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Cheap flights from Pennsylvania to Chicago from $69

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 8/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Pennsylvania to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
4:45 pm - 10:47 pm
PHL
-
MDW
7h 02m
1 stop
Frontier Logo
11:50 am - 10:33 pm
MDW
-
PHL
9h 43m
1 stop
$180Frontier
Thu, Aug 27 - Thu, Sep 3
Delta Logo
6:30 am - 11:47 am
PIT
-
MDW
6h 17m
1 stop
Delta Logo
12:27 pm - 6:05 pm
MDW
-
PIT
4h 38m
1 stop
$188Delta
Sat, Oct 17 - Mon, Oct 26
Delta Logo
11:35 am - 6:19 pm
PIT
-
MDW
7h 44m
1 stop
Delta Logo
7:01 pm - 11:58 pm
MDW
-
PIT
3h 57m
1 stop
$188Delta
Wed, Sep 23 - Mon, Sep 28
Delta Logo
5:40 pm - 10:44 pm
PIT
-
MDW
6h 04m
1 stop
Delta Logo
1:19 pm - 6:58 pm
MDW
-
PIT
4h 39m
1 stop
$193Delta
Sat, Sep 12 - Thu, Sep 17
Frontier Logo
7:50 am - 5:51 pm
IAD
-
MDW
11h 01m
1 stop
Frontier Logo
6:25 am - 5:18 pm
MDW
-
IAD
9h 53m
1 stop
$200Frontier
Sat, Sep 12 - Fri, Sep 18
Frontier Logo
6:20 am - 10:55 am
IAD
-
MDW
5h 35m
1 stop
Frontier Logo
6:05 am - 5:14 pm
MDW
-
IAD
10h 09m
1 stop
$200Frontier
Fri, Aug 28 - Sat, Aug 29
Southwest Logo
3:15 pm - 6:55 pm
DCA
-
MDW
4h 40m
1 stop
Southwest Logo
8:15 am - 2:55 pm
MDW
-
DCA
5h 40m
1 stop
$202Southwest
Fri, Sep 11 - Mon, Sep 14
Southwest Logo
1:00 pm - 5:50 pm
DCA
-
MDW
5h 50m
2 stops
Southwest Logo
8:50 am - 3:00 pm
MDW
-
DCA
5h 10m
1 stop
$202Southwest
Mon, Aug 24 - Wed, Aug 26
Multiple Airlines Logo
11:35 am - 5:46 pm
EWR
-
MDW
7h 11m
1 stop
Multiple Airlines Logo
9:24 pm - 11:05 am
MDW
-
EWR
12h 41m
1 stop
$258Multiple Airlines
Tue, Sep 22 - Fri, Oct 2
Multiple Airlines Logo
11:35 am - 5:46 pm
EWR
-
MDW
7h 11m
1 stop
Multiple Airlines Logo
9:24 pm - 11:05 am
MDW
-
EWR
12h 41m
1 stop
$262Multiple Airlines
Thu, Sep 24 - Fri, Oct 2

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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 23
PIT11:35 amPittsburgh
7h 44m
1 stop
MDW6:19 pmChicago Midway
Sep 28
MDW7:01 pmChicago Midway
3h 57m
1 stop
PIT11:58 pmPittsburgh
$188
Delta
Sep 12
PIT5:40 pmPittsburgh
6h 04m
1 stop
MDW10:44 pmChicago Midway
Sep 17
MDW1:19 pmChicago Midway
4h 39m
1 stop
PIT6:58 pmPittsburgh
$193
Delta
Sep 6
IAD11:10 amWashington, D.C. Dulles Intl
6h 49m
1 stop
MDW4:59 pmChicago Midway
Sep 8
MDW5:37 pmChicago Midway
4h 37m
1 stop
IAD11:14 pmWashington, D.C. Dulles Intl
$202

Southwest flights from Pennsylvania to Chicago Midway Airport

Our best Southwest deals on Pennsylvania to Chicago Midway Airport flight tickets
Southwest
Sep 16
DCA6:00 amWashington, D.C. Reagan-National
7h 05m
2 stops
MDW12:05 pmChicago Midway
Sep 22
MDW10:10 amChicago Midway
5h 00m
1 stop
DCA4:10 pmWashington, D.C. Reagan-National
$202
Southwest
Oct 6
DCA6:05 amWashington, D.C. Reagan-National
7h 00m
2 stops
MDW12:05 pmChicago Midway
Oct 7
MDW3:30 pmChicago Midway
7h 25m
2 stops
DCA11:55 pmWashington, D.C. Reagan-National
$203
Southwest
Aug 17
PIT7:30 pmPittsburgh
1h 20m
MDW7:50 pmChicago Midway
Aug 20
MDW7:40 pmChicago Midway
1h 25m
PIT10:05 pmPittsburgh
$207

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 July 30, 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

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 8/27

4:45 pm-10:47 pm

1 stop7h 02m

Chicago Midway

Thu 9/3

11:50 am-10:33 pm

1 stop9h 43m

$180

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 10/17

6:30 am-11:47 am

1 stop6h 17m

Chicago Midway

Mon 10/26

12:27 pm-6:05 pm

1 stop4h 38m

$188

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 9/23

11:35 am-6:19 pm

1 stop7h 44m

Chicago Midway

Mon 9/28

7:01 pm-11:58 pm

1 stop3h 57m

$188

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 9/12

5:40 pm-10:44 pm

1 stop6h 04m

Chicago Midway

Thu 9/17

1:19 pm-6:58 pm

1 stop4h 39m

$193

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 9/12

7:50 am-5:51 pm

1 stop11h 01m

Chicago Midway

Fri 9/18

6:25 am-5:18 pm

1 stop9h 53m

$200

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 8/28

6:20 am-10:55 am

1 stop5h 35m

Chicago Midway

Sat 8/29

6:05 am-5:14 pm

1 stop10h 09m

$200
Quickest round-trip

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Fri 9/11

3:15 pm-6:55 pm

1 stop4h 40m

Chicago Midway

Mon 9/14

8:15 am-2:55 pm

1 stop5h 40m

$202

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Mon 8/24

1:00 pm-5:50 pm

2 stops5h 50m

Chicago Midway

Wed 8/26

8:50 am-3:00 pm

1 stop5h 10m

$202

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 9/22

11:35 am-5:46 pm

1 stop7h 11m

Chicago Midway

Fri 10/2

9:24 pm-11:05 am

1 stop12h 41m

$258

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 9/24

11:35 am-5:46 pm

1 stop7h 11m

Chicago Midway

Fri 10/2

9:24 pm-11:05 am

1 stop12h 41m

$262

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 $231. If you are unable to visit Chicago Midway Airport during the month of November, then departing from Pennsylvania during the month October is also very affordable. Most momondo users find prices during this month for around $234.

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 $338. 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 $459.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Pennsylvania at noon is the least expensive time of day to depart. momondo users have found prices as low as $340 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $390. 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 from Pennsylvania 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 $327 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 $225 on momondo.

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

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

$184

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 $184. The best round-trip flight deal from Pennsylvania to Chicago Midway Airport found on momondo in the last 72 hours is $344.
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 $82Free CancellationRating
5.6
2,748 reviews
Search Frontier flights
SouthwestPriceFrom $131Free CancellationRating
8.0
4,227 reviews
Search Southwest flights
DeltaPriceFrom $186Free CancellationRating
7.8
8,488 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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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