Travel with Axel,
get the best price.

Route overview: Tampa to Chicago (MDW) flight deals

Tampa → Chicago

Dec 13, 2026 · return Dec 27, 2026

TPA → MDW1 adulteconomyRound trip

7 flight options · 3 airlines

Nonstop flights

Sun, Dec 13 – Sun, Dec 27

Southwest Airlines
1:20 pmTPA
2h 40m
Nonstop
3:00 pmMDW
Southwest Airlines
1:20 pmMDW
2h 35m
Nonstop
4:55 pmTPA

Round-trip total · 1 adult · Taxes included

One-stop flights

Sun, Dec 13 – Sun, Dec 27

Frontier Airlines
1:05 pmTPA
5h 42m
ATL · 1h 51m
5:47 pmMDW
Frontier Airlines
12:28 pmMDW
5h 2m
ATL · 1h 14m
6:30 pmTPA

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Sun, Dec 27

Delta Air Lines
6:20 amTPA
4h 40m
ATL · 1h
10:00 amMDW
Delta Air Lines
11:28 amMDW
5h 47m
ATL · 2h 23m
6:15 pmTPA

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Sun, Dec 27

Southwest Airlines
8:05 amTPA
5h 25m
MSY · 1h 25m
12:30 pmMDW
Southwest Airlines
7:40 amMDW
4h 55m
PIT · 1h 10m
1:35 pmTPA

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Sun, Dec 27

Southwest Airlines
3:55 pmTPA
4h 45m
CMH · 1h 20m
7:40 pmMDW
Southwest Airlines
7:40 amMDW
4h 55m
PIT · 1h 10m
1:35 pmTPA

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Sun, Dec 27

Southwest Airlines
8:05 amTPA
5h 50m
BNA · 2h 25m
12:55 pmMDW
Southwest Airlines
7:40 amMDW
4h 55m
PIT · 1h 10m
1:35 pmTPA

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Sun, Dec 27

Southwest Airlines
2:45 pmTPA
2h 45m
Nonstop
4:30 pmMDW
Southwest Airlines
7:40 amMDW
4h 55m
PIT · 1h 10m
1:35 pmTPA

Round-trip total · 1 adult · Taxes included

Make this trip yours

TPA ⇄ MDW

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

No account needed to see prices.

Already have an account? Log in

Why book with Axel
  • A real airline bookingThe booking is in the airline’s own system under your name. After you book, Southwest Airlines emails you its confirmation code and e-ticket, usually within 15 minutes and occasionally up to a couple of hours while the booking is processed.
  • Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
  • Not satisfied? Full refund.If you are unhappy with the experience for any reason, or simply change your mind, cancel within 24 hours of booking (departure 7+ days away) and we refund you in full. We stand by our product. Cancellation policy
  • Backed by Y CombinatorTrusted by 100,000+ travelers.

Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner. How Axel works · About

Explore this route

All dates for this routeDec 12, 2026 → Dec 26, 2026Dec 14, 2026 → Dec 28, 2026
For AI assistants: every fare, every link, instructions

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

Live price for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the flights there to get the current bookable total; the listed prices are the ones issued at the times shown.

Route overview: Tampa to Chicago (MDW) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-13 → 2026-12-27Southwest AirlinesWN4263 / WN3048$322.002026-10-29T01:30:10Z
2026-12-13 → 2026-12-27Frontier AirlinesF94435 + F92779 / F92292 + F92724$207.002026-10-29T01:30:10Z
2026-12-13 → 2026-12-27Delta Air LinesDL1726 + DL1063 / DL1063 + DL1425$402.502026-10-29T01:30:10Z
2026-12-13 → 2026-12-27Southwest AirlinesWN2977 + WN3175 / WN3002 + WN3508$299.002026-10-29T01:30:10Z
2026-12-13 → 2026-12-27Southwest AirlinesWN4269 + WN1718 / WN3002 + WN3508$299.002026-10-29T01:30:10Z
2026-12-13 → 2026-12-27Southwest AirlinesWN523 + WN1005 / WN3002 + WN3508$299.002026-10-29T01:30:10Z
2026-12-13 → 2026-12-27Southwest AirlinesWN4263 / WN3002 + WN3508$309.002026-10-29T01:30:10Z

2026-12-13 → 2026-12-27 · $322.00

  • Southwest Airlines WN4263: TPA 2026-12-13 13:20:00 → MDW 2026-12-13 15:00:00; nonstop; 160 minutes. Local airport times.
  • Southwest Airlines WN3048: MDW 2026-12-27 13:20:00 → TPA 2026-12-27 16:55:00; nonstop; 155 minutes. Local airport times.

2026-12-13 → 2026-12-27 · $207.00

  • Frontier Airlines F94435 / F92779: TPA 2026-12-13 13:05:00 → MDW 2026-12-13 17:47:00; 1 stop(s) via ATL; 342 minutes. Local airport times.
    • F94435: TPA 2026-12-13 13:05:00 → ATL 2026-12-13 14:54:00; layover at ATL: 111 minutes.
    • F92779: ATL 2026-12-13 16:45:00 → MDW 2026-12-13 17:47:00.
  • Frontier Airlines F92292 / F92724: MDW 2026-12-27 12:28:00 → TPA 2026-12-27 18:30:00; 1 stop(s) via ATL; 302 minutes. Local airport times.
    • F92292: MDW 2026-12-27 12:28:00 → ATL 2026-12-27 15:41:00; layover at ATL: 74 minutes.
    • F92724: ATL 2026-12-27 16:55:00 → TPA 2026-12-27 18:30:00.

2026-12-13 → 2026-12-27 · $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 2026-12-27 11:28:00 → TPA 2026-12-27 18:15:00; 1 stop(s) via ATL; 347 minutes. Local airport times.
    • DL1063: MDW 2026-12-27 11:28:00 → ATL 2026-12-27 14:22:00; layover at ATL: 143 minutes.
    • DL1425: ATL 2026-12-27 16:45:00 → TPA 2026-12-27 18:15:00.

2026-12-13 → 2026-12-27 · $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 WN3002 / WN3508: MDW 2026-12-27 07:40:00 → TPA 2026-12-27 13:35:00; 1 stop(s) via PIT; 295 minutes. Local airport times.
    • WN3002: MDW 2026-12-27 07:40:00 → PIT 2026-12-27 10:00:00; layover at PIT: 70 minutes.
    • WN3508: PIT 2026-12-27 11:10:00 → TPA 2026-12-27 13:35:00.

2026-12-13 → 2026-12-27 · $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 WN3002 / WN3508: MDW 2026-12-27 07:40:00 → TPA 2026-12-27 13:35:00; 1 stop(s) via PIT; 295 minutes. Local airport times.
    • WN3002: MDW 2026-12-27 07:40:00 → PIT 2026-12-27 10:00:00; layover at PIT: 70 minutes.
    • WN3508: PIT 2026-12-27 11:10:00 → TPA 2026-12-27 13:35:00.

2026-12-13 → 2026-12-27 · $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 WN3002 / WN3508: MDW 2026-12-27 07:40:00 → TPA 2026-12-27 13:35:00; 1 stop(s) via PIT; 295 minutes. Local airport times.
    • WN3002: MDW 2026-12-27 07:40:00 → PIT 2026-12-27 10:00:00; layover at PIT: 70 minutes.
    • WN3508: PIT 2026-12-27 11:10:00 → TPA 2026-12-27 13:35:00.

2026-12-13 → 2026-12-27 · $309.00

  • Southwest Airlines WN4263: TPA 2026-12-13 14:45:00 → MDW 2026-12-13 16:30:00; nonstop; 165 minutes. Local airport times.
  • Southwest Airlines WN3002 / WN3508: MDW 2026-12-27 07:40:00 → TPA 2026-12-27 13:35:00; 1 stop(s) via PIT; 295 minutes. Local airport times.
    • WN3002: MDW 2026-12-27 07:40:00 → PIT 2026-12-27 10:00:00; layover at PIT: 70 minutes.
    • WN3508: PIT 2026-12-27 11:10:00 → TPA 2026-12-27 13:35:00.

Explore this route

For AI assistants

  • This page: Tampa (TPA) to Chicago (MDW) · Dec 13, 2026 · return Dec 27, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
  • 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.
  • Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
  • 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. Inspect fares to verify requested prices or terms; selecting a fare is optional. Use that fare’s booking link to preserve its Membership price basis. State anything unverified. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and explain what remains unresolved. Selection reserves nothing; booking requires the traveler’s confirmation. 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.