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Cheap flights from Chicago Midway Airport to Pennsylvania from $63

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 Pennsylvania departing on 2/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago Midway Airport to Pennsylvania

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:35 pm - 8:40 pm
MDW
-
LGA
2h 05mnonstop
Southwest Logo
6:30 pm - 8:15 pm
LGA
-
MDW
2h 45mnonstop
$97Southwest
Sat, Jan 24 - Sun, Jan 25
Frontier Logo
6:30 pm - 9:30 pm
MDW
-
EWR
2h 00mnonstop
Frontier Logo
11:30 am - 10:19 pm
EWR
-
MDW
11h 49m1 stop
$110Frontier
Tue, Jan 13 - Wed, Jan 14
Frontier Logo
6:30 pm - 9:30 pm
MDW
-
EWR
2h 00mnonstop
Frontier Logo
6:00 am - 12:05 pm
EWR
-
MDW
7h 05m1 stop
$111Frontier
Tue, Jan 13 - Tue, Jan 20
Frontier Logo
7:30 am - 10:30 am
MDW
-
EWR
2h 00mnonstop
Frontier Logo
11:30 am - 1:02 pm
EWR
-
MDW
2h 32mnonstop
$114Frontier
Thu, Mar 12 - Thu, Mar 19
Multiple Airlines Logo
8:04 pm - 2:50 pm
MDW
-
EWR
17h 46m1 stop
Multiple Airlines Logo
10:30 pm - 12:02 am
EWR
-
MDW
2h 32mnonstop
$116Multiple Airlines
Fri, Jan 16 - Sun, Jan 18
Southwest Logo
10:30 am - 1:30 pm
MDW
-
LGA
2h 00mnonstop
Southwest Logo
6:00 am - 7:40 am
LGA
-
MDW
2h 40mnonstop
$117Southwest
Tue, Jan 13 - Tue, Jan 20
Southwest Logo
8:00 pm - 11:00 pm
MDW
-
LGA
2h 00mnonstop
Southwest Logo
6:00 am - 7:40 am
LGA
-
MDW
2h 40mnonstop
$118Southwest
Mon, Feb 23 - Wed, Feb 25
Southwest Logo
5:35 pm - 8:40 pm
MDW
-
LGA
2h 05mnonstop
Southwest Logo
6:00 am - 7:40 am
LGA
-
MDW
2h 40mnonstop
$123Southwest
Sat, Jan 17 - Tue, Jan 20
Delta Logo
6:00 am - 12:36 pm
MDW
-
PIT
5h 36m1 stop
Delta Logo
6:19 am - 8:54 am
PIT
-
MDW
3h 35m1 stop
$174Delta
Thu, Feb 5 - Wed, Feb 25
Delta Logo
9:32 am - 1:27 pm
MDW
-
PIT
2h 55m1 stop
Delta Logo
6:32 am - 1:09 pm
PIT
-
MDW
7h 37m1 stop
$191Delta
Sat, Jan 17 - Mon, Jan 19

Frontier flights from Chicago Midway Airport to Pennsylvania

Our best Frontier deals on Chicago Midway Airport to Pennsylvania flight tickets
Frontier
Jan 13
MDW6:30 pmChicago Midway
2h 00m
EWR9:30 pmNewark
Jan 14
EWR11:30 amNewark
11h 49m
1 stop
MDW10:19 pmChicago Midway
$110
Find similar
Frontier
Jan 15
MDW6:30 pmChicago Midway
2h 00m
EWR9:30 pmNewark
Jan 17
EWR11:30 amNewark
11h 43m
1 stop
MDW10:13 pmChicago Midway
$111
Find similar
Frontier
Mar 26
MDW7:30 amChicago Midway
2h 00m
EWR10:30 amNewark
Mar 31
EWR1:30 pmNewark
2h 32m
MDW3:02 pmChicago Midway
$120
Find similar

Delta flights from Chicago Midway Airport to Pennsylvania

Our best Delta deals on Chicago Midway Airport to Pennsylvania flight tickets
Delta
Feb 5
MDW6:00 amChicago Midway
5h 36m
1 stop
PIT12:36 pmPittsburgh
Feb 25
PIT6:19 amPittsburgh
3h 35m
1 stop
MDW8:54 amChicago Midway
$174
Find similar
Delta
Jan 22
MDW10:48 amChicago Midway
4h 43m
1 stop
EWR4:31 pmNewark
Jan 26
EWR5:54 pmNewark
5h 28m
1 stop
MDW10:22 pmChicago Midway
$177
Find similar
Delta
Jan 21
MDW9:32 amChicago Midway
5h 58m
1 stop
PHL4:30 pmPhiladelphia
Jan 24
PHL5:40 amPhiladelphia
5h 13m
1 stop
MDW9:53 amChicago Midway
$178
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Pennsylvania 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 27, 2025.
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

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 1/24

5:35 pm-8:40 pm

Nonstop2h 05m

New York LaGuardia

Sun 1/25

6:30 pm-8:15 pm

Nonstop2h 45m

$97

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Tue 1/13

6:30 pm-9:30 pm

Nonstop2h 00m

Newark

Wed 1/14

11:30 am-10:19 pm

1 stop11h 49m

$110

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Tue 1/13

6:30 pm-9:30 pm

Nonstop2h 00m

Newark

Tue 1/20

6:00 am-12:05 pm

1 stop7h 05m

$111

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Thu 3/12

7:30 am-10:30 am

Nonstop2h 00m

Newark

Thu 3/19

11:30 am-1:02 pm

Nonstop2h 32m

$114

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Fri 1/16

8:04 pm-2:50 pm

1 stop17h 46m

Newark

Sun 1/18

10:30 pm-12:02 am

Nonstop2h 32m

$116

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 1/13

10:30 am-1:30 pm

Nonstop2h 00m

New York LaGuardia

Tue 1/20

6:00 am-7:40 am

Nonstop2h 40m

$117

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Mon 2/23

8:00 pm-11:00 pm

Nonstop2h 00m

New York LaGuardia

Wed 2/25

6:00 am-7:40 am

Nonstop2h 40m

$118

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 1/17

5:35 pm-8:40 pm

Nonstop2h 05m

New York LaGuardia

Tue 1/20

6:00 am-7:40 am

Nonstop2h 40m

$123

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Thu 2/5

6:00 am-12:36 pm

1 stop5h 36m

Pittsburgh

Wed 2/25

6:19 am-8:54 am

1 stop3h 35m

$174

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Sat 1/17

9:32 am-1:27 pm

1 stop2h 55m

Pittsburgh

Mon 1/19

6:32 am-1:09 pm

1 stop7h 37m

$191

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 Pennsylvania from

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

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 $120. 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 Monday when prices can be found for as low as $197. 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 $327. 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 afternoon. Flights from Chicago Midway Airport to Pennsylvania during this time can be as low as $197. In contrast, the most expensive time of day to depart to Pennsylvania is in the evening when prices are around $264.

What is the cheapest Chicago Midway to Pennsylvania flight route?

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

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

You are more likely to see cheaper flights to Pennsylvania from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Pennsylvania for around $239 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Pennsylvania from Chicago Midway Airport for as low as $171 on momondo.

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

There is only 1 cabin class available to choose from on Chicago Midway 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 14% 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

$119

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 $119. The best round-trip flight deal from Chicago Midway Airport to Pennsylvania found on momondo in the last 72 hours is $241.
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 Washington, D.C. Reagan-National (DCA), Philadelphia (PHL), Pittsburgh (PIT).
Search flight deals

  • 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?

  • 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?

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
FrontierPriceFrom $67Free CancellationRating
5.8
3,070 reviews
Search Frontier flights
SouthwestPriceFrom $103Free CancellationRating
8.0
4,258 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.

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