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Cheap flights from Philadelphia to Chicago Midway Airport from $39

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 4/1. 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.
7:38 pm - 9:04 pmPHL-MDW
2h 26mnonstop
7:30 am - 6:21 pmMDW-PHL
9h 51m1 stop
$98Frontier
Find Deal
Mon, Jan 6 - Thu, Jan 9
6:03 pm - 11:29 pmPHL-MDW
6h 26m1 stop
4:48 pm - 12:01 amMDW-PHL
6h 13m1 stop
$106Frontier
Find Deal
Sat, Feb 8 - Sat, Feb 15
1:41 pm - 6:26 pmPHL-MDW
5h 45m1 stop
6:15 am - 7:26 pmMDW-PHL
12h 11m1 stop
$108Frontier
Find Deal
Thu, Feb 6 - Mon, Feb 10
6:05 am - 3:02 pmPHL-MDW
9h 57m1 stop
7:30 am - 4:48 pmMDW-PHL
8h 18m1 stop
$115Frontier
Find Deal
Mon, Jan 20 - Sat, Jan 25
1:50 pm - 3:05 pmPHL-MDW
2h 15mnonstop
6:15 pm - 9:05 pmMDW-PHL
1h 50mnonstop
$175Southwest
Find Deal
Wed, Jan 29 - Wed, Jan 29
1:50 pm - 3:05 pmPHL-MDW
2h 15mnonstop
12:25 pm - 3:15 pmMDW-PHL
1h 50mnonstop
$181Southwest
Find Deal
Wed, Jan 22 - Wed, Jan 29
5:40 am - 10:12 amPHL-MDW
5h 32m1 stop
10:19 am - 5:51 pmMDW-PHL
6h 32m1 stop
$196Delta
Find Deal
Tue, Jan 14 - Tue, Jan 21
9:33 am - 1:08 pmPHL-MDW
4h 35m1 stop
6:28 pm - 11:20 pmMDW-PHL
3h 52m1 stop
$198Delta
Find Deal
Fri, Jan 17 - Mon, Jan 20
5:15 pm - 3:11 pmPHL-MDW
22h 56m2 stops
6:28 pm - 11:20 pmMDW-PHL
3h 52m1 stop
Fri, Jan 3 - Mon, Jan 6
5:15 pm - 3:11 pmPHL-MDW
22h 56m2 stops
8:41 pm - 7:46 pmMDW-PHL
22h 05m3 stops
Fri, Jan 3 - Mon, Jan 6
6:31 pm - 7:51 pmPHL-MDW
2h 20mnonstop
$39Frontier
Find Deal
Tue, Apr 1
3:19 pm - 9:29 pmPHL-MDW
7h 10m1 stop
$53Frontier
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Thu, Feb 27
6:03 pm - 11:29 pmPHL-MDW
6h 26m1 stop
$54Frontier
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Sat, Jan 25
6:03 pm - 11:29 pmPHL-MDW
6h 26m1 stop
$55Frontier
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Sat, Feb 1
1:50 pm - 3:05 pmPHL-MDW
2h 15mnonstop
$91Southwest
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Wed, Jan 22
10:33 am - 4:21 pmPHL-MDW
6h 48m1 stop
$98Delta
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Tue, Jan 14
6:00 am - 12:46 pmPHL-MDW
7h 46m1 stop
$100Delta
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Wed, Jan 22
6:20 pm - 7:35 pmPHL-MDW
2h 15mnonstop
$111Southwest
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Thu, Jan 23
12:20 pm - 5:30 pmPHL-MDW
30h 10m3 stops
Wed, Feb 26
12:20 pm - 5:30 pmPHL-MDW
30h 10m3 stops
Wed, Feb 26
5:15 am - 6:39 amPHL-MDW
2h 24mnonstop
7:34 am - 10:37 amMDW-PHL
2h 03mnonstop
$282Frontier
Find Deal
Sun, Dec 29 - Sun, Jan 5
5:15 am - 6:39 amPHL-MDW
2h 24mnonstop
7:30 am - 6:21 pmMDW-PHL
9h 51m1 stop
$290Frontier
Find Deal
Sun, Dec 29 - Thu, Jan 9
5:15 am - 6:39 amPHL-MDW
2h 24mnonstop
7:45 am - 10:48 amMDW-PHL
2h 03mnonstop
$304Frontier
Find Deal
Thu, Dec 26 - Tue, Dec 31
5:15 am - 6:39 amPHL-MDW
2h 24mnonstop
4:08 pm - 8:41 amMDW-PHL
15h 33m1 stop
$305Frontier
Find Deal
Thu, Dec 26 - Tue, Dec 31
6:00 am - 8:50 amPHL-MDW
3h 50m1 stop
6:00 am - 12:04 pmMDW-PHL
5h 04m1 stop
$558Delta
Find Deal
Sat, Dec 28 - Tue, Jan 7
4:50 pm - 10:06 pmPHL-MDW
6h 16m1 stop
9:34 am - 3:55 pmMDW-PHL
5h 21m1 stop
$578Delta
Find Deal
Sat, Dec 28 - Thu, Jan 9
12:55 pm - 2:05 pmPHL-MDW
2h 10mnonstop
12:15 pm - 3:10 pmMDW-PHL
1h 55mnonstop
$606Southwest
Find Deal
Wed, Dec 25 - Tue, Dec 31
7:00 am - 8:10 amPHL-MDW
2h 10mnonstop
8:30 am - 11:25 amMDW-PHL
1h 55mnonstop
$623Southwest
Find Deal
Sun, Dec 29 - Wed, Jan 1
6:15 am - 10:10 amPHL-MDW
4h 55m1 stop
9:50 am - 9:45 pmMDW-PHL
10h 55m2 stops
$630Southwest
Find Deal
Wed, Dec 25 - Tue, Dec 31
5:38 am - 11:21 amPHL-MDW
6h 43m1 stop
6:00 am - 12:04 pmMDW-PHL
5h 04m1 stop
$756Delta
Find Deal
Sat, Dec 28 - Fri, Jan 10
8:23 pm - 9:40 pmPHL-MDW
2h 17mnonstop
4:30 pm - 7:28 pmMDW-PHL
1h 58mnonstop
$139Frontier
Find Deal
Thu, Apr 3 - Sun, Apr 6
1:50 pm - 3:05 pmPHL-MDW
2h 15mnonstop
6:15 pm - 9:05 pmMDW-PHL
1h 50mnonstop
$175Southwest
Find Deal
Wed, Jan 29 - Wed, Jan 29
1:50 pm - 3:05 pmPHL-MDW
2h 15mnonstop
12:25 pm - 3:15 pmMDW-PHL
1h 50mnonstop
$181Southwest
Find Deal
Wed, Jan 22 - Wed, Jan 29
1:50 pm - 3:05 pmPHL-MDW
2h 15mnonstop
8:00 am - 10:55 amMDW-PHL
1h 55mnonstop
$201Southwest
Find Deal
Tue, Feb 25 - Thu, Feb 27
1:44 pm - 3:06 pmPHL-MDW
2h 22mnonstop
9:59 pm - 12:58 amMDW-PHL
1h 59mnonstop
$219Frontier
Find Deal
Fri, Jan 3 - Mon, Jan 6
3:55 pm - 5:05 pmPHL-MDW
2h 10mnonstop
6:15 pm - 9:05 pmMDW-PHL
1h 50mnonstop
$221Southwest
Find Deal
Mon, Jan 6 - Thu, Jan 9
12:32 pm - 1:46 pmPHL-MDW
2h 14mnonstop
2:44 pm - 5:55 pmMDW-PHL
2h 11mnonstop
$243Frontier
Find Deal
Wed, May 28 - Sat, May 31
6:15 am - 7:45 amPHL-MDW
2h 30mnonstop
8:35 am - 11:30 amMDW-PHL
1h 55mnonstop
$256Southwest
Find Deal
Thu, Jan 16 - Mon, Jan 20
6:20 pm - 7:35 pmPHL-MDW
2h 15mnonstop
10:05 am - 1:00 pmMDW-PHL
1h 55mnonstop
$267Southwest
Find Deal
Fri, Jan 24 - Mon, Jan 27
12:32 pm - 1:46 pmPHL-MDW
2h 14mnonstop
2:44 pm - 5:55 pmMDW-PHL
2h 11mnonstop
$285Frontier
Find Deal
Sat, Jun 14 - Sat, Jun 21

Frontier flights from Philadelphia to Chicago Midway Airport

Our best Frontier deals on Philadelphia to Chicago Midway Airport flight tickets
Frontier
Jan 6
PHL7:38 pmPhiladelphia
2h 26m
MDW9:04 pmChicago Midway
Jan 9
MDW7:30 amChicago Midway
9h 51m
1 stop
PHL6:21 pmPhiladelphia
Frontier
Feb 8
PHL6:03 pmPhiladelphia
6h 26m
1 stop
MDW11:29 pmChicago Midway
Feb 15
MDW4:48 pmChicago Midway
6h 13m
1 stop
PHL12:01 amPhiladelphia
Frontier
Feb 6
PHL1:41 pmPhiladelphia
5h 45m
1 stop
MDW6:26 pmChicago Midway
Feb 10
MDW6:15 amChicago Midway
12h 11m
1 stop
PHL7:26 pmPhiladelphia

Southwest flights from Philadelphia to Chicago Midway Airport

Our best Southwest deals on Philadelphia to Chicago Midway Airport flight tickets
Southwest
Jan 29
PHL1:50 pmPhiladelphia
2h 15m
MDW3:05 pmChicago Midway
Jan 29
MDW6:15 pmChicago Midway
1h 50m
PHL9:05 pmPhiladelphia
Southwest
Jan 22
PHL1:50 pmPhiladelphia
2h 15m
MDW3:05 pmChicago Midway
Jan 29
MDW12:25 pmChicago Midway
1h 50m
PHL3:15 pmPhiladelphia
Southwest
Feb 20
PHL7:05 pmPhiladelphia
2h 20m
MDW8:25 pmChicago Midway
Feb 25
MDW10:05 amChicago Midway
1h 55m
PHL1:00 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 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 $104. 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 $109. 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 $186.

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 $134 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $179. 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 $168. 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 35% 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 December 2024, prices for Philadelphia to Chicago Midway Airport flights are approximately 24% 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

$39

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 $39. The best round-trip flight deal from Philadelphia to Chicago Midway Airport found on momondo in the last 72 hours is $98.
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
6.1
3,468 reviews
Search Frontier flights
SouthwestPriceFrom $150Free CancellationRating
8.1
4,765 reviews
Search Southwest flights
DeltaPriceFrom $188Free CancellationRating
8.0
8,580 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 22 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 $238. Our users have rated Southwest at 8.1/10.

  • Frontier Flights From Philadelphia to Chicago Midway Airport

    Frontier (6.1/10 from 3,468 reviews) operates around 2 flights from Philadelphia to Chicago Midway Airport in any given week. The average Frontier airfare for this route is around $138, 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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