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Cheap flights from Philadelphia to Chicago from $38

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Philadelphia to Chicago departing on 9/7. 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 Philadelphia to Chicago (PHL-MDW)

Cheap round-trip flights

Frontier Logo
6:00 am - 7:11 amPHL-MDW
2h 11mnonstop
Frontier Logo
8:15 am - 11:16 amMDW-PHL
2h 01mnonstop
$73Frontier
Find Deal
Thu, Sep 11 - Mon, Sep 15
Frontier Logo
6:00 am - 7:11 amPHL-MDW
2h 11mnonstop
Frontier Logo
8:06 am - 11:07 amMDW-PHL
2h 01mnonstop
$74Frontier
Find Deal
Mon, Sep 29 - Sun, Oct 5
Frontier Logo
6:00 am - 7:11 amPHL-MDW
2h 11mnonstop
Frontier Logo
8:06 am - 11:07 amMDW-PHL
2h 01mnonstop
$75Frontier
Find Deal
Thu, Sep 18 - Sun, Sep 21
Frontier Logo
6:00 am - 7:11 amPHL-MDW
2h 11mnonstop
Frontier Logo
8:06 am - 11:07 amMDW-PHL
2h 01mnonstop
$76Frontier
Find Deal
Fri, Oct 3 - Sun, Oct 5
Frontier Logo
6:00 am - 7:11 amPHL-MDW
2h 11mnonstop
Frontier Logo
8:06 am - 11:07 amMDW-PHL
2h 01mnonstop
$77Frontier
Find Deal
Fri, Sep 26 - Sun, Sep 28
Frontier Logo
6:00 am - 7:11 amPHL-MDW
2h 11mnonstop
Frontier Logo
8:15 am - 11:16 amMDW-PHL
2h 01mnonstop
$90Frontier
Find Deal
Mon, Sep 8 - Thu, Sep 11
Frontier Logo
6:00 am - 7:11 amPHL-MDW
2h 11mnonstop
Frontier Logo
8:15 am - 11:16 amMDW-PHL
2h 01mnonstop
$91Frontier
Find Deal
Thu, Sep 11 - Mon, Sep 15
Frontier Logo
6:00 am - 7:11 amPHL-MDW
2h 11mnonstop
Frontier Logo
8:15 am - 11:16 amMDW-PHL
2h 01mnonstop
$93Frontier
Find Deal
Thu, Sep 11 - Mon, Sep 15
Frontier Logo
6:00 am - 7:11 amPHL-MDW
2h 11mnonstop
Frontier Logo
8:15 am - 11:16 amMDW-PHL
2h 01mnonstop
$94Frontier
Find Deal
Thu, Sep 4 - Fri, Sep 5
Southwest Logo
5:25 pm - 6:35 pmPHL-MDW
2h 10mnonstop
Southwest Logo
2:40 pm - 5:40 pmMDW-PHL
2h 00mnonstop
$139Southwest
Find Deal
Sat, Sep 20 - Wed, Sep 24

Frontier flights from Philadelphia to Chicago Midway Airport

Our best Frontier deals on Philadelphia to Chicago Midway Airport flight tickets
Frontier
Sep 11
PHL6:00 amPhiladelphia
2h 11m
MDW7:11 amChicago Midway
Sep 15
MDW8:15 amChicago Midway
2h 01m
PHL11:16 amPhiladelphia
$73
Find similar
Frontier
Sep 29
PHL6:00 amPhiladelphia
2h 11m
MDW7:11 amChicago Midway
Oct 5
MDW8:06 amChicago Midway
2h 01m
PHL11:07 amPhiladelphia
$74
Find similar
Frontier
Sep 18
PHL6:00 amPhiladelphia
2h 11m
MDW7:11 amChicago Midway
Sep 21
MDW8:06 amChicago Midway
2h 01m
PHL11:07 amPhiladelphia
$75
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Philadelphia 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 15, 2025.
Use the filters below to find and compare flights from Philadelphia to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 9/11

6:00 am-7:11 am

Nonstop2h 11m

Chicago Midway

Mon 9/15

8:15 am-11:16 am

Nonstop2h 01m

$73

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Mon 9/29

6:00 am-7:11 am

Nonstop2h 11m

Chicago Midway

Sun 10/5

8:06 am-11:07 am

Nonstop2h 01m

$74

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 9/18

6:00 am-7:11 am

Nonstop2h 11m

Chicago Midway

Sun 9/21

8:06 am-11:07 am

Nonstop2h 01m

$75

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 10/3

6:00 am-7:11 am

Nonstop2h 11m

Chicago Midway

Sun 10/5

8:06 am-11:07 am

Nonstop2h 01m

$76

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 9/26

6:00 am-7:11 am

Nonstop2h 11m

Chicago Midway

Sun 9/28

8:06 am-11:07 am

Nonstop2h 01m

$77

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Mon 9/8

6:00 am-7:11 am

Nonstop2h 11m

Chicago Midway

Thu 9/11

8:15 am-11:16 am

Nonstop2h 01m

$90

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 9/11

6:00 am-7:11 am

Nonstop2h 11m

Chicago Midway

Mon 9/15

8:15 am-11:16 am

Nonstop2h 01m

$91

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 9/11

6:00 am-7:11 am

Nonstop2h 11m

Chicago Midway

Mon 9/15

8:15 am-11:16 am

Nonstop2h 01m

$93

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 9/4

6:00 am-7:11 am

Nonstop2h 11m

Chicago Midway

Fri 9/5

8:15 am-11:16 am

Nonstop2h 01m

$94

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Sat 9/20

5:25 pm-6:35 pm

Nonstop2h 10m

Chicago Midway

Wed 9/24

2:40 pm-5:40 pm

Nonstop2h 00m

$139

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 Philadelphia 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 Philadelphia, with most prices found around $150. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Philadelphia 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 Philadelphia. 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 Philadelphia 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 Philadelphia in the evening is the least expensive time of day to depart. momondo users have found prices as low as $221 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $338. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Philadelphia to Chicago Midway flight route?

Fly from Philadelphia to Chicago Midway for the best Philadelphia - 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 Philadelphia 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 Philadelphia for as low as $160 on momondo.

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

There are 1 cabin classes available to choose from on Philadelphia to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Philadelphia to Chicago Midway Airport flight prices changed over time?

As of August 2025, prices for Philadelphia to Chicago Midway Airport flights are approximately 39% more expensive when compared to flights at the same time last year.

When to book flights from Philadelphia to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Philadelphia to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Philadelphia to Chicago Midway Airport (PHL to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Philadelphia to Chicago Midway Airport

Best Price Found

$38

Fastest flight time

2h 05m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Philadelphia in the past 72 hours is $38. The best round-trip flight deal from Philadelphia to Chicago Midway Airport found on momondo in the last 72 hours is $73.
The fastest flight from Philadelphia to Chicago Midway Airport takes 2h 05m
Direct flights go from Philadelphia to Chicago Midway Airport every day.
Search flight deals

  • How far is Philadelphia to Chicago Midway by plane?

    The straight-line distance from Philadelphia to Chicago Midway is 668.8 mi. In terms of flight time, this usually takes a little over 2h 10m.

  • When did momondo last update prices for flights from Philadelphia Airport to Chicago Midway Airport?

    Prices for flights from Philadelphia Airport to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from Philadelphia Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Philadelphia Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Philadelphia Airport 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 Philadelphia to Chicago Midway Airport?

  • What is the most popular airline from Philadelphia to Chicago Midway Airport?

Best airlines flying from Philadelphia to Chicago Midway Airport

Compare and see reviews for airlines that fly from Philadelphia to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $55Free CancellationRating
5.8
3,217 reviews
Search Frontier flights
United AirlinesPriceFrom $144Free CancellationRating
7.4
8,915 reviews
Search United Airlines flights
SouthwestPriceFrom $163Free CancellationRating
8.0
4,244 reviews
Search Southwest flights

  • Southwest Flights From Philadelphia to Chicago Midway Airport

    Southwest is one of the most popular airlines flying from Philadelphia to Chicago Midway Airport, operating 25 flights/week on average for this route. A good Southwest flight deal for Philadelphia to Chicago Midway Airport starts from $163 round-trip, up to an average price of $296. Our users have rated Southwest at 8.0/10.

  • Frontier Flights From Philadelphia to Chicago Midway Airport

    Frontier (5.8/10 from 3,217 reviews) operates around 2 flights from Philadelphia to Chicago Midway Airport in any given week. The average Frontier airfare for this route is around $157, with deals from around $55 rare but found on momondo. Referenced prices are for round-trip Philadelphia to Chicago Midway Airport flight searches in the last 72 hours.

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 Philadelphia to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Philadelphia to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Philadelphia to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Philadelphia which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Philadelphia to Chicago?

Once all potential Philadelphia to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Philadelphia to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Philadelphia and alert you when they change.

An easier way to manage your Chicago Midway Airport trip

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