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Cheap flights from Philadelphia to Chicago Midway Airport 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 Midway Airport departing on 5/5. 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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0 bags

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Find the cheapest flights from Philadelphia to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Philadelphia to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.
8:23 pm - 9:40 pmPHL-MDW
2h 17mnonstop
2:36 pm - 5:36 pmMDW-PHL
2h 00mnonstop
$63Frontier
Find Deal
Thu, Apr 3 - Tue, Apr 8
12:48 pm - 7:35 pmPHL-MDW
7h 47m1 stop
2:36 pm - 5:36 pmMDW-PHL
2h 00mnonstop
$94Frontier
Find Deal
Mon, Mar 24 - Tue, Apr 1
1:29 pm - 5:48 pmPHL-MDW
5h 19m1 stop
12:15 pm - 3:17 pmMDW-PHL
2h 02mnonstop
$97Frontier
Find Deal
Sat, May 17 - Mon, May 19
8:23 pm - 9:40 pmPHL-MDW
2h 17mnonstop
7:50 am - 4:55 pmMDW-PHL
8h 05m1 stop
$99Frontier
Find Deal
Thu, Apr 3 - Tue, Apr 8
1:45 pm - 3:00 pmPHL-MDW
2h 15mnonstop
7:00 pm - 9:55 pmMDW-PHL
1h 55mnonstop
$197Southwest
Find Deal
Thu, Feb 27 - Mon, Mar 3
5:25 pm - 10:30 pmPHL-MDW
6h 05m1 stop
7:00 pm - 9:55 pmMDW-PHL
1h 55mnonstop
$207Southwest
Find Deal
Thu, Feb 27 - Mon, Mar 3
9:33 am - 1:05 pmPHL-MDW
4h 32m1 stop
10:57 am - 5:02 pmMDW-PHL
5h 05m1 stop
$217Delta
Find Deal
Tue, Feb 18 - Wed, Feb 26
5:25 am - 4:05 pmPHL-MDW
11h 40m2 stops
5:30 am - 1:40 pmMDW-PHL
7h 10m1 stop
$222Southwest
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Tue, Apr 29 - Wed, Apr 30
6:56 pm - 8:45 amPHL-MDW
14h 49m1 stop
6:42 pm - 11:16 pmMDW-PHL
3h 34m1 stop
$241Delta
Find Deal
Mon, Mar 24 - Mon, Mar 31
6:00 am - 12:36 pmPHL-MDW
7h 36m1 stop
4:59 pm - 12:45 amMDW-PHL
6h 46m1 stop
$270Delta
Find Deal
Thu, Mar 27 - Tue, Apr 1

Frontier flights from Philadelphia to Chicago Midway Airport

Our best Frontier deals on Philadelphia to Chicago Midway Airport flight tickets
Frontier
Apr 3
PHL8:23 pmPhiladelphia
2h 17m
MDW9:40 pmChicago Midway
Apr 8
MDW2:36 pmChicago Midway
2h 00m
PHL5:36 pmPhiladelphia
Frontier
Mar 24
PHL12:48 pmPhiladelphia
7h 47m
1 stop
MDW7:35 pmChicago Midway
Apr 1
MDW2:36 pmChicago Midway
2h 00m
PHL5:36 pmPhiladelphia
Frontier
May 17
PHL1:29 pmPhiladelphia
5h 19m
1 stop
MDW5:48 pmChicago Midway
May 19
MDW12:15 pmChicago Midway
2h 02m
PHL3:17 pmPhiladelphia

Southwest flights from Philadelphia to Chicago Midway Airport

Our best Southwest deals on Philadelphia to Chicago Midway Airport flight tickets
Southwest
Feb 27
PHL1:45 pmPhiladelphia
2h 15m
MDW3:00 pmChicago Midway
Mar 3
MDW7:00 pmChicago Midway
1h 55m
PHL9:55 pmPhiladelphia
Southwest
Feb 27
PHL5:25 pmPhiladelphia
6h 05m
1 stop
MDW10:30 pmChicago Midway
Mar 3
MDW7:00 pmChicago Midway
1h 55m
PHL9:55 pmPhiladelphia
Southwest
Apr 29
PHL5:25 amPhiladelphia
11h 40m
2 stops
MDW4:05 pmChicago Midway
Apr 30
MDW5:30 amChicago Midway
7h 10m
1 stop
PHL1:40 pmPhiladelphia

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 typical price of a round-trip flight between Philadelphia and Chicago Midway Airport?

What is the cheapest month to fly to Chicago Midway Airport?

The month of May is, on average, the cheapest month to fly to Chicago Midway Airport from Philadelphia, with most prices found around $105. If you are unable to visit Chicago Midway Airport during the month of May, then departing from Philadelphia during the month August is also very affordable. Most momondo users find prices during this month for around $133.

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 Philadelphia. The lowest ticket price found for a Saturday departure recently was $132. 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 Philadelphia because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $194.

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 $121 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $221. 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 11 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $172 when searching 11 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 $110 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 January 2025, prices for Philadelphia to Chicago Midway Airport flights are approximately 317% 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 $63.
The fastest flight from Philadelphia to Chicago Midway Airport takes 2h 05m
Direct flights go from Philadelphia to Chicago Midway Airport every day.

  • 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 05m.

  • 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
6.0
3,434 reviews
Search Frontier flights
SouthwestPriceFrom $151Free CancellationRating
8.1
4,615 reviews
Search Southwest flights
DeltaPriceFrom $186Free CancellationRating
8.0
8,485 reviews
Search Delta flights
American AirlinesPriceFrom $199Free CancellationRating
7.2
10,000 reviews
Search American Airlines 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 21 flights/week on average for this route. A good Southwest flight deal for Philadelphia to Chicago Midway Airport starts from $151 round-trip, up to an average price of $254. Our users have rated Southwest at 8.1/10.


Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Hammond
New Buffalo
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Munster
Crown Point
Schererville
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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.


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