MDW - MIA

$105 Find Cheap Flights from Chicago Midway Airport to Miami - Compare and Save

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 Miami departing on 8/25. 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
1 adult, Economy, 0 bags

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Miami, 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 Miami, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$232
Typical prices: $185-$542
Frontier
Sat 9/5Tue 9/8
MDW - MIA • 1 stop
Cheapest non-stop
$237
Typical prices: $292-$502
Southwest
Wed 9/23Mon 9/28
MDW - MIA • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Frontier Basic Fare includes only a personal item; Economy Bundle adds more.
Southwest includes a free carry-on, while checked bags now cost extra.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $232 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 3h 00m
Direct flights
Direct flights
+1
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Direct flights
Direct flights
+1
Avoid delays
Most punctual • 83% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $267 (round-trip)
Shortest trip • 4h 25m (one-way)
Insights
Insights
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Insights
When to travel
Cheapest • 55% price drop
Most popular
Good to know
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Flight Deals

Cheap Flights from Midway to Miami (MDW-MIA)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Miami 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Miami

Sat, Sep 5 - Tue, Sep 8
Frontier Logo
11:45 am - 8:29 pm
MDW
-
MIA
7h 44m
1 stop
Frontier Logo
5:28 pm - 10:47 pm
MIA
-
MDW
6h 19m
1 stop
$232Frontier
Thu, Aug 20 - Mon, Aug 24
Southwest Logo
1:20 pm - 10:05 pm
MDW
-
MIA
7h 45m
2 stops
Southwest Logo
7:00 am - 2:05 pm
MIA
-
MDW
8h 05m
2 stops
$233Southwest
Sat, Oct 24 - Wed, Oct 28
Frontier Logo
6:40 am - 6:22 pm
MDW
-
MIA
10h 42m
1 stop
Frontier Logo
6:45 am - 10:58 am
MIA
-
MDW
5h 13m
1 stop
$234Frontier
Wed, Jul 29 - Wed, Aug 5
Frontier Logo
6:05 am - 1:53 pm
MDW
-
MIA
6h 48m
1 stop
Frontier Logo
6:50 am - 3:50 pm
MIA
-
MDW
10h 00m
1 stop
$235Frontier
Sat, Jul 18 - Wed, Jul 22
Frontier Logo
12:11 pm - 8:29 pm
MDW
-
MIA
7h 18m
1 stop
Frontier Logo
5:28 pm - 10:03 pm
MIA
-
MDW
5h 35m
1 stop
$236Frontier
Mon, Aug 3 - Wed, Aug 5
Frontier Logo
6:05 am - 4:33 pm
MDW
-
MIA
9h 28m
1 stop
Frontier Logo
6:50 am - 3:50 pm
MIA
-
MDW
10h 00m
1 stop
$237Frontier
Mon, Sep 7 - Tue, Sep 15
Frontier Logo
6:05 am - 4:21 pm
MDW
-
MIA
9h 16m
1 stop
Frontier Logo
6:45 am - 10:58 am
MIA
-
MDW
5h 13m
1 stop
$238Frontier
Thu, Sep 3 - Tue, Sep 8
Frontier Logo
11:50 am - 11:05 pm
MDW
-
MIA
10h 15m
1 stop
Frontier Logo
5:28 pm - 10:47 pm
MIA
-
MDW
6h 19m
1 stop
$239Frontier
Fri, Aug 7 - Tue, Aug 11
Frontier Logo
6:05 am - 1:53 pm
MDW
-
MIA
6h 48m
1 stop
Frontier Logo
10:50 am - 10:03 pm
MIA
-
MDW
12h 13m
1 stop
$240Frontier
Tue, Jul 21 - Tue, Jul 28
Frontier Logo
6:05 am - 1:53 pm
MDW
-
MIA
6h 48m
1 stop
Frontier Logo
5:28 pm - 10:03 pm
MIA
-
MDW
5h 35m
1 stop
$241Frontier
Booking Insights

KAYAK's insights & trends for Midway to Miami flights

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

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

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Miami departing in September.

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

The average price of all round-trip flights from Chicago Midway Airport to Miami clicked on KAYAK for each day over the last 12 months.

When flying from Chicago Midway Airport to Miami, you should consider leaving on a Thursday and avoid Saturdays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Thursdays and the most expensive ones on Sundays.

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

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 Miami, 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 Miami is October, where tickets cost $149 (return) on average. On the other hand, the most expensive months are June and July, where the average cost of round-trip tickets is $400 and $399 respectively.

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

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $321 on average.

How far in advance should I book a flight from Chicago Midway Airport to Miami?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago Midway Airport to Miami, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago Midway Airport to Miami, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Expert advice

Expert advice for your flight from Midway to Miami

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Frontier, MDW and MIA

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.

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.

Good to know

Low seasonSeptember
Cheapest flight$105
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 14% lower on average.
Flight from Chicago Midway Airport to Miami

When to book flights from Midway to Miami

Are your dates flexible? Find out the best times to travel from Midway to Miami 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 Miami flights

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

    In the last 5 days, the lowest price for a flight from Chicago Midway Airport to Miami was $105 for a one-way ticket and $232 for a round-trip.

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

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

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

    American Airlines, JetBlue, and Delta offer inflight Wi-Fi service on the Chicago Midway Airport to Miami flight route.

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

    The Airbus A321neo is the aircraft model that flies most regularly on the Chicago Midway Airport to Miami flight route.

  • Which airline alliances offer flights from Chicago Midway Airport to Miami?

    oneworld, and SkyTeam are the airline alliances operating flights between Chicago Midway Airport and Miami, with oneworld being the most commonly used for this route.

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

    There are nonstop flights from Chicago Midway Airport to Miami on a daily basis.

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

    The two airlines most popular with KAYAK users for flights from Chicago to Miami are Southwest and Delta. With an average price for the route of $406 and an overall rating of 7.9, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $415 and an overall rating of 7.8.

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

    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 Miami.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Miami 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 Miami?

    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 Miami with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and MIA 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 Miami?

    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 Miami from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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

  • Looking for a cheap flight? 25% of our users found flights on this route for $187 or less one-way and $253 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Miami?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to Miami.
Find which airlines fly direct from Chicago Midway Airport to Miami Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to Miami

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

Miami 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

Reviews of the top 4 airlines serving from Midway to Miami

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Miami. 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 Miami? 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.
7.9
SouthwestOverall score based on 4246 reviews
8.1Boarding
8.6Crew
7.0Food
8.0Comfort
7.5Entertainment
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

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 experience. WiFi worked on this leg of My trip

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

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

I truly love flying with Delta. They have always treated me with the upmost respect

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

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.

First time travel in economy and the worst experience I ever had ! Shame on paying 600 dollars to be in a tuna can ! Service was terrible no even water no even class no even matters your flight attendants were lazy and sloppy very bad experience! After all these years traveling in first and once I try this cause I need to go to a destination for an emergency wow shame on you !

The Delta flight was delayed for maintenance issue. The crew is also delayed and I’ve been there at the same time as I was so it was really outside the hands of crew directly. However, where Delta failed was there was about eight other ways for me to get to my final destination and they did not offer changes beyond the initial one. The flight was delayed five hours when they had to change my connecting flight they had to downgrade my premium class for so far zero compensation and I’m still waiting on the results of a formal complaint. All in all this was the worst experience I’ve had with Delta in quite some time. Carrying the review for my first light over to this one, I was downgraded a class and because of my status I’ve only flown comfort plus or higher in some years I was unaware of things like drink vouchers, or anything like that, as far as I knew drinks were complimentary. The attendant was unnecessarily nasty towards me when I was just asking her to explain how it works and I showed her my first class ticket even though I was in the back of the plane and she was still equally unhelpful and frustrated. I’m not saying that the first class ticket should allow better treatment. I’m saying that I was showing that normally I would’ve had it for free beverage and so I didn’t know what she was talking about, she didn’t need to be so frustrated. Outside of that if the flight was 2 1/2 hours and the snack and beverage options did not become available until the final 30 minutes of the flight when we were on the descent, so any snacks and drinks were quickly rushed away. I do not know if this is common for what main cabin normally experiences but I hope it isn’t because that level of customer service and tending to the needs of the passengers is below what I would call essential.

I was flying from nyc jfk home to Miami and I used a flight credit from delta since they destroyed my bag earlier that year. On this return flight I landed retrieved my bag and noticed when I got home that delta ripped a hole in my bag and got one of my belongings caught up wrapped around the wheel of my Tumi bag!!! Oh and now their policy says they won’t replace it.

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

My experience with American Airlines was great. Unfortunately my stroller was not located and has not been given to me and or reached out in return for in regard to information.

The plane was large, not full, but one with 3 seats near each window and 4 in a row in the middle of the plane. There were screens on the backs of the seats for entertainment and information. To use the entertainment one needs ear plugs that physically plug into the screen. My husband had some he let me use as I only had blue tooth type. The stewards gave out some headphones to some, but when my neighbor asked for some, the steward said no. So maybe they ran out? Idk. Bring the old kind of headphones or earbuds if you want entertainment in case this is the type of entertainment offered. We had a very tight connection in Miami. 43 minutes. The other economy passengers allowed us to get ahead of them because I asked if we could since we were near boarding time for our next flight and 35 gates away. They were extremely kind. First class wasn’t going to allow us to pass through. We did make the next flight. Our baggage didn’t, but they were delivered to us the next day and we were prepared with essentials in our carry on packs.

So overall the flight was just average and nothing special. They overbooked some of the flights and they ended up running out of overhead storage space so we had to check our carry-ons which wasn't terrible but we were inconvenienced because of the second connecting flight with a long layover we couldn't get our bags until the final destination. Most of the flight attendants were pretty good and overall the meals were not that great because the chicken was dry and overcooked. They also didn't provide butter or any kind of spread with the bread which is cheap and concerning. The American airlines staff at the check-in counter was kind of unprofessional because this lady just started singing in the middle of checking us in and that's weird. The worst part of the flights was the terrible conditions of the bathrooms which were unclean and did not have toilet paper or toilet tissue available which is kind of insane for a 14-hour and 8 and 1/2 hour flight.

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

Very disappointing. Flight was delayed by 1.5 hours and food options are very underwhelming even for first class seats (same food given to economy seats)

Was not able to do a online check-in because the American Airlines system doesn't store our visa or other passport information, allowing us to have a trouble-free check-in. We were forced to have to check-in at the counter which Changes are upgrade status given that we were not able to check in much earlier.

I would have liked vegetarian and gluten free options for evening dinner time flight. I would have like a pillow on the international overnight flight . The veg wrap and oaten desert on the international flight was good

We hoarded. Then we deplaned. Then we waited for 10 hours in the MSP airport due to a wheel misfunction. We understand safety but communication between crew and airport staff was horrible. When we did finally board, we were rushed on and because we were waiting for a “fresh” pilot and crew, we sat in a roasting plane with no A/C for an hour. My question is why was this flight not cancelled right away when they knew this would be a huge issue OR, why did AA not get a substitute plane, considering this was already a full flight? To me, this appears to be a complete breakdown in leadership and utter systems failure. The compensation for completely disrupting travel plans for hundreds, which we paid dearly for, was measly. While we appreciated the lodging for the night, $12 in meal vouchers isn’t going to sustain anyone for over 12 hours. “We apologize; our hands are tied” is no longer an acceptable explanation. We are so completely turned off by this experience and will definitely seek alternative avenues when we need to fly.

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

Better than expected. Staff were friendly and nice on both flights.

2 hour delay due to late plane, wrong size plane causing overbooking, and people getting off and on the plane after boarding was completed.

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

I chose the seats when booked the flight and paid for them. However after checking in I found we were assigned different seats!

Since they are a budget airline, I wasn’t expecting too much but they did some things well. They were on time, the plane was clean, boarding was fairly straightforward and the staff was cheerful and friendly. The only downside was comfort. The seats were fairly hard and after a 2 hour flight your rear end is not feeling so great. Maybe a little more cushion in the seats, Frontier!

It was horrible. My plane was delayed until the next day resulting in me losing a day of work. It’s absolutely unacceptable and I won’t be flying with you any more and I will strongly caution others to avoid your airline as well.

The personal at boarding are rude and try to steel people with their rule of personal item , really bad experience for us

Connecting from an international flight in Miami was horrible. We had to take check luggage on the way out go to the frontier counter and there was no one there to receive it for our domestic connecting flight we almost missed the flight because they had no Personnel on site

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Flying frontier reminded me of flying with my family in the 80’s in all of the worst ways possible. From poor customer service to little to no technology. The plane was dirty old and also stuck in the 80’s. From their seatbelts to not having anywhere to charge our phones the seats and the equipment I wasn’t sure if I was being punked or thrown back in time. Needless to say I don’t see myself flying frontier ever again.

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

Information on your arrival and departure airports