$49 Cheap Flights from Miami (MIA) to Chicago (MDW)

View $49 flight on Thu, Oct 16, 2025Opens in a new window

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

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • one key icon

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Miami to Chicago (MIA-MDW)

Prices were available within the past 7 days and start at $49 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
Mon, Oct 20 - Mon, Oct 27
MIA
Miami
MDW
Chicago
$108 Roundtrip, found 3 days ago
$108
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Oct 20 from Miami to Chicago, returning Mon, Oct 27, priced at $108 found 3 days ago
Southwest Airlines
Thu, Oct 23 - Mon, Oct 27
MIA
Miami
MDW
Chicago
$128 Roundtrip, found 22 hours ago
$128
Roundtrip
found 22 hours ago
Select Southwest Airlines flight, departing Thu, Oct 23 from Miami to Chicago, returning Mon, Oct 27, priced at $128 found 22 hours ago
Southwest Airlines
Thu, Sep 4 - Mon, Sep 8
MIA
Miami
MDW
Chicago
$137 Roundtrip, just found
$137
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Sep 4 from Miami to Chicago, returning Mon, Sep 8, priced at $137 just found
Frontier Airlines
Thu, Oct 16 - Mon, Oct 27
MIA
Miami
MDW
Chicago
$138 Roundtrip, found 5 days ago
$138
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Oct 16 from Miami to Chicago, returning Mon, Oct 27, priced at $138 found 5 days ago
Frontier Airlines
Thu, Oct 23 - Mon, Oct 27
MIA
Miami
MDW
Chicago
$140 Roundtrip, found 22 hours ago
$140
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Thu, Oct 23 from Miami to Chicago, returning Mon, Oct 27, priced at $140 found 22 hours ago
Southwest Airlines
Sat, Oct 18 - Mon, Oct 20
MIA
Miami
MDW
Chicago
$142 Roundtrip, found 6 days ago
$142
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Oct 18 from Miami to Chicago, returning Mon, Oct 20, priced at $142 found 6 days ago
Southwest Airlines
Thu, Sep 4 - Mon, Sep 8
MIA
Miami
MDW
Chicago
$147 Roundtrip, just found
$147
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Sep 4 from Miami to Chicago, returning Mon, Sep 8, priced at $147 just found
Southwest Airlines
Tue, Sep 23 - Mon, Sep 29
MIA
Miami
MDW
Chicago
$152 Roundtrip, found 21 hours ago
$152
Roundtrip
found 21 hours ago
Select Southwest Airlines flight, departing Tue, Sep 23 from Miami to Chicago, returning Mon, Sep 29, priced at $152 found 21 hours ago
Frontier Airlines
Thu, Oct 23 - Mon, Oct 27
MIA
Miami
MDW
Chicago
$154 Roundtrip, found 2 hours ago
$154
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Oct 23 from Miami to Chicago, returning Mon, Oct 27, priced at $154 found 2 hours ago
Delta
Thu, Sep 18 - Sun, Sep 21
MIA
Miami
MDW
Chicago
$177 Roundtrip, found 3 hours ago
$177
Roundtrip
found 3 hours ago
Select Delta flight, departing Thu, Sep 18 from Miami to Chicago, returning Sun, Sep 21, priced at $177 found 3 hours ago

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

February is typically the cheapest month to fly

From $78 - $298 per traveler.

Graph displaying average flight prices per month

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 $133
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $133
Flights from Miami (MIA) to Chicago (MDW)
Origin airport
Miami Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$102
Distance
1183 mi
Average flight time
2 hours 6 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 $49 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?
Cheap round-trip flights from Miami Intl. Airport (MIA) to Midway Intl. Airport (MDW) start from $123. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines and Spirit Airlines flight leaving MIA on August 3 2025 and touching down at MDW. The price was last updated on July 23 2025 and has not changed since.
What is the cheapest month to fly from MIA to MDW?
The cheapest flights from MIA to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
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 MIA to MDW?
Book a flight from MIA to MDW with Southwest Airlines. This carrier currently has the cheapest one-way fare for this route, starting from $69. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MIA on October 10 2025. Prices were last updated on July 23 2025 and have not changed since.
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.

Explore a world of travel with Expedia

*Available to One Key members.