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Cheap flights from Pennsylvania to Chicago from $58

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 3/8. 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

Enter your travel dates to find the best prices.
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
$94Frontier
Thu, Apr 16 - Sun, Apr 19
Frontier Logo
10:29 pm - 10:26 pm
EWR
-
MDW
24h 57m
1 stop
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
$95Frontier
Thu, Apr 16 - Mon, Apr 20
Multiple Airlines Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
Multiple Airlines Logo
7:34 pm - 8:12 am
MDW
-
EWR
11h 38m
1 stop
$96Multiple Airlines
Tue, Apr 14 - Sat, Apr 25
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
$97Frontier
Wed, Apr 15 - Sat, Apr 25
Frontier Logo
11:30 am - 1:02 pm
EWR
-
MDW
2h 32mnonstop
Frontier Logo
7:30 am - 10:30 am
MDW
-
EWR
2h 00mnonstop
$98Frontier
Sun, Mar 8 - Thu, Mar 12
Southwest Logo
6:00 am - 7:25 am
LGA
-
MDW
2h 25mnonstop
Southwest Logo
7:25 pm - 10:30 pm
MDW
-
LGA
2h 05mnonstop
$136Southwest
Wed, Apr 15 - Wed, Apr 22
Southwest Logo
6:00 am - 7:25 am
LGA
-
MDW
2h 25mnonstop
Southwest Logo
5:20 am - 8:20 am
MDW
-
LGA
2h 00mnonstop
$141Southwest
Wed, Apr 29 - Sun, May 3
Delta Logo
6:00 am - 8:47 am
IAD
-
MDW
3h 47m
1 stop
Delta Logo
6:38 pm - 11:03 pm
MDW
-
IAD
3h 25m
1 stop
$188Delta
Fri, Apr 17 - Mon, Apr 20
Delta Logo
12:29 pm - 5:54 pm
DCA
-
MDW
6h 25m
1 stop
Delta Logo
6:34 pm - 10:51 pm
MDW
-
DCA
3h 17m
1 stop
$188Delta
Wed, Apr 8 - Fri, Apr 10
Multiple Airlines Logo
10:25 pm - 1:00 pm
IAD
-
MDW
15h 35m
2 stops
Multiple Airlines Logo
2:15 pm - 12:36 am
MDW
-
IAD
9h 21m
1 stop
$197Multiple Airlines
Mon, Apr 13 - Wed, Apr 15

Southwest flights from Pennsylvania to Chicago Midway Airport

Our best Southwest deals on Pennsylvania to Chicago Midway Airport flight tickets
Southwest
Apr 15
LGA6:00 amNew York LaGuardia
2h 25m
MDW7:25 amChicago Midway
Apr 22
MDW7:25 pmChicago Midway
2h 05m
LGA10:30 pmNew York LaGuardia
$136
Southwest
Apr 29
LGA6:00 amNew York LaGuardia
2h 25m
MDW7:25 amChicago Midway
May 2
MDW6:10 pmChicago Midway
2h 05m
LGA9:15 pmNew York LaGuardia
$141
Southwest
Mar 31
LGA9:30 pmNew York LaGuardia
2h 30m
MDW11:00 pmChicago Midway
Apr 14
MDW9:30 amChicago Midway
2h 05m
LGA12:35 pmNew York LaGuardia
$146

Frontier flights from Pennsylvania to Chicago Midway Airport

Our best Frontier deals on Pennsylvania to Chicago Midway Airport flight tickets
Frontier
Apr 16
EWR11:30 amNewark
2h 30m
MDW1:00 pmChicago Midway
Apr 19
MDW7:30 amChicago Midway
2h 08m
EWR10:38 amNewark
$94
Frontier
Mar 8
EWR11:30 amNewark
2h 32m
MDW1:02 pmChicago Midway
Mar 17
MDW7:30 amChicago Midway
2h 00m
EWR10:30 amNewark
$95
Frontier
Apr 15
EWR11:30 amNewark
2h 30m
MDW1:00 pmChicago Midway
Apr 25
MDW7:30 amChicago Midway
2h 08m
EWR10:38 amNewark
$97

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 February 26, 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

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 4/16

11:30 am-1:00 pm

Nonstop2h 30m

Chicago Midway

Sun 4/19

7:30 am-10:38 am

Nonstop2h 08m

$94

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 4/16

10:29 pm-10:26 pm

1 stop24h 57m

Chicago Midway

Mon 4/20

7:30 am-10:38 am

Nonstop2h 08m

$95

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 4/14

11:30 am-1:00 pm

Nonstop2h 30m

Chicago Midway

Sat 4/25

7:34 pm-8:12 am

1 stop11h 38m

$96

NewarkChicago

EWR - MDW

EWRMDW

Newark

Wed 4/15

11:30 am-1:00 pm

Nonstop2h 30m

Chicago Midway

Sat 4/25

7:30 am-10:38 am

Nonstop2h 08m

$97

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sun 3/8

11:30 am-1:02 pm

Nonstop2h 32m

Chicago Midway

Thu 3/12

7:30 am-10:30 am

Nonstop2h 00m

$98

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 4/15

6:00 am-7:25 am

Nonstop2h 25m

Chicago Midway

Wed 4/22

7:25 pm-10:30 pm

Nonstop2h 05m

$136

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 4/29

6:00 am-7:25 am

Nonstop2h 25m

Chicago Midway

Sun 5/3

5:20 am-8:20 am

Nonstop2h 00m

$141

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 4/17

6:00 am-8:47 am

1 stop3h 47m

Chicago Midway

Mon 4/20

6:38 pm-11:03 pm

1 stop3h 25m

$188

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 4/8

12:29 pm-5:54 pm

1 stop6h 25m

Chicago Midway

Fri 4/10

6:34 pm-10:51 pm

1 stop3h 17m

$188

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 4/13

10:25 pm-1:00 pm

2 stops15h 35m

Chicago Midway

Wed 4/15

2:15 pm-12:36 am

1 stop9h 21m

$197

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 $253. 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 $390.

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 $257 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $359. 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 $288 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 $190 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 19% 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

$179

Fastest flight time

1h 25m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Pennsylvania in the past 72 hours is $179. The best round-trip flight deal from Pennsylvania to Chicago Midway Airport found on momondo in the last 72 hours is $318.
The fastest flight from Pennsylvania to Chicago Midway Airport takes 1h 25m
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 $90Free CancellationRating
5.7
3,040 reviews
Search Frontier flights
SouthwestPriceFrom $97Free CancellationRating
8.0
4,299 reviews
Search Southwest flights
United AirlinesPriceFrom $188Free CancellationRating
7.4
9,347 reviews
Search United Airlines flights
DeltaPriceFrom $228Free CancellationRating
7.9
8,237 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
Munster
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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