Chicago (MDW) to Miami (MIA): 1,184 miles (1,905 km) great-circle, about 2h 50m nonstop by our estimate. Cheapest fare observed: $138 round-trip on Southwest, with 1 stop, departing May 13, 2026.
$138 round-trip, Southwest WN2630, departing 2026-05-13 at 08:15, returning 2026-05-17. The recorded itinerary left on a Wednesday, returning on a Sunday 4 nights later; the fare was observed 18 days before departure. "Book this flight" opens Kiwi.com with the same airline and dates.
At $138, it ranked 2nd of the 30 round-trip fares we recorded from MDW (median $316). That is 11.7 cents per great-circle mile (round-trip price over one-way distance), below the MDW median of 22.1 cents across 30 round-trip routes.
Routes from MDW of similar length: Fort Lauderdale (1,169 mi) at $160 and Tampa (998 mi) at $178.
Southwest had the cheapest fare on 12 of 30 MDW routes. It is the 21st longest of the 30 routes we track from MDW.
Of 30 departure airports with a fare to Miami, Chicago (MDW) ranked 8th at $138. Lowest: $72 from Atlanta (ATL); highest: $1627 from Wellington (WLG); 10 nonstop. Cheapest-fare airlines (routes): Frontier (13), Spirit (4), Southwest (3), American Airlines (2), Arajet (2) and Avianca (1), plus 5 more.
The reverse, Miami (MIA) to Chicago (CHI), was $165 round-trip on Spirit, nonstop, departing May 22, 2026. Miami to Chicago flights.
Travelpayouts fares (cheapest per route, observed April 25, 2026); OurAirports coordinates and elevations; IANA zones America/Chicago, America/New_York; flight time is our estimate.