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Cheap flights from Pennsylvania to Chicago from $59

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 4/25. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
Frontier Logo
2:15 pm - 1:16 am
MDW
-
EWR
10h 01m
1 stop
$134Frontier
Sat, May 2 - Mon, May 4
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
Frontier Logo
2:15 pm - 9:29 pm
MDW
-
EWR
6h 14m
1 stop
$135Frontier
Fri, May 1 - Mon, May 4
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
Frontier Logo
2:15 pm - 9:29 pm
MDW
-
EWR
6h 14m
1 stop
$136Frontier
Sat, May 2 - Mon, May 4
Multiple Airlines Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
Multiple Airlines Logo
2:15 pm - 11:36 am
MDW
-
EWR
20h 21m
1 stop
$142Multiple Airlines
Sat, May 2 - Sun, May 3
Southwest Logo
6:25 am - 2:55 pm
PIT
-
MDW
9h 30m
2 stops
Southwest Logo
10:10 am - 5:55 pm
MDW
-
PIT
6h 45m
2 stops
$173Southwest
Tue, May 12 - Tue, May 19
Multiple Airlines Logo
8:00 am - 4:13 pm
LGA
-
MDW
9h 13m
1 stop
Multiple Airlines Logo
11:59 am - 7:29 pm
MDW
-
LGA
6h 30m
1 stop
$175Multiple Airlines
Sat, May 2 - Sat, May 9
Southwest Logo
8:00 pm - 8:30 pm
PIT
-
MDW
1h 30mnonstop
Southwest Logo
6:55 pm - 9:20 pm
MDW
-
PIT
1h 25mnonstop
$177Southwest
Thu, May 7 - Mon, May 11
Delta Logo
11:55 am - 4:26 pm
PIT
-
MDW
5h 31m
1 stop
Delta Logo
9:27 am - 3:05 pm
MDW
-
PIT
4h 38m
1 stop
$201Delta
Sat, May 2 - Wed, May 6
Delta Logo
6:00 pm - 10:28 pm
DCA
-
MDW
5h 28m
1 stop
Delta Logo
1:24 pm - 6:59 pm
MDW
-
DCA
4h 35m
1 stop
$226Delta
Wed, Apr 29 - Wed, May 6
Allegiant Air Logo
10:00 am - 8:26 am
ABE
-
MDW
23h 26m
1 stop
Allegiant Air Logo
9:16 am - 9:44 am
MDW
-
ABE
23h 28m
1 stop
$327Allegiant Air
Wed, Apr 29 - Sun, May 3

Frontier flights from Pennsylvania to Chicago Midway Airport

Our best Frontier deals on Pennsylvania to Chicago Midway Airport flight tickets
Frontier
Apr 22
EWR11:30 amNewark
2h 30m
MDW1:00 pmChicago Midway
May 1
MDW7:30 amChicago Midway
2h 08m
EWR10:38 amNewark
$132
Frontier
May 2
EWR11:30 amNewark
2h 30m
MDW1:00 pmChicago Midway
May 8
MDW12:04 pmChicago Midway
8h 25m
1 stop
EWR9:29 pmNewark
$134
Frontier
Apr 24
EWR11:30 amNewark
2h 30m
MDW1:00 pmChicago Midway
May 2
MDW7:30 amChicago Midway
2h 08m
EWR10:38 amNewark
$135

Southwest flights from Pennsylvania to Chicago Midway Airport

Our best Southwest deals on Pennsylvania to Chicago Midway Airport flight tickets
Southwest
May 12
PIT6:25 amPittsburgh
9h 30m
2 stops
MDW2:55 pmChicago Midway
May 19
MDW10:10 amChicago Midway
6h 45m
2 stops
PIT5:55 pmPittsburgh
$173
Southwest
Jun 11
LGA6:00 amNew York LaGuardia
2h 20m
MDW7:20 amChicago Midway
Jun 16
MDW5:15 amChicago Midway
2h 00m
LGA8:15 amNew York LaGuardia
$177
Southwest
Jun 6
LGA9:10 pmNew York LaGuardia
2h 35m
MDW10:45 pmChicago Midway
Jun 11
MDW5:15 amChicago Midway
2h 00m
LGA8:15 amNew York LaGuardia
$182

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 April 17, 2026.
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

Cheapest round-trip

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sat 5/2

11:30 am-1:00 pm

Nonstop2h 30m

Chicago Midway

Mon 5/4

2:15 pm-1:16 am

1 stop10h 01m

$134

NewarkChicago

EWR - MDW

EWRMDW

Newark

Fri 5/1

11:30 am-1:00 pm

Nonstop2h 30m

Chicago Midway

Mon 5/4

2:15 pm-9:29 pm

1 stop6h 14m

$135

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sat 5/2

11:30 am-1:00 pm

Nonstop2h 30m

Chicago Midway

Mon 5/4

2:15 pm-9:29 pm

1 stop6h 14m

$136

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sat 5/2

11:30 am-1:00 pm

Nonstop2h 30m

Chicago Midway

Sun 5/3

2:15 pm-11:36 am

1 stop20h 21m

$142

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 5/12

6:25 am-2:55 pm

2 stops9h 30m

Chicago Midway

Tue 5/19

10:10 am-5:55 pm

2 stops6h 45m

$173

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 5/2

8:00 am-4:13 pm

1 stop9h 13m

Chicago Midway

Sat 5/9

11:59 am-7:29 pm

1 stop6h 30m

$175
Quickest round-trip

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 5/7

8:00 pm-8:30 pm

Nonstop1h 30m

Chicago Midway

Mon 5/11

6:55 pm-9:20 pm

Nonstop1h 25m

$177

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 5/2

11:55 am-4:26 pm

1 stop5h 31m

Chicago Midway

Wed 5/6

9:27 am-3:05 pm

1 stop4h 38m

$201

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 4/29

6:00 pm-10:28 pm

1 stop5h 28m

Chicago Midway

Wed 5/6

1:24 pm-6:59 pm

1 stop4h 35m

$226

AllentownChicago

ABE - MDW

ABEMDW

Allentown-Bethlehem

Wed 4/29

10:00 am-8:26 am

1 stop23h 26m

Chicago Midway

Sun 5/3

9:16 am-9:44 am

1 stop23h 28m

$327

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 $202. If you are unable to visit Chicago Midway Airport during the month of November, then departing from Pennsylvania during the month September is also very affordable. Most momondo users find prices during this month for around $208.

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 $260. 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, Sunday 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 $428.

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 $264 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $363. 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 Philadelphia 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 $286 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 $191 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?

You could potentially save up to 28% on your flight if you consider stops on a Pennsylvania to Chicago Midway Airport flight.

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

$197

Fastest flight time

1h 20m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Pennsylvania in the past 72 hours is $197. The best round-trip flight deal from Pennsylvania to Chicago Midway Airport found on momondo in the last 72 hours is $326.
The fastest flight from Pennsylvania to Chicago Midway Airport takes 1h 20m
Direct flights go from Pennsylvania to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Pennsylvania to Chicago Midway Airport

  • 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 $83Free CancellationRating
5.7
2,987 reviews
Search Frontier flights
SouthwestPriceFrom $97Free CancellationRating
8.0
4,328 reviews
Search Southwest flights
DeltaPriceFrom $228Free CancellationRating
7.9
8,406 reviews
Search Delta flights
United AirlinesPriceFrom $297Free CancellationRating
7.4
9,602 reviews
Search United Airlines flights

Traveling to a place near Chicago?

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