$90 Cheap Flights from Miami (MIA) to Chicago (MDW)

View $90 flight on Wed, Jul 2, 2025Opens in a new window

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

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Find available prices by choosing your travel dates.

Cheap Flights from Miami to Chicago (MIA-MDW)

Prices were available within the past 7 days and start at $90 for one-way flights and $188 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Sat, May 24 - Sun, Jun 1
MIA
Miami
MDW
Chicago
$188 Roundtrip, just found
$188
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, May 24 from Miami to Chicago, returning Sun, Jun 1, priced at $188 just found
Southwest Airlines
Tue, Jul 1 - Sat, Jul 5
MIA
Miami
MDW
Chicago
$189 Roundtrip, found 8 hours ago
$189
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Tue, Jul 1 from Miami to Chicago, returning Sat, Jul 5, priced at $189 found 8 hours ago
Southwest Airlines
Tue, Jun 17 - Sun, Jun 22
MIA
Miami
MDW
Chicago
$197 Roundtrip, just found
$197
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Jun 17 from Miami to Chicago, returning Sun, Jun 22, priced at $197 just found
Southwest Airlines
Fri, Jul 4 - Tue, Jul 8
MIA
Miami
MDW
Chicago
$198 Roundtrip, found 7 hours ago
$198
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Fri, Jul 4 from Miami to Chicago, returning Tue, Jul 8, priced at $198 found 7 hours ago
Southwest Airlines
Sat, May 24 - Tue, May 27
MIA
Miami
MDW
Chicago
$199 Roundtrip, found 10 hours ago
$199
Roundtrip
found 10 hours ago
Select Southwest Airlines flight, departing Sat, May 24 from Miami to Chicago, returning Tue, May 27, priced at $199 found 10 hours ago
Southwest Airlines
Wed, Jul 2 - Wed, Jul 9
MIA
Miami
MDW
Chicago
$202 Roundtrip, found 7 hours ago
$202
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Wed, Jul 2 from Miami to Chicago, returning Wed, Jul 9, priced at $202 found 7 hours ago
Delta
Tue, Jun 17 - Sun, Jun 22
MIA
Miami
MDW
Chicago
$207 Roundtrip, just found
$207
Roundtrip
just found
Select Delta flight, departing Tue, Jun 17 from Miami to Chicago, returning Sun, Jun 22, priced at $207 just found
Southwest Airlines
Sun, Jun 29 - Wed, Jul 2
MIA
Miami
MDW
Chicago
$208 Roundtrip, found 18 hours ago
$208
Roundtrip
found 18 hours ago
Select Southwest Airlines flight, departing Sun, Jun 29 from Miami to Chicago, returning Wed, Jul 2, priced at $208 found 18 hours ago
Southwest Airlines
Sat, May 17 - Wed, May 21
MIA
Miami
MDW
Chicago
$209 Roundtrip, found 7 hours ago
$209
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Sat, May 17 from Miami to Chicago, returning Wed, May 21, priced at $209 found 7 hours ago
Frontier Airlines
Fri, May 16 - Tue, May 20
MIA
Miami
MDW
Chicago
$220 Roundtrip, just found
$220
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, May 16 from Miami to Chicago, returning Tue, May 20, priced at $220 just found

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 $138. 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 May 17 2025 and touching down at MDW. The price was last updated on April 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 $89. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MIA on May 20 2025. Prices were last updated on April 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.
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