Chicago (MDW) to Tampa (TPA): 998 miles (1,607 km) great-circle, about 2h 30m nonstop by our estimate. Cheapest fare observed: $178 round-trip on Frontier, with 1 stop, departing May 27, 2026.
$178 round-trip, Frontier F92780, departing 2026-05-27 at 12:04, returning 2026-05-30. The recorded itinerary left on a Wednesday, returning on a Saturday 3 nights later; the fare was observed 32 days before departure. "Book this flight" opens Kiwi.com with the same airline and dates.
At $178, it ranked 6th of the 30 round-trip fares we recorded from MDW (median $316). That is 17.8 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: Orlando (983 mi) at $154 and Houston (938 mi) at $253.
Frontier had the cheapest fare on 11 of 30 MDW routes. It is the 23rd longest of the 30 routes we track from MDW.
Of 14 departure airports with a fare to Tampa, Chicago (MDW) ranked 6th at $178. Lowest: $101 from Fort Lauderdale (FLL); highest: $400 from Las Vegas (LAS); 4 nonstop. Cheapest-fare airlines (routes): Frontier (6), American Airlines (2), Spirit (2), Air Canada (1), Allegiant Air (1) and Southwest (1), plus 1 more.
The reverse, Tampa (TPA) to Chicago (CHI), was $178 round-trip on Spirit, nonstop, departing July 1, 2026. Tampa 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.