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Cheap flights from Philadelphia to Chicago Midway Airport from $28

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 12/17. 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

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.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Philadelphia to Chicago.

Cheap last minute flights

Planning a quick getaway from Philadelphia to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Philadelphia to Chicago

Find recent round-trip train or bus tickets from Philadelphia to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
11:43 am - 1:09 pmPHL-MDW
2h 26mnonstop
7:45 am - 10:48 amMDW-PHL
2h 03mnonstop
$57Frontier
Find Deal
Tue, Dec 17 - Tue, Dec 24
11:43 am - 1:09 pmPHL-MDW
2h 26mnonstop
7:45 am - 10:48 amMDW-PHL
2h 03mnonstop
$58Frontier
Find Deal
Tue, Dec 17 - Tue, Dec 24
11:43 am - 1:09 pmPHL-MDW
2h 26mnonstop
7:34 am - 10:37 amMDW-PHL
2h 03mnonstop
$67Frontier
Find Deal
Tue, Dec 17 - Thu, Dec 19
11:43 am - 1:09 pmPHL-MDW
2h 26mnonstop
7:45 am - 10:48 amMDW-PHL
2h 03mnonstop
$73Frontier
Find Deal
Tue, Dec 17 - Tue, Dec 31
5:25 pm - 6:35 pmPHL-MDW
2h 10mnonstop
6:00 pm - 8:55 pmMDW-PHL
1h 55mnonstop
$172Southwest
Find Deal
Sat, Dec 7 - Sat, Dec 14
6:40 pm - 7:50 pmPHL-MDW
2h 10mnonstop
8:15 pm - 11:10 pmMDW-PHL
1h 55mnonstop
$185Southwest
Find Deal
Tue, Dec 10 - Fri, Dec 13
7:35 am - 8:45 amPHL-MDW
2h 10mnonstop
8:05 am - 11:00 amMDW-PHL
1h 55mnonstop
$195Southwest
Find Deal
Wed, Dec 11 - Sun, Dec 15
4:44 pm - 10:06 pmPHL-MDW
6h 22m1 stop
5:51 pm - 11:14 pmMDW-PHL
4h 23m1 stop
$196Delta
Find Deal
Sat, Dec 14 - Tue, Dec 31
11:43 am - 6:32 pmPHL-MDW
7h 49m1 stop
4:58 pm - 12:55 amMDW-PHL
6h 57m1 stop
$216Delta
Find Deal
Wed, Dec 11 - Sat, Dec 14
5:30 am - 9:50 amPHL-MDW
5h 20m1 stop
9:30 am - 4:32 pmMDW-PHL
6h 02m1 stop
$236Delta
Find Deal
Sun, Dec 8 - Tue, Dec 10
11:43 am - 1:09 pmPHL-MDW
2h 26mnonstop
$28Frontier
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Tue, Dec 17
11:43 am - 1:09 pmPHL-MDW
2h 26mnonstop
$29Frontier
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Tue, Dec 17
10:57 pm - 12:20 amPHL-MDW
2h 23mnonstop
$37Frontier
Find Deal
Fri, Dec 6
10:57 pm - 12:20 amPHL-MDW
2h 23mnonstop
$38Frontier
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Fri, Dec 6
7:35 am - 8:45 amPHL-MDW
2h 10mnonstop
$86Southwest
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Wed, Dec 11
12:55 pm - 2:05 pmPHL-MDW
2h 10mnonstop
$89Southwest
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Wed, Dec 25
9:33 am - 1:08 pmPHL-MDW
4h 35m1 stop
$98Delta
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Tue, Jan 7
10:48 am - 8:41 amPHL-MDW
22h 53m3 stops
Mon, Jan 6
6:00 am - 8:50 amPHL-MDW
3h 50m1 stop
$197Delta
Find Deal
Fri, Dec 27
5:10 am - 8:56 amPHL-MDW
28h 46m3 stops
Tue, Nov 26
4:21 pm - 5:38 pmPHL-MDW
2h 17mnonstop
10:28 am - 1:23 pmMDW-PHL
1h 55mnonstop
$136Frontier
Find Deal
Tue, Nov 26 - Thu, Nov 28
4:21 pm - 5:38 pmPHL-MDW
2h 17mnonstop
10:28 am - 1:23 pmMDW-PHL
1h 55mnonstop
$144Frontier
Find Deal
Tue, Nov 26 - Thu, Nov 28
4:21 pm - 5:38 pmPHL-MDW
2h 17mnonstop
11:16 am - 2:18 pmMDW-PHL
2h 02mnonstop
$155Frontier
Find Deal
Tue, Nov 26 - Wed, Nov 27
4:21 pm - 5:38 pmPHL-MDW
2h 17mnonstop
6:53 pm - 9:54 pmMDW-PHL
2h 01mnonstop
$164Frontier
Find Deal
Tue, Nov 26 - Fri, Nov 29
7:00 am - 8:10 amPHL-MDW
2h 10mnonstop
12:15 pm - 3:10 pmMDW-PHL
1h 55mnonstop
$520Southwest
Find Deal
Fri, Nov 22 - Wed, Dec 4
12:55 pm - 5:50 pmPHL-MDW
5h 55m1 stop
12:15 pm - 3:10 pmMDW-PHL
1h 55mnonstop
$529Southwest
Find Deal
Fri, Nov 22 - Wed, Dec 4
8:00 am - 11:58 amPHL-MDW
4h 58m1 stop
9:31 am - 4:44 pmMDW-PHL
6h 13m1 stop
$586Delta
Find Deal
Tue, Nov 26 - Tue, Dec 3
5:10 am - 8:41 amPHL-MDW
28h 31m3 stops
6:16 pm - 1:17 amMDW-PHL
30h 01m3 stops
Mon, Nov 25 - Wed, Nov 27
1:25 pm - 1:23 pmPHL-MDW
24h 58m3 stops
9:21 am - 1:17 amMDW-PHL
14h 56m2 stops
Sun, Nov 24 - Tue, Nov 26
6:00 am - 8:50 amPHL-MDW
3h 50m1 stop
6:49 pm - 12:54 amMDW-PHL
5h 05m1 stop
$743Delta
Find Deal
Tue, Nov 26 - Mon, Dec 2
11:43 am - 1:09 pmPHL-MDW
2h 26mnonstop
7:45 am - 10:48 amMDW-PHL
2h 03mnonstop
$57Frontier
Find Deal
Tue, Dec 17 - Tue, Dec 24
11:43 am - 1:09 pmPHL-MDW
2h 26mnonstop
7:45 am - 10:48 amMDW-PHL
2h 03mnonstop
$58Frontier
Find Deal
Tue, Dec 17 - Tue, Dec 24
11:43 am - 1:09 pmPHL-MDW
2h 26mnonstop
7:34 am - 10:37 amMDW-PHL
2h 03mnonstop
$67Frontier
Find Deal
Tue, Dec 17 - Thu, Dec 19
11:43 am - 1:09 pmPHL-MDW
2h 26mnonstop
7:45 am - 10:48 amMDW-PHL
2h 03mnonstop
$73Frontier
Find Deal
Tue, Dec 17 - Tue, Dec 31
10:57 pm - 12:20 amPHL-MDW
2h 23mnonstop
8:15 am - 11:18 amMDW-PHL
2h 03mnonstop
$76Frontier
Find Deal
Fri, Dec 13 - Mon, Dec 16
10:57 pm - 12:20 amPHL-MDW
2h 23mnonstop
8:15 am - 11:18 amMDW-PHL
2h 03mnonstop
$77Frontier
Find Deal
Fri, Dec 6 - Mon, Dec 9
4:50 pm - 6:12 pmPHL-MDW
2h 22mnonstop
12:36 pm - 3:42 pmMDW-PHL
2h 06mnonstop
$78Frontier
Find Deal
Thu, Dec 12 - Sun, Dec 15
12:14 pm - 1:40 pmPHL-MDW
2h 26mnonstop
4:01 pm - 7:05 pmMDW-PHL
2h 04mnonstop
$82Frontier
Find Deal
Mon, Dec 16 - Fri, Jan 3
5:25 pm - 6:35 pmPHL-MDW
2h 10mnonstop
6:00 pm - 8:55 pmMDW-PHL
1h 55mnonstop
$172Southwest
Find Deal
Sat, Dec 7 - Sat, Dec 14
3:55 pm - 5:05 pmPHL-MDW
2h 10mnonstop
8:30 am - 11:25 amMDW-PHL
1h 55mnonstop
$178Southwest
Find Deal
Wed, Dec 25 - Wed, Jan 1

Frontier flights from Philadelphia to Chicago Midway Airport

Our best Frontier deals on Philadelphia to Chicago Midway Airport flight tickets
Frontier
Dec 17
PHL11:43 amPhiladelphia
2h 26m
MDW1:09 pmChicago Midway
Dec 24
MDW7:45 amChicago Midway
2h 03m
PHL10:48 amPhiladelphia
Frontier
Dec 17
PHL11:43 amPhiladelphia
2h 26m
MDW1:09 pmChicago Midway
Dec 24
MDW7:45 amChicago Midway
2h 03m
PHL10:48 amPhiladelphia
Frontier
Dec 17
PHL11:43 amPhiladelphia
2h 26m
MDW1:09 pmChicago Midway
Dec 19
MDW7:34 amChicago Midway
2h 03m
PHL10:37 amPhiladelphia

Southwest flights from Philadelphia to Chicago Midway Airport

Our best Southwest deals on Philadelphia to Chicago Midway Airport flight tickets
Southwest
Dec 7
PHL5:25 pmPhiladelphia
2h 10m
MDW6:35 pmChicago Midway
Dec 14
MDW6:00 pmChicago Midway
1h 55m
PHL8:55 pmPhiladelphia
Southwest
Dec 10
PHL6:40 pmPhiladelphia
2h 10m
MDW7:50 pmChicago Midway
Dec 13
MDW8:15 pmChicago Midway
1h 55m
PHL11:10 pmPhiladelphia
Southwest
Dec 11
PHL7:35 amPhiladelphia
2h 10m
MDW8:45 amChicago Midway
Dec 15
MDW8:05 amChicago Midway
1h 55m
PHL11:00 amPhiladelphia

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 May is, on average, the cheapest month to fly to Chicago Midway Airport from Philadelphia, with most prices found around $103. If you are unable to visit Chicago Midway Airport during the month of May, then departing from Philadelphia during the month June is also very affordable. Most momondo users find prices during this month for around $130.

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 $108. 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 $195.

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 $132 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $166. 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?

We recommend purchasing flights from Philadelphia to Chicago Midway Airport 46 days ahead of your departure date because this is when momondo users tend to see the best flight rates. On average, our users have found flights to Chicago Midway Airport for $163. In the past 72 hours, momondo users found flights from Philadelphia to Chicago Midway Airport for as low as $48.

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.

Can stopping save me money on Philadelphia to Chicago Midway Airport flights?

You could potentially save up to 89% on your flight if you consider stops on a Philadelphia to Chicago Midway Airport flight.

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

As of November 2024, prices for Philadelphia to Chicago Midway Airport flights are approximately 42% 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

$28

Fastest flight time

2h 10m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Philadelphia in the past 72 hours is $28. The best round-trip flight deal from Philadelphia to Chicago Midway Airport found on momondo in the last 72 hours is $57.
The fastest flight from Philadelphia to Chicago Midway Airport takes 2h 10m
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 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
6.1
3,536 reviews
Search Frontier flights
SouthwestPriceFrom $150Free CancellationRating
8.1
5,005 reviews
Search Southwest flights
DeltaPriceFrom $188Free CancellationRating
8.0
8,755 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 18 flights/week on average for this route. A good Southwest flight deal for Philadelphia to Chicago Midway Airport starts from $150 round-trip, up to an average price of $235. Our users have rated Southwest at 8.1/10.

  • Frontier Flights From Philadelphia to Chicago Midway Airport

    Frontier (6.1/10 from 3,536 reviews) operates around 3 flights from Philadelphia to Chicago Midway Airport in any given week. The average Frontier airfare for this route is around $137, 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.


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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