Tampa (TPA) to Chicago (MDW) · Dec 5, 2026 · return Dec 12, 2026

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.

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights: the lowest 3★, 4★, 5★ stay totals among the city's featured hotels, Axel's price for 2 adults in 1 room, each opening that hotel's page for those dates with the rooms and the booking link.

• Hotels in Chicago for these nights (Dec 5–12, 2026 · 7 nights · 2 adults, 1 room): 3★ Chicago Lake Shore Hotel, $804 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $1,068 total · 5★ Nobu Hotel Chicago, $2,855 total

All hotels in Chicago

Route overview: Tampa to Chicago (MDW) flight deals

2026-12-05 → 2026-12-12 · Axel-exclusive $180.00

• Frontier Airlines F94435 / F92779: TPA 2026-12-05 13:05:00 → MDW 2026-12-05 17:47:00; 1 stop(s) via ATL; 342 minutes. Local airport times.
  • F94435: TPA 2026-12-05 13:05:00 → ATL 2026-12-05 14:54:00; layover at ATL: 111 minutes.
  • F92779: ATL 2026-12-05 16:45:00 → MDW 2026-12-05 17:47:00.
• Frontier Airlines F92292 / F92724: MDW 2026-12-12 12:28:00 → TPA 2026-12-12 18:30:00; 1 stop(s) via ATL; 302 minutes. Local airport times.
  • F92292: MDW 2026-12-12 12:28:00 → ATL 2026-12-12 15:41:00; layover at ATL: 74 minutes.
  • F92724: ATL 2026-12-12 16:55:00 → TPA 2026-12-12 18:30:00.

2026-12-05 → 2026-12-12 · Axel-exclusive $260.00

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

2026-12-05 → 2026-12-12 · Axel-exclusive $350.00

• Delta Air Lines DL1726 / DL1063: TPA 2026-12-05 06:20:00 → MDW 2026-12-05 10:00:00; 1 stop(s) via ATL; 280 minutes. Local airport times.
  • DL1726: TPA 2026-12-05 06:20:00 → ATL 2026-12-05 07:55:00; layover at ATL: 60 minutes.
  • DL1063: ATL 2026-12-05 08:55:00 → MDW 2026-12-05 10:00:00.
• Delta Air Lines DL1063 / DL1425: MDW 2026-12-12 11:28:00 → TPA 2026-12-12 18:15:00; 1 stop(s) via ATL; 347 minutes. Local airport times.
  • DL1063: MDW 2026-12-12 11:28:00 → ATL 2026-12-12 14:22:00; layover at ATL: 143 minutes.
  • DL1425: ATL 2026-12-12 16:45:00 → TPA 2026-12-12 18:15:00.

2026-12-05 → 2026-12-12 · Axel-exclusive $260.00

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

2026-12-05 → 2026-12-12 · Axel-exclusive $260.00

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

2026-12-05 → 2026-12-12 · Axel-exclusive $270.00

• Southwest Airlines WN3029: TPA 2026-12-05 16:30:00 → MDW 2026-12-05 18:15:00; nonstop; 165 minutes. Local airport times.
• Southwest Airlines WN1742 / WN2718: MDW 2026-12-12 17:10:00 → TPA 2026-12-12 23:55:00; 1 stop(s) via MCI; 345 minutes. Local airport times.
  • WN1742: MDW 2026-12-12 17:10:00 → MCI 2026-12-12 18:40:00; layover at MCI: 100 minutes.
  • WN2718: MCI 2026-12-12 20:20:00 → TPA 2026-12-12 23:55:00.

Explore this route

• All dates for this route
• Dec 4, 2026 · Return options
• Dec 6, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Tampa (TPA) to Chicago (MDW) · Dec 5, 2026 · return Dec 12, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Chicago for exactly those nights: the lowest 3★, 4★ and 5★ stay totals for 2 adults in 1 room, each linking to that hotel's page for those dates.
• Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
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• If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Tampa to Chicago (MDW) flight deals · Flight search guide.
• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

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