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Cheap flights from Pennsylvania to Chicago from $39

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 9/10. 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
6:25 am - 6:50 amPIT-MDW
1h 25mnonstop
Southwest Logo
9:15 pm - 11:40 pmMDW-PIT
1h 25mnonstop
$77Southwest
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Thu, Sep 4 - Mon, Sep 8
Southwest Logo
7:00 pm - 7:25 pmPIT-MDW
1h 25mnonstop
Southwest Logo
5:10 am - 12:10 pmMDW-PIT
6h 00m1 stop
$87Southwest
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Thu, Sep 4 - Mon, Sep 8
Southwest Logo
10:10 am - 10:35 amPIT-MDW
1h 25mnonstop
Southwest Logo
3:25 pm - 10:45 pmMDW-PIT
6h 20m2 stops
$92Southwest
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Thu, Sep 4 - Mon, Sep 8
Frontier Logo
10:00 pm - 11:25 pmEWR-MDW
2h 25mnonstop
Frontier Logo
5:56 pm - 9:00 pmMDW-EWR
2h 04mnonstop
$97Frontier
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Tue, Oct 7 - Tue, Oct 14
Frontier Logo
10:00 pm - 11:25 pmEWR-MDW
2h 25mnonstop
Frontier Logo
5:56 pm - 9:00 pmMDW-EWR
2h 04mnonstop
$98Frontier
Find Deal
Tue, Oct 14 - Tue, Oct 21
Delta Logo
6:00 am - 8:35 amEWR-MDW
3h 35m1 stop
Delta Logo
6:17 pm - 11:12 pmMDW-EWR
3h 55m1 stop
$157Delta
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Wed, Sep 3 - Wed, Sep 3
Delta Logo
6:00 am - 8:35 amEWR-MDW
3h 35m1 stop
Delta Logo
6:17 pm - 11:32 pmMDW-EWR
4h 15m1 stop
$162Delta
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Wed, Sep 3 - Sat, Sep 6
Logo
5:15 am - 3:58 pmEWR-MDW
11h 43m1 stop
Logo
5:56 pm - 9:00 pmMDW-EWR
2h 04mnonstop
$168
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Tue, Sep 30 - Tue, Oct 7
Logo
5:15 am - 3:58 pmEWR-MDW
11h 43m1 stop
Logo
2:32 pm - 12:34 amMDW-EWR
9h 02m1 stop
$173
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Wed, Sep 10 - Tue, Sep 16
Allegiant Air Logo
6:00 am - 7:00 pmABE-MDW
14h 00m2 stops
Allegiant Air Logo
12:50 pm - 10:55 amMDW-ABE
21h 05m2 stops
$337Allegiant Air
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Fri, Sep 5 - Mon, Sep 8

Southwest flights from Pennsylvania to Chicago Midway Airport

Our best Southwest deals on Pennsylvania to Chicago Midway Airport flight tickets
Southwest
Sep 4
PIT6:25 amPittsburgh
1h 25m
MDW6:50 amChicago Midway
Sep 8
MDW9:15 pmChicago Midway
1h 25m
PIT11:40 pmPittsburgh
$77
Find similar
Southwest
Sep 4
PIT7:00 pmPittsburgh
1h 25m
MDW7:25 pmChicago Midway
Sep 8
MDW5:10 amChicago Midway
6h 00m
1 stop
PIT12:10 pmPittsburgh
$87
Find similar
Southwest
Sep 4
PIT10:10 amPittsburgh
1h 25m
MDW10:35 amChicago Midway
Sep 8
MDW3:25 pmChicago Midway
6h 20m
2 stops
PIT10:45 pmPittsburgh
$92
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Delta flights from Pennsylvania to Chicago Midway Airport

Our best Delta deals on Pennsylvania to Chicago Midway Airport flight tickets
Delta
Sep 3
EWR6:00 amNewark
3h 35m
1 stop
MDW8:35 amChicago Midway
Sep 3
MDW6:17 pmChicago Midway
3h 55m
1 stop
EWR11:12 pmNewark
$157
Find similar
Delta
Sep 3
EWR6:00 amNewark
3h 35m
1 stop
MDW8:35 amChicago Midway
Sep 6
MDW6:17 pmChicago Midway
4h 15m
1 stop
EWR11:32 pmNewark
$162
Find similar
Delta
Sep 20
EWR9:51 amNewark
3h 37m
1 stop
MDW12:28 pmChicago Midway
Sep 24
MDW6:15 pmChicago Midway
4h 16m
1 stop
EWR11:31 pmNewark
$167
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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 August 11, 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

Thu 9/4

6:25 am-6:50 am

Nonstop1h 25m

Chicago Midway

Mon 9/8

9:15 pm-11:40 pm

Nonstop1h 25m

$77

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 9/4

7:00 pm-7:25 pm

Nonstop1h 25m

Chicago Midway

Mon 9/8

5:10 am-12:10 pm

1 stop6h 00m

$87

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 9/4

10:10 am-10:35 am

Nonstop1h 25m

Chicago Midway

Mon 9/8

3:25 pm-10:45 pm

2 stops6h 20m

$92

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 10/7

10:00 pm-11:25 pm

Nonstop2h 25m

Chicago Midway

Tue 10/14

5:56 pm-9:00 pm

Nonstop2h 04m

$97

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 10/14

10:00 pm-11:25 pm

Nonstop2h 25m

Chicago Midway

Tue 10/21

5:56 pm-9:00 pm

Nonstop2h 04m

$98

NewarkChicago

EWR - MDW

EWRMDW

Newark

Wed 9/3

6:00 am-8:35 am

1 stop3h 35m

Chicago Midway

Wed 9/3

6:17 pm-11:12 pm

1 stop3h 55m

$157

NewarkChicago

EWR - MDW

EWRMDW

Newark

Wed 9/3

6:00 am-8:35 am

1 stop3h 35m

Chicago Midway

Sat 9/6

6:17 pm-11:32 pm

1 stop4h 15m

$162

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 9/30

5:15 am-3:58 pm

1 stop11h 43m

Chicago Midway

Tue 10/7

5:56 pm-9:00 pm

Nonstop2h 04m

$168

NewarkChicago

EWR - MDW

EWRMDW

Newark

Wed 9/10

5:15 am-3:58 pm

1 stop11h 43m

Chicago Midway

Tue 9/16

2:32 pm-12:34 am

1 stop9h 02m

$173

AllentownChicago

ABE - MDW

ABEMDW

Allentown-Bethlehem

Fri 9/5

6:00 am-7:00 pm

2 stops14h 00m

Chicago Midway

Mon 9/8

12:50 pm-10:55 am

2 stops21h 05m

$337

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 September is, on average, the cheapest month to fly to Chicago Midway Airport from Pennsylvania, with most prices found around $150. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Pennsylvania during the month November is also very affordable. Most momondo users find prices during this month for around $153.

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 $234. 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 $368.

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 $215 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $332. 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 $244 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 $160 on momondo.

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

There are 1 cabin classes 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

$39

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 $39. The best round-trip flight deal from Pennsylvania to Chicago Midway Airport found on momondo in the last 72 hours is $77.
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 $55Free CancellationRating
5.8
3,221 reviews
Search Frontier flights
SouthwestPriceFrom $126Free CancellationRating
8.0
4,248 reviews
Search Southwest flights
United AirlinesPriceFrom $144Free CancellationRating
7.4
8,920 reviews
Search United Airlines flights
DeltaPriceFrom $228Free CancellationRating
8.0
7,979 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
Lansing
Portage
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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