MDW - MIA

$90 Find Cheap Flights from Chicago Midway Airport to Miami

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 6/18. 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.
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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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Cheap Flights from Midway to Miami

 
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.

Recent round-trip flight deals from Midway to Miami

KAYAK's recommended round-trip deals from the most popular airlines that fly from Midway to Miami.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southwest Logo
8:40 pm - 12:40 amMDW-MIA
3h 00mnonstop
Southwest Logo
7:00 am - 9:10 amMIA-MDW
3h 10mnonstop
$197Southwest
Find Deal
Sun, Jun 1 - Wed, Jun 4
Southwest Logo
6:45 pm - 10:40 pmMDW-MIA
2h 55mnonstop
Southwest Logo
5:45 am - 7:50 amMIA-MDW
3h 05mnonstop
$208Southwest
Find Deal
Sat, May 31 - Sat, Jun 7
Southwest Logo
5:10 pm - 9:05 pmMDW-MIA
2h 55mnonstop
Southwest Logo
7:00 am - 9:10 amMIA-MDW
3h 10mnonstop
$209Southwest
Find Deal
Wed, May 28 - Wed, Jun 4
Delta Logo
12:44 pm - 9:16 pmMDW-MIA
7h 32m1 stop
Delta Logo
5:30 am - 9:41 amMIA-MDW
5h 11m1 stop
$217Delta
Find Deal
Tue, Jun 10 - Tue, Jun 17
Frontier Logo
8:03 pm - 5:22 amMDW-MIA
8h 19m1 stop
Frontier Logo
8:46 am - 1:34 pmMIA-MDW
5h 48m1 stop
$220Frontier
Find Deal
Mon, May 12 - Thu, May 15
Delta Logo
9:16 am - 6:07 pmMDW-MIA
7h 51m1 stop
Delta Logo
8:40 am - 12:28 pmMIA-MDW
4h 48m1 stop
$229Delta
Find Deal
Sun, Jun 1 - Sat, Jun 7
Frontier Logo
6:10 am - 10:09 pmMDW-MIA
14h 59m1 stop
Frontier Logo
10:37 am - 1:29 pmMIA-MDW
27h 52m1 stop
$235Frontier
Find Deal
Sat, May 31 - Sun, Jun 1
Delta Logo
9:16 am - 6:07 pmMDW-MIA
7h 51m1 stop
Delta Logo
3:59 pm - 9:27 pmMIA-MDW
6h 28m1 stop
$237Delta
Find Deal
Mon, Jun 2 - Wed, Jun 4
Frontier Logo
6:10 am - 10:09 pmMDW-MIA
14h 59m1 stop
Frontier Logo
10:59 pm - 10:16 pmMIA-MDW
24h 17m1 stop
$260Frontier
Find Deal
Sat, May 31 - Sun, Jun 1
Frontier Logo
6:25 am - 5:40 amMDW-MIA
22h 15m1 stop
Frontier Logo
7:24 pm - 7:31 pmMIA-MDW
25h 07m1 stop
$279Frontier
Find Deal
Fri, May 30 - Sun, Jun 1
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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.

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 Wednesday 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 June, where tickets cost $158 (return) on average. On the other hand, the most expensive months are November and March, where the average cost of round-trip tickets is $357 and $337 respectively.

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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonAugust
High seasonDecember
Cheapest flight$90
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 28% increase in price.
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 3 days, the lowest price for a flight from Chicago Midway Airport to Miami was $90 for a one-way ticket and $197 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?

    Only American Airlines offers 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 A320neo is the aircraft model that flies most regularly on the Chicago Midway Airport to Miami flight 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 $436 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 $457 and an overall rating of 8.0.

  • 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 $119 or less one-way and $223 or less round-trip.

Prefer to fly direct from Chicago Midway Airport 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
See more direct flights

Top 5 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.
8.0
SouthwestOverall score based on 4294 reviews
8.0Comfort
8.2Boarding
7.6Entertainment
8.6Crew
7.1Food
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

Plz don't take away free bags and free seating

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.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

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.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Would have thought that they would gas up plane before everyone got on board

The flights were terribly delayed and then cancelled which forced us booking another night at the hotel. Very poor management from American Airlines

Crew was late. Baggage was late. 2hs inside the plane waiting fro de-icing and traffic. A 3:30hs flight ended up being almost 6hs inside the airplane.

Checking in at the counter was very disappointing. The lady had a very bad attitude and smart at me. She had no smile, did not greet me by name, or acknowledge me as a valued customer. Poor reflection of the airline.

Miami lounges were overcrowded and we were unable to get in. We only had a short time. But the banks are too tight in all American hubs

Boarded over an hour late, no communication, the sign just changed, no attendant to answer questions - she disappeared forever (hiding). Small plane and couldn’t hear the overhead nor understand.

Two issues. The plane was old and dirty. The armrest looked like an old car that had the vinyl rubbed off. The Seats in these aircraft are about as hard and uncomfortable. I want to tour Italy for a month and I want to buy a one-way ticket to Thailand but I will not sit in the seats these planes have. It is seriously stupid how hard they are.

Check bag location is full of rude employees who are unwilling to assist with issues after talking to AA on the phone and relaying messages. The boarding was good. While on the flight it got really hot. Asked flight attendant if there’s a way to drop the temp and make it more comfortable as we are flying from DC to Miami so flying from cold to hot weather. No changes made. Stayed hot and uncomfortable on the plane. When asked again about the AC being down the flight attendant said no the WiFi was down but not the AC. I mentioned it was still hot. No changes.

There was a delay that affected all passengers with connecting flights.

I love to flight american however my carry on had to be sent with regular luggage and it was broken. Don't appreciate that. If when I buy a ticket says I can take a carry on and a hand item there should be space for mwsy stuff and not be basically forced to send the item even if it's at no charge. A.A. needs to work on that. Everything else excellent.

It’s what we expected from Spirit..reasonable cost, good for a 2-3 hour flight. Disappointed that we had a 2 hour delay in departure from DFW for a maintenance issue, but the pilot handled it well once we were outbound on a different Airbus.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

In a word, it was horrible. The flight crew timed out and this, apparently was not accounted for by management. This meant that our 10:15 departure turned into a 1:30am departure the next DAY!!! And some brainchild decided to email us 12$ food vouchers set to expire the 9th, but they sent them after EVERY VENDOR WAS CLOSED in the Miami airport and obviously none would be open in New Orleans. I found this to be another sterling example of, at best, shitty management…at worst an absolute lack of empathy for your customers. Triplt Pro: Check-in may be avail for NK222 dep MIA 4/8/2025 10:16pm. Conf#RGSUMI. https://tripit.com/t/. e106fd644e0a; Today 6:16 PM TripIt Pro: NK222 ON TIME. MIA dep 10:16pm term C, gate F5. MSY arr 11:38pm. Today 8:59 PM Tript Pro: NK222 DELAYED. MIA dep 1:00am term C, gate F5. MSY arr 2:18am. Alternate flights: https:// www.tripit.com/t/b2903869f438 Triplt Pro: NK222 PULLED IN. MIA dep 12:30am term C, gate F5. MSY arr 1:48am. Alternate flights: https:/// www.tripit.com/t/834d176c630b Tript Pro: NK222 DELAYED. MIA dep 1:00am term C, gate F5. MSY arr 1:48am. Alternate flights: https:/// www.tripit.com/t/0441e41a9dd3 Triplt Pro: NK222 PULLED IN. MIA dep 12:30am term C, gate F5. MSY arr 1:48am. Alternate flights: https:// www.tripit.com/t/92ac2157ef54 The sender is not in your contact

Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

No leg room AT all extremely uncomfortable flight water even cost 5 dollars

Good crew and safe. However, comfort and being nickeled-and-dimed are my issues. $75 each way for luggage is exhortation. The space to the next seat is so close you cannot open a laptop. The magazine rack doesn’t hold your items. Not a fan.

WiFi could have been a little more consistent - otherwise a phenomenal and positive experience. The 1000 mile giveaway was awesome!!!

Flight was on time It was a good flight overall

Needs legroom for tall people. Needs to offer a glass of water.

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!

It was a no frills flight. Would have liked to be able to charge my device

Seats were extremely uncomfortable and it was very hot on the plane.

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!

Check in at Philadelphia international was absolutely terrible! I fly 2 to 3 times a month and avoid frontier at all cost and will never fly Frontier again! The night before travel, I tried checking in however, the app was giving me an error, so I went to the desktop, which instructed you that you need to use the app. The next day I presented at the check-in gate after trying at least a half dozen times prior to getting into the airport and continuing to getting the error in the app. I actually had rebooted my phone numerous times and reinstall the app just in case. My phone is only one generation older than the current model. It has no problems completing a frontier flight purchase or any other app issues. There was only three frontier employees working at check-in and a huge line while I was in line I continued to try and check in via the app. As I approach the desk, I was dreading dealing with the agent. He was extremely unprofessional, anti-semantic & very ignorant, and mean to the people in front of me, as well as the people who ended up being behind me. He literally told people “Man I don’t care bout y’all” in his native dialect! Maintaining my composure I approached and explained the situation. To which he replied, you’re gonna have to pay then! I don’t understand. It’s an issue with their app not allowing me to check in! Not my issue! He told me if I pay cash it would be $15, $25 if I pay credit card. I don’t understand a $10 difference for paying with a credit card? I am completely cashless so I continued to try using the app to avoid the $25 fee, Which I still don’t believe that I should be responsible for since it was Frontier’s technical issue!!! I continued to check in via the app a couple more times after he verified I was doing everything right he proceeded to continue to belittle the people behind me. Yelling at them saying I don’t care about you people! I cannot believe that this is the way that businesses would treat its customers! Unfortunately, the black mail with dreadlocks did not have a name tag all he had was a frontier sweater on! For the $25 fee that I ended up getting charged on my credit card. I should’ve just booked originally with Spirit or any other carrier! I have no problem paying fees that I should be responsible for, but when it’s due to a technical failure of a company, the customer should not be responsible for it! I cannot believe that it’s not frontier going out of business!

they delayed my flight which ended up, causing my layover flight to leave without me, resulting in me missing a flight and having to stay overnight in Houston international. I got no compensation other than a flight to my original location only a day later. i’ve never experienced such a unprofessional situation

Our flight was suppose to leave at 9pm and we didn’t board until after 3am. We lost a whole day at our hotel and half a day at a park we paid a lot of money for.

Boarding was organized and flight was on time. Overall very satisfied with my flight.

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.

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