MIA - MDW

$101 Find Cheap Flights from Miami to Chicago Midway Airport - 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 Miami to Midway departing on 8/22. 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

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Everything you should know

Cheapest round-trip
$191
Typical prices: $197-$307
Southwest
Mon 8/24Thu 8/27
MIA - MDW • 1 stop
Cheapest non-stop
$221
Typical prices: $310-$337
Southwest
Tue 9/8Fri 9/11
MIA - MDW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Frontier Economy Bundle adds a carry-on and seat choice for budget value.
Southwest includes free snacks and Wi-Fi; Frontier Premium Bundle adds legroom.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $191 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
You can fly direct with Southwest. Average duration is 3h 05m
Direct flights
Direct flights
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Direct flights
Direct flights
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Avoid delays
Most punctual • 78% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $256 (round-trip)
Shortest trip • 4h 55m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 65% price drop
Most popular
Good to know
Good to know
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We hope you love your trip to Midway!
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Flight Deals

Cheap Flights from Miami to Midway (MIA-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Miami to Midway 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 Miami to Midway

Mon, Aug 24 - Thu, Aug 27
Southwest Logo
4:00 pm - 11:45 pm
MIA
-
MDW
8h 45m
1 stop
Southwest Logo
7:55 am - 4:10 pm
MDW
-
MIA
7h 15m
1 stop
$191Southwest
Thu, Sep 10 - Thu, Sep 17
Southwest Logo
6:25 pm - 10:25 pm
MIA
-
MDW
5h 00m
1 stop
Southwest Logo
8:00 am - 12:10 pm
MDW
-
MIA
3h 10mnonstop
$191Southwest
Wed, Sep 2 - Sun, Sep 6
Southwest Logo
2:20 pm - 10:50 pm
MIA
-
MDW
9h 30m
2 stops
Southwest Logo
1:30 pm - 5:30 pm
MDW
-
MIA
3h 00mnonstop
$191Southwest
Thu, Sep 17 - Mon, Sep 21
Southwest Logo
6:25 pm - 10:25 pm
MIA
-
MDW
5h 00m
1 stop
Southwest Logo
7:25 am - 3:20 pm
MDW
-
MIA
6h 55m
1 stop
$191Southwest
Wed, Sep 2 - Tue, Sep 8
Delta Logo
6:00 am - 9:59 am
MIA
-
MDW
4h 59m
1 stop
Delta Logo
9:29 am - 5:37 pm
MDW
-
MIA
7h 08m
1 stop
$217Delta
Tue, Sep 1 - Wed, Sep 9
Delta Logo
6:00 am - 9:59 am
MIA
-
MDW
4h 59m
1 stop
Delta Logo
11:35 am - 5:20 pm
MDW
-
MIA
4h 45m
1 stop
$217Delta
Tue, Sep 1 - Sat, Sep 5
Delta Logo
6:00 am - 9:59 am
MIA
-
MDW
4h 59m
1 stop
Delta Logo
4:39 pm - 12:47 am
MDW
-
MIA
7h 08m
1 stop
$217Delta
Thu, Oct 8 - Wed, Oct 14
Frontier Logo
6:00 am - 12:07 pm
MIA
-
MDW
7h 07m
1 stop
Frontier Logo
6:40 am - 6:22 pm
MDW
-
MIA
10h 42m
1 stop
$242Frontier
Thu, Aug 27 - Thu, Sep 3
Frontier Logo
5:28 pm - 10:47 pm
MIA
-
MDW
6h 19m
1 stop
Frontier Logo
11:50 am - 11:05 pm
MDW
-
MIA
10h 15m
1 stop
$242Frontier
Sat, Aug 29 - Thu, Sep 10
Frontier Logo
5:28 pm - 10:47 pm
MIA
-
MDW
6h 19m
1 stop
Frontier Logo
12:54 pm - 10:00 pm
MDW
-
MIA
8h 06m
1 stop
$242Frontier
Booking Insights

KAYAK's insights & trends for Miami to Midway flights

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

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

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

Flight prices are below average for this route right now.

Flights to Chicago Midway Airport from Miami usually cost between $197 and $307 in September.
The lowest price found in the past 5 days was $191 on Southwest (Sep 10-Sep 14).

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

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

For Miami to Chicago Midway Airport, Thursday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Chicago Midway Airport back to Miami, the best deals are generally found on Thursday, with Saturday being the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Miami to Chicago Midway Airport, 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 Miami to Chicago Midway Airport is October, where tickets cost $89 (return) on average. On the other hand, the most expensive months are March and June, where the average cost of round-trip tickets is $459 and $393 respectively.

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

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 $247, prices are generally cheapest when you fly direct.

Expert advice

Expert advice for your flight from Miami to Midway

 
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 season

April

Cheapest flight

$101
Best time to beat the crowds but there is an average 18% increase in price.
Most popular time to fly and prices are also 50% lower on average.
Flight from Miami to Chicago Midway Airport

When to book flights from Miami to Midway

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

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

    In the last 5 days, the lowest price for a flight from Miami to Chicago Midway Airport was $101 for a one-way ticket and $191 for a round-trip.

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

    A passport is not required to fly from Miami to Chicago Midway Airport.

  • Which airports will I be using when flying from Miami to Chicago Midway Airport?

    When flying out of Miami you will be using Miami. You will be landing at Chicago Midway Airport, also known as Chicago Midway.

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

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

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

    The Boeing 737-800 is the aircraft model that flies most regularly on the Miami to Chicago Midway Airport flight route.

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

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

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

    The two airlines most popular with KAYAK users for flights from Miami to Chicago are Southwest and Frontier. With an average price for the route of $306 and an overall rating of 8.0, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $145 and an overall rating of 5.6.

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

    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 Miami to Chicago Midway Airport.

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

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

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

    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 Chicago Midway Airport from Miami 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 Miami to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $194 or less one-way and $203 or less round-trip.

Prefer to fly direct from Miami to Chicago Midway Airport?

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

Direct departures

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

Direct returns

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

Reviews of the top airlines flying from Miami to Midway

 
See real verified KAYAK customer reviews for airlines flying from Miami to Chicago. 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 Miami to Midway? 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 4228 reviews
8.1Boarding
7.5Entertainment
8.6Crew
7.0Food
8.0Comfort
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

The flight was great. We were not offered any beverages though. And there was no real turbulence, so not sure why.

Not good.,At first delayed due to weather, then still had to load all the luggage, then a mechanical issue. Upon finally arriving, clothes wet as suitcases sat out in the rain. In a hard side suitcase! Ruined some paper items inside. Not happy!

The flight itself was good. We were delayed 1 1/2 hours which was not good.

Flight was fine but new boarding policy was a drag Xtra time passenger group And Waiting until entire bridge empties before calling a list preferred... Waste of time

Wish that they would space out the boarding a little. COVID is still around and is real. No entertainment. Miss the peanuts.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Severe turbulence. Captain never came on to reassure passengers after things settled down.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

The flight itself was ok and the pilot was very communicative. However, our flight was delayed for almost 3 hours, the gate was changed 3 times and there was no communication as we were waiting. The flight staff was overall a little crabby...I understand as they probably had a long day but we all did.

After waiting several minutes to be acknowledged by 3 employees on their phones, was told we had missed our flight because the doors were closed at that literal moment. Had they given any actual service or help while we were standing there we would have been on with time to spare. More than 10 people were turned away in this fashion claiming there was no way they could let us on the plane, even though it was still sitting connected to the terminal. After the desk agents let us know they didn't care about the situation we were forced to pay more than twice the price of our original tickets as no credits were given for the price of the "missed" flight. And the icing on the cake was after being treated poorly, fleeced for another few hundred dollars for new tickets? We waited on the next plane for 25 minutes passed the "doors closed" time, letting almost an extra dozen passengers on board. You're company has lazy, disinterested employees and your lack of any real help will ensure this was the first and last time we fly Frontier. Awful.

terrible cascading delays and unhelpful customer service. uncomfortable plane. crew was great, however!

The trip was unremarkable which is good. Crew was very professional and courteous.

I was singled out for being a Latina flying solo and the attendants took me out of line to put my luggage in the personal item bin to see if it would fly. Keep In mind I had just flown with the same luggage with no problem not even 5 days ago. The tag was sticking out a bit and the attendant was belligerent about charging me $100. I could not refuse because I didn’t wanna cause a scene. But today I felt targeted and embarrassed. I went online and found out that this happens a lot with this airline and to many minority women.

Nothing I missed my first flight because my boarding pass said one thing and another passenger on the same flight said another. I didn’t get notified of a gate change until 8:39 pm which was one minute before the flight departed at 8:40pm when we explained this to gate agent Dorsey prior to the flight departing she was extremely short and had nasty attitude. Some of the passengers in my party including myself needed to catch that flight due work the next which included presentations and court litigation. We were deeply saddened and frustrated how Frontier handled this situation. We were told that the flight was over booked by 19 seats and they constantly change gates to make people miss their flight. If that is true I will ensure there will be a class action lawsuit against frontier airlines.

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

Information on your arrival and departure airports