Tampa (TPA) to Chicago (MDW), Dec 7–18, 2026: from $260 round trip

Tampa (TPA) to Chicago (MDW), Dec 7–18, 2026: from $260 round trip on Axel, checked Nov 11, 2026. Lowest published fare: $260 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Dec 7–18, 2026, 1 adult, economy, checked Nov 11, 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 link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Chicago for these nights (Dec 7–18, 2026 · 11 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $95 a night, $1,046 for 11 nights · 4★ Warwick Allerton - Chicago, $97 a night, $1,062 for 11 nights · 5★ Waldorf Astoria Chicago, $520 a night, $5,718 for 11 nights

All hotels in Chicago

Route overview: Tampa to Chicago (MDW) flight deals

2026-12-07 → 2026-12-18 · Axel-exclusive $260.00

• Southwest Airlines WN523 / WN1005: TPA 2026-12-07 08:05:00 → MDW 2026-12-07 12:55:00; 1 stop(s) via BNA; 350 minutes. Local airport times.
  • WN523: TPA 2026-12-07 08:05:00 → BNA 2026-12-07 09:00:00; layover at BNA: 145 minutes.
  • WN1005: BNA 2026-12-07 11:25:00 → MDW 2026-12-07 12:55:00.
• Southwest Airlines WN2886 / WN314: MDW 2026-12-18 13:20:00 → TPA 2026-12-18 18:55:00; 1 stop(s) via ATL; 275 minutes. Local airport times.
  • WN2886: MDW 2026-12-18 13:20:00 → ATL 2026-12-18 16:10:00; layover at ATL: 80 minutes.
  • WN314: ATL 2026-12-18 17:30:00 → TPA 2026-12-18 18:55:00.

2026-12-07 → 2026-12-18 · Axel-exclusive $350.00

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

2026-12-07 → 2026-12-18 · Axel-exclusive $260.00

• Southwest Airlines WN2977 / WN3175: TPA 2026-12-07 08:05:00 → MDW 2026-12-07 12:30:00; 1 stop(s) via MSY; 325 minutes. Local airport times.
  • WN2977: TPA 2026-12-07 08:05:00 → MSY 2026-12-07 08:45:00; layover at MSY: 85 minutes.
  • WN3175: MSY 2026-12-07 10:10:00 → MDW 2026-12-07 12:30:00.
• Southwest Airlines WN2886 / WN314: MDW 2026-12-18 13:20:00 → TPA 2026-12-18 18:55:00; 1 stop(s) via ATL; 275 minutes. Local airport times.
  • WN2886: MDW 2026-12-18 13:20:00 → ATL 2026-12-18 16:10:00; layover at ATL: 80 minutes.
  • WN314: ATL 2026-12-18 17:30:00 → TPA 2026-12-18 18:55:00.

2026-12-07 → 2026-12-18 · Axel-exclusive $260.00

• Southwest Airlines WN4269 / WN1718: TPA 2026-12-07 15:55:00 → MDW 2026-12-07 19:40:00; 1 stop(s) via CMH; 285 minutes. Local airport times.
  • WN4269: TPA 2026-12-07 15:55:00 → CMH 2026-12-07 18:10:00; layover at CMH: 80 minutes.
  • WN1718: CMH 2026-12-07 19:30:00 → MDW 2026-12-07 19:40:00.
• Southwest Airlines WN2886 / WN314: MDW 2026-12-18 13:20:00 → TPA 2026-12-18 18:55:00; 1 stop(s) via ATL; 275 minutes. Local airport times.
  • WN2886: MDW 2026-12-18 13:20:00 → ATL 2026-12-18 16:10:00; layover at ATL: 80 minutes.
  • WN314: ATL 2026-12-18 17:30:00 → TPA 2026-12-18 18:55:00.

2026-12-07 → 2026-12-18 · Axel-exclusive $260.00

• Southwest Airlines WN186 / WN4770: TPA 2026-12-07 18:05:00 → MDW 2026-12-07 23:00:00; 1 stop(s) via STL; 355 minutes. Local airport times.
  • WN186: TPA 2026-12-07 18:05:00 → STL 2026-12-07 19:40:00; layover at STL: 130 minutes.
  • WN4770: STL 2026-12-07 21:50:00 → MDW 2026-12-07 23:00:00.
• Southwest Airlines WN2886 / WN314: MDW 2026-12-18 13:20:00 → TPA 2026-12-18 18:55:00; 1 stop(s) via ATL; 275 minutes. Local airport times.
  • WN2886: MDW 2026-12-18 13:20:00 → ATL 2026-12-18 16:10:00; layover at ATL: 80 minutes.
  • WN314: ATL 2026-12-18 17:30:00 → TPA 2026-12-18 18:55:00.

2026-12-07 → 2026-12-18 · Axel-exclusive $270.00

• Southwest Airlines WN3016: TPA 2026-12-07 19:50:00 → MDW 2026-12-07 21:35:00; nonstop; 165 minutes. Local airport times.
• Southwest Airlines WN2886 / WN314: MDW 2026-12-18 13:20:00 → TPA 2026-12-18 18:55:00; 1 stop(s) via ATL; 275 minutes. Local airport times.
  • WN2886: MDW 2026-12-18 13:20:00 → ATL 2026-12-18 16:10:00; layover at ATL: 80 minutes.
  • WN314: ATL 2026-12-18 17:30:00 → TPA 2026-12-18 18:55:00.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

Explore this route

• All dates for this route
• Dec 6, 2026 · Return options
• Dec 8, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Tampa (TPA) to Chicago (MDW) · Dec 7, 2026 · return Dec 18, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date. Under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in each star tier for those dates.
• Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
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