Tampa (TPA) to Chicago (MDW), Dec 13–25, 2026: from $299 round trip
Tampa (TPA) to Chicago (MDW), Dec 13–25, 2026: from $299 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $299 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Dec 13–25, 2026, 1 adult, economy, checked Oct 29, 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.
| Exact travel dates | Airline | Flights | Times, duration, stops | Total price | Price issued (UTC) |
|---|---|---|---|---|---|
| 2026-12-13 → 2026-12-25 | Southwest Airlines | WN4265 / WN4567 | 19:20:00→21:10:00 2h 50m nonstop · 16:40:00→20:15:00 2h 35m nonstop | Axel-exclusive $322.00 | 2026-10-29T01:30:10Z |
| 2026-12-13 → 2026-12-25 | Delta Air Lines | DL1726 + DL1063 / DL1063 + DL1425 | 06:20:00→10:00:00 4h 40m 1 stop via ATL · 11:28:00→18:15:00 5h 47m 1 stop via ATL | Axel-exclusive $402.50 | 2026-10-29T01:30:10Z |
| 2026-12-13 → 2026-12-25 | Southwest Airlines | WN186 + WN4770 / WN2886 + WN314 | 18:05:00→23:00:00 5h 55m 1 stop via STL · 13:20:00→18:55:00 4h 35m 1 stop via ATL | Axel-exclusive $299.00 | 2026-10-29T01:30:10Z |
| 2026-12-13 → 2026-12-25 | Southwest Airlines | WN2977 + WN3175 / WN2886 + WN314 | 08:05:00→12:30:00 5h 25m 1 stop via MSY · 13:20:00→18:55:00 4h 35m 1 stop via ATL | Axel-exclusive $299.00 | 2026-10-29T01:30:10Z |
| 2026-12-13 → 2026-12-25 | Southwest Airlines | WN4269 + WN1718 / WN2886 + WN314 | 15:55:00→19:40:00 4h 45m 1 stop via CMH · 13:20:00→18:55:00 4h 35m 1 stop via ATL | Axel-exclusive $299.00 | 2026-10-29T01:30:10Z |
| 2026-12-13 → 2026-12-25 | Southwest Airlines | WN523 + WN1005 / WN2886 + WN314 | 08:05:00→12:55:00 5h 50m 1 stop via BNA · 13:20:00→18:55:00 4h 35m 1 stop via ATL | Axel-exclusive $299.00 | 2026-10-29T01:30:10Z |
| 2026-12-13 → 2026-12-25 | Southwest Airlines | WN4265 / WN2886 + WN314 | 20:20:00→22:05:00 2h 45m nonstop · 13:20:00→18:55:00 4h 35m 1 stop via ATL | Axel-exclusive $309.00 | 2026-10-29T01:30:10Z |
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 lowest saved total among the shortlisted hotels in that star tier for those dates.
- Hotels in Chicago for these nights (Dec 13–25, 2026 · 12 nights · 2 adults, 1 room): 3★ Hotel Versey, $1,092 total · 4★ Warwick Allerton - Chicago, $1,154 total · 5★ Sofitel Chicago Magnificent Mile, $2,576 total
Route overview: Tampa to Chicago (MDW) flight deals
2026-12-13 → 2026-12-25 · Axel-exclusive $322.00
- Southwest Airlines WN4265: TPA 2026-12-13 19:20:00 → MDW 2026-12-13 21:10:00; nonstop; 170 minutes. Local airport times.
- Southwest Airlines WN4567: MDW 2026-12-25 16:40:00 → TPA 2026-12-25 20:15:00; nonstop; 155 minutes. Local airport times.
2026-12-13 → 2026-12-25 · Axel-exclusive $402.50
- Delta Air Lines DL1726 / DL1063: TPA 2026-12-13 06:20:00 → MDW 2026-12-13 10:00:00; 1 stop(s) via ATL; 280 minutes. Local airport times.
- DL1726: TPA 2026-12-13 06:20:00 → ATL 2026-12-13 07:55:00; layover at ATL: 60 minutes.
- DL1063: ATL 2026-12-13 08:55:00 → MDW 2026-12-13 10:00:00.
- Delta Air Lines DL1063 / DL1425: MDW 2026-12-25 11:28:00 → TPA 2026-12-25 18:15:00; 1 stop(s) via ATL; 347 minutes. Local airport times.
- DL1063: MDW 2026-12-25 11:28:00 → ATL 2026-12-25 14:22:00; layover at ATL: 143 minutes.
- DL1425: ATL 2026-12-25 16:45:00 → TPA 2026-12-25 18:15:00.
2026-12-13 → 2026-12-25 · Axel-exclusive $299.00
- Southwest Airlines WN186 / WN4770: TPA 2026-12-13 18:05:00 → MDW 2026-12-13 23:00:00; 1 stop(s) via STL; 355 minutes. Local airport times.
- WN186: TPA 2026-12-13 18:05:00 → STL 2026-12-13 19:40:00; layover at STL: 130 minutes.
- WN4770: STL 2026-12-13 21:50:00 → MDW 2026-12-13 23:00:00.
- Southwest Airlines WN2886 / WN314: MDW 2026-12-25 13:20:00 → TPA 2026-12-25 18:55:00; 1 stop(s) via ATL; 275 minutes. Local airport times.
- WN2886: MDW 2026-12-25 13:20:00 → ATL 2026-12-25 16:10:00; layover at ATL: 80 minutes.
- WN314: ATL 2026-12-25 17:30:00 → TPA 2026-12-25 18:55:00.
2026-12-13 → 2026-12-25 · Axel-exclusive $299.00
- Southwest Airlines WN2977 / WN3175: TPA 2026-12-13 08:05:00 → MDW 2026-12-13 12:30:00; 1 stop(s) via MSY; 325 minutes. Local airport times.
- WN2977: TPA 2026-12-13 08:05:00 → MSY 2026-12-13 08:45:00; layover at MSY: 85 minutes.
- WN3175: MSY 2026-12-13 10:10:00 → MDW 2026-12-13 12:30:00.
- Southwest Airlines WN2886 / WN314: MDW 2026-12-25 13:20:00 → TPA 2026-12-25 18:55:00; 1 stop(s) via ATL; 275 minutes. Local airport times.
- WN2886: MDW 2026-12-25 13:20:00 → ATL 2026-12-25 16:10:00; layover at ATL: 80 minutes.
- WN314: ATL 2026-12-25 17:30:00 → TPA 2026-12-25 18:55:00.
2026-12-13 → 2026-12-25 · Axel-exclusive $299.00
- Southwest Airlines WN4269 / WN1718: TPA 2026-12-13 15:55:00 → MDW 2026-12-13 19:40:00; 1 stop(s) via CMH; 285 minutes. Local airport times.
- WN4269: TPA 2026-12-13 15:55:00 → CMH 2026-12-13 18:10:00; layover at CMH: 80 minutes.
- WN1718: CMH 2026-12-13 19:30:00 → MDW 2026-12-13 19:40:00.
- Southwest Airlines WN2886 / WN314: MDW 2026-12-25 13:20:00 → TPA 2026-12-25 18:55:00; 1 stop(s) via ATL; 275 minutes. Local airport times.
- WN2886: MDW 2026-12-25 13:20:00 → ATL 2026-12-25 16:10:00; layover at ATL: 80 minutes.
- WN314: ATL 2026-12-25 17:30:00 → TPA 2026-12-25 18:55:00.
2026-12-13 → 2026-12-25 · Axel-exclusive $299.00
- Southwest Airlines WN523 / WN1005: TPA 2026-12-13 08:05:00 → MDW 2026-12-13 12:55:00; 1 stop(s) via BNA; 350 minutes. Local airport times.
- WN523: TPA 2026-12-13 08:05:00 → BNA 2026-12-13 09:00:00; layover at BNA: 145 minutes.
- WN1005: BNA 2026-12-13 11:25:00 → MDW 2026-12-13 12:55:00.
- Southwest Airlines WN2886 / WN314: MDW 2026-12-25 13:20:00 → TPA 2026-12-25 18:55:00; 1 stop(s) via ATL; 275 minutes. Local airport times.
- WN2886: MDW 2026-12-25 13:20:00 → ATL 2026-12-25 16:10:00; layover at ATL: 80 minutes.
- WN314: ATL 2026-12-25 17:30:00 → TPA 2026-12-25 18:55:00.
2026-12-13 → 2026-12-25 · Axel-exclusive $309.00
- Southwest Airlines WN4265: TPA 2026-12-13 20:20:00 → MDW 2026-12-13 22:05:00; nonstop; 165 minutes. Local airport times.
- Southwest Airlines WN2886 / WN314: MDW 2026-12-25 13:20:00 → TPA 2026-12-25 18:55:00; 1 stop(s) via ATL; 275 minutes. Local airport times.
- WN2886: MDW 2026-12-25 13:20:00 → ATL 2026-12-25 16:10:00; layover at ATL: 80 minutes.
- WN314: ATL 2026-12-25 17:30:00 → TPA 2026-12-25 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.
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- All dates for this route
- Dec 12, 2026 · Return options
- Dec 14, 2026 · Return options
- Hotels in Chicago with Axel
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- This page: Tampa (TPA) to Chicago (MDW) · Dec 13, 2026 · return Dec 25, 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 link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates.
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