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Cheap flights from Pennsylvania to Chicago from $89

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.
Delta Logo
6:05 am - 9:32 amIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
4h 27m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:44 pm - 11:16 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
3h 32m1 stop Detroit Metropolitan Wayne County
$179Delta
Tue, Oct 20 - Sat, Oct 24
Delta Logo
6:00 am - 9:42 amIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
4h 42m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:00 am - 11:37 amMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
4h 37m1 stop Atlanta Hartsfield-Jackson
$179Delta
Tue, Nov 10 - Wed, Nov 11
Delta Logo
6:05 am - 9:32 amIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
4h 27m1 stop Detroit Metropolitan Wayne County
Delta Logo
4:19 pm - 12:42 amMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
7h 23m1 stop Atlanta Hartsfield-Jackson
$179Delta
Sat, Oct 17 - Sat, Oct 24
Frontier Logo
5:22 pm - 11:43 pmPHL  Philadelphia-MDW Chicago Midway
7h 21m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:40 pm - 7:21 amMDW  Chicago Midway-PHL Philadelphia
11h 41m1 stop Atlanta Hartsfield-Jackson
$180Frontier
Wed, Oct 21 - Thu, Oct 22
Frontier Logo
6:00 am - 12:17 pmPHL  Philadelphia-MDW Chicago Midway
7h 17m1 stop Dallas/Fort Worth
Frontier Logo
6:42 pm - 7:11 amMDW  Chicago Midway-PHL Philadelphia
11h 29m1 stop Atlanta Hartsfield-Jackson
$182Frontier
Thu, Oct 22 - Wed, Oct 28
Frontier Logo
12:36 pm - 11:47 pmPHL  Philadelphia-MDW Chicago Midway
12h 11m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:16 am - 6:19 pmMDW  Chicago Midway-PHL Philadelphia
11h 03m1 stop Atlanta Hartsfield-Jackson
$182Frontier
Wed, Nov 18 - Thu, Nov 19
Southwest Logo
6:20 pm - 7:35 pmPHL  Philadelphia-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
8:10 am - 11:05 amMDW  Chicago Midway-PHL Philadelphia
1h 55mnonstop
$185Southwest
Wed, Dec 2 - Wed, Dec 9
Southwest Logo
1:05 pm - 2:15 pmPHL  Philadelphia-MDW Chicago Midway
2h 10mnonstop
Southwest Logo
6:25 pm - 9:20 pmMDW  Chicago Midway-PHL Philadelphia
1h 55mnonstop
$185Southwest
Sat, Dec 5 - Tue, Dec 8
Multiple Airlines Logo
9:55 am - 11:47 pmEWR  Newark-MDW Chicago Midway
14h 52m2 stops Cincinnati Cinci./N. Kentucky Atlanta Hartsfield-Jackson
Multiple Airlines Logo
7:25 am - 9:19 pmMDW  Chicago Midway-EWR Newark
12h 54m1 stop Atlanta Hartsfield-Jackson
$288Multiple Airlines
Thu, Nov 12 - Sat, Nov 14
Multiple Airlines Logo
11:35 am - 5:46 pmEWR  Newark-MDW Chicago Midway
7h 11m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
9:24 pm - 11:05 amMDW  Chicago Midway-EWR Newark
12h 41m1 stop Valparaiso Destin-Ft Walton Beach
$291Multiple Airlines
Tue, Sep 29 - Fri, Oct 2

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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
Oct 14
PHL11:25 amPhiladelphia
2h 05m
MDW12:30 pmChicago Midway
Oct 20
MDW7:45 amChicago Midway
1h 55m
PHL10:40 amPhiladelphia
$185
Southwest
Oct 13
PHL5:30 pmPhiladelphia
2h 05m
MDW6:35 pmChicago Midway
Oct 20
MDW6:00 pmChicago Midway
2h 05m
PHL9:05 pmPhiladelphia
$186
Southwest
Oct 28
PHL6:00 amPhiladelphia
5h 55m
1 stop
MDW10:55 amChicago Midway
Oct 31
MDW12:55 pmChicago Midway
2h 05m
PHL4:00 pmPhiladelphia
$195

Frontier flights from Pennsylvania to Chicago Midway Airport

Our best Frontier deals on Pennsylvania to Chicago Midway Airport flight tickets
Frontier
Oct 21
PHL5:22 pmPhiladelphia
7h 21m
1 stop
MDW11:43 pmChicago Midway
Oct 22
MDW6:40 pmChicago Midway
11h 41m
1 stop
PHL7:21 amPhiladelphia
$180
Frontier
Oct 22
PHL6:00 amPhiladelphia
7h 17m
1 stop
MDW12:17 pmChicago Midway
Oct 28
MDW6:42 pmChicago Midway
11h 29m
1 stop
PHL7:11 amPhiladelphia
$182
Frontier
Nov 3
PHL12:36 pmPhiladelphia
6h 11m
1 stop
MDW5:47 pmChicago Midway
Nov 10
MDW6:42 pmChicago Midway
11h 39m
1 stop
PHL7:21 amPhiladelphia
$183

momondo Fare Finder

 
Use the filters below to find and compare flights from Pennsylvania to Chicago Midway Airport that are best for you.

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Route

Depart

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Price

Cheapest round-trip

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Tue 10/20

6:05 am-9:32 am

1 stop4h 27m

Chicago Midway

Sat 10/24

6:44 pm-11:16 pm

1 stop3h 32m

$179

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Tue 11/10

6:00 am-9:42 am

1 stop4h 42m

Chicago Midway

Wed 11/11

6:00 am-11:37 am

1 stop4h 37m

$179

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Sat 10/17

6:05 am-9:32 am

1 stop4h 27m

Chicago Midway

Sat 10/24

4:19 pm-12:42 am

1 stop7h 23m

$179

PhiladelphiaChicago

PHL Philadelphia - MDW Chicago Midway

PHLMDW

Philadelphia

Wed 10/21

5:22 pm-11:43 pm

1 stop7h 21m

Chicago Midway

Thu 10/22

6:40 pm-7:21 am

1 stop11h 41m

$180

PhiladelphiaChicago

PHL Philadelphia - MDW Chicago Midway

PHLMDW

Philadelphia

Thu 10/22

6:00 am-12:17 pm

1 stop7h 17m

Chicago Midway

Wed 10/28

6:42 pm-7:11 am

1 stop11h 29m

$182

PhiladelphiaChicago

PHL Philadelphia - MDW Chicago Midway

PHLMDW

Philadelphia

Wed 11/18

12:36 pm-11:47 pm

1 stop12h 11m

Chicago Midway

Thu 11/19

6:16 am-6:19 pm

1 stop11h 03m

$182

PhiladelphiaChicago

PHL Philadelphia - MDW Chicago Midway

PHLMDW

Philadelphia

Wed 12/2

6:20 pm-7:35 pm

Nonstop2h 15m

Chicago Midway

Wed 12/9

8:10 am-11:05 am

Nonstop1h 55m

$185
Quickest round-trip

PhiladelphiaChicago

PHL Philadelphia - MDW Chicago Midway

PHLMDW

Philadelphia

Sat 12/5

1:05 pm-2:15 pm

Nonstop2h 10m

Chicago Midway

Tue 12/8

6:25 pm-9:20 pm

Nonstop1h 55m

$185

NewarkChicago

EWR Newark - MDW Chicago Midway

EWRMDW

Newark

Thu 11/12

9:55 am-11:47 pm

2 stops14h 52m

Chicago Midway

Sat 11/14

7:25 am-9:19 pm

1 stop12h 54m

$288

NewarkChicago

EWR Newark - MDW Chicago Midway

EWRMDW

Newark

Tue 9/29

11:35 am-5:46 pm

1 stop7h 11m

Chicago Midway

Fri 10/2

9:24 pm-11:05 am

1 stop12h 41m

$291

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 $230. 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 $272.

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

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Pennsylvania. The lowest ticket price found for a Saturday departure recently was $362. 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 $470.

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 $355 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $427. 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 $344 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 $286 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

$89

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 $89. The best round-trip flight deal from Pennsylvania to Chicago Midway Airport found on momondo in the last 72 hours is $179.
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 $73Free CancellationRating
5.6
2,598 reviews
Search Frontier flights
SouthwestPriceFrom $137Free CancellationRating
8.0
4,192 reviews
Search Southwest flights
DeltaPriceFrom $148Free CancellationRating
7.8
8,584 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
Porter
Crown Point
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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