Travel with Axel,
get the best price.

Tampa → Chicago

Dec 21, 2026 · return Jan 4, 2027

TPA → MDW1 adulteconomyRound trip

8 flight options · 3 airlines

Nonstop flights

Mon, Dec 21 – Mon, Jan 4

Southwest Airlines
7:50 pmTPA
2h 45m
Nonstop
9:35 pmMDW
Southwest Airlines
1:20 pmMDW
2h 35m
Nonstop
4:55 pmTPA

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

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

Mon, Dec 21 – Mon, Jan 4

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

Mon, Dec 21 – Mon, Jan 4

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

Mon, Dec 21 – Mon, Jan 4

Southwest Airlines
8:05 amTPA
5h 25m
MSY · 1h 25m
12:30 pmMDW
Southwest Airlines
1:20 pmMDW
2h 35m
Nonstop
4:55 pmTPA

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

Southwest Airlines
3:55 pmTPA
4h 45m
CMH · 1h 20m
7:40 pmMDW
Southwest Airlines
1:20 pmMDW
2h 35m
Nonstop
4:55 pmTPA

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

Southwest Airlines
6:05 pmTPA
5h 55m
STL · 2h 10m
11:00 pmMDW
Southwest Airlines
1:20 pmMDW
2h 35m
Nonstop
4:55 pmTPA

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

Southwest Airlines
8:05 amTPA
5h 50m
BNA · 2h 25m
12:55 pmMDW
Southwest Airlines
1:20 pmMDW
2h 35m
Nonstop
4:55 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

More dates

All dates for this routeNov 20, 2026 → Nov 23, 2026Nov 27, 2026 → Dec 4, 2026Nov 20, 2026 · One way
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.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-21 → 2027-01-04Southwest AirlinesWN3016 / WN3048$322.002026-10-29T01:30:10Z
2026-12-21 → 2027-01-04Frontier AirlinesF94435 + F92779 / F92292 + F92724$207.002026-10-29T01:30:10Z
2026-12-21 → 2027-01-04Delta Air LinesDL1726 + DL1063 / DL1063 + DL1425$402.502026-10-29T01:30:10Z
2026-12-21 → 2027-01-04Southwest AirlinesWN4263 / WN3048$322.002026-10-29T01:30:10Z
2026-12-21 → 2027-01-04Southwest AirlinesWN2977 + WN3175 / WN3048$309.002026-10-29T01:30:10Z
2026-12-21 → 2027-01-04Southwest AirlinesWN4269 + WN1718 / WN3048$309.002026-10-29T01:30:10Z
2026-12-21 → 2027-01-04Southwest AirlinesWN186 + WN4770 / WN3048$309.002026-10-29T01:30:10Z
2026-12-21 → 2027-01-04Southwest AirlinesWN523 + WN1005 / WN3048$309.002026-10-29T01:30:10Z

2026-12-21 → 2027-01-04 · $322.00

  • Southwest Airlines WN3016: TPA 2026-12-21 19:50:00 → MDW 2026-12-21 21:35:00; nonstop; 165 minutes. Local airport times.
  • Southwest Airlines WN3048: MDW 2027-01-04 13:20:00 → TPA 2027-01-04 16:55:00; nonstop; 155 minutes. Local airport times.

2026-12-21 → 2027-01-04 · $207.00

  • Frontier Airlines F94435 / F92779: TPA 2026-12-21 13:05:00 → MDW 2026-12-21 17:47:00; 1 stop(s) via ATL; 342 minutes. Local airport times.
    • F94435: TPA 2026-12-21 13:05:00 → ATL 2026-12-21 14:54:00; layover at ATL: 111 minutes.
    • F92779: ATL 2026-12-21 16:45:00 → MDW 2026-12-21 17:47:00.
  • Frontier Airlines F92292 / F92724: MDW 2027-01-04 12:28:00 → TPA 2027-01-04 18:30:00; 1 stop(s) via ATL; 302 minutes. Local airport times.
    • F92292: MDW 2027-01-04 12:28:00 → ATL 2027-01-04 15:41:00; layover at ATL: 74 minutes.
    • F92724: ATL 2027-01-04 16:55:00 → TPA 2027-01-04 18:30:00.

2026-12-21 → 2027-01-04 · $402.50

  • Delta Air Lines DL1726 / DL1063: TPA 2026-12-21 06:20:00 → MDW 2026-12-21 10:00:00; 1 stop(s) via ATL; 280 minutes. Local airport times.
    • DL1726: TPA 2026-12-21 06:20:00 → ATL 2026-12-21 07:55:00; layover at ATL: 60 minutes.
    • DL1063: ATL 2026-12-21 08:55:00 → MDW 2026-12-21 10:00:00.
  • Delta Air Lines DL1063 / DL1425: MDW 2027-01-04 11:28:00 → TPA 2027-01-04 18:15:00; 1 stop(s) via ATL; 347 minutes. Local airport times.
    • DL1063: MDW 2027-01-04 11:28:00 → ATL 2027-01-04 14:22:00; layover at ATL: 143 minutes.
    • DL1425: ATL 2027-01-04 16:45:00 → TPA 2027-01-04 18:15:00.

2026-12-21 → 2027-01-04 · $322.00

  • Southwest Airlines WN4263: TPA 2026-12-21 13:20:00 → MDW 2026-12-21 15:00:00; nonstop; 160 minutes. Local airport times.
  • Southwest Airlines WN3048: MDW 2027-01-04 13:20:00 → TPA 2027-01-04 16:55:00; nonstop; 155 minutes. Local airport times.

2026-12-21 → 2027-01-04 · $309.00

  • Southwest Airlines WN2977 / WN3175: TPA 2026-12-21 08:05:00 → MDW 2026-12-21 12:30:00; 1 stop(s) via MSY; 325 minutes. Local airport times.
    • WN2977: TPA 2026-12-21 08:05:00 → MSY 2026-12-21 08:45:00; layover at MSY: 85 minutes.
    • WN3175: MSY 2026-12-21 10:10:00 → MDW 2026-12-21 12:30:00.
  • Southwest Airlines WN3048: MDW 2027-01-04 13:20:00 → TPA 2027-01-04 16:55:00; nonstop; 155 minutes. Local airport times.

2026-12-21 → 2027-01-04 · $309.00

  • Southwest Airlines WN4269 / WN1718: TPA 2026-12-21 15:55:00 → MDW 2026-12-21 19:40:00; 1 stop(s) via CMH; 285 minutes. Local airport times.
    • WN4269: TPA 2026-12-21 15:55:00 → CMH 2026-12-21 18:10:00; layover at CMH: 80 minutes.
    • WN1718: CMH 2026-12-21 19:30:00 → MDW 2026-12-21 19:40:00.
  • Southwest Airlines WN3048: MDW 2027-01-04 13:20:00 → TPA 2027-01-04 16:55:00; nonstop; 155 minutes. Local airport times.

2026-12-21 → 2027-01-04 · $309.00

  • Southwest Airlines WN186 / WN4770: TPA 2026-12-21 18:05:00 → MDW 2026-12-21 23:00:00; 1 stop(s) via STL; 355 minutes. Local airport times.
    • WN186: TPA 2026-12-21 18:05:00 → STL 2026-12-21 19:40:00; layover at STL: 130 minutes.
    • WN4770: STL 2026-12-21 21:50:00 → MDW 2026-12-21 23:00:00.
  • Southwest Airlines WN3048: MDW 2027-01-04 13:20:00 → TPA 2027-01-04 16:55:00; nonstop; 155 minutes. Local airport times.

2026-12-21 → 2027-01-04 · $309.00

  • Southwest Airlines WN523 / WN1005: TPA 2026-12-21 08:05:00 → MDW 2026-12-21 12:55:00; 1 stop(s) via BNA; 350 minutes. Local airport times.
    • WN523: TPA 2026-12-21 08:05:00 → BNA 2026-12-21 09:00:00; layover at BNA: 145 minutes.
    • WN1005: BNA 2026-12-21 11:25:00 → MDW 2026-12-21 12:55:00.
  • Southwest Airlines WN3048: MDW 2027-01-04 13:20:00 → TPA 2027-01-04 16:55:00; nonstop; 155 minutes. Local airport times.

More dates for this route