Cheap Flights from Philadelphia International PA to Chicago Midway IL from $127

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Flight deals from Philadelphia International to Chicago Midway

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

Chicago.$127 per passenger.Departing Tue, Aug 19, returning Fri, Aug 22.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Philadelphia International on Tue, Aug 19, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Fri, Aug 22, arriving in Philadelphia International.Price includes taxes and charges.From $127, select.

Chicago.$127 per passenger.Departing Sat, Nov 8, returning Tue, Nov 11.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Philadelphia International on Sat, Nov 8, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Tue, Nov 11, arriving in Philadelphia International.Price includes taxes and charges.From $127, select.

Chicago.$127 per passenger.Departing Tue, Sep 9, returning Tue, Sep 16.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Philadelphia International on Tue, Sep 9, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Tue, Sep 16, arriving in Philadelphia International.Price includes taxes and charges.From $127, select.

Chicago.$140 per passenger.Departing Wed, Aug 27, returning Wed, Sep 3.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Philadelphia International on Wed, Aug 27, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Wed, Sep 3, arriving in Philadelphia International.Price includes taxes and charges.From $140, select.

Chicago.$149 per passenger.Departing Thu, Oct 9, returning Sun, Oct 12.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Philadelphia International on Thu, Oct 9, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Sun, Oct 12, arriving in Philadelphia International.Price includes taxes and charges.From $149, select.

Chicago.$158 per passenger.Departing Fri, Jul 25, returning Fri, Aug 1.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Philadelphia International on Fri, Jul 25, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Fri, Aug 1, arriving in Philadelphia International.Price includes taxes and charges.From $158, select.

Chicago.$158 per passenger.Departing Fri, Jun 13, returning Mon, Jun 16.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Philadelphia International on Fri, Jun 13, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Mon, Jun 16, arriving in Philadelphia International.Price includes taxes and charges.From $158, select.

Chicago.$158 per passenger.Departing Mon, Jun 30, returning Mon, Jul 7.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Philadelphia International on Mon, Jun 30, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Mon, Jul 7, arriving in Philadelphia International.Price includes taxes and charges.From $158, 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 August.

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Direct flights from Philadelphia International to Chicago Midway

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.

Philadelphia to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$127
Cheapest month to fly	November
Average flight time	2 hrs, 9 mins
Most popular airline	Southwest Airlines
Average flights per week	32

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

How much are round-trip flights from Philadelphia International to Chicago Midway?

The best price we found for a round-trip flight from Philadelphia International to Chicago Midway is $127. 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 International to Chicago Midway?

2 hours and 9 minutes is the average flight time from Philadelphia International to Chicago Midway.

Which airlines fly direct from Philadelphia International to Chicago Midway?

Southwest Airlines and Frontier Airlines fly direct from Philadelphia International to Chicago Midway.

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

There are 32 flights per week flying from Philadelphia International to Chicago Midway, as of June 2025.

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

The cheapest month to fly from Philadelphia International to Chicago Midway is usually June 2025.

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

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 Saturday, November 8, 2025.

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

Yes – the average flight time is 2 hours and 9 minutes.

How can I find the best flight deal to Chicago Midway?

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.

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.

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

Currently, Southwest Airlines offers the cheapest flight tickets to Chicago Midway.

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

The average time for a direct flight from Philadelphia International Airport to Chicago Midway International Airport is 2 hours 10 minutes.
Chicago is one hour behind Philadelphia and follows the UTC-5 timezone.
Every week, there are 31 Philadelphia International Airport to Chicago Midway International Airport flights. If you'd like to be on board as soon as possible, pick the 05:30 Southwest Airlines flight. If you'd rather make the most of your time before flying, the last departure is at 21:55 with Southwest Airlines.
Arriving two hours before an international flight and one hour ahead of a domestic departure are golden rules for stress-free travel. Be at the airport on time to board your PHL to MDW flight.
During popular months like August, it's a good idea to get to the airport earlier. Plan to arrive two hours before domestic departures and four hours ahead for an international flight when you travel during peak periods in general.
Frontier Airlines offers direct flights from Philadelphia International Airport to Chicago Midway International Airport. Book with this popular airline, then get ready to check out the sights in Chicago — and maybe even more of United States if you have time.
The airline that passengers book most often on this route is Frontier Airlines.
With 77.78% of services arriving as planned, Frontier Airlines is the most punctual carrier operating PHL to MDW flights.
We make it a piece of cake to book a flight with a stopover. To see all your options for tickets from Philadelphia International Airport to Chicago Midway International Airport, deselect 'Direct flights only.' Then, pick a flight offering a stop long enough to tour the city of your choice. Top stopovers between PHL and MDW include:
- Detroit Metropolitan Wayne County Airport
- Buffalo Niagara International Airport
- Gerald R. Ford International Airport

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

The lowest price we've seen for a one-way Philadelphia International Airport to Chicago Midway International Airport flight is $63. A round-trip ticket is currently $127. Depending on the availability and when you book, these fares can change.
Book six months before flying. After looking at the numbers on our calendar, this is how far you should book ahead to secure cheap tickets from PHL to MDW.
Plan your trip for May. That's the cheapest month for flights from Philadelphia International Airport to Chicago Midway International Airport. If you're flexible with your dates, use the 'Whole month' tool to find the lowest airfare across each month.
Finding cheap flights from PHL to MDW is easy with Price Alerts. All you need to do is set up one of these automatic alerts and we'll let you know as soon as a new discounted fare appears.
Pick your preferred arrival and departure 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 International Airport.

Handy information about Philadelphia International Airport (PHL)

PHL is located at Industrial Highway and Island Road.
78.93% of flights leaving from Philadelphia International Airport touch down at their destination on schedule.
Central Philadelphia to Philadelphia International Airport is approximately 19 kilometers. Depending on traffic, it'll take about 15 minutes to get there if you're catching a cab, ride-sharing or driving.
Catching public transport? You can expect a journey time of around 45 minutes.
Get your break off to a relaxed start by staying near PHL. Whether you're boarding an early flight from Philadelphia International Airport to Chicago Midway International Airport or want to avoid feeling rushed, these hotels have you covered:

Arriving at Chicago Midway International Airport (MDW)

The last thing you need is a long trip to your hotel if you're arriving on a late Philadelphia International Airport to Chicago Midway International Airport flight. Book one of these accommodation options near MDW instead:
Get your adventure underway by picking up a Chicago Midway International Airport rental car. Grab your wheels from Dollar, Hertz or Budget and explore beyond Chicago's usual tourist stops.
Get the best deal by reserving your vehicle from Chicago Midway International Airport around four weeks before your departure date.

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

MDW is located at 5700 South Cicero.
Chicago Midway International Airport to the center of Chicago has a drive time of around 20 minutes. It's approximately 19 kilometers away.
It typically takes 45 minutes if you're using public transport.

When to fly to Chicago Midway International Airport (MDW)

The quietest month for a flight from Philadelphia International Airport to Chicago Midway International Airport is May, while July is the most popular. Pick the ideal time to visit Chicago based on whether you prefer a laid-back vibe or a more bustling atmosphere.
Before locking in your flight from Philadelphia International Airport to Chicago Midway International Airport, consider the kind of weather you enjoy. July is the warmest month in Chicago, with the temperature ranging from 15ºC (59ºF) to 29ºC (84ºF).
January has average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Look for cheap tickets from PHL to MDW around that time if you'd rather travel in cooler conditions.

Explore more of United States

Columbus is just one of the many places in United States waiting to be explored once you've seen the sights of Chicago. Around 451 kilometers away to the south-east, top sights here include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.
If you're looking to explore another major destination in United States, head for Indianapolis, about 257 kilometers south-east of Chicago. The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo are highlights.