Find cheap flights from Philadelphia to Chicago Midway Airport

PHL - MDW

Find cheap flights from Philadelphia to Chicago Midway Airport

Round-trip
Economy
Philadelphia (PHL)
Chicago Midway
Tue 12/1
Tue 12/8
Any month
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Good to know

Low season

August Best time to beat the crowds with an average 47% drop in price.

High season

March Most popular time to fly with an average 23% increase in price.

Average price round-trip

$271 (avg. price over the last 2 weeks)

Good deal round-trip

$219 or less

Good deal one-way

$143 or less

When to book flights from Philadelphia to Chicago Midway

Estimated round-trip price
Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for finding a cheap flight

  • Looking for a cheap flight? 25% of our users found flights on this route for $143 or less one-way and $219 or less round-trip.
  • The cheapest flight from Philadelphia to Chicago Midway Airport was found 14 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be February, March and April. The cheapest month to fly is August.
  • Morning departure is around 12% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for booking Philadelphia to Chicago Midway Airport flights

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Top airline flying Philadelphia to Chicago Midway

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 28,799 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Pros: "Friendly crew. Landed early."

Cons: "Safe and happy travel!"

Pros: "Good customer service in person"

Cons: "I had a 4 hour layover in Minneapolis, there was another flight to Denver that I meant I could’ve been home three hours earlier had I done standby, but because I had a cheaper ticket I was not allowed that opportunity. That makes absolutely no sense to me seeing as my flight was packed. I’m sorry my flight saved me money"

Pros: "Not like"
Cons: "I have Sky Team Elite Plus Platinum but not fare anything!"

Pros: "Ease of check in and friendly people"
Cons: "Marta"

Pros: "Did not wait for luggage."
Cons: "Food was marginal. Equipment had low ceiling under carry on shelf. No entertainment."

Pros: "Delta provided great entertainment options and it felt like endless food and drinks. The seats were also a bit more spacious than usual"

Cons: "They cancelled my ticket and did not inform me. Horrible exlefywith JustFly.com Beware of this organization"

Pros: "The exit row seat on this leg out of PHL to SLC did recline! No need for Delta Comfort+ unless you want to get off of the plane ... faster."
Cons: "For some reason, the pilot couldn't figure out how to adjust the cabin temperature for the first hour or so. This made the flight (and I was sitting in an exit row seat, right by the door which is usually cooler) uncomfortably hot and muggy. Food? No food. Thank goodness for Delta Lounge (even if it was the one in PHL). Just snacks make this a poor option for many. I don't know what is up, but the USB charger on the two monitors didn't work and neither did the outlet between the seats. And I have two different sets of cables "just in case" and they're the 3-in-1 so I can try to charge multiple devices (Apple, Android and Samsung) but nothing worked."

Pros: "Staff personalities"
Cons: "Waited extra 20 mins after door closed to-complete loading luggage"

Pros: "Staff was very courteous, the flight was smooth."
Cons: "There was no TV's on this flight."

Pros: "There was one helpful lady"
Cons: "Flight was rerouted and rebooked twice. I’m stuck in Detroit overnight, and won’t be getting to Monterrey until tomorrow afternoon. Thanks, delta!"

Cons: "Flight delayed 2 hrs"

Pros: "After almost every airline cancelled. Delta still took me to where I needed to go with not one single problem. That pilot was amazing. I forget his name. But the plane didn't slide or anything during take off. Amazing."
Cons: "What was there not to like. We were a little bit late but I wasn't in a rush. I planned well ahead. Delta moved my flight from 10 a.m. to 6 a.m. and that was perfectly fine with me."

Pros: "Uneventful flight - boarding was great and there were no hassles."
Cons: "No food. No onboard entertainment."

Pros: "Flight attendants were really kind"
Cons: "We were an hour late to leave so I missed my connecting flight and am currently stuck in Minneapolis for nearly 8 hours now"

Pros: "Stewardesses were sympathetic but could do nothing."
Cons: "A few flurries out of Philadelphia and flight is delayed 2.5 hrs, we therefore miss our connection and all they wanted us to do was spend 2 days in airport until next flight. Finally reached a compassionate soul at customer service who got creative and routed us to BCN via ATL, Miami and Madrid."

Pros: "Got upgraded to 1st / Business class."
Cons: "Due to weather the power outage in ATL, the flight out of PHL was delayed by about 30 minutes. No movies. No meals."

Pros: "Was initially hoping to fly a US airline but will now look for Aeromexico first. Exceeded my expectations!"
Cons: "The layover in Mexico City was a bit long and the airport was not so great"

Pros: "We were probably in the air for 30 mins; great short flight. Plane wasn’t filled so had plenty of space."

Pros: "Crew was very attentive and curtious. Boarding was a bit more chaotic than usual and the gate agent made no announcement about boarding procedure, which certainly contributed to the scrum resulting. I arrived from the Skyclub several minutes prior to boarding time and was unable to find a path through to the Priority Boarding Lane. As boarding began she had to redirect at least seventy-five percent of those in front of me as they were not in First Class. Had she made one or more clear announcements about boarding procedure I rather doubt such a misunderstanding would have occurred with so many."
Cons: "For the third Delta flight in a row (all First Class) the crew did not make any effort to keep economy class cuctomers form storing bags in the First Class overhead or using the only First Class laveratory during flight. This flight I was unable to utilize the laveratory even once due to this excessive and continuous useage. Trying to do my bit to reduce our carbon footprint, yet I am sorely tempted to return to charter service when disrespect of the airlines own basic service class rules gets piled on top of TSA hassles."

Pros: "I had a window seat"
Cons: "bumpy flight"

Pros: "Boarding, checking in etc. The usual stuff, nothign spectacular."
Cons: "Seats are getting too crowded!"

Pros: "Flight attendant insisted to take my jacket. She didn’t return led. I forgot jacket in Cincinnati"
Cons: "I need my jacket"

Pros: "As usual, Delta staff and crew did their best to make the flight quite enjoyable and smooth."

Pros: "The crew was beyond friendly and courteous. Lots of leg room."
Cons: "I was an older plane, it was louder than our flight down to Atlanta. Nothing they could do about it, but a slight annoyance."

Pros: "one i got to gate i could relax"
Cons: "scary making connection from AA flight arriving int'l terminal"

Pros: "Friendly and informative flight attendants kept the passengers in reasonable spirit."
Cons: "Left nearly an hour late after confusion related to oversold seats and upgrades. The gate agent entered the plane multiple times. The landing was rough, the brakes were loud."

Pros: "I appreciated the kindness of the staff at each of our stops. From beginning to end they were polite, helpful, and kind!"

Pros: "All crew was great"
Cons: "We lost checked bag or it was taken, will loss a half day shopping for replacements. Compensation policy very unclear, not counting on getting any."

Pros: "Arrived on time crew worked had"
Cons: "my seat was BAD , no recline- right by bathroom one of which was out of order."

Cons: "Compared to such airlines like Turkish or etihad, service and comfort was lacking behind."

Cons: "On time"

Pros: "Liked the plane and the leg room. Had to switch itenary due to weather and the gate agent did a great job."

Pros: "The crew was friendly and accommodating, and service was good"
Cons: "I purchased a basic economy ticket and upon checking in, my Delta app said my seat was unassigned and I had to get my boarding pass at the airport. I checked back later and the app had me as number 7 on the standby list. I called Delta (wait time 3+ hours... my flight was in 3), and then the Delta app support where I was able to get through to someone. She told me that the ticket I purchased over a month in advance did not guarantee me a seat on the plane (???). She said that if I was bumped from the flight they would reschedule me for the next morning. She was pretty rude and made it seem like I had a 50/50 shot of getting on this plane. I rushed to the airport in hopes that I would be the first from Standby there, and the gate agent told me that I was fine and would board right after first class and be assigned a seat then. Great. Once I got my seat assignment, I board to find out there is someone else sitting in my seat...... They eventually called the desk and had her moved, but it was the weirdest boarding experience I've had.. and I've flown Spirit. These planes that Delta fly's are SO OLD. Both times I have flown Delta the "turbulence" has been so bad and cold air was blowing right on my the whole flight with no option to turn it off (it wasn't from one of the vents, but from the side). Someone close to me works for Delta and I know for a fact that some of their engines blow mid-flight.. and they tell the passengers that it's turbulence.. so that doesn't make me feel very safe. I won't fly Delta again if there is another comparable option."

Pros: "Airplane was good, boarding was fast."

Cons: "The original flight was canceled and a new one substituted - basically they wanted to fly a smaller aircraft (via a different regional carrier) so the flight number changed. PHL did not have the new flight info displayed at the Departures board or on the screen at the gate. Caused a little anxiety."

Cons: "Cramped, uncomfortable tin can of an airplane. Barely tolerable for even an hour’s flight."

Cons: "Flight attendants were a little snobby and didn't treat all passengers equally, in my humble opinion (note: I was sitting in 1st class)."

Cons: "Delta Flight #1661 I paid for 1st class. My first flight was late so I arrived at the gate after boarding began. When the gate attendant scanned my ticket another printed. When he handed me the ticket my seat had changed to seat 25E. I told the attendant that I had paid for first class. He asked me to step aside while he contacted his supervisor, Joe. Then I had to wait until ENTIRE flight had boarded which defeated part of the reason I paid for the upgrade. This was on top of the fact I was so thirsty because 1st flight didn't have drink service and because it was late I had to book it to the connection arriving sweaty, hot and needing to use the bathroom. I was told they had given my seat away to someone as a free upgrade. Joe offered me a $100 voucher to take other seat which was less than I paid for 1st class, plus the seat was a middle seat in the rear of the plane. When I told him as much, he tried to manipulate me by telling me that they would have to kick someone out of my seat. When I declined the downgrade, they made me stand by while they kicked someone out of my seat which was embarrassing and humiliating. Then, when they handed me a new boarding pass, it was not the seat I had paid for and selected, instead it was in the first row, which I’ve always hated because there is no under seat storage and I cannot keep my backpack with me. When I pay for first class, it is primarily so that I can board first and so that I have extra room to work (which I need access to my bag to do). While I was trying to take out the minimum of the things I needed from my bag and figure out how to manage without it, 3 times a flight attendant told me they had to take my bag (since I was the last person to board they tried to prevent me from using the bathroom and they were anxious to leave early). I tried to explain that Delta had prevented me from boarding earlier and that they gave away the seat I paid for which was NOT the first row."

Pros: "Service was great. Seating was OK. It was a brand new vehicle, so the (climate/air handling) was great."
Cons: "Boarding was not well organized."

Pros: "I liked that I didn't have to pay for a carry on and the blanket they gave me in flight to stay warm it was a great flight."
Cons: "Only dislike was that the flight was ending other than that no problems"

Pros: "Flight left on time despite the problems"
Cons: "We waited for one hour to be able to board. The system crashed so we were very lucky to arrive very early to the airport"

Pros: "This was a routine fight that was handled well but Delta and crew."

Pros: "Always have great experience with Delta flight attendants and staff. The entertainment on mobile phone was a really nice add-on, I had never seen before."
Cons: "Flight was delayed in taking off, waiting for connecting passengers. Plane was old, which is most Delta planes, but this one showed it. The tray table looked like it was from the 70s or 80s. Flying into Midway instead of O'hare was anticlimactic."

Pros: "Even though we had to tax over to the de-Icing pad before we could take off from Philadelphia, we were still in the air by our original departure time. Our flight was accompanied by tail winds that got us to Detroit early giving me plenty of time to make my connecting flight."

Pros: "Everything was perfect!"
Cons: "Not one negative!!"

Pros: "The travel time was excellent, layover was quick, TSA was not bad at all.... The only problem I had was seat size... I'm 6'4 and both aisle seat was not I had was not comfortable... The layover flight from ATL to HOU wasn't assigned until I got to the desk before the flight... I guess I got to do a better job buying seats in the future"

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Philadelphia to Chicago Midway

Airlines flying from Philadelphia to Chicago Midway have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Philadelphia to Chicago Midway

Mandatory masks

Masks required on board, masks provided on flights from Philadelphia to Chicago Midway

Social distancing seating

Middle seats unavailable to book on flights from Philadelphia to Chicago Midway

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Philadelphia to Chicago Midway

Book cheap flights from Philadelphia to Chicago Midway Airport

Recent round-trip flight deals

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Recent one-way flight deals

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