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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 11/13. 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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Find the cheapest flights from Pennsylvania to Chicago

Cheap round-trip flights

Southwest Logo
4:30 pm - 4:55 pmPIT-MDW
1h 25mnonstop
Southwest Logo
5:20 pm - 11:35 pmMDW-PIT
5h 15m1 stop
$107Southwest
Find Deal
qui, out 16 - seg, out 20
Southwest Logo
5:50 pm - 11:15 pmPIT-MDW
6h 25m2 stops
Southwest Logo
9:55 pm - 12:15 amMDW-PIT
1h 20mnonstop
$112Southwest
Find Deal
qui, out 16 - seg, out 20
Frontier Logo
6:00 am - 7:11 amPHL-MDW
2h 11mnonstop
Frontier Logo
8:25 am - 11:27 amMDW-PHL
2h 02mnonstop
$113Frontier
Find Deal
dom, out 5 - qui, out 16
Frontier Logo
9:48 pm - 11:03 pmPHL-MDW
2h 15mnonstop
Frontier Logo
6:15 am - 6:44 pmMDW-PHL
11h 29m1 stop
$114Frontier
Find Deal
sex, out 24 - sáb, out 25
Frontier Logo
6:10 am - 7:25 amPHL-MDW
2h 15mnonstop
Frontier Logo
8:25 am - 11:27 amMDW-PHL
2h 02mnonstop
$115Frontier
Find Deal
qui, out 23 - dom, out 26
Frontier Logo
1:19 pm - 2:33 pmPHL-MDW
2h 14mnonstop
Frontier Logo
10:12 am - 7:30 amMDW-PHL
20h 18m1 stop
$116Frontier
Find Deal
qui, out 30 - dom, nov 2
Multiple Airlines Logo
10:55 pm - 1:38 pmEWR-MDW
15h 43m2 stops
Multiple Airlines Logo
5:56 pm - 9:00 pmMDW-EWR
2h 04mnonstop
$168Multiple Airlines
Find Deal
seg, out 6 - ter, out 7
Multiple Airlines Logo
5:54 am - 1:38 pmEWR-MDW
8h 44m1 stop
Multiple Airlines Logo
11:31 am - 11:07 pmMDW-EWR
10h 36m1 stop
$170Multiple Airlines
Find Deal
ter, out 14 - sáb, out 18
Delta Logo
6:00 am - 9:40 amPIT-MDW
4h 40m1 stop
Delta Logo
9:20 am - 3:53 pmMDW-PIT
5h 33m1 stop
$177Delta
Find Deal
ter, out 28 - qua, out 29
Delta Logo
6:00 am - 8:40 amEWR-MDW
3h 40m1 stop
Delta Logo
4:23 pm - 11:56 pmMDW-EWR
6h 33m1 stop
$188Delta
Find Deal
qua, out 8 - sáb, out 25

Southwest flights from Pennsylvania to Chicago Midway Airport

Our best Southwest deals on Pennsylvania to Chicago Midway Airport flight tickets
Southwest
Oct 16
PIT4:30 pmPittsburgh
1h 25m
MDW4:55 pmChicago Midway
Oct 20
MDW5:20 pmChicago Midway
5h 15m
1 stop
PIT11:35 pmPittsburgh
$107
Find similar
Southwest
Oct 16
PIT5:50 pmPittsburgh
6h 25m
2 stops
MDW11:15 pmChicago Midway
Oct 20
MDW9:55 pmChicago Midway
1h 20m
PIT12:15 amPittsburgh
$112
Find similar
Southwest
Oct 16
PIT6:10 amPittsburgh
3h 55m
1 stop
MDW9:05 amChicago Midway
Oct 21
MDW5:50 amChicago Midway
6h 45m
1 stop
PIT1:35 pmPittsburgh
$117
Find similar

Frontier flights from Pennsylvania to Chicago Midway Airport

Our best Frontier deals on Pennsylvania to Chicago Midway Airport flight tickets
Frontier
Oct 5
PHL6:00 amPhiladelphia
2h 11m
MDW7:11 amChicago Midway
Oct 16
MDW8:25 amChicago Midway
2h 02m
PHL11:27 amPhiladelphia
$113
Find similar
Frontier
Oct 24
PHL9:48 pmPhiladelphia
2h 15m
MDW11:03 pmChicago Midway
Oct 25
MDW6:15 amChicago Midway
11h 29m
1 stop
PHL6:44 pmPhiladelphia
$114
Find similar
Frontier
Oct 23
PHL6:10 amPhiladelphia
2h 15m
MDW7:25 amChicago Midway
Oct 26
MDW8:25 amChicago Midway
2h 02m
PHL11:27 amPhiladelphia
$115
Find similar

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 setembro 25, 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

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

qui 10/16

4:30 pm-4:55 pm

Nonstop1h 25m

Chicago Midway

seg 10/20

5:20 pm-11:35 pm

1 stop5h 15m

$107

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

qui 10/16

5:50 pm-11:15 pm

2 stops6h 25m

Chicago Midway

seg 10/20

9:55 pm-12:15 am

Nonstop1h 20m

$112

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

dom 10/5

6:00 am-7:11 am

Nonstop2h 11m

Chicago Midway

qui 10/16

8:25 am-11:27 am

Nonstop2h 02m

$113

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

sex 10/24

9:48 pm-11:03 pm

Nonstop2h 15m

Chicago Midway

sáb 10/25

6:15 am-6:44 pm

1 stop11h 29m

$114

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

qui 10/23

6:10 am-7:25 am

Nonstop2h 15m

Chicago Midway

dom 10/26

8:25 am-11:27 am

Nonstop2h 02m

$115

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

qui 10/30

1:19 pm-2:33 pm

Nonstop2h 14m

Chicago Midway

dom 11/2

10:12 am-7:30 am

1 stop20h 18m

$116

NewarkChicago

EWR - MDW

EWRMDW

Newark

seg 10/6

10:55 pm-1:38 pm

2 stops15h 43m

Chicago Midway

ter 10/7

5:56 pm-9:00 pm

Nonstop2h 04m

$168

NewarkChicago

EWR - MDW

EWRMDW

Newark

ter 10/14

5:54 am-1:38 pm

1 stop8h 44m

Chicago Midway

sáb 10/18

11:31 am-11:07 pm

1 stop10h 36m

$170

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

ter 10/28

6:00 am-9:40 am

1 stop4h 40m

Chicago Midway

qua 10/29

9:20 am-3:53 pm

1 stop5h 33m

$177

NewarkChicago

EWR - MDW

EWRMDW

Newark

qua 10/8

6:00 am-8:40 am

1 stop3h 40m

Chicago Midway

sáb 10/25

4:23 pm-11:56 pm

1 stop6h 33m

$188

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 $164. 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 $182.

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 $379.

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 $243 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $344. 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 $252 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 $159 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

$109

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 $109. 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 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 $61Free CancellationRating
5.8
3,163 reviews
Search Frontier flights
SouthwestPriceFrom $97Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
United AirlinesPriceFrom $194Free CancellationRating
7.4
8,928 reviews
Search United Airlines flights
DeltaPriceFrom $218Free CancellationRating
7.9
7,973 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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