Southwest® flights from Miami to Chicago (O'Hare) from $129

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Low fares from Miami to Chicago (O'Hare)

$

Miami (MIA)to

Chicago (Midway) (MDW)
Depart: 03/07/2026

One-way

Choice

From
$79
Seen: 23 hrs ago

Miami (MIA)to

Chicago (Midway) (MDW)
Depart: 03/05/2026

One-way

Choice

From
$79
Seen: 1 minute ago

Miami (MIA)to

Chicago (Midway) (MDW)
Depart: 04/08/2026

One-way

Choice

From
$99
Seen: 23 hrs ago

Miami (MIA)to

Chicago (Midway) (MDW)
Depart: 03/17/2026

One-way

Choice

From
$99
Seen: 14 hrs ago

Miami (MIA)to

Chicago (Midway) (MDW)
Depart: 03/18/2026

One-way

Choice

From
$99
Seen: 8 hrs ago

Miami (MIA)to

Chicago (Midway) (MDW)
Depart: 03/25/2026

One-way

Choice

From
$99
Seen: 5 hrs ago

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Explore flights from Miami to Chicago (O'Hare)

*Fares displayed have been collected within the last 24 hours and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply. Modifying this information may result in a different fare. To find the most updated fare, please visit Southwest.com. Fares listed are Basic, which are subject to additional terms and conditions.

Flight Details

Departing from:
Miami International Airport
Arriving at:
O'Hare International Airport
Distance:
1197 miles

Route Information

35† Weekly flights

† Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.

‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.

Questions we hear the most

There are 35 weekly flights from Miami to Chicago (O'Hare) on Southwest Airlines.
To find the lowest fares by day and time to fly Miami to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
You can rent a car at O'Hare International Airport book yours with your flight.
Yes! Flights from Miami to Chicago (O'Hare)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
Check the status of your upcoming Southwest flight.
Check out the Southwest Airlines® Help Center for answers about everything Southwest.

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