What is the cheapest airline that flies from Philadelphia to Chicago Midway?

Southwest and Delta are the most popular carriers operating from Philadelphia to Chicago Midway

What airlines fly to Chicago Midway Airport?

Southwest, Frontier and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Philadelphia according to our data. Southwest is the first choice among our users, with 63% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 4 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

Which airline has the best punctuality record on Philadelphia to Chicago flights?

According to our data, Frontier have had the least number of delays on this route over the last 12 months; with about 18% of their flights experiencing any sort of delay.

How often are flights from Philadelphia to Chicago delayed?

Historically, on average around 19% of flights between Philadelphia and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 126 minutes.

How many flights depart from Philadelphia to Chicago Midway Airport on average per week?

As of December 2025, 23 flights take off from Philadelphia and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.

What day of the week experiences the fewest flight delays on this route?

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Friday has historically seen more delays on average compared to the rest of the week.

How many flights depart from Philadelphia to Chicago Midway Airport on average per day?

As of December 2025, 3 flights take off from Philadelphia and land in Chicago Midway Airport each day. The most common flight departure time for this route is 5:00AM, with 45% of daily flights taking off in the afternoon.

What is the most punctual flight time for Philadelphia to Chicago flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

When did momondo last update prices for flights from Philadelphia Airport to Chicago Midway Airport?

Prices for flights from Philadelphia Airport to Chicago Midway Airport are updated daily.

How many operators does momondo search for flights from Philadelphia Airport to Chicago Midway Airport?

The number of operators available for flights from Philadelphia Airport to Chicago Midway Airport is 3 as of December 2025.

How old do you have to be to fly from Philadelphia Airport to Chicago Midway Airport?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Philadelphia Airport to Chicago Midway Airport.

What documentation or ID do you need to fly to Chicago Midway Airport?

The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$64 Cheap Flights from Philadelphia to Chicago Midway Airport in 2025/26

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6:00 am - 12:05 pm

PHL

MDW

7h 05m1 stop

1:20 pm - 12:52 am

MDW

PHL

10h 32m1 stop

$128Frontier

Wed, Jan 21 - Wed, Jan 28

5:50 am - 7:05 am

PHL

MDW

2h 15mnonstop

5:30 pm - 8:20 pm

MDW

PHL

1h 50mnonstop

$139Southwest

Sat, Jan 17 - Tue, Jan 20

11:40 am - 7:07 pm

PHL

MDW

8h 27m1 stop

6:25 am - 6:11 pm

MDW

PHL

10h 46m1 stop

$142Frontier

Wed, Feb 25 - Sat, Feb 28

12:06 pm - 7:09 pm

PHL

MDW

8h 03m1 stop

1:20 pm - 12:52 am

MDW

PHL

10h 32m1 stop

$145Frontier

Thu, Jan 15 - Wed, Jan 21

5:40 am - 7:00 am

PHL

MDW

2h 20mnonstop

10:00 am - 12:55 pm

MDW

PHL

1h 55mnonstop

$149Southwest

Wed, Jan 14 - Sun, Jan 18

5:45 pm - 7:00 pm

PHL

MDW

2h 15mnonstop

10:00 am - 12:55 pm

MDW

PHL

1h 55mnonstop

$158Southwest

Tue, Jan 20 - Fri, Jan 23

5:40 am - 7:00 am

PHL

MDW

2h 20mnonstop

6:10 am - 11:30 am

MDW

PHL

4h 20m1 stop

$159Southwest

Wed, Jan 14 - Sun, Jan 18

3:45 pm - 10:19 pm

PHL

MDW

7h 34m1 stop

9:13 am - 6:46 pm

MDW

PHL

8h 33m1 stop

$162Frontier

Wed, Jan 14 - Thu, Jan 15

5:30 am - 11:45 am

PHL

MDW

7h 15m1 stop

5:01 pm - 12:52 am

MDW

PHL

6h 51m1 stop

$163Frontier

Thu, Jan 22 - Thu, Jan 29

1:38 pm - 11:09 pm

PHL

MDW

10h 31m1 stop

6:10 am - 4:28 pm

MDW

PHL

9h 18m1 stop

$164Frontier

Mon, Jan 12 - Wed, Jan 14

Frontier flights from Philadelphia to Chicago Midway Airport

Our best Frontier deals on Philadelphia to Chicago Midway Airport flight tickets

Frontier

Jan 21

PHL6:00 amPhiladelphia

7h 05m

1 stop

MDW12:05 pmChicago Midway

Jan 28

MDW1:20 pmChicago Midway

10h 32m

1 stop

PHL12:52 amPhiladelphia

$128

Find similar

Frontier

Feb 25

PHL11:40 amPhiladelphia

8h 27m

1 stop

MDW7:07 pmChicago Midway

Feb 28

MDW6:25 amChicago Midway

10h 46m

1 stop

PHL6:11 pmPhiladelphia

$142

Find similar

Frontier

Jan 15

PHL12:06 pmPhiladelphia

8h 03m

1 stop

MDW7:09 pmChicago Midway

Jan 21

MDW1:20 pmChicago Midway

10h 32m

1 stop

PHL12:52 amPhiladelphia

$145

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Southwest flights from Philadelphia to Chicago Midway Airport

Our best Southwest deals on Philadelphia to Chicago Midway Airport flight tickets

Southwest

Jan 17

PHL5:50 amPhiladelphia

2h 15m

MDW7:05 amChicago Midway

Jan 20

MDW5:30 pmChicago Midway

1h 50m

PHL8:20 pmPhiladelphia

$139

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Southwest

Jan 14

PHL5:40 amPhiladelphia

2h 20m

MDW7:00 amChicago Midway

Jan 18

MDW10:00 amChicago Midway

1h 55m

PHL12:55 pmPhiladelphia

$149

Find similar

Southwest

Jan 20

PHL5:45 pmPhiladelphia

2h 15m

MDW7:00 pmChicago Midway

Jan 23

MDW10:00 amChicago Midway

1h 55m

PHL12:55 pmPhiladelphia

$158

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momondo Fare Finder

Use the filters below to find and compare flights from Philadelphia to Chicago Midway Airport that are best for you.

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Fly to

Route

Depart

Return

Price

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 1/21

6:00 am-12:05 pm

1 stop7h 05m

Chicago Midway

Wed 1/28

1:20 pm-12:52 am

1 stop10h 32m

$128

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Sat 1/17

5:50 am-7:05 am

Nonstop2h 15m

Chicago Midway

Tue 1/20

5:30 pm-8:20 pm

Nonstop1h 50m

$139

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 2/25

11:40 am-7:07 pm

1 stop8h 27m

Chicago Midway

Sat 2/28

6:25 am-6:11 pm

1 stop10h 46m

$142

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 1/15

12:06 pm-7:09 pm

1 stop8h 03m

Chicago Midway

Wed 1/21

1:20 pm-12:52 am

1 stop10h 32m

$145

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 1/14

5:40 am-7:00 am

Nonstop2h 20m

Chicago Midway

Sun 1/18

10:00 am-12:55 pm

Nonstop1h 55m

$149

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Tue 1/20

5:45 pm-7:00 pm

Nonstop2h 15m

Chicago Midway

Fri 1/23

10:00 am-12:55 pm

Nonstop1h 55m

$158

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 1/14

5:40 am-7:00 am

Nonstop2h 20m

Chicago Midway

Sun 1/18

6:10 am-11:30 am

1 stop4h 20m

$159

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 1/14

3:45 pm-10:19 pm

1 stop7h 34m

Chicago Midway

Thu 1/15

9:13 am-6:46 pm

1 stop8h 33m

$162

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 1/22

5:30 am-11:45 am

1 stop7h 15m

Chicago Midway

Thu 1/29

5:01 pm-12:52 am

1 stop6h 51m

$163

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Mon 1/12

1:38 pm-11:09 pm

1 stop10h 31m

Chicago Midway

Wed 1/14

6:10 am-4:28 pm

1 stop9h 18m

$164

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How to get the cheapest flight ticket from Philadelphia to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Delays

Other information

What is the cheapest month to fly to Chicago Midway Airport?

The month of November is, on average, the cheapest month to fly to Chicago Midway Airport from Philadelphia, with most prices found around $202. If you are unable to visit Chicago Midway Airport during the month of November, then departing from Philadelphia during the month September is also very affordable. Most momondo users find prices during this month for around $217.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Philadelphia. The lowest ticket price found for a Friday departure recently was $266. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Philadelphia because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $394.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Philadelphia in the evening is the least expensive time of day to depart. momondo users have found prices as low as $276 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $365. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Philadelphia to Chicago Midway flight route?

Fly from Philadelphia to Chicago Midway for the best Philadelphia - Chicago Midway flight prices

How far in advance should I book a flight to Chicago Midway Airport?

You are more likely to see cheaper flights to Chicago Midway Airport from Philadelphia when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $265 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Philadelphia for as low as $218 on momondo.

What cabin class options are available on Philadelphia to Chicago Midway flights?

There is only 1 cabin class available to choose from on Philadelphia to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Philadelphia to Chicago Midway Airport flight prices changed over time?

As of December 2025, prices for Philadelphia to Chicago Midway Airport flights are approximately 41% more expensive when compared to flights at the same time last year.

When to book flights from Philadelphia to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Philadelphia to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Philadelphia to Chicago Midway Airport (PHL to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Philadelphia to Chicago Midway Airport

Best Price Found	$186
Fastest flight time	2h 05m
Direct flights	Every day

The best one-way flight to Chicago Midway Airport from Philadelphia in the past 72 hours is $186. The best round-trip flight deal from Philadelphia to Chicago Midway Airport found on momondo in the last 72 hours is $309.

The fastest flight from Philadelphia to Chicago Midway Airport takes 2h 05m

Direct flights go from Philadelphia to Chicago Midway Airport every day.

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How far is Philadelphia to Chicago Midway by plane?
The straight-line distance from Philadelphia to Chicago Midway is 668.8 mi. In terms of flight time, this usually takes a little over 2h 05m.
When did momondo last update prices for flights from Philadelphia Airport to Chicago Midway Airport?
Prices for flights from Philadelphia Airport to Chicago Midway Airport are updated daily.
How many operators does momondo search for flights from Philadelphia Airport to Chicago Midway Airport?
The number of operators available for flights from Philadelphia Airport to Chicago Midway Airport is 3 as of December 2025.
How old do you have to be to fly from Philadelphia Airport to Chicago Midway Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Philadelphia Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Philadelphia to Chicago Midway Airport?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Philadelphia to Chicago Midway Airport is Boeing 737-800 (18.56% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (11.78%), Airbus A320neo (9.48%), and Boeing 737-800 Passenger/BBJ2 (winglets) (9.30%).
What is the most popular airline from Philadelphia to Chicago Midway Airport?
momondo data reveals that the most frequently booked airline on the route from Philadelphia to Chicago Midway Airport is Southwest, representing 63% of all bookings. The subsequent popular airlines are Frontier at 36% and United Airlines at 1%.

Best airlines flying from Philadelphia to Chicago Midway Airport

Compare and see reviews for airlines that fly from Philadelphia to Chicago Midway Airport with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $92	Free Cancellation	Rating 5.8 3,070 reviews	Search Frontier flights
Southwest	PriceFrom $162	Free Cancellation	Rating 8.0 4,258 reviews	Search Southwest flights
United Airlines	PriceFrom $297	Free Cancellation	Rating 7.4 9,116 reviews	Search United Airlines flights

Southwest Flights From Philadelphia to Chicago Midway Airport
Southwest is one of the most popular airlines flying from Philadelphia to Chicago Midway Airport, operating 23 flights/week on average for this route. A good Southwest flight deal for Philadelphia to Chicago Midway Airport starts from $162 round-trip, up to an average price of $320. Our users have rated Southwest at 8.0/10.

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Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

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momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Philadelphia to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Philadelphia to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Philadelphia which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Philadelphia to Chicago?

Once all potential Philadelphia to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Philadelphia to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Philadelphia and alert you when they change.

An easier way to manage your Chicago Midway Airport trip

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Cheap flights from Philadelphia to Chicago from $64

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Philadelphia to Chicago departing on 1/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Frontier flights from Philadelphia to Chicago Midway Airport

Our best Frontier deals on Philadelphia to Chicago Midway Airport flight tickets

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Our best Southwest deals on Philadelphia to Chicago Midway Airport flight tickets

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Use the filters below to find and compare flights from Philadelphia to Chicago Midway Airport that are best for you.

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How to get the cheapest flight ticket from Philadelphia to Chicago Midway Airport

What is the cheapest month to fly to Chicago Midway Airport?

What is the cheapest day to depart on your flight to Chicago Midway Airport?

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

What is the cheapest Philadelphia to Chicago Midway flight route?

Fly from Philadelphia to Chicago Midway for the best Philadelphia - Chicago Midway flight prices

How far in advance should I book a flight to Chicago Midway Airport?

What cabin class options are available on Philadelphia to Chicago Midway flights?

There is only 1 cabin class available to choose from on Philadelphia to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Philadelphia to Chicago Midway Airport flight prices changed over time?

As of December 2025, prices for Philadelphia to Chicago Midway Airport flights are approximately 41% more expensive when compared to flights at the same time last year.

What is the cheapest airline that flies from Philadelphia to Chicago Midway?

Southwest and Delta are the most popular carriers operating from Philadelphia to Chicago Midway

What airlines fly to Chicago Midway Airport?

How often are flights from Philadelphia to Chicago delayed?

Historically, on average around 19% of flights between Philadelphia and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 126 minutes.

What is the most punctual flight time for Philadelphia to Chicago flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Friday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Philadelphia to Chicago flights?

According to our data, Frontier have had the least number of delays on this route over the last 12 months; with about 18% of their flights experiencing any sort of delay.

How many flights depart from Philadelphia to Chicago Midway Airport on average per day?

As of December 2025, 3 flights take off from Philadelphia and land in Chicago Midway Airport each day. The most common flight departure time for this route is 5:00AM, with 45% of daily flights taking off in the afternoon.

How many flights depart from Philadelphia to Chicago Midway Airport on average per week?

As of December 2025, 23 flights take off from Philadelphia and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.

When to book flights from Philadelphia to Chicago Midway Airport

Cheap Philadelphia to Chicago Midway Airport (PHL to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Philadelphia to Chicago Midway Airport

Best Price Found

Fastest flight time

Direct flights

How far is Philadelphia to Chicago Midway by plane?

When did momondo last update prices for flights from Philadelphia Airport to Chicago Midway Airport?

How many operators does momondo search for flights from Philadelphia Airport to Chicago Midway Airport?

How old do you have to be to fly from Philadelphia Airport to Chicago Midway Airport?

What documentation or ID do you need to fly to Chicago Midway Airport?

What is the most popular plane model from Philadelphia to Chicago Midway Airport?

What is the most popular airline from Philadelphia to Chicago Midway Airport?

Best airlines flying from Philadelphia to Chicago Midway Airport

Compare and see reviews for airlines that fly from Philadelphia to Chicago Midway Airport with momondo

Southwest Flights From Philadelphia to Chicago Midway Airport

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Philadelphia to Chicago?

Can I find flights from Philadelphia to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Philadelphia to Chicago?

I’m not ready to book a flight from Philadelphia to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Chicago

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Popular flights according to clicks in the last 7 days on momondo