$56 Cheap Flights from Miami (MIA) to Chicago (MDW)

View $56 flight on Sat, Nov 8, 2025Opens in a new window

Popular airlines from Miami Intl. Airport (MIA) to Chicago Midway Airport (MDW)

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Cheap Flights from Miami to Chicago (MIA-MDW)

Prices were available within the past 7 days and start at $56 for one-way flights and $108 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Fri, Oct 10 - Mon, Oct 13
MIA
Miami
MDW
Chicago
$108 Roundtrip, just found
$108
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Oct 10 from Miami to Chicago, returning Mon, Oct 13, priced at $108 just found
Frontier Airlines
Fri, Oct 17 - Sat, Nov 1
MIA
Miami
MDW
Chicago
$112 Roundtrip, found 6 days ago
$112
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Fri, Oct 17 from Miami to Chicago, returning Sat, Nov 1, priced at $112 found 6 days ago
Frontier Airlines
Mon, Oct 13 - Mon, Oct 20
MIA
Miami
MDW
Chicago
$123 Roundtrip, just found
$123
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Oct 13 from Miami to Chicago, returning Mon, Oct 20, priced at $123 just found
Frontier Airlines
Mon, Oct 20 - Mon, Nov 3
MIA
Miami
MDW
Chicago
$131 Roundtrip, just found
$131
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Oct 20 from Miami to Chicago, returning Mon, Nov 3, priced at $131 just found
Southwest Airlines
Wed, Nov 5 - Tue, Nov 11
MIA
Miami
MDW
Chicago
$133 Roundtrip, found 3 days ago
$133
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Nov 5 from Miami to Chicago, returning Tue, Nov 11, priced at $133 found 3 days ago
Southwest Airlines
Tue, Oct 14 - Fri, Oct 17
MIA
Miami
MDW
Chicago
$134 Roundtrip, found 3 days ago
$134
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Oct 14 from Miami to Chicago, returning Fri, Oct 17, priced at $134 found 3 days ago
Frontier Airlines
Fri, Oct 17 - Mon, Oct 20
MIA
Miami
MDW
Chicago
$136 Roundtrip, found 1 hour ago
$136
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Oct 17 from Miami to Chicago, returning Mon, Oct 20, priced at $136 found 1 hour ago
Southwest Airlines
Tue, Nov 4 - Sat, Nov 8
MIA
Miami
MDW
Chicago
$137 Roundtrip, found 1 hour ago
$137
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Tue, Nov 4 from Miami to Chicago, returning Sat, Nov 8, priced at $137 found 1 hour ago
Southwest Airlines
Tue, Oct 14 - Fri, Oct 17
MIA
Miami
MDW
Chicago
$138 Roundtrip, found 3 days ago
$138
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Oct 14 from Miami to Chicago, returning Fri, Oct 17, priced at $138 found 3 days ago
Southwest Airlines
Tue, Oct 14 - Fri, Oct 17
MIA
Miami
MDW
Chicago
$138 Roundtrip, found 3 days ago
$138
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Oct 14 from Miami to Chicago, returning Fri, Oct 17, priced at $138 found 3 days ago

Find the cheapest month to fly from Miami (MIA) to Chicago (MDW)

February is typically the cheapest month to fly

From $78 - $352 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $138
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $138
Flights from Miami (MIA) to Chicago (MDW)
Origin airport
Miami Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$106
Distance
1183 mi
Average flight time
2 hours 8 mins

Miami to Chicago Flights

The cheapest times to fly from Miami to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Miami to Chicago are during the month of October. You can find some of the cheapest flights from Miami to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Miami to Chicago

Sunday is one of the best days to book for cheap flights from Miami to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Miami to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Miami to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $56 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Miami to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Miami to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Miami Intl. Airport (MIA) to Midway Intl. Airport (MDW) cost?
Grab a cheap one-way flight from $56 or cheap return flight from $108 from Miami Intl. Airport (MIA) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Miami Intl. Airport (MIA) to Midway Intl. Airport (MDW)?
The cheapest month to fly from MIA to MDW is October, when demand is low. Off-peak season is usually when airlines offer lower prices between these airports.
Which airlines fly direct from Miami Intl. Airport (MIA) to Midway Intl. Airport (MDW)?
Hop on a nonstop flight with Southwest Airlines and head straight from Miami Intl. Airport (MIA) to Midway Intl. Airport (MDW).
What is the cheapest airline that flies from Miami Intl. Airport (MIA) to Midway Intl. Airport (MDW)?
While prices can change depending on when you travel, Frontier Airlines and Southwest Airlines are popular options for flights between Miami Intl. Airport (MIA) and Midway Intl. Airport (MDW). You can also compare carriers on Expedia and use the "Sort by" filter to find the best deal for your MIA to MDW flight.
How many flights per day from Miami Intl. Airport (MIA) to Midway Intl. Airport (MDW)?
On average, only 1 nonstop flight departs daily from Miami Intl. Airport (MIA) to Midway Intl. Airport (MDW). Need other options? Use Expedia's filters to find flights with layovers and add a new stop to your trip.
What are the most popular departure times for flights from Miami Intl. Airport (MIA) to Midway Intl. Airport (MDW)?
More travelers fly between MIA and MDW at 4 PM than at any other time. Rather go when it's quieter? Pick a flight outside the busiest times and you could save on your fare as well.
What day of the week has the most flights from MIA to MDW?
Saturday has the most flights from Miami Intl. Airport (MIA) to Midway Intl. Airport (MDW). Consider taking off on this day and you'll have the best chance of finding a departure that fits your plans.
What is the earliest flight from Miami Intl. Airport (MIA) to Midway Intl. Airport (MDW)?
Miami Intl. Airport (MIA)'s earliest flight to Midway Intl. Airport (MDW) is at approximately 8:10AM UTC-5. With a total travel time of 3h 10m, you'll arrive at around 10:20AM UTC-6.
How long does it take to fly from Miami Intl. Airport (MIA) to Midway Intl. Airport (MDW)?
Flights from MIA to MDW have an average travel time of 3 hours and 19 minutes. The distance between these two airports is 1,200 mi.
What is the best time to fly from Miami Intl. Airport (MIA) to Midway Intl. Airport (MDW)?
Select a flight from Miami Intl. Airport (MIA) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the risk of cancellations and delays. Later departures have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Miami Intl. Airport (MIA)?
You'll touch down at O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW) when traveling to Chicago on a direct flight from Miami Intl. Airport (MIA).
Is it cheaper to buy a plane ticket from Miami Intl. Airport (MIA) to Midway Intl. Airport (MDW) last-minute?
Waiting until right before your break to book a ticket from MIA to MDW generally means paying more. While you might find some last-minute discounts, they aren't always guaranteed. Keep your travel schedule open for the best chance of scoring a bargain.
Is it cheaper to book a MIA to MDW flight and hotel package?
Booking a MIA to MDW flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels all in one place. Pick from our wide range of stays and then add activities, car rentals and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Miami Intl. Airport (MIA) to Midway Intl. Airport (MDW)?
If you booked your MIA to MDW flight in the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for further details.

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*Available to One Key members.