MIA - MDW

$102 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 8/4. 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 Chicago Midway Airport

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

Cheapest round-trip
$207
Typical prices: $350-$258
Southwest
Wed 8/26Wed 9/2
MIA - MDW • Non-stop
Cheapest non-stop
$207
Typical prices: $445-$307
Southwest
Wed 8/12Tue 8/18
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 $207 (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 07m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Most punctual • 79% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $283 (round-trip)
Shortest trip • 5h 05m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 48% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
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Expert advice
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

Wed, Aug 26 - Wed, Sep 2
Southwest Logo
4:00 pm - 6:05 pm
MIA
-
MDW
3h 05mnonstop
Southwest Logo
9:25 am - 1:25 pm
MDW
-
MIA
3h 00mnonstop
$207Southwest
Wed, Aug 26 - Wed, Sep 2
Southwest Logo
2:20 pm - 8:40 pm
MIA
-
MDW
7h 20m
1 stop
Southwest Logo
9:25 am - 1:25 pm
MDW
-
MIA
3h 00mnonstop
$217Southwest
Wed, Aug 26 - Wed, Sep 2
Southwest Logo
6:45 am - 3:30 pm
MIA
-
MDW
9h 45m
2 stops
Southwest Logo
9:25 am - 1:25 pm
MDW
-
MIA
3h 00mnonstop
$222Southwest
Wed, Jul 29 - Tue, Aug 4
Southwest Logo
4:00 pm - 6:10 pm
MIA
-
MDW
3h 10mnonstop
Southwest Logo
9:25 am - 1:25 pm
MDW
-
MIA
3h 00mnonstop
$223Southwest
Tue, Jul 28 - Tue, Sep 8
Southwest Logo
4:00 pm - 6:10 pm
MIA
-
MDW
3h 10mnonstop
Southwest Logo
9:25 am - 1:25 pm
MDW
-
MIA
3h 00mnonstop
$224Southwest
Tue, Jul 7 - Tue, Jul 14
Frontier Logo
6:50 am - 4:51 pm
MIA
-
MDW
11h 01m
1 stop
Frontier Logo
6:05 am - 4:33 pm
MDW
-
MIA
9h 28m
1 stop
$226Frontier
Tue, Jul 14 - Tue, Jul 21
Frontier Logo
5:28 pm - 10:03 pm
MIA
-
MDW
5h 35m
1 stop
Frontier Logo
6:05 am - 1:53 pm
MDW
-
MIA
6h 48m
1 stop
$228Frontier
Wed, Jul 22 - Wed, Jul 29
Frontier Logo
11:19 am - 10:03 pm
MIA
-
MDW
11h 44m
1 stop
Frontier Logo
6:05 am - 1:53 pm
MDW
-
MIA
6h 48m
1 stop
$229Frontier
Wed, Jul 29 - Tue, Aug 4
Frontier Logo
11:19 am - 10:03 pm
MIA
-
MDW
11h 44m
1 stop
Frontier Logo
12:11 pm - 11:05 pm
MDW
-
MIA
9h 54m
1 stop
$230Frontier
Wed, Jul 29 - Tue, Aug 4
Southwest Logo
4:20 pm - 11:15 pm
MIA
-
MDW
7h 55m
1 stop
Southwest Logo
9:25 am - 1:25 pm
MDW
-
MIA
3h 00mnonstop
$233Southwest
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 August.

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 Sunday, 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 January, where tickets cost $128 (return) on average. On the other hand, the most expensive months are March and June, where the average cost of round-trip tickets is $368 and $357 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 seasonApril
Cheapest flight$102
Best time to beat the crowds but there is an average 21% increase in price.
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 $102 for a one-way ticket and $207 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, Delta, JetBlue, 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 MAX 8 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 $327 and an overall rating of 7.9, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $151 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 $187 or less one-way and $399 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.
7.9
SouthwestOverall score based on 4235 reviews
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
Airline reviews

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

8.0 ExcellentAnonymous, May 2026
BDL - MDW
Read more Southwest reviews

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.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

I liked it better when you were truer to your roots Am paying more for less fun

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

It was an early flight and most people napped/slept and the crew let us which was nice.

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

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.

Flight got delayed for 5 hours no good explanation was offered ;(

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

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

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

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

Information on your arrival and departure airports