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

3 flights are operational daily from Chicago Midway Airport to Pennsylvania as of October 2026. The most popular departure time for this route is 8:00AM, with 40% of flights per day taking off at noon.

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

23 flights are operational weekly from Chicago Midway Airport to Pennsylvania as of October 2026. The most popular departure day for this route is Mon, with 26% of flights per week taking off on this day.

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

Southwest, Delta, and Allegiant Air are the most popular carriers operating from Chicago Midway to Pennsylvania

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

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

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

As of October 2026, there are 2 operators available to choose from for flights from Chicago Midway Airport to Pennsylvania.

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

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Pennsylvania.

What documentation or ID do you need to fly to Pennsylvania?

The travel and health documents required for your trip to Pennsylvania 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 Pennsylvania. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$99 Cheap Flights from Chicago Midway Airport to Pennsylvania in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago Midway Airport to Pennsylvania

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

3:50 pm - 11:05 pmMDW Chicago Midway-PHL Philadelphia

6h 15m1 stop Atlanta Hartsfield-Jackson

8:34 am - 2:55 pmPHL Philadelphia-MDW Chicago Midway

7h 21m1 stop Atlanta Hartsfield-Jackson

$169Frontier

Fri, Dec 4 - Sun, Dec 6

6:42 pm - 7:21 amMDW Chicago Midway-PHL Philadelphia

11h 39m1 stop Atlanta Hartsfield-Jackson

5:22 pm - 11:47 pmPHL Philadelphia-MDW Chicago Midway

7h 25m1 stop Atlanta Hartsfield-Jackson

$169Frontier

Fri, Oct 30 - Fri, Nov 6

6:42 pm - 7:21 amMDW Chicago Midway-PHL Philadelphia

11h 39m1 stop Atlanta Hartsfield-Jackson

12:36 pm - 11:47 pmPHL Philadelphia-MDW Chicago Midway

12h 11m1 stop Atlanta Hartsfield-Jackson

$169Frontier

Fri, Oct 30 - Wed, Nov 4

6:42 pm - 7:21 amMDW Chicago Midway-PHL Philadelphia

11h 39m1 stop Atlanta Hartsfield-Jackson

5:22 pm - 11:47 pmPHL Philadelphia-MDW Chicago Midway

7h 25m1 stop Atlanta Hartsfield-Jackson

$171Frontier

Fri, Oct 30 - Fri, Nov 6

4:10 pm - 7:05 pmMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

1:25 pm - 2:40 pmPHL Philadelphia-MDW Chicago Midway

2h 15mnonstop

$257Southwest

Sat, Oct 31 - Tue, Nov 3

7:50 am - 10:50 amMDW Chicago Midway-PHL Philadelphia

2h 00mnonstop

3:20 pm - 4:25 pmPHL Philadelphia-MDW Chicago Midway

2h 05mnonstop

$257Southwest

Thu, Oct 29 - Thu, Oct 29

12:10 pm - 3:05 pmMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

6:20 pm - 7:35 pmPHL Philadelphia-MDW Chicago Midway

2h 15mnonstop

$257Southwest

Sat, Nov 14 - Mon, Nov 16

9:30 am - 4:35 pmMDW Chicago Midway-PHL Philadelphia

6h 05m1 stop Detroit Metropolitan Wayne County

6:00 am - 11:25 amPHL Philadelphia-MDW Chicago Midway

6h 25m1 stop Detroit Metropolitan Wayne County

$277Delta

Mon, Nov 23 - Thu, Nov 26

6:00 am - 2:33 pmMDW Chicago Midway-PHL Philadelphia

7h 33m1 stop Atlanta Hartsfield-Jackson

6:00 am - 9:37 amPHL Philadelphia-MDW Chicago Midway

4h 37m1 stop Detroit Metropolitan Wayne County

$277Delta

Mon, Dec 14 - Tue, Dec 15

9:29 am - 4:44 pmMDW Chicago Midway-PHL Philadelphia

6h 15m1 stop Detroit Metropolitan Wayne County

5:16 pm - 10:33 pmPHL Philadelphia-MDW Chicago Midway

6h 17m1 stop Atlanta Hartsfield-Jackson

$277Delta

Sat, Oct 24 - Mon, Oct 26

Cheap last minute flights

Enter your travel dates to find the best prices.

6:25 am - 6:14 pmMDW Chicago Midway-PHL Philadelphia

10h 49m1 stop Atlanta Hartsfield-Jackson

12:35 pm - 11:43 pmPHL Philadelphia-MDW Chicago Midway

12h 08m1 stop Atlanta Hartsfield-Jackson

$292Frontier

Tue, Oct 6 - Tue, Oct 13

6:25 am - 6:14 pmMDW Chicago Midway-PHL Philadelphia

10h 49m1 stop Atlanta Hartsfield-Jackson

6:00 am - 2:35 pmPHL Philadelphia-MDW Chicago Midway

9h 35m1 stop Dallas/Fort Worth

$308Frontier

Wed, Oct 7 - Wed, Oct 14

6:25 am - 6:14 pmMDW Chicago Midway-PHL Philadelphia

10h 49m1 stop Atlanta Hartsfield-Jackson

6:00 am - 2:35 pmPHL Philadelphia-MDW Chicago Midway

9h 35m1 stop Dallas/Fort Worth

$308Frontier

Tue, Oct 6 - Tue, Oct 13

6:25 am - 6:14 pmMDW Chicago Midway-PHL Philadelphia

10h 49m1 stop Atlanta Hartsfield-Jackson

6:00 am - 2:35 pmPHL Philadelphia-MDW Chicago Midway

9h 35m1 stop Dallas/Fort Worth

$309Frontier

Wed, Oct 7 - Sat, Oct 17

12:26 pm - 8:45 pmMDW Chicago Midway-PHL Philadelphia

7h 19m1 stop Knoxville McGhee Tyson

12:36 pm - 11:47 pmPHL Philadelphia-MDW Chicago Midway

12h 11m1 stop Atlanta Hartsfield-Jackson

$331Multiple Airlines

Fri, Oct 9 - Wed, Nov 4

12:26 pm - 8:45 pmMDW Chicago Midway-PHL Philadelphia

7h 19m1 stop Knoxville McGhee Tyson

5:22 pm - 11:47 pmPHL Philadelphia-MDW Chicago Midway

7h 25m1 stop Atlanta Hartsfield-Jackson

$338Multiple Airlines

Fri, Oct 9 - Fri, Nov 6

11:45 am - 2:40 pmMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

11:45 am - 1:00 pmPHL Philadelphia-MDW Chicago Midway

2h 15mnonstop

$370Southwest

Fri, Oct 9 - Wed, Nov 4

11:45 am - 2:40 pmMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

1:50 pm - 3:05 pmPHL Philadelphia-MDW Chicago Midway

2h 15mnonstop

$379Southwest

Fri, Oct 9 - Fri, Nov 6

4:40 pm - 7:35 pmMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

6:00 am - 3:30 pmPHL Philadelphia-MDW Chicago Midway

10h 30m1 stop Lambert-St Louis

$386Southwest

Fri, Oct 9 - Wed, Nov 4

12:26 pm - 8:45 pmMDW Chicago Midway-PHL Philadelphia

7h 19m1 stop Knoxville McGhee Tyson

5:22 pm - 11:43 pmPHL Philadelphia-MDW Chicago Midway

7h 21m1 stop Atlanta Hartsfield-Jackson

$405Multiple Airlines

Fri, Oct 9 - Tue, Oct 13

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Frontier flights from Chicago Midway Airport to Pennsylvania

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

Frontier

Oct 30

MDW6:42 pmChicago Midway

11h 39m

1 stop

PHL7:21 amPhiladelphia

Nov 6

PHL5:22 pmPhiladelphia

7h 25m

1 stop

MDW11:47 pmChicago Midway

$169

Frontier

Oct 30

MDW6:42 pmChicago Midway

11h 39m

1 stop

PHL7:21 amPhiladelphia

Nov 6

PHL5:22 pmPhiladelphia

7h 25m

1 stop

MDW11:47 pmChicago Midway

$171

Frontier

Oct 22

MDW6:22 amChicago Midway

10h 53m

1 stop

PHL6:15 pmPhiladelphia

Oct 26

PHL5:22 pmPhiladelphia

7h 21m

1 stop

MDW11:43 pmChicago Midway

$182

Southwest flights from Chicago Midway Airport to Pennsylvania

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

Southwest

Oct 22

MDW7:45 pmChicago Midway

1h 25m

PIT10:10 pmPittsburgh

Oct 26

PIT1:40 pmPittsburgh

1h 30m

MDW2:10 pmChicago Midway

$277

Southwest

Oct 22

MDW7:45 pmChicago Midway

1h 25m

PIT10:10 pmPittsburgh

Oct 26

PIT6:00 pmPittsburgh

5h 00m

1 stop

MDW10:00 pmChicago Midway

$287

Southwest

Oct 22

MDW1:20 pmChicago Midway

1h 20m

PIT3:40 pmPittsburgh

Oct 26

PIT4:20 pmPittsburgh

8h 35m

2 stops

MDW11:55 pmChicago Midway

$292

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPhiladelphia

MDW Chicago Midway - PHL Philadelphia

MDWPHL

Chicago Midway

Fri 12/4

3:50 pm-11:05 pm

1 stop6h 15m

Philadelphia

Sun 12/6

8:34 am-2:55 pm

1 stop7h 21m

$169

ChicagoPhiladelphia

MDW Chicago Midway - PHL Philadelphia

MDWPHL

Chicago Midway

Fri 10/30

6:42 pm-7:21 am

1 stop11h 39m

Philadelphia

Fri 11/6

5:22 pm-11:47 pm

1 stop7h 25m

$169

ChicagoPhiladelphia

MDW Chicago Midway - PHL Philadelphia

MDWPHL

Chicago Midway

Fri 10/30

6:42 pm-7:21 am

1 stop11h 39m

Philadelphia

Wed 11/4

12:36 pm-11:47 pm

1 stop12h 11m

$169

ChicagoPhiladelphia

MDW Chicago Midway - PHL Philadelphia

MDWPHL

Chicago Midway

Fri 10/30

6:42 pm-7:21 am

1 stop11h 39m

Philadelphia

Fri 11/6

5:22 pm-11:47 pm

1 stop7h 25m

$171

ChicagoPhiladelphia

MDW Chicago Midway - PHL Philadelphia

MDWPHL

Chicago Midway

Sat 10/31

4:10 pm-7:05 pm

Nonstop1h 55m

Philadelphia

Tue 11/3

1:25 pm-2:40 pm

Nonstop2h 15m

$257

Quickest round-trip

ChicagoPhiladelphia

MDW Chicago Midway - PHL Philadelphia

MDWPHL

Chicago Midway

Thu 10/29

7:50 am-10:50 am

Nonstop2h 00m

Philadelphia

Thu 10/29

3:20 pm-4:25 pm

Nonstop2h 05m

$257

ChicagoPhiladelphia

MDW Chicago Midway - PHL Philadelphia

MDWPHL

Chicago Midway

Sat 11/14

12:10 pm-3:05 pm

Nonstop1h 55m

Philadelphia

Mon 11/16

6:20 pm-7:35 pm

Nonstop2h 15m

$257

ChicagoPhiladelphia

MDW Chicago Midway - PHL Philadelphia

MDWPHL

Chicago Midway

Mon 11/23

9:30 am-4:35 pm

1 stop6h 05m

Philadelphia

Thu 11/26

6:00 am-11:25 am

1 stop6h 25m

$277

ChicagoPhiladelphia

MDW Chicago Midway - PHL Philadelphia

MDWPHL

Chicago Midway

Mon 12/14

6:00 am-2:33 pm

1 stop7h 33m

Philadelphia

Tue 12/15

6:00 am-9:37 am

1 stop4h 37m

$277

ChicagoPhiladelphia

MDW Chicago Midway - PHL Philadelphia

MDWPHL

Chicago Midway

Sat 10/24

9:29 am-4:44 pm

1 stop6h 15m

Philadelphia

Mon 10/26

5:16 pm-10:33 pm

1 stop6h 17m

$277

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

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

Other information

What is the cheapest month to fly to Pennsylvania?

The month of October is, on average, the cheapest month to fly to Pennsylvania from Chicago Midway Airport, with most prices found around $160. If you don’t want to visit Pennsylvania in October, then you should wait until January to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $168.

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

The cheapest day to depart on your flight to Pennsylvania is on a Thursday when prices can be found for as low as $271. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around $401. These prices are subject to change though, so be sure to set up a Price Alert for flights to Pennsylvania.

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

Our most recent data shows that the best time of day to fly to Pennsylvania is in the evening. Flights from Chicago Midway Airport to Pennsylvania during this time can be as low as $284. In contrast, the most expensive time of day to depart to Pennsylvania is at noon when prices are around $362.

What is the cheapest Chicago Midway to Pennsylvania flight route?

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

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

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

Can stopping save me money on Chicago Midway Airport to Pennsylvania flights?

You could potentially save up to 39% on your flight if you consider stops on a Chicago Midway Airport to Pennsylvania flight.

Cheap Chicago Midway Airport to Pennsylvania flight deals and tips

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

Best Price Found	$99
Fastest flight time	1h 20m
Direct flights	Every day
Airports in Pennsylvania	152 airports

The best one-way flight to Pennsylvania from Chicago Midway Airport in the past 72 hours is $99. The best round-trip flight deal from Chicago Midway Airport to Pennsylvania found on momondo in the last 72 hours is $169.

The fastest flight from Chicago Midway Airport to Pennsylvania takes 1h 20m

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

There are 152 airports in Pennsylvania. From Chicago Midway Airport there are direct flights to Philadelphia (PHL), Pittsburgh (PIT).

Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Pennsylvania

When did momondo last update prices for flights from Chicago Midway Airport to Pennsylvania?
Prices for flights from Chicago Midway Airport to Pennsylvania are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago Midway Airport to Pennsylvania?
As of October 2026, there are 2 operators available to choose from for flights from Chicago Midway Airport to Pennsylvania.
How old do you have to be to fly from Chicago Midway Airport to Pennsylvania?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Pennsylvania.
What documentation or ID do you need to fly to Pennsylvania?
The travel and health documents required for your trip to Pennsylvania 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 Pennsylvania. 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 Chicago Midway Airport to Pennsylvania?
momondo data reveals that the most frequently booked plane model on the route from Chicago Midway Airport to Pennsylvania is Boeing 737 MAX 8, representing 14.43% of all bookings. The subsequent popular models are Boeing 737-800 at 14.14%, Boeing 737-800 Passenger/BBJ2 (winglets) at 10.55%, and Boeing 737-900 at 9.91%.

Best airlines flying from Chicago Midway Airport to Pennsylvania

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

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $89	Free Cancellation	Rating 5.5 2,556 reviews		Search Frontier flights
Southwest	PriceFrom $137	Free Cancellation	Rating 7.9 4,216 reviews		Search Southwest flights

Why use momondo?

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

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

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

Yes. All flights to Pennsylvania from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once you have performed a search for Chicago to Pennsylvania flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes. momondo can track prices for Chicago to Pennsylvania flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.