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 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 60% 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.

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 130 minutes.

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

As of November 2025, 27 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 19% of weekly flights taking off on this day.

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

Saturday 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.

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

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

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

As of November 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 12:00PM, with 55% of daily flights taking off in the afternoon.

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

According to our data, Air Canada have had the least number of delays on this route over the last 12 months; with no flights being classified as delayed.

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 2 as of November 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.

$68 Cheap Flights from Philadelphia to Chicago Midway Airport in 2025/26

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5:00 pm - 6:20 pmPHL-MDW

2h 20mnonstop

7:10 pm - 10:06 pmMDW-PHL

1h 56mnonstop

$102Frontier

Find Deal

Wed, Nov 26 - Mon, Dec 1

4:50 pm - 6:06 pmPHL-MDW

2h 16mnonstop

8:41 pm - 11:38 pmMDW-PHL

1h 57mnonstop

$104Frontier

Find Deal

Mon, Nov 24 - Fri, Nov 28

4:50 pm - 6:06 pmPHL-MDW

2h 16mnonstop

5:30 pm - 11:20 amMDW-PHL

16h 50m1 stop

$106Frontier

Find Deal

Mon, Nov 24 - Wed, Nov 26

5:44 pm - 7:04 pmPHL-MDW

2h 20mnonstop

8:41 pm - 11:38 pmMDW-PHL

1h 57mnonstop

$109Frontier

Find Deal

Tue, Nov 25 - Fri, Nov 28

6:00 am - 12:05 pmPHL-MDW

7h 05m1 stop

9:48 am - 7:13 pmMDW-PHL

8h 25m1 stop

$110Frontier

Find Deal

Wed, Jan 28 - Sat, Jan 31

3:30 pm - 12:13 amPHL-MDW

9h 43m1 stop

8:41 pm - 11:38 pmMDW-PHL

1h 57mnonstop

$111Frontier

Find Deal

Thu, Nov 27 - Fri, Nov 28

5:44 pm - 7:04 pmPHL-MDW

2h 20mnonstop

5:30 pm - 11:27 amMDW-PHL

16h 57m1 stop

$112Frontier

Find Deal

Tue, Nov 25 - Thu, Nov 27

1:00 pm - 10:17 pmPHL-MDW

10h 17m1 stop

2:47 pm - 1:14 amMDW-PHL

9h 27m1 stop

$117Frontier

Find Deal

Thu, Jan 8 - Mon, Jan 12

7:16 am - 4:57 pmPHL-MDW

10h 41m1 stop

7:10 pm - 10:06 pmMDW-PHL

1h 56mnonstop

$120Frontier

Find Deal

Wed, Nov 26 - Mon, Dec 1

1:46 pm - 7:42 pmPHL-MDW

6h 56m1 stop

3:10 pm - 12:40 amMDW-PHL

8h 30m1 stop

$123Frontier

Find Deal

Fri, Dec 12 - Mon, Dec 15

Frontier flights from Philadelphia to Chicago Midway Airport

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

Frontier

Nov 26

PHL5:00 pmPhiladelphia

2h 20m

MDW6:20 pmChicago Midway

Dec 1

MDW7:10 pmChicago Midway

1h 56m

PHL10:06 pmPhiladelphia

$102

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Frontier

Nov 24

PHL4:50 pmPhiladelphia

2h 16m

MDW6:06 pmChicago Midway

Nov 28

MDW8:41 pmChicago Midway

1h 57m

PHL11:38 pmPhiladelphia

$104

Find similar

Frontier

Nov 22

PHL6:07 pmPhiladelphia

2h 22m

MDW7:29 pmChicago Midway

Nov 24

MDW7:10 pmChicago Midway

1h 56m

PHL10:06 pmPhiladelphia

$105

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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 10

PHL12:40 pmPhiladelphia

2h 10m

MDW1:50 pmChicago Midway

Jan 14

MDW5:30 pmChicago Midway

1h 50m

PHL8:20 pmPhiladelphia

$139

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Southwest

Jan 11

PHL6:20 pmPhiladelphia

2h 15m

MDW7:35 pmChicago Midway

Jan 14

MDW5:30 pmChicago Midway

1h 50m

PHL8:20 pmPhiladelphia

$158

Find similar

Southwest

Dec 6

PHL2:20 pmPhiladelphia

2h 10m

MDW3:30 pmChicago Midway

Dec 9

MDW11:05 amChicago Midway

1h 55m

PHL2:00 pmPhiladelphia

$159

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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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Depart

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Price

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 11/26

5:00 pm-6:20 pm

Nonstop2h 20m

Chicago Midway

Mon 12/1

7:10 pm-10:06 pm

Nonstop1h 56m

$102

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Mon 11/24

4:50 pm-6:06 pm

Nonstop2h 16m

Chicago Midway

Fri 11/28

8:41 pm-11:38 pm

Nonstop1h 57m

$104

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Mon 11/24

4:50 pm-6:06 pm

Nonstop2h 16m

Chicago Midway

Wed 11/26

5:30 pm-11:20 am

1 stop16h 50m

$106

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Tue 11/25

5:44 pm-7:04 pm

Nonstop2h 20m

Chicago Midway

Fri 11/28

8:41 pm-11:38 pm

Nonstop1h 57m

$109

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 1/28

6:00 am-12:05 pm

1 stop7h 05m

Chicago Midway

Sat 1/31

9:48 am-7:13 pm

1 stop8h 25m

$110

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 11/27

3:30 pm-12:13 am

1 stop9h 43m

Chicago Midway

Fri 11/28

8:41 pm-11:38 pm

Nonstop1h 57m

$111

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Tue 11/25

5:44 pm-7:04 pm

Nonstop2h 20m

Chicago Midway

Thu 11/27

5:30 pm-11:27 am

1 stop16h 57m

$112

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 1/8

1:00 pm-10:17 pm

1 stop10h 17m

Chicago Midway

Mon 1/12

2:47 pm-1:14 am

1 stop9h 27m

$117

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 11/26

7:16 am-4:57 pm

1 stop10h 41m

Chicago Midway

Mon 12/1

7:10 pm-10:06 pm

Nonstop1h 56m

$120

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 12/12

1:46 pm-7:42 pm

1 stop6h 56m

Chicago Midway

Mon 12/15

3:10 pm-12:40 am

1 stop8h 30m

$123

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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 $198. If you are unable to visit Chicago Midway Airport during the month of November, then departing from Philadelphia during the month December is also very affordable. Most momondo users find prices during this month for around $198.

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 $267. 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 $383.

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 $267 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $358. 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 $261 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 November 2025, prices for Philadelphia to Chicago Midway Airport flights are approximately 19% 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	$142
Fastest flight time	2h 10m
Direct flights	Every day

The best one-way flight to Chicago Midway Airport from Philadelphia in the past 72 hours is $142. The best round-trip flight deal from Philadelphia to Chicago Midway Airport found on momondo in the last 72 hours is $149.

The fastest flight from Philadelphia to Chicago Midway Airport takes 2h 10m

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 10m.
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 2 as of November 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 (19.28% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (13.37%), Airbus A320neo (10.43%), and Airbus A319 (8.65%).
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 56% of all bookings. The subsequent popular airline is Frontier at 44%.

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 $61	Free Cancellation	Rating 5.8 3,109 reviews		Search Frontier flights
Southwest	PriceFrom $167	Free Cancellation	Rating 8.0 4,242 reviews		Search Southwest 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 24 flights/week on average for this route. A good Southwest flight deal for Philadelphia to Chicago Midway Airport starts from $167 round-trip, up to an average price of $322. Our users have rated Southwest at 8.0/10.
Frontier Flights From Philadelphia to Chicago Midway Airport
Frontier (5.8/10 from 3,109 reviews) operates around 3 flights from Philadelphia to Chicago Midway Airport in any given week. The average Frontier airfare for this route is around $179, with deals from around $61 rare but found on momondo. Referenced prices are for round-trip Philadelphia to Chicago Midway Airport flight searches in the last 72 hours.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

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

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 $68

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 1/25. 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

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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

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

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 November 2025, prices for Philadelphia to Chicago Midway Airport flights are approximately 19% more expensive when compared to flights at the same time last year.

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

Frontier, 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 130 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?

Saturday 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, Air Canada have had the least number of delays on this route over the last 12 months; with no flights being classified as delayed.

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

As of November 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 12:00PM, with 55% of daily flights taking off in the afternoon.

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

As of November 2025, 27 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 19% 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

Frontier 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