Tampa (TPA) to Chicago (MDW) · Dec 27, 2026 · return Jan 2, 2027

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Route overview: Tampa to Chicago (MDW) flight deals

2026-12-27 → 2027-01-02 · Axel-exclusive $364.00

• Southwest Airlines WN4263: TPA 2026-12-27 13:20:00 → MDW 2026-12-27 15:00:00; nonstop; 160 minutes. Local airport times.
• Southwest Airlines WN4567: MDW 2027-01-02 16:40:00 → TPA 2027-01-02 20:15:00; nonstop; 155 minutes. Local airport times.

2026-12-27 → 2027-01-02 · Axel-exclusive $455.00

• Delta Air Lines DL1726 / DL1063: TPA 2026-12-27 06:20:00 → MDW 2026-12-27 10:00:00; 1 stop(s) via ATL; 280 minutes. Local airport times.
  • DL1726: TPA 2026-12-27 06:20:00 → ATL 2026-12-27 07:55:00; layover at ATL: 60 minutes.
  • DL1063: ATL 2026-12-27 08:55:00 → MDW 2026-12-27 10:00:00.
• Delta Air Lines DL1063 / DL1425: MDW 2027-01-02 11:28:00 → TPA 2027-01-02 18:15:00; 1 stop(s) via ATL; 347 minutes. Local airport times.
  • DL1063: MDW 2027-01-02 11:28:00 → ATL 2027-01-02 14:22:00; layover at ATL: 143 minutes.
  • DL1425: ATL 2027-01-02 16:45:00 → TPA 2027-01-02 18:15:00.

2026-12-27 → 2027-01-02 · Axel-exclusive $338.00

• Southwest Airlines WN2977 / WN3175: TPA 2026-12-27 08:05:00 → MDW 2026-12-27 12:30:00; 1 stop(s) via MSY; 325 minutes. Local airport times.
  • WN2977: TPA 2026-12-27 08:05:00 → MSY 2026-12-27 08:45:00; layover at MSY: 85 minutes.
  • WN3175: MSY 2026-12-27 10:10:00 → MDW 2026-12-27 12:30:00.
• Southwest Airlines WN1742 / WN2718: MDW 2027-01-02 17:10:00 → TPA 2027-01-02 23:55:00; 1 stop(s) via MCI; 345 minutes. Local airport times.
  • WN1742: MDW 2027-01-02 17:10:00 → MCI 2027-01-02 18:40:00; layover at MCI: 100 minutes.
  • WN2718: MCI 2027-01-02 20:20:00 → TPA 2027-01-02 23:55:00.

2026-12-27 → 2027-01-02 · Axel-exclusive $338.00

• Southwest Airlines WN523 / WN1005: TPA 2026-12-27 08:05:00 → MDW 2026-12-27 12:55:00; 1 stop(s) via BNA; 350 minutes. Local airport times.
  • WN523: TPA 2026-12-27 08:05:00 → BNA 2026-12-27 09:00:00; layover at BNA: 145 minutes.
  • WN1005: BNA 2026-12-27 11:25:00 → MDW 2026-12-27 12:55:00.
• Southwest Airlines WN1742 / WN2718: MDW 2027-01-02 17:10:00 → TPA 2027-01-02 23:55:00; 1 stop(s) via MCI; 345 minutes. Local airport times.
  • WN1742: MDW 2027-01-02 17:10:00 → MCI 2027-01-02 18:40:00; layover at MCI: 100 minutes.
  • WN2718: MCI 2027-01-02 20:20:00 → TPA 2027-01-02 23:55:00.

2026-12-27 → 2027-01-02 · Axel-exclusive $338.00

• Southwest Airlines WN4269 / WN1718: TPA 2026-12-27 15:55:00 → MDW 2026-12-27 19:40:00; 1 stop(s) via CMH; 285 minutes. Local airport times.
  • WN4269: TPA 2026-12-27 15:55:00 → CMH 2026-12-27 18:10:00; layover at CMH: 80 minutes.
  • WN1718: CMH 2026-12-27 19:30:00 → MDW 2026-12-27 19:40:00.
• Southwest Airlines WN1742 / WN2718: MDW 2027-01-02 17:10:00 → TPA 2027-01-02 23:55:00; 1 stop(s) via MCI; 345 minutes. Local airport times.
  • WN1742: MDW 2027-01-02 17:10:00 → MCI 2027-01-02 18:40:00; layover at MCI: 100 minutes.
  • WN2718: MCI 2027-01-02 20:20:00 → TPA 2027-01-02 23:55:00.

2026-12-27 → 2027-01-02 · Axel-exclusive $338.00

• Southwest Airlines WN186 / WN4770: TPA 2026-12-27 18:05:00 → MDW 2026-12-27 23:00:00; 1 stop(s) via STL; 355 minutes. Local airport times.
  • WN186: TPA 2026-12-27 18:05:00 → STL 2026-12-27 19:40:00; layover at STL: 130 minutes.
  • WN4770: STL 2026-12-27 21:50:00 → MDW 2026-12-27 23:00:00.
• Southwest Airlines WN1742 / WN2718: MDW 2027-01-02 17:10:00 → TPA 2027-01-02 23:55:00; 1 stop(s) via MCI; 345 minutes. Local airport times.
  • WN1742: MDW 2027-01-02 17:10:00 → MCI 2027-01-02 18:40:00; layover at MCI: 100 minutes.
  • WN2718: MCI 2027-01-02 20:20:00 → TPA 2027-01-02 23:55:00.

2026-12-27 → 2027-01-02 · Axel-exclusive $351.00

• Southwest Airlines WN4263: TPA 2026-12-27 14:45:00 → MDW 2026-12-27 16:30:00; nonstop; 165 minutes. Local airport times.
• Southwest Airlines WN1742 / WN2718: MDW 2027-01-02 17:10:00 → TPA 2027-01-02 23:55:00; 1 stop(s) via MCI; 345 minutes. Local airport times.
  • WN1742: MDW 2027-01-02 17:10:00 → MCI 2027-01-02 18:40:00; layover at MCI: 100 minutes.
  • WN2718: MCI 2027-01-02 20:20:00 → TPA 2027-01-02 23:55:00.

Explore this route

• All dates for this route
• Dec 26, 2026 · Return options
• Dec 28, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Tampa (TPA) to Chicago (MDW) · Dec 27, 2026 · return Jan 2, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
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