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Cheap flights from Pennsylvania to Chicago from $49

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Pennsylvania to Chicago departing on 12/25. 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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Cheap round-trip flights

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Frontier Logo
4:50 pm - 6:06 pmPHL-MDW
2h 16mnonstop
Frontier Logo
8:29 pm - 11:26 pmMDW-PHL
1h 57mnonstop
$103Frontier
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Mon, Nov 24 - Sat, Nov 29
Frontier Logo
4:50 pm - 6:06 pmPHL-MDW
2h 16mnonstop
Frontier Logo
7:10 pm - 10:06 pmMDW-PHL
1h 56mnonstop
$104Frontier
Find Deal
Mon, Nov 24 - Mon, Nov 24
Frontier Logo
6:25 am - 12:05 pmLGA-MDW
6h 40m1 stop
Frontier Logo
2:15 pm - 11:08 pmMDW-LGA
7h 53m1 stop
$105Frontier
Find Deal
Wed, Jan 21 - Wed, Jan 21
Frontier Logo
1:00 pm - 6:08 pmJFK-MDW
6h 08m1 stop
Frontier Logo
2:59 pm - 12:07 amMDW-JFK
8h 08m1 stop
$109Frontier
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Thu, Dec 4 - Sat, Dec 6
Multiple Airlines Logo
5:39 pm - 8:03 amEWR-MDW
15h 24m1 stop
Multiple Airlines Logo
5:25 pm - 9:30 pmMDW-EWR
3h 05mnonstop
$115Multiple Airlines
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Sat, Jan 17 - Sun, Jan 18
Southwest Logo
6:15 am - 6:55 amPIT-MDW
1h 40mnonstop
Southwest Logo
5:15 pm - 11:45 pmMDW-PIT
5h 30m1 stop
$178Southwest
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Fri, Nov 21 - Mon, Nov 24
Multiple Airlines Logo
5:05 pm - 8:46 amPIT-MDW
16h 41m2 stops
Multiple Airlines Logo
7:24 pm - 6:01 pmMDW-PIT
21h 37m1 stop
$181Multiple Airlines
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Tue, Dec 9 - Sun, Dec 14
Southwest Logo
5:30 am - 8:50 amPIT-MDW
4h 20m1 stop
Southwest Logo
5:15 pm - 11:45 pmMDW-PIT
5h 30m1 stop
$188Southwest
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Fri, Nov 21 - Mon, Nov 24
Delta Logo
5:58 pm - 10:44 pmABE-MDW
5h 46m1 stop
Delta Logo
10:53 am - 5:18 pmMDW-ABE
5h 25m1 stop
$229Delta
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Sat, Feb 21 - Wed, Feb 25
Delta Logo
5:58 pm - 10:44 pmABE-MDW
5h 46m1 stop
Delta Logo
9:34 am - 5:18 pmMDW-ABE
6h 44m2 stops
$234Delta
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Sat, Feb 21 - Wed, Feb 25

Frontier flights from Pennsylvania to Chicago Midway Airport

Our best Frontier deals on Pennsylvania to Chicago Midway Airport flight tickets
Frontier
Nov 24
PHL4:50 pmPhiladelphia
2h 16m
MDW6:06 pmChicago Midway
Nov 29
MDW8:29 pmChicago Midway
1h 57m
PHL11:26 pmPhiladelphia
$103
Find similar
Frontier
Nov 24
PHL4:50 pmPhiladelphia
2h 16m
MDW6:06 pmChicago Midway
Nov 24
MDW7:10 pmChicago Midway
1h 56m
PHL10:06 pmPhiladelphia
$104
Find similar
Frontier
Jan 21
LGA6:25 amNew York LaGuardia
6h 40m
1 stop
MDW12:05 pmChicago Midway
Jan 21
MDW2:15 pmChicago Midway
7h 53m
1 stop
LGA11:08 pmNew York LaGuardia
$105
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Southwest flights from Pennsylvania to Chicago Midway Airport

Our best Southwest deals on Pennsylvania to Chicago Midway Airport flight tickets
Southwest
Dec 6
LGA8:35 amNew York LaGuardia
2h 25m
MDW10:00 amChicago Midway
Dec 9
MDW5:55 pmChicago Midway
2h 05m
LGA9:00 pmNew York LaGuardia
$137
Find similar
Southwest
Jan 21
LGA6:00 amNew York LaGuardia
2h 40m
MDW7:40 amChicago Midway
Jan 24
MDW5:35 pmChicago Midway
2h 05m
LGA8:40 pmNew York LaGuardia
$139
Find similar
Southwest
Dec 5
LGA6:00 amNew York LaGuardia
2h 30m
MDW7:30 amChicago Midway
Dec 8
MDW7:15 pmChicago Midway
2h 05m
LGA10:20 pmNew York LaGuardia
$143
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momondo Fare Finder

 
Customize your flight search to find flights from Pennsylvania to Chicago Midway Airport 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 November 17, 2025.
Use the filters below to find and compare flights from Pennsylvania to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Mon 11/24

4:50 pm-6:06 pm

Nonstop2h 16m

Chicago Midway

Sat 11/29

8:29 pm-11:26 pm

Nonstop1h 57m

$103

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Mon 11/24

4:50 pm-6:06 pm

Nonstop2h 16m

Chicago Midway

Mon 11/24

7:10 pm-10:06 pm

Nonstop1h 56m

$104

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 1/21

6:25 am-12:05 pm

1 stop6h 40m

Chicago Midway

Wed 1/21

2:15 pm-11:08 pm

1 stop7h 53m

$105

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Thu 12/4

1:00 pm-6:08 pm

1 stop6h 08m

Chicago Midway

Sat 12/6

2:59 pm-12:07 am

1 stop8h 08m

$109

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sat 1/17

5:39 pm-8:03 am

1 stop15h 24m

Chicago Midway

Sun 1/18

5:25 pm-9:30 pm

Nonstop3h 05m

$115

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Fri 11/21

6:15 am-6:55 am

Nonstop1h 40m

Chicago Midway

Mon 11/24

5:15 pm-11:45 pm

1 stop5h 30m

$178

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 12/9

5:05 pm-8:46 am

2 stops16h 41m

Chicago Midway

Sun 12/14

7:24 pm-6:01 pm

1 stop21h 37m

$181

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Fri 11/21

5:30 am-8:50 am

1 stop4h 20m

Chicago Midway

Mon 11/24

5:15 pm-11:45 pm

1 stop5h 30m

$188

AllentownChicago

ABE - MDW

ABEMDW

Allentown-Bethlehem

Sat 2/21

5:58 pm-10:44 pm

1 stop5h 46m

Chicago Midway

Wed 2/25

10:53 am-5:18 pm

1 stop5h 25m

$229

AllentownChicago

ABE - MDW

ABEMDW

Allentown-Bethlehem

Sat 2/21

5:58 pm-10:44 pm

1 stop5h 46m

Chicago Midway

Wed 2/25

9:34 am-5:18 pm

2 stops6h 44m

$234

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 Chicago from

How to get the cheapest flight ticket from Pennsylvania 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?

The month of November is, on average, the cheapest month to fly to Chicago Midway Airport from Pennsylvania, with most prices found around $188. If you are unable to visit Chicago Midway Airport during the month of November, then departing from Pennsylvania 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 Pennsylvania. 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 Pennsylvania 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 Pennsylvania 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 Pennsylvania to Chicago Midway flight route?

Fly from Pittsburgh to Chicago Midway for the best Pennsylvania - 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 Pennsylvania when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $260 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 Pennsylvania for as low as $218 on momondo.

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

There is only 1 cabin class available to choose from on Pennsylvania to Chicago Midway 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 Pennsylvania to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Pennsylvania to Chicago Midway Airport.

Cheap Pennsylvania to Chicago Midway Airport flight deals and tips

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

Best Price Found

$142

Fastest flight time

1h 30m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Pennsylvania in the past 72 hours is $142. The best round-trip flight deal from Pennsylvania to Chicago Midway Airport found on momondo in the last 72 hours is $149.
The fastest flight from Pennsylvania to Chicago Midway Airport takes 1h 30m
Direct flights go from Pennsylvania to Chicago Midway Airport every day.
Search flight deals

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

    Prices for flights from Pennsylvania to Chicago Midway Airport refresh daily.

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

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

    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 Pennsylvania 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 Pennsylvania to Chicago Midway Airport?

Best airlines flying from Pennsylvania to Chicago Midway Airport

Compare and see reviews for airlines that fly from Pennsylvania to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $61Free CancellationRating
5.8
3,108 reviews
Search Frontier flights
SouthwestPriceFrom $97Free CancellationRating
8.0
4,244 reviews
Search Southwest flights
DeltaPriceFrom $228Free CancellationRating
7.9
8,006 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

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

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

All flight searches from Pennsylvania to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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

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 Pennsylvania to Chicago.

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

Price alerts on flights to Chicago from Pennsylvania 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.

An easier way to manage your Chicago Midway Airport trip

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