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Cheap flights from Pennsylvania to Chicago from $90

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
6:37 pm - 11:46 pmPHL  Philadelphia-MDW Chicago Midway
6h 09m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
1:18 pm - 12:28 amMDW  Chicago Midway-PHL Philadelphia
10h 10m1 stop Atlanta Hartsfield-Jackson
$176Frontier
Sat, Jan 23 - Wed, Jan 27
Frontier Logo
6:37 pm - 11:46 pmPHL  Philadelphia-MDW Chicago Midway
6h 09m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
1:18 pm - 12:28 amMDW  Chicago Midway-PHL Philadelphia
10h 10m1 stop Atlanta Hartsfield-Jackson
$176Frontier
Sat, Jan 23 - Wed, Jan 27
Frontier Logo
6:37 pm - 11:46 pmPHL  Philadelphia-MDW Chicago Midway
6h 09m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
1:18 pm - 12:28 amMDW  Chicago Midway-PHL Philadelphia
10h 10m1 stop Atlanta Hartsfield-Jackson
$179Frontier
Wed, Jan 20 - Sat, Jan 23
Southwest Logo
3:55 pm - 5:10 pmPHL  Philadelphia-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
1:25 pm - 4:20 pmMDW  Chicago Midway-PHL Philadelphia
1h 55mnonstop
$199Southwest
Sat, Jan 23 - Wed, Jan 27
Southwest Logo
7:50 am - 9:00 amPHL  Philadelphia-MDW Chicago Midway
2h 10mnonstop
Southwest Logo
12:00 pm - 3:00 pmMDW  Chicago Midway-PHL Philadelphia
2h 00mnonstop
$199Southwest
Wed, Jan 20 - Sat, Jan 23
Southwest Logo
7:30 am - 8:50 amPHL  Philadelphia-MDW Chicago Midway
2h 20mnonstop
Southwest Logo
6:25 pm - 9:25 pmMDW  Chicago Midway-PHL Philadelphia
2h 00mnonstop
$199Southwest
Tue, Dec 8 - Tue, Dec 8
Delta Logo
9:43 am - 1:01 pmPHL  Philadelphia-MDW Chicago Midway
4h 18m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:41 pm - 11:27 pmMDW  Chicago Midway-PHL Philadelphia
3h 46m1 stop Detroit Metropolitan Wayne County
$220Delta
Sat, Dec 5 - Sat, Dec 12
Delta Logo
9:43 am - 1:01 pmPHL  Philadelphia-MDW Chicago Midway
4h 18m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:41 pm - 7:30 pmMDW  Chicago Midway-PHL Philadelphia
4h 49m1 stop Detroit Metropolitan Wayne County
$235Delta
Sat, Dec 5 - Mon, Dec 7
Multiple Airlines Logo
5:15 am - 2:26 pmPHL  Philadelphia-MDW Chicago Midway
10h 11m2 stops Orlando Knoxville McGhee Tyson
Multiple Airlines Logo
12:28 pm - 11:09 pmMDW  Chicago Midway-PHL Philadelphia
9h 41m1 stop Atlanta Hartsfield-Jackson
$420Multiple Airlines
Fri, Nov 13 - Wed, Dec 2
Multiple Airlines Logo
9:12 pm - 5:16 pmMDT  Harrisburg-MDW Chicago Midway
21h 04m1 stop Orlando Sanford Intl
Multiple Airlines Logo
12:28 pm - 10:49 amMDW  Chicago Midway-MDT Harrisburg
21h 21m2 stops Atlanta Hartsfield-Jackson Orlando
$474Multiple Airlines
Thu, Dec 10 - Tue, Dec 15

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Southwest flights from Pennsylvania to Chicago Midway Airport

Our best Southwest deals on Pennsylvania to Chicago Midway Airport flight tickets
Southwest
Jan 23
PHL7:55 amPhiladelphia
2h 10m
MDW9:05 amChicago Midway
Jan 26
MDW8:10 amChicago Midway
2h 05m
PHL11:15 amPhiladelphia
$199
Southwest
Jan 23
PHL7:55 amPhiladelphia
2h 10m
MDW9:05 amChicago Midway
Jan 26
MDW3:25 pmChicago Midway
4h 30m
1 stop
PHL8:55 pmPhiladelphia
$209
Southwest
Dec 10
PHL11:45 amPhiladelphia
2h 15m
MDW1:00 pmChicago Midway
Dec 12
MDW3:40 pmChicago Midway
1h 55m
PHL6:35 pmPhiladelphia
$215

Delta flights from Pennsylvania to Chicago Midway Airport

Our best Delta deals on Pennsylvania to Chicago Midway Airport flight tickets
Delta
Nov 19
PIT10:24 amPittsburgh
3h 27m
1 stop
MDW12:51 pmChicago Midway
Nov 20
MDW12:30 pmChicago Midway
5h 05m
1 stop
PIT6:35 pmPittsburgh
$283
Delta
Dec 4
PIT11:17 amPittsburgh
6h 33m
1 stop
MDW4:50 pmChicago Midway
Dec 8
MDW5:30 pmChicago Midway
4h 48m
1 stop
PIT11:18 pmPittsburgh
$297
Delta
Dec 3
PIT6:10 amPittsburgh
4h 27m
1 stop
MDW9:37 amChicago Midway
Dec 7
MDW5:30 pmChicago Midway
4h 48m
1 stop
PIT11:18 pmPittsburgh
$298

momondo Fare Finder

 
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 Philadelphia - MDW Chicago Midway

PHLMDW

Philadelphia

Sat 1/23

6:37 pm-11:46 pm

1 stop6h 09m

Chicago Midway

Wed 1/27

1:18 pm-12:28 am

1 stop10h 10m

$176

PhiladelphiaChicago

PHL Philadelphia - MDW Chicago Midway

PHLMDW

Philadelphia

Sat 1/23

6:37 pm-11:46 pm

1 stop6h 09m

Chicago Midway

Wed 1/27

1:18 pm-12:28 am

1 stop10h 10m

$176

PhiladelphiaChicago

PHL Philadelphia - MDW Chicago Midway

PHLMDW

Philadelphia

Wed 1/20

6:37 pm-11:46 pm

1 stop6h 09m

Chicago Midway

Sat 1/23

1:18 pm-12:28 am

1 stop10h 10m

$179
Quickest round-trip

PhiladelphiaChicago

PHL Philadelphia - MDW Chicago Midway

PHLMDW

Philadelphia

Sat 1/23

3:55 pm-5:10 pm

Nonstop2h 15m

Chicago Midway

Wed 1/27

1:25 pm-4:20 pm

Nonstop1h 55m

$199

PhiladelphiaChicago

PHL Philadelphia - MDW Chicago Midway

PHLMDW

Philadelphia

Wed 1/20

7:50 am-9:00 am

Nonstop2h 10m

Chicago Midway

Sat 1/23

12:00 pm-3:00 pm

Nonstop2h 00m

$199

PhiladelphiaChicago

PHL Philadelphia - MDW Chicago Midway

PHLMDW

Philadelphia

Tue 12/8

7:30 am-8:50 am

Nonstop2h 20m

Chicago Midway

Tue 12/8

6:25 pm-9:25 pm

Nonstop2h 00m

$199

PhiladelphiaChicago

PHL Philadelphia - MDW Chicago Midway

PHLMDW

Philadelphia

Sat 12/5

9:43 am-1:01 pm

1 stop4h 18m

Chicago Midway

Sat 12/12

6:41 pm-11:27 pm

1 stop3h 46m

$220

PhiladelphiaChicago

PHL Philadelphia - MDW Chicago Midway

PHLMDW

Philadelphia

Sat 12/5

9:43 am-1:01 pm

1 stop4h 18m

Chicago Midway

Mon 12/7

1:41 pm-7:30 pm

1 stop4h 49m

$235

PhiladelphiaChicago

PHL Philadelphia - MDW Chicago Midway

PHLMDW

Philadelphia

Fri 11/13

5:15 am-2:26 pm

2 stops10h 11m

Chicago Midway

Wed 12/2

12:28 pm-11:09 pm

1 stop9h 41m

$420

HarrisburgChicago

MDT Harrisburg - MDW Chicago Midway

MDTMDW

Harrisburg

Thu 12/10

9:12 pm-5:16 pm

1 stop21h 04m

Chicago Midway

Tue 12/15

12:28 pm-10:49 am

2 stops21h 21m

$474

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 $287. If you are unable to visit Chicago Midway Airport during the month of November, then departing from Pennsylvania during the month January is also very affordable. Most momondo users find prices during this month for around $306.

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

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Pennsylvania. The lowest ticket price found for a Wednesday departure recently was $364. 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 $481.

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 afternoon is the least expensive time of day to depart. momondo users have found prices as low as $374 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $463. 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 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 $363 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 $291 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?

You could potentially save up to 5% 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

$90

Fastest flight time

1h 30m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Pennsylvania in the past 72 hours is $90. The best round-trip flight deal from Pennsylvania to Chicago Midway Airport found on momondo in the last 72 hours is $176.
The fastest flight from Pennsylvania to Chicago Midway Airport takes 1h 30m
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 $105Free CancellationRating
5.5
2,513 reviews
Search Frontier flights
SouthwestPriceFrom $137Free CancellationRating
8.0
4,215 reviews
Search Southwest flights
DeltaPriceFrom $186Free CancellationRating
7.8
8,696 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
Lansing
Saint Joseph
Benton Harbor
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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