MDW - MIA

$62 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 10/27. 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

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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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

Fri, Oct 17 - Mon, Oct 20
Frontier Logo
12:13 pm - 7:59 pmMDW-MIA
6h 46m1 stop
Frontier Logo
7:20 am - 9:33 amMIA-MDW
3h 13mnonstop
$117Frontier
Find Deal
Sun, Nov 9 - Sat, Nov 15
Frontier Logo
5:40 am - 5:48 pmMDW-MIA
11h 08m1 stop
Frontier Logo
7:05 pm - 9:22 pmMIA-MDW
3h 17mnonstop
$118Frontier
Find Deal
Sat, Nov 1 - Mon, Nov 10
Frontier Logo
2:05 pm - 6:05 pmMDW-MIA
3h 00mnonstop
Frontier Logo
10:30 am - 5:15 pmMIA-MDW
7h 45m1 stop
$120Frontier
Find Deal
Sun, Oct 12 - Fri, Oct 17
Frontier Logo
8:25 am - 7:59 pmMDW-MIA
10h 34m1 stop
Frontier Logo
7:20 am - 9:33 amMIA-MDW
3h 13mnonstop
$121Frontier
Find Deal
Fri, Oct 10 - Mon, Oct 13
Frontier Logo
12:13 pm - 7:59 pmMDW-MIA
6h 46m1 stop
Frontier Logo
9:26 pm - 11:46 pmMIA-MDW
3h 20mnonstop
$122Frontier
Find Deal
Fri, Oct 10 - Fri, Oct 17
Frontier Logo
12:13 pm - 7:59 pmMDW-MIA
6h 46m1 stop
Frontier Logo
7:20 am - 9:33 amMIA-MDW
3h 13mnonstop
$124Frontier
Find Deal
Fri, Oct 10 - Mon, Oct 13
Frontier Logo
12:13 pm - 7:59 pmMDW-MIA
6h 46m1 stop
Frontier Logo
9:26 pm - 11:46 pmMIA-MDW
3h 20mnonstop
$125Frontier
Find Deal
Fri, Oct 10 - Fri, Oct 17
Frontier Logo
12:28 pm - 4:29 pmMDW-MIA
3h 01mnonstop
Frontier Logo
7:20 am - 9:33 amMIA-MDW
3h 13mnonstop
$126Frontier
Find Deal
Fri, Oct 24 - Sat, Nov 1
Frontier Logo
12:18 pm - 4:19 pmMDW-MIA
3h 01mnonstop
Frontier Logo
7:05 pm - 9:22 pmMIA-MDW
3h 17mnonstop
$129Frontier
Find Deal
Mon, Nov 10 - Wed, Nov 12
Southwest Logo
9:30 am - 1:35 pmMDW-MIA
3h 05mnonstop
Southwest Logo
1:05 pm - 3:20 pmMIA-MDW
3h 15mnonstop
$167Southwest
Find Deal
Expert advice

Expert advice for your flight from Midway to Miami

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
Frontier

Frontier's Basic Fare includes only a personal item; carry-ons cost extra.


Frontier's Economy Bundle offers a carry-on and seat choice, avoiding change fees.

Read more about Frontierby Stefanie Waldek
Southwest

Southwest offers free carry-on and personal item, but checked bags now incur fees.


Southwest's cancellation policy allows changes up to 10 minutes before departure.

Read more about Southwestby Blane Bachelor
Airports
MDW

Midway offers a compact terminal with easy navigation, making it ideal for quick departures. Enjoy local dining options like Billy Goat Tavern before your flight.

Read more about MDWby Stefanie Waldek
MIA

For a quick trip downtown, take the Metrorail's Orange Line from MIA. It connects directly to the city center in about 15 minutes.

Read more about MIAby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Frontier, MDW and MIA

Stefanie Waldek

Stefanie Waldek

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.

Read more
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor

Blane Bachelor

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.

Read more
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.

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 Monday 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 Fridays 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 $173 (return) on average. On the other hand, the most expensive months are June and November, where the average cost of round-trip tickets is $439 and $365 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.

No, with an average price for the route of $263, prices are generally cheapest when you fly direct.

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, which saves you about 46% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonJuly
Cheapest flight$62
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly and prices are also 0% 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 3 days, the lowest price for a flight from Chicago Midway Airport to Miami was $62 for a one-way ticket and $117 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, Spirit Airlines, 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 Boeing 737-800 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?

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

  • 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 $424 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 $398 and an overall rating of 7.9.

  • 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 $128 or less one-way and $160 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, Frontier

Southwest, Frontier

Thursday

Southwest

Southwest

Friday

Southwest, Frontier

Southwest, Frontier

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Miami to Chicago Midway

Monday

Southwest, Frontier

Southwest, Frontier

Thursday

Southwest

Southwest

Friday

Southwest, Frontier

Southwest, Frontier

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the 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 4243 reviews
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
8.6Crew
Airline reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

10.0 ExcellentKevin, Jul 2025MDW - PUJ
Read more Southwest reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

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.

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!

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

this crew didn't care much. bumping carts into seats more times than i care to remember

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

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.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

Wow truly top notch airline Efficient nice snacks courteous staff Fast boarding !

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

The flight times got delayed multiple times due to weather which is understandable, but later the time got prepared 30min. Made to the flight barely but got stressed too much.

you guys canceled my flight last minute and lost my luggage.

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

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

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

Since you have to pay for overhead bags then they shouldn't be running out of space and asking individuals who paid to remove stuff from the overhead

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

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.

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