelphia to Chicago is usually November.

Which is the cheapest airport to fly into in Chicago?

If you're flying from Philadelphia, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.5 km away from the centre of Chicago. We've found flights into this airport from R 1,636.

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

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Philadelphia to Chicago on Monday, 16 November 2026.

Can I get a direct flight from Philadelphia to Chicago?

Yes – the average flight time is 2 hours and 24 minutes.

How can I get the best flight deal from Philadelphia to Chicago?

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.

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.

What’s the weather like in Chicago?

In August, the average temperature is usually around 22°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.

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

The cheapest airline that flies to Chicago is Frontier Airlines .

Travelling from Philadelphia to Chicago: what you need to know

Embark on your next adventure from one of Philadelphia's main airports, Philadelphia International Airport (PHL) or Philadelphia Trenton-Mercer Airport (TTN). Check out your options for booking a flight from Philadelphia to Chicago departing from either of these bases.
Chicago O'Hare International Airport (ORD) and Chicago Midway Airport (MDW) are the primary entry points to Chicago.
Jump on a direct Philadelphia to Chicago flight and you'll be travelling for an average of 2 hours 20 minutes.
The timezone in Chicago is UTC-6, which is one hour behind Philadelphia.
With 105 flights a week between the two airports, Philadelphia International Airport (PHL) to Chicago O'Hare International Airport (ORD) is the busiest route. Hop on the first flight from Philadelphia to Chicago with American Airlines at 05:00. If you'd like to get more out of your day before jetting off, the last departure from PHL to ORD is with American Airlines at 21:40.
Give yourself plenty of time to catch your Philadelphia to Chicago flight. It's generally best to arrive at least two hours before international departures and an hour ahead for domestic flights.
Flying during a peak month like August? Public holidays and other popular periods can lead to longer lines at check-in and security. Be extra cautious and arrive up to four hours ahead of an international flight and two hours before domestic departures.

How to find the cheapest flights from Philadelphia to Chicago

To pick up cheap Philadelphia to Chicago flights, book early. Airlines tend to offer the most competitive fares when flights are first released.
If you're willing to be flexible with your travel plans, use the 'Whole month' search tool. It'll give you the cheapest price across the month when searching for your plane ticket from Philadelphia to Chicago.
Finding a cheap flight from Philadelphia to Chicago is easy with Price Alerts. Simply create one of these automatic alerts and we'll get in touch as soon as the price has dropped.
Find a cheap Philadelphia to Chicago flight with the help of our filters. Select your ideal times, number of stops and airlines, then sort the results by 'Cheapest' for the best deals.

Flying from Philadelphia

Philadelphia International Airport (PHL)

Begin your trip at Philadelphia International Airport (PHL), which has a range of direct flights from Philadelphia to Chicago. From PHL, you can fly seamlessly to Chicago O'Hare International Airport (ORD) or Chicago Midway Airport (MDW).
Top airlines that offer direct Philadelphia to Chicago plane tickets departing from PHL include:
PHL is around 11 kilometres from central Philadelphia. If you're catching a taxi, driving or ride-sharing from the centre, it'll take you 20 minutes or so to get there, depending on traffic conditions. If you're taking public transport, expect the journey time to be around 30 minutes.
In search of a convenient hotel close to Philadelphia International Airport? If you're boarding an early flight from Philadelphia to Chicago, these accommodation options will have you sleeping nice and close to your departure gate:
77% of flights that take off from Philadelphia International Airport make it to their destination on time.
PHL is located at 8500 Essington Ave.

Arriving in Chicago

Chicago O'Hare International Airport (ORD)

The distance from Chicago O'Hare International Airport (ORD) to central Chicago is approximately 26 kilometres. It takes around 30 minutes to get to the centre driving.
If you're travelling on public transport, expect a journey time of roughly 45 minutes.
The last thing you need is a lengthy journey to your hotel if you're arriving on a late flight from Philadelphia to Chicago. Stay at one of these accommodation options near ORD instead:
Get your adventure underway by picking up a Chicago O'Hare International Airport rental car. Grab your wheels from Routes Car Rentals, Dollar or Budget and explore beyond Chicago's main sights.
Lock in the best deal by reserving your vehicle from Chicago O'Hare International Airport about four weeks ahead of your trip.
ORD is located at 10000 West O'Hare.

Chicago Midway Airport (MDW)

Once your flight from Philadelphia to Chicago has hit the tarmac, you can reach the city centre in about 25 minutes by car. Central Chicago is approximately 14 kilometres from Chicago Midway Airport (MDW).
Public transport will get you there in about 30 minutes.
Hang the 'Do not disturb' sign on your door and rest at a hotel close to MDW. Here are a few options where you can put your feet up after your flight from Philadelphia to Chicago:
The fastest way to reach your destination is with a Chicago Midway Airport rental car. Pick up a set of wheels from Dollar, Hertz or Budget and get going in the blink of an eye.
Avoid paying more than you need to. Securing your ride four weeks before your arrival at MDW can land you a better rate.
Chicago Midway Airport is located at 5700 South Cicero.

Chicago Rockford Airport (RFD)

Make your way to the city centre after your flight from Philadelphia to Chicago has arrived. Central Chicago is about 129 kilometres from Chicago Rockford Airport (RFD) and takes roughly 1 hour 40 minutes to get there in a car.
If you're using public transport, expect a journey of around 2 hours.
Begin your travels without stressing about how to reach your destination with a Chicago Rockford Airport rental car. Book your wheels with reliable companies here like Budget, Alamo and National.
Booking a couple of weeks in advance of your flight from Philadelphia to Chicago is a smart way to go. Along with better deals, you'll have a wider selection of vehicle makes and models at RFD.
The street address for Chicago Rockford Airport is 2 Airport Cir.

Best time to go to Chicago

It's time to pick your trip dates for your flight from Philadelphia to Chicago. July is the most popular month to visit Chicago. If you want a quieter vibe, go in March.
The warmest month in Chicago is July, with temperatures ranging between 16ºC (61ºF) and 28ºC (82ºF). Book your Philadelphia to Chicago ticket then if this is the type of weather you enjoy.
Look for cheap flights from Philadelphia to Chicago in January if you'd rather travel when it's cooler. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

When it comes to searching for somewhere to lay your head, you'll find the best places to stay in Chicago right here. Browse these options after locking in your flight from Philadelphia to Chicago:
Every great holiday has to include some sightseeing. Millennium Park, The Art Institute of Chicago and Willis Tower are attractions you won't want to skip in Chicago.

Explore more of the United States

Chicago has its own special appeal, but there are so many other parts of the United States just waiting to be discovered. About 451 kilometres southeast of Chicago, a visit to Columbus will keep you on the move. Check out popular attractions like Franklin Park Conservatory and Botanical Gardens, Columbus Park of Roses and Ohio Theatre.
If you're eager to discover another major destination in the United States, head for Indianapolis, roughly 257 kilometres southeast of Chicago. Lucas Oil Stadium, Eiteljorg Museum of American Indians and Western Art and The Children's Museum of Indianapolis are among its highlights.