MDW - PNS

$115 Find Cheap Flights from Chicago Midway Airport to Pensacola

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Pensacola departing on 4/18. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult

KAYAK searches hundreds of travel sites at once for deals on flights to Pensacola

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Pensacola, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Pensacola, as well as popular online travel agencies
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Cheap Flight Deals from Midway to Pensacola (MDW-PNS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Pensacola that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Midway to Pensacola

KAYAK's recommended round-trip deals from the most popular airlines that fly from Midway to Pensacola.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Southwest Logo
10:45 am - 1:00 pmMDW-PNS
2h 15mnonstop
Southwest Logo
11:30 am - 5:05 pmPNS-MDW
5h 35m1 stop
$219Southwest
Find Deal
Sun, Apr 27 - Tue, Apr 29
Southwest Logo
5:25 pm - 9:55 pmMDW-PNS
4h 30m1 stop
Southwest Logo
5:30 pm - 11:30 pmPNS-MDW
6h 00m1 stop
$229Southwest
Find Deal
Sat, Jun 14 - Sat, Jun 21
Southwest Logo
11:15 am - 4:25 pmMDW-PNS
5h 10m1 stop
Southwest Logo
3:15 pm - 10:55 pmPNS-MDW
7h 40m1 stop
$234Southwest
Find Deal
Sun, May 11 - Thu, May 15
Southwest Logo
5:25 pm - 9:55 pmMDW-PNS
4h 30m1 stop
Southwest Logo
6:10 pm - 12:10 amPNS-MDW
6h 00m1 stop
$239Southwest
Find Deal
Sat, Jun 21 - Thu, Jun 26
Delta Logo
4:15 pm - 9:36 pmMDW-PNS
5h 21m1 stop
Delta Logo
4:03 pm - 9:38 pmPNS-MDW
5h 35m1 stop
$249Delta
Find Deal
Sat, Jun 7 - Wed, Jul 2
Delta Logo
6:04 am - 9:54 amMDW-PNS
3h 50m1 stop
Delta Logo
7:05 am - 11:53 amPNS-MDW
4h 48m1 stop
$259Delta
Find Deal
Mon, Apr 28 - Thu, May 8
Frontier Logo
8:03 pm - 3:28 pmMDW-PNS
19h 25m1 stop
Frontier Logo
4:30 pm - 7:08 pmPNS-MDW
26h 38m1 stop
$320Frontier
Find Deal
Thu, May 8 - Sun, May 11
Frontier Logo
2:44 pm - 3:34 pmMDW-PNS
24h 50m1 stop
Frontier Logo
4:29 pm - 8:54 pmPNS-MDW
28h 25m1 stop
$332Frontier
Find Deal
Thu, Jul 31 - Mon, Aug 4
 Logo
10:59 am - 3:04 pmMDW-PNS
28h 05m3 stops
 Logo
6:00 am - 9:58 amPNS-MDW
27h 58m3 stops
Mon, May 5 - Sat, May 10
 Logo
8:04 pm - 10:20 pmMDW-PNS
26h 16m2 stops
 Logo
6:14 pm - 7:14 pmPNS-MDW
25h 00m3 stops
Fri, May 23 - Thu, May 29

KAYAK's insights & trends for Midway to Pensacola flights

Get data-powered insights and trends into flights from Midway to Pensacola to help you find the cheapest flights, the best time to fly and much more.

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

The average price of all round-trip flights from Chicago Midway Airport to Pensacola clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Pensacola on a Thursday and more expensive on a Monday. On your return trip to Chicago Midway Airport, you should consider flying back on a Tuesday, and avoid Sundays for better deals.

What is the cheapest month to fly from Chicago Midway Airport to Pensacola?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Pensacola, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago Midway Airport to Pensacola is January, where tickets cost $228 (return) on average. On the other hand, the most expensive months are November and March, where the average cost of round-trip tickets is $458 and $431 respectively.

Can I save money by flying with a layover from Chicago Midway Airport to Pensacola?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.
No, with an average price for the route of $268, prices are generally cheapest when you fly direct.

Good to know

Low season

February

High season

March

Cheapest flight

$115
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly with an average 23% increase in price.
Flight from Chicago Midway Airport to Pensacola

When to book flights from Midway to Pensacola

Are your dates flexible? Find out the best times to travel from Midway to Pensacola based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Pensacola flights

  • What is the cheapest flight from Chicago Midway Airport to Pensacola?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Pensacola was $115 for a one-way ticket and $219 for a round-trip.

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

    No, a passport isn't needed to fly from Chicago Midway Airport to Pensacola. However, local authorities might ask for an official ID.

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Pensacola?

    Only American Airlines offers inflight Wi-Fi service on the Chicago Midway Airport to Pensacola flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Pensacola?

    The Boeing 737-800 Passenger/BBJ2 (winglets) is the aircraft model that flies most regularly on the Chicago Midway Airport to Pensacola flight route.

  • On which days can I fly direct from Chicago Midway Airport to Pensacola?

    You can catch a nonstop flight from Chicago Midway Airport to Pensacola on Monday, Thursday, Friday, Saturday, and Sunday.

  • Which is the best airline for flights from Chicago to Pensacola, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to Pensacola are Southwest and Delta. With an average price for the route of $404 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $362 and an overall rating of 8.0.

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

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Pensacola.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Pensacola?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Pensacola from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

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

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Pensacola with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and PNS can sometimes prove cheaper using this method.

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

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Pensacola from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to Pensacola

  • Looking for a cheap flight? 25% of our users found flights on this route for $203 or less one-way and $305 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Pensacola?

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

Direct departures

Chicago Midway to Pensacola

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

Pensacola 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
See more direct flights

Top airlines flying from Midway to Pensacola

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Pensacola. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Pensacola? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4277 reviews
8.0Comfort
8.7Crew
8.2Boarding
7.6Entertainment
7.1Food
Airline reviews

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

10.0 ExcellentReginald, Mar 2025MDW - LGA
Read more Southwest reviews

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

It went well. Plane wasn't full. Will be great when assigned seating is in place

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Excellent experience. WiFi worked on this leg of My trip

Flight was great, but golf bag never made it until later in the day. Even though I had a nonstop flight it was placed on a different one. They made it right with flight credits and I was able to get it the same day.

Pretty standard flight. We left late, but arrived early. The wifi entertainment is always nice. The free snacks and beverages are simple, but appreciated. I'm tall and the seats are an issue. I can deal with a short flight, but any longer, I have to find another airline where I know beforehand I have extra legroom.

The flight attendant was proactive in helping with placing carry on in overhead bins. This was the first time I had ever been offered help without asking or obviously struggling. Many on the flight were older people like myself and vertically challenged. I would hope this would be the norm on all flights.

wifi wasn't working correctly so couldn't watch live tv

Flight was delayed by 12 minutes. Boarding wasn’t fun. The crew was nice though.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Terrible and im avoiding them in the future. My initial flight was delayed causing me to rebook my flight and when speaking with the representative to rebook I explained this is the second time my flights were delayed and they did nothing to help me. I wasn't booked to comfort plus or given a voucher or anything. I was almost late for my meeting that I needed to attend on Monday because of the games delta played delaying my flights even more and putting me in the very back of the plane next to an extremely intoxicated passenger

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

This was a code share Latam Airlines flight - everything very good except there was no seatback entertainment

Don't waste your money or points on first class. Delta first class is a joke. The seats were rickety, the food was awful, and nothing worked, wifi, my light, the power plug - and it was dirty - the fold out table was gross. For 2-3 hours, tough it out in Economy.

Loyal Delta traveler, but last nights flight was a train wreck. Seated in 1B after multiple delays. Then we couldn’t takeoff because of an issue with the passenger that was ‘not in compliance’ and had to deplane along with the threat if they did not deplane, all the passengers would be required to do so. Finally they were escorted off, but the experience threw off the crew. Disruptive for everyone. Service was a mess, televisions didn’t work, bathroom door kept swinging open during the entire flight whenever empty …

My flight was cancelled twice and the third time I tried to rebook it online I cancelled the flight because it looked like I would get a refund to my credit card. Instead I now have a credit. I was also on hold for three hours waiting for a representative and then disconnected. I will never fly delta again.

It was very cold because the air conditioner was on high power, and my son got sick.

Everything you need to know for your flight from Midway to Pensacola

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