MDW - PHL

$97 Find Cheap Flights from Chicago Midway Airport to Philadelphia - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 25% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$170
Typical prices: $261-$398
Frontier
Sun 11/11Sat 11/17
MDW - PHL • 1 stop
Cheapest non-stop
$257
Typical prices: $264-$403
Southwest
Mon 11/12Sat 11/17
MDW - PHL • Non-stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 1h 56m
Direct flights
+1
Direct flights
+1
When to book
11 weeks
in advance
Our data shows that travelers who book at least 11 weeks in advance save around 28% compared to booking last minute.
Insights
Insights
When to travel
January
Cheapest • 48% price drop
October
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Orlando (MCO)
Cheapest • Avg $188 (round-trip)
Detroit Metropolitan Wayne County (DTW)
Shortest trip • 3h 39m (one-way)
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Philadelphia!

Cheap Flights from Midway to Philadelphia (MDW-PHL)

 

Cheap flights from Midway to Philadelphia with top airlines, updated regularly. Compare round-trip, one-way, direct and last-minute deals.

Wed, Nov 11 - Tue, Nov 17
Frontier Logo
6:08 am - 11:16 pmMDW  Chicago Midway-PHL Philadelphia
16h 08m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
5:14 pm - 11:47 pmPHL  Philadelphia-MDW Chicago Midway
7h 33m1 stop Atlanta Hartsfield-Jackson
$170Frontier
Fri, Nov 13 - Tue, Nov 17
Frontier Logo
6:42 pm - 7:21 amMDW  Chicago Midway-PHL Philadelphia
11h 39m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
5:14 pm - 11:47 pmPHL  Philadelphia-MDW Chicago Midway
7h 33m1 stop Atlanta Hartsfield-Jackson
$175Frontier
Thu, Nov 12 - Tue, Nov 17
Frontier Logo
6:08 am - 6:19 pmMDW  Chicago Midway-PHL Philadelphia
11h 11m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
12:36 pm - 5:47 pmPHL  Philadelphia-MDW Chicago Midway
6h 11m1 stop Atlanta Hartsfield-Jackson
$178Frontier
Thu, Nov 12 - Sat, Nov 14
Frontier Logo
6:42 pm - 7:21 amMDW  Chicago Midway-PHL Philadelphia
11h 39m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
5:14 pm - 11:47 pmPHL  Philadelphia-MDW Chicago Midway
7h 33m1 stop Atlanta Hartsfield-Jackson
$178Frontier
Thu, Nov 12 - Tue, Nov 17
Southwest Logo
3:50 pm - 6:45 pmMDW  Chicago Midway-PHL Philadelphia
1h 55mnonstop
Southwest Logo
1:25 pm - 2:40 pmPHL  Philadelphia-MDW Chicago Midway
2h 15mnonstop
$257Southwest
Thu, Nov 12 - Thu, Nov 26
Southwest Logo
7:25 pm - 10:20 pmMDW  Chicago Midway-PHL Philadelphia
1h 55mnonstop
Southwest Logo
7:55 am - 9:10 amPHL  Philadelphia-MDW Chicago Midway
2h 15mnonstop
$257Southwest
Thu, Nov 5 - Mon, Nov 9
Southwest Logo
3:50 pm - 6:45 pmMDW  Chicago Midway-PHL Philadelphia
1h 55mnonstop
Southwest Logo
1:50 pm - 3:05 pmPHL  Philadelphia-MDW Chicago Midway
2h 15mnonstop
$257Southwest
Tue, Nov 3 - Thu, Nov 5
Delta Logo
11:39 am - 8:30 pmMDW  Chicago Midway-PHL Philadelphia
7h 51m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:10 am - 9:32 amPHL  Philadelphia-MDW Chicago Midway
4h 22m1 stop Detroit Metropolitan Wayne County
$277Delta
Wed, Nov 11 - Thu, Nov 26
Delta Logo
1:31 pm - 7:19 pmMDW  Chicago Midway-PHL Philadelphia
4h 48m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:00 am - 11:25 amPHL  Philadelphia-MDW Chicago Midway
6h 25m1 stop Detroit Metropolitan Wayne County
$277Delta
Sat, Nov 7 - Sat, Nov 7
Delta Logo
6:04 am - 12:53 pmMDW  Chicago Midway-PHL Philadelphia
5h 49m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:13 pm - 10:33 pmPHL  Philadelphia-MDW Chicago Midway
5h 20m1 stop Atlanta Hartsfield-Jackson
$277Delta

Price, demand and travel trends for Chicago Midway Airport to Philadelphia flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Chicago Midway Airport to Philadelphia?

Round-trip flights from Chicago Midway Airport to Philadelphia typically range from $261 to $398. The lowest price found in the past 5 days was $170, on Frontier.

What's the cheapest day of the week to fly from Chicago Midway Airport to Philadelphia?

Based on deals KAYAK users found in the last 12 months, Thursday is the cheapest day of the week to fly from Chicago Midway Airport to Philadelphia. It’s 11% cheaper than the average day, while Tuesday is the most expensive, with prices 12% higher.

What’s the cheapest month to fly from Chicago Midway Airport to Philadelphia?

•January is the cheapest month to fly from Chicago Midway Airport to Philadelphia at $168 round-trip.
•June ($413) and February ($403) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 145% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Chicago Midway Airport to Philadelphia the cheapest?

Flights from Chicago Midway Airport to Philadelphia are cheapest 11 weeks before departure. Booking in this window typically costs about 28% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Find deals

Expert advice for your flight from Midway to Philadelphia

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on Frontier and MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Harriet Baskas

Harriet Baskas

Expert on PHL

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more

Key details for Chicago Midway Airport to Philadelphia flights

Low season

January

Cheapest flight

$97
Beat the crowds with an average 66% drop in travelers.
The most popular month to fly with an average 44% increase in travelers.
One-way flight from Chicago Midway Airport to Philadelphia

When to book flights from Midway to Philadelphia

Are your dates flexible? Find out the best times to travel from Midway to Philadelphia based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago Midway Airport to Philadelphia flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Chicago Midway Airport to Philadelphia?

    These are the earliest and latest flight times available from Chicago Midway Airport to Philadelphia:

    • Earliest: departs at 6:20 am and lands at 8:16 am
    • Latest: departs at 8:30 pm and lands at 10:26 pm.

    The flight takes about 1h 56m.

  • What cabin classes can I book on flights from Chicago Midway Airport to Philadelphia?

    Only Economy Class is available on flights from Chicago Midway Airport to Philadelphia.

  • How long is a flight from Chicago Midway Airport to Philadelphia?

    A nonstop flight from Chicago Midway Airport to Philadelphia takes 1h 56m, covering 666 miles.

  • Do I need a passport to fly from Chicago Midway Airport to Philadelphia?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Chicago Midway Airport to Philadelphia flight?

    Round-trip flights from Chicago Midway Airport to Philadelphia range from $261 to $398, with an average of $324 over the past 12 months. Anything below $261 counts as a good deal.

  • How expensive are last-minute Chicago Midway Airport to Philadelphia flights?

    Last-minute fares on this route (booked within two weeks of departure) run 16% above the $324 route average. Book 11 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Chicago Midway Airport to Philadelphia?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $188 round-trip via Orlando (MCO), compared to $327 for nonstop.

  • What is the standard checked-bag allowance on flights from Chicago Midway Airport to Philadelphia?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$91 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Chicago Midway Airport to Philadelphia?

    The Boeing 737-800 family is used most often on this route, operated mainly by American Airlines and United Airlines. Other aircraft seen on the route include Boeing 737 MAX 8 variants.

  • How are flight departures from Chicago Midway Airport to Philadelphia spread across the day?

    Afternoon is the busiest departure period on Chicago Midway Airport to Philadelphia flights, with 50% of flights leaving in that window. Morning departures account for 25%, evening flights for 25%, and night flights for 0%.

  • Have flight prices from Chicago Midway Airport to Philadelphia changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $178 to $1,464. That means the highest observed fare was about 8x higher than the lowest one.

  • How are flight prices from Chicago Midway Airport to Philadelphia looking right now?

    One-way fares from Chicago Midway Airport to Philadelphia are currently lower than usual. Average one-way flight prices are about $119, which is 44% below the typical average for this route.

  • What car rental options are available at Philadelphia Airport (PHL)?

    Philadelphia Airport (PHL) hosts 5 major car rental companies, with daily rates starting from around $28 for economy cars. Top options include:

    • Payless
    • Dollar
    • Hertz
    • Thrifty
    • Alamo

  • Which airports can I use when flying from Chicago Midway Airport to Philadelphia?

    Flights from Chicago Midway Airport to Philadelphia usually depart from Chicago Midway (MDW) and arrive at Philadelphia (PHL).

  • Which airports do connecting flights from Chicago Midway Airport to Philadelphia pass through?

    One-stop flights from Chicago Midway Airport to Philadelphia most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 91% of one-stop connections
    • Detroit Metropolitan Wayne County (DTW) - 5% of one-stop connections
    • Orlando (MCO) - 5% of one-stop connections

  • Can I save money by using flexible dates for flights from Chicago Midway Airport to Philadelphia?

    Yes. Flexible dates can save you up to 21% on flights from Chicago Midway Airport to Philadelphia. Thursday is the cheapest departure day at $289 round-trip on average, while Tuesday is the most expensive at $363, a difference of $74.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Chicago Midway Airport to Philadelphia?

    Only Southwest operates flights between Chicago Midway Airport and Philadelphia.

  • How much time can I save by choosing a different layover airport from Chicago Midway Airport to Philadelphia?

    Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 3h 39m, compared with 6h 30m via Atlanta Hartsfield-Jackson (ATL) and 10h 32m via Orlando (MCO).

  • What is the time difference between Chicago Midway Airport and Philadelphia?

    Philadelphia is 1 hour ahead of Chicago Midway Airport (Eastern Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Philadelphia?

    Some of the most popular sights in Philadelphia are Philadelphia Convention Center, Rittenhouse Square and Philadelphia Stadium. These are among the most viewed places in Philadelphia on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Chicago Midway Airport to Philadelphia flights?

    Among airlines operating Chicago Midway Airport to Philadelphia flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Chicago Midway Airport to Philadelphia flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Chicago Midway Airport to Philadelphia flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Thursday departure and avoid flying on Tuesday. On this route, Thursday flights average $289, about $74 less than Tuesday fares (20% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 11 weeks before you fly. On this route, that window historically saves about 28% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago Midway Airport to Philadelphia trip for January. Fares historically average $168 round-trip in that month - typically $245 less than the most expensive month, which is June (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Orlando Airport (MCO) can be cheaper than flying direct. The cheapest layover option averages $188 round-trip on this route - about $139 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Philadelphia Airport.

    • Embassy Suites by Hilton Philadelphia Airport
    • Sonesta Select Philadelphia Airport
    • Microtel Inn & Suites by Wyndham Philadelphia Airport

Prefer to fly direct from Chicago Midway Airport to Philadelphia?

 
Find which airlines fly direct from Chicago Midway Airport to Philadelphia Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to Philadelphia

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Philadelphia to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

More options for your flight from Midway to Philadelphia

Complete your trip to Philadelphia with a hotel stay or car rental

Car rentals in Philadelphia
Hotels in Philadelphia
Vacations in Philadelphia