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Cheap flights from Chicago Midway Airport to Philadelphia from $61

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Philadelphia departing on 12/16. 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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0 bags

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Find the cheapest flights from Chicago Midway Airport to Philadelphia

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:30 pm - 8:20 pm
MDW
-
PHL
1h 50mnonstop
Southwest Logo
5:45 pm - 7:00 pm
PHL
-
MDW
2h 15mnonstop
$125Southwest
Wed, Jan 21 - Wed, Jan 28
Frontier Logo
5:01 pm - 12:52 am
MDW
-
PHL
6h 51m1 stop
Frontier Logo
5:30 am - 11:45 am
PHL
-
MDW
7h 15m1 stop
$128Frontier
Fri, Jan 30 - Sun, Feb 1
Frontier Logo
9:38 am - 7:13 pm
MDW
-
PHL
8h 35m1 stop
Frontier Logo
5:30 am - 11:45 am
PHL
-
MDW
7h 15m1 stop
$129Frontier
Sat, Jan 31 - Mon, Feb 2
Southwest Logo
5:30 pm - 8:20 pm
MDW
-
PHL
1h 50mnonstop
Southwest Logo
4:15 pm - 5:30 pm
PHL
-
MDW
2h 15mnonstop
$134Southwest
Thu, Jan 8 - Sat, Jan 10
Frontier Logo
5:01 pm - 12:52 am
MDW
-
PHL
6h 51m1 stop
Frontier Logo
5:30 am - 11:45 am
PHL
-
MDW
7h 15m1 stop
$135Frontier
Thu, Jan 22 - Sun, Jan 25
Frontier Logo
8:42 pm - 10:50 am
MDW
-
PHL
13h 08m1 stop
Frontier Logo
6:37 pm - 8:46 am
PHL
-
MDW
15h 09m1 stop
$136Frontier
Mon, Dec 15 - Tue, Dec 16
Southwest Logo
5:30 pm - 8:20 pm
MDW
-
PHL
1h 50mnonstop
Southwest Logo
5:45 pm - 7:00 pm
PHL
-
MDW
2h 15mnonstop
$137Southwest
Fri, Jan 30 - Wed, Feb 4
Southwest Logo
12:45 pm - 3:35 pm
MDW
-
PHL
1h 50mnonstop
Southwest Logo
5:40 am - 7:00 am
PHL
-
MDW
2h 20mnonstop
$144Southwest
Sat, Jan 31 - Mon, Feb 2
Frontier Logo
1:20 pm - 12:42 am
MDW
-
PHL
10h 22m1 stop
Frontier Logo
5:30 am - 11:45 am
PHL
-
MDW
7h 15m1 stop
$145Frontier
Tue, Jan 20 - Thu, Jan 22
Frontier Logo
5:01 pm - 12:52 am
MDW
-
PHL
6h 51m1 stop
Frontier Logo
3:54 pm - 7:52 pm
PHL
-
MDW
28h 58m1 stop
$146Frontier
Thu, Feb 5 - Sat, Feb 7

Frontier flights from Chicago Midway Airport to Philadelphia

Our best Frontier deals on Chicago Midway Airport to Philadelphia flight tickets
Frontier
Jan 30
MDW5:01 pmChicago Midway
6h 51m
1 stop
PHL12:52 amPhiladelphia
Feb 1
PHL5:30 amPhiladelphia
7h 15m
1 stop
MDW11:45 amChicago Midway
$128
Find similar
Frontier
Jan 31
MDW9:38 amChicago Midway
8h 35m
1 stop
PHL7:13 pmPhiladelphia
Feb 2
PHL5:30 amPhiladelphia
7h 15m
1 stop
MDW11:45 amChicago Midway
$129
Find similar
Frontier
Jan 22
MDW5:01 pmChicago Midway
6h 51m
1 stop
PHL12:52 amPhiladelphia
Jan 25
PHL5:30 amPhiladelphia
7h 15m
1 stop
MDW11:45 amChicago Midway
$135
Find similar

Southwest flights from Chicago Midway Airport to Philadelphia

Our best Southwest deals on Chicago Midway Airport to Philadelphia flight tickets
Southwest
Jan 21
MDW5:30 pmChicago Midway
1h 50m
PHL8:20 pmPhiladelphia
Jan 28
PHL5:45 pmPhiladelphia
2h 15m
MDW7:00 pmChicago Midway
$125
Find similar
Southwest
Jan 8
MDW5:30 pmChicago Midway
1h 50m
PHL8:20 pmPhiladelphia
Jan 10
PHL4:15 pmPhiladelphia
2h 15m
MDW5:30 pmChicago Midway
$134
Find similar
Southwest
Jan 30
MDW5:30 pmChicago Midway
1h 50m
PHL8:20 pmPhiladelphia
Feb 4
PHL5:45 pmPhiladelphia
2h 15m
MDW7:00 pmChicago Midway
$137
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Philadelphia that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated December 4, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Philadelphia that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Wed 1/21

5:30 pm-8:20 pm

Nonstop1h 50m

Philadelphia

Wed 1/28

5:45 pm-7:00 pm

Nonstop2h 15m

$125

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Fri 1/30

5:01 pm-12:52 am

1 stop6h 51m

Philadelphia

Sun 2/1

5:30 am-11:45 am

1 stop7h 15m

$128

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Sat 1/31

9:38 am-7:13 pm

1 stop8h 35m

Philadelphia

Mon 2/2

5:30 am-11:45 am

1 stop7h 15m

$129

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Thu 1/8

5:30 pm-8:20 pm

Nonstop1h 50m

Philadelphia

Sat 1/10

4:15 pm-5:30 pm

Nonstop2h 15m

$134

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Thu 1/22

5:01 pm-12:52 am

1 stop6h 51m

Philadelphia

Sun 1/25

5:30 am-11:45 am

1 stop7h 15m

$135

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Mon 12/15

8:42 pm-10:50 am

1 stop13h 08m

Philadelphia

Tue 12/16

6:37 pm-8:46 am

1 stop15h 09m

$136

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Fri 1/30

5:30 pm-8:20 pm

Nonstop1h 50m

Philadelphia

Wed 2/4

5:45 pm-7:00 pm

Nonstop2h 15m

$137

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Sat 1/31

12:45 pm-3:35 pm

Nonstop1h 50m

Philadelphia

Mon 2/2

5:40 am-7:00 am

Nonstop2h 20m

$144

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Tue 1/20

1:20 pm-12:42 am

1 stop10h 22m

Philadelphia

Thu 1/22

5:30 am-11:45 am

1 stop7h 15m

$145

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Thu 2/5

5:01 pm-12:52 am

1 stop6h 51m

Philadelphia

Sat 2/7

3:54 pm-7:52 pm

1 stop28h 58m

$146

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Philadelphia from

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

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 Philadelphia?

The cheapest month to fly to Philadelphia from Chicago Midway Airport is in October. Flight prices, which tend to average around $120, are often lower during this time because this is during the off-season. The month of December is another great option to travel to Philadelphia, with average flight prices from Chicago Midway Airport averaging around $166.

What is the cheapest day to depart on your flight to Philadelphia?

The cheapest day to depart from Chicago Midway Airport to Philadelphia is on a Thursday. Travelers who choose to depart for Philadelphia on a Thursday will often find tickets for as low as $272. On the other hand, Sunday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $384.

What is the cheapest time of day to depart on your flight to Philadelphia?

According to our data, the cheapest time of day to fly to Philadelphia is in the evening. momondo users have found flights departing from Chicago Midway Airport to Philadelphia in the evening for as low as $257. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Philadelphia is in the afternoon when prices are around $409.

What is the cheapest Chicago Midway to Philadelphia flight route?

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

How far in advance should I book a flight to Philadelphia?

You are more likely to see cheaper flights to Philadelphia from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Philadelphia for around $239 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Philadelphia from Chicago Midway Airport for as low as $159 on momondo.

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

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

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

As of December 2025, prices for Chicago Midway Airport to Philadelphia flights are approximately 316% more expensive when compared to flights at the same time last year.

When to book flights from Chicago Midway Airport to Philadelphia

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

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

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

Best Price Found

$88

Fastest flight time

1h 50m

Direct flights

Every day

Airports in Philadelphia

1 airport
The best one-way flight to Philadelphia from Chicago Midway Airport in the past 72 hours is $88. The best round-trip flight deal from Chicago Midway Airport to Philadelphia found on momondo in the last 72 hours is $189.
The fastest flight from Chicago Midway Airport to Philadelphia takes 1h 50m
Direct flights go from Chicago Midway Airport to Philadelphia every day.
There is 1 airport near Philadelphia: Philadelphia (PHL)
Search flight deals

  • How far is Chicago Midway to Philadelphia by plane?

    Philadelphia is 668.8 mi away from Chicago Midway. 1h 50m is a normal flight duration for this route.

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

    Prices for flights from Chicago Midway Airport to Philadelphia Airport are refreshed on a daily basis.

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

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

  • What documentation or ID do you need to fly to Philadelphia Airport?

    The necessary travel and health documents for your Philadelphia Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

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

Best airlines flying from Chicago Midway Airport to Philadelphia

Compare and see reviews for airlines that fly from Chicago Midway Airport to Philadelphia with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $80Free CancellationRating
5.8
3,092 reviews
Search Frontier flights
SouthwestPriceFrom $177Free CancellationRating
8.0
4,252 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Philadelphia

    The lowest priced Southwest flight from Chicago Midway Airport to Philadelphia from the last 72 hours was $177. Generally, Southwest has 20 flights on this route every week with an average price of $308. Southwest is rated 8.0/10 by our users.

Traveling to a place near Philadelphia?

Book flights to Philadelphia if you plan to visit one of these locations
Wildwood
Cape May
Rehoboth Beach
Ocean City
Wildwood Crest
King of Prussia
Cherry Hill
Newark
Dewey Beach
Reading
North Wildwood
Avalon
Dover
Lewes
Stone Harbor
Essington
Vineland
Pottstown
Somers Point
Elkton

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Philadelphia for you.

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

Flights from Chicago to Philadelphia with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Philadelphia.

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

Price alerts on flights to Philadelphia from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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