Find cheap flights from Pensacola to Chicago Midway Airport

PNS - MDW

Find cheap flights from Pensacola to Chicago Midway Airport

Round-trip
Economy
Pensacola (PNS)
Chicago Midway
Sun 1/24
Sun 1/31
Any month
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Good to know

Low season

June Best time to beat the crowds with an average 56% drop in price.

High season

December Most popular time to fly with an average 42% increase in price.

Average price round-trip

$354 (avg. price over the last 2 weeks)

Good deal round-trip

$338 or less

Good deal one-way

$168 or less

When to book flights from Pensacola to Chicago Midway

Estimated round-trip price
Average price per month

Top tips for finding a cheap flight

  • Looking for a cheap flight? 25% of our users found flights on this route for $168 or less one-way and $338 or less round-trip.
  • High season is considered to be November, December and January. The cheapest month to fly is June.
  • Morning departure is around 41% 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 Pensacola to Chicago Midway Airport flights

Are there Chicago Midway Airport travel restrictions currently due to Coronavirus?

How long does a flight from Pensacola to Chicago Midway Airport take?

Which airlines provide the cheapest flights from Pensacola to Chicago Midway Airport?

Do I need a passport to fly between Pensacola and Chicago Midway Airport?

What’s the cheapest day of the week to fly Pensacola to Chicago Midway Airport?

How does KAYAK find such low prices on flights from Pensacola to Chicago Midway Airport?

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What is the Hacker Fare option on flights from Pensacola to Chicago Midway Airport?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Pensacola to Chicago Midway Airport?

Top airline flying Pensacola to Chicago Midway

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 28,923 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Cons: "Just water and coffee. Needed some variety."

Pros: "Quick boarding process! Everything was on time as estimated."

Pros: "nice crew and newer plane"

Pros: "Nice crew, easy process"
Cons: "Everything was fine"

Cons: "Filthy plane, and delayed too long"

Pros: "Wow. I have been flying American and United for years. Delta is friendly, competent, professsional and enjoyable. They treated us like friends instead of like cattle. It was great! Great job Delta. Oh, and for the first time in 50 years of flying my bags arrived sky first. Yes! They get it!"
Cons: "Perfect experience. Well done. Treat people like friends. Simple. Works."

Pros: "Nothing exceptional stands out"
Cons: "Flight was not on time"

Pros: "Everything met my expectations"
Cons: "Refreshments"

Pros: "Flights were both timely"
Cons: "WiFi on flight from Atl to Tallahassee wasn’t working at first"

Cons: "WiFi didn't work"

Pros: "It was fine. They didn't charge me for the exit row, so that was nice"
Cons: "N/a. It was fine"

Pros: "The seat was comfortable"
Cons: "Seats could be a couple of inches wider"

Pros: "Very smooth and friendly TSA personnel at the security point. Very friendly and respectful of the military. My husband is a Vietnam veteran."

Pros: "Boarding was smooth"
Cons: "Awful flight attendant that was rude in not passing a snack to us and then not handing a bottle of water to me when snacks were being stroked to the passengers. When asking her why she didn't provide us a snack she said that this is a plane and when the captain says we have to land that she doesn't have to pass out snacks. The interesting thing is that all the other passengers around us receive snacks and bottled water except us. When we were leaving the plane after it landed my mom had to stay behind while I went to the front of the plane a good wheelchair assistance. The same stewardess said why did your son leave you and my mother had to correct her and say that he went to the front to get wheelchair assistance. The lady was very rude and didn't know proper manners."

Pros: "see above"

Pros: "No surprises. On time. Courteous. I suppose the most amazing thing is their app. It tells you when your bags get on! Also I forgot that I had a knife in my pocket. I ran back to the desk and she went back, found my bag, put the knife in there. Wow. What service. Also I notice that Atlanta is a lot nicer than it use to be. Attendants are more friendly and loading is more organized. Way to go Delta."

Pros: "Great employees, genuine, quick drink service, early arrival, available entertainment"
Cons: "Boarding process was slow and backed up due to extra baggage needing to be checked involuntarily"

Pros: "We flew Delta from Rome to Atlanta. Everyone was very accommodating and we had no problem with our tickets"

Pros: "Nothing"
Cons: "The fact that I sat on an airplane for over three hours due to a delay and couldnt get off"

Pros: "The flight was good but the air didn’t work again plane was warm the space was limited but the movies were good the flight attendants were OK"

Pros: "Clean and spacious plane, relaxed and organized gate cre"
Cons: "Crew member passing out ear buds ran out and never came back"

Pros: "Large jet, attentive crew, on time."

Pros: "20 minutes ahead of schedule"

Pros: "Everything was very standard, good crew, good gate agents, smooth flight."
Cons: "I purchase tickets using credit card points and was not allowed to have seat assignments until 24 hours before the flight. This is NOT going to work for me in the future"

Cons: "The boarding process is quite confusing with all the different categories of people prior to the actual listed "zone" boarding. As an example, if you have a "Zone 2" boarding pass, you think you will be second to board when in reality that means you are second to last to board. After those who need extra time, those with small children, active military, premier, whatever.... all that covers about 2/3 of the passengers. Then of course there's all the stepping over those who already boarded which seems to slow the process overall. It would be better to ask these questions when making your reservation. Then, the zones would be appropriate based on how you made your reservation to begin with."

Cons: "Flight delayed 2 hrs"

Pros: "No issues boarding as a group of 6, including one child. We all had at least a personal item and/or a carry-on to stow. The flight was easy, comfortable, and the free movies were current and definitely helped pass the time."
Cons: "We were seated right behind the delta comfort+ and saw the special snacks they got. Being teased by that is not a huge deal, just a little disappointed by the regular snack selection, the snack mix was definitely subpar."

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: "Nicest crew"

Cons: "Force me to take a bad seat"

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"

Cons: "Courtesy, on time and good communication."

Cons: "Took forever to board and get off the plan."

Pros: "Not much"
Cons: "Security line, waiting an hour to take off, no time for drink service. Awful flight"

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

Cons: "Hurricane Irma, I was lucky enough to get a refund do to the natural disaster."

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: "Boarding was quick and efficient. Landed early!"
Cons: "Food was Meh but fine"

Cons: "Long delay due to maintenance of oxygen masks issue. Why hadn't this been taken care of with preventive maintenance?"

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."

Cons: "Seating close and uncomfortable especially next to a big ol' boy."

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."

Cons: "Connection flight from LAX to Seattle was dropped off of booking completely. When Delta was able to fix the changes in Sydney Australia they put my husbands ticket as a standby instead of putting him in an assigned seat and reported that they couldn't fix it that we would have to wait and get to LAX before the changes could be made again. There was a one and a half hour flight delay from LAX to Seattle. From Sydney Australia to LAX entertainment system didn't work the whole entire flight, they were screaming children the entire flight, and Delta had double booked seats on several different people. There were no apologies and no compensation for any of the incidences."

Cons: "The flight attendant looked like she was mad throughout the whole 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: "Boarding was inefficient. Plane was packed to the last seat. No food for purchase."

Pros: "The plane was changed so some people had new seat and some not. The crew assigned tickets quickly at the entrance. Arrived 20 min earlier, which is great!"
Cons: "The peanut bad is now contains 13 peanuts, I counted them :).Where is a good food for a 3.5 hours flight?"

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: "Very good boarding process and on time for out international flight."

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Pensacola to Chicago Midway

Airlines flying from Pensacola 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 Pensacola to Chicago Midway

Mandatory masks

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

Social distancing seating

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

Pre-flight testing

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

Book cheap flights from Pensacola to Chicago Midway Airport

Recent round-trip flight deals

2/16
Tue
1 stop
Delta
3h 58m
PNS - MDW
2/23
Tue
1 stop
Delta
4h 47m
MDW - PNS
2/26
Fri
1 stop
Delta
5h 02m
PNS - MDW
2/27
Sat
1 stop
Delta
4h 02m
MDW - PNS
2/17
Wed
1 stop
Delta
4h 15m
PNS - MDW
3/4
Thu
1 stop
Delta
5h 38m
MDW - PNS
3/12
Fri
1 stop
Delta
8h 16m
PNS - MDW
3/14
Sun
1 stop
Delta
5h 38m
MDW - PNS
2/26
Fri
1 stop
Delta
6h 59m
PNS - MDW
2/27
Sat
1 stop
Delta
16h 02m
MDW - PNS
7/22
Thu
1 stop
Delta
3h 56m
PNS - MDW
7/25
Sun
1 stop
Delta
4h 16m
MDW - PNS
7/22
Thu
2 stops
Delta
7h 20m
PNS - MDW
7/25
Sun
1 stop
Delta
4h 16m
MDW - PNS
2/15
Mon
1 stop
Delta
5h 02m
PNS - MDW
2/18
Thu
1 stop
Delta
3h 53m
MDW - PNS
1/28
Thu
1 stop
Delta
4h 05m
PNS - MDW
2/4
Thu
1 stop
Delta
3h 53m
MDW - PNS
1/29
Fri
1 stop
Delta
4h 00m
PNS - MDW
1/31
Sun
1 stop
Delta
5h 20m
MDW - PNS
2/17
Wed
2 stops
Multiple Airlines
25h 43m
PNS - MDW
3/4
Thu
2 stops
Multiple Airlines
39h 07m
MDW - PNS
2/17
Wed
3 stops
Multiple Airlines
30h 13m
PNS - MDW
3/4
Thu
3 stops
Multiple Airlines
26h 06m
MDW - PNS
2/17
Wed
3 stops
Multiple Airlines
30h 13m
PNS - MDW
3/4
Thu
2 stops
Multiple Airlines
26h 06m
MDW - PNS
2/14
Sun
1 stop
Delta
5h 02m
PNS - MDW
2/28
Sun
1 stop
Delta
3h 53m
MDW - PNS
6/12
Sat
1 stop
Delta
4h 27m
PNS - MDW
6/26
Sat
1 stop
Delta
5h 38m
MDW - PNS
6/12
Sat
2 stops
Delta
6h 10m
PNS - MDW
6/26
Sat
1 stop
Delta
7h 13m
MDW - PNS
2/22
Mon
1 stop
Delta
6h 59m
PNS - MDW
2/26
Fri
1 stop
Delta
4h 47m
MDW - PNS
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Recent one-way flight deals

2/16
Tue
1 stop
Delta
5h 25m
PNS - MDW
2/6
Sat
1 stop
Delta
3h 53m
PNS - MDW
2/1
Mon
1 stop
Delta
6h 59m
PNS - MDW
2/20
Sat
2 stops
Multiple Airlines
31h 23m
PNS - MDW
1/29
Fri
1 stop
Delta
5h 02m
PNS - MDW
2/17
Wed
3 stops
Multiple Airlines
30h 13m
PNS - MDW
2/6
Sat
3 stops
Multiple Airlines
47h 28m
PNS - MDW
2/15
Mon
1 stop
Delta
5h 02m
PNS - MDW
2/19
Fri
3 stops
Multiple Airlines
48h 09m
PNS - MDW
4/3
Sat
3 stops
Multiple Airlines
31h 58m
PNS - MDW
3/18
Thu
3 stops
Multiple Airlines
31h 14m
PNS - MDW
2/16
Tue
3 stops
Multiple Airlines
54h 13m
PNS - MDW
1/29
Fri
3 stops
Multiple Airlines
23h 37m
PNS - MDW
2/14
Sun
3 stops
Multiple Airlines
52h 29m
PNS - MDW
2/1
Mon
3 stops
Multiple Airlines
47h 37m
PNS - MDW
4/3
Sat
2 stops
Delta
7h 20m
PNS - MDW
2/1
Mon
2 stops
Linear Air Taxi
26h 18m
PNS - MDW
1/29
Fri
2 stops
Linear Air Taxi
10h 03m
PNS - MDW
2/17
Wed
2 stops
Linear Air Taxi
10h 03m
PNS - MDW
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