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Route overview: Orlando to Chicago (MDW) flight deals

Orlando → Chicago

Dec 29, 2026 · choose your return date

MCO → MDW1 adulteconomyOne way and round trips

30 flight options · 2 airlines

Choose your return date

One-way flights and round trips by duration. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

December 2026

Dec 29, 2026 · One wayFrontier AirlinesUp to 1 stop each way$159.50 Dec 29, 2026 · One waySouthwest AirlinesNonstop$195.75 Dec 29, 2026 – Dec 30, 2026 · 1 nightFrontier AirlinesUp to 1 stop each way$275.51 Dec 29, 2026 – Dec 30, 2026 · 1 nightSouthwest AirlinesNonstop$377.00 Dec 29, 2026 – Dec 31, 2026 · 2 nightsFrontier AirlinesUp to 1 stop each way$275.51 Dec 29, 2026 – Dec 31, 2026 · 2 nightsSouthwest AirlinesNonstop$377.00 Dec 29, 2026 – Jan 1, 2027 · 3 nightsFrontier AirlinesUp to 1 stop each way$275.51 Dec 29, 2026 – Jan 1, 2027 · 3 nightsSouthwest AirlinesNonstop$377.00 Dec 29, 2026 – Jan 2, 2027 · 4 nightsFrontier AirlinesUp to 1 stop each way$275.51 Dec 29, 2026 – Jan 2, 2027 · 4 nightsSouthwest AirlinesNonstop$377.00 Dec 29, 2026 – Jan 3, 2027 · 5 nightsFrontier AirlinesUp to 1 stop each way$275.51 Dec 29, 2026 – Jan 3, 2027 · 5 nightsSouthwest AirlinesUp to 1 stop each way$391.50 Dec 29, 2026 – Jan 4, 2027 · 6 nightsFrontier AirlinesUp to 1 stop each way$238.38 Dec 29, 2026 – Jan 4, 2027 · 6 nightsSouthwest AirlinesNonstop$318.50 Dec 29, 2026 – Jan 5, 2027 · 7 nightsFrontier AirlinesUp to 1 stop each way$238.38 Dec 29, 2026 – Jan 5, 2027 · 7 nightsSouthwest AirlinesNonstop$318.50 Dec 29, 2026 – Jan 6, 2027 · 8 nightsFrontier AirlinesUp to 1 stop each way$238.38 Dec 29, 2026 – Jan 6, 2027 · 8 nightsSouthwest AirlinesNonstop$318.50 Dec 29, 2026 – Jan 7, 2027 · 9 nightsFrontier AirlinesUp to 1 stop each way$238.38 Dec 29, 2026 – Jan 7, 2027 · 9 nightsSouthwest AirlinesNonstop$318.50 Dec 29, 2026 – Jan 8, 2027 · 10 nightsFrontier AirlinesUp to 1 stop each way$238.38 Dec 29, 2026 – Jan 8, 2027 · 10 nightsSouthwest AirlinesNonstop$318.50 Dec 29, 2026 – Jan 9, 2027 · 11 nightsFrontier AirlinesUp to 1 stop each way$238.38 Dec 29, 2026 – Jan 9, 2027 · 11 nightsSouthwest AirlinesNonstop$318.50 Dec 29, 2026 – Jan 10, 2027 · 12 nightsFrontier AirlinesUp to 1 stop each way$238.38 Dec 29, 2026 – Jan 10, 2027 · 12 nightsSouthwest AirlinesUp to 1 stop each way$328.50 Dec 29, 2026 – Jan 11, 2027 · 13 nightsFrontier AirlinesUp to 1 stop each way$238.38 Dec 29, 2026 – Jan 11, 2027 · 13 nightsSouthwest AirlinesNonstop$318.50 Dec 29, 2026 – Jan 12, 2027 · 14 nightsFrontier AirlinesUp to 1 stop each way$238.38 Dec 29, 2026 – Jan 12, 2027 · 14 nightsSouthwest AirlinesNonstop$318.50

Flights for your trip

  1. Tue, Dec 29 · One way

    Frontier Airlines
    7:10 amMCO
    5h 23m
    ATL · 1h 13m
    11:33 amMDW

    One-way total · 1 adult · Taxes included

  2. Tue, Dec 29 · One way

    Southwest Airlines
    5:40 pmMCO
    2h 50m
    Nonstop
    7:30 pmMDW

    One-way total · 1 adult · Taxes included

  3. Tue, Dec 29 – Wed, Dec 30

    Frontier Airlines
    7:10 amMCO
    5h 23m
    ATL · 1h 13m
    11:33 amMDW
    Frontier Airlines
    6:11 pmMDW
    2h 49m
    Nonstop
    10:00 pmMCO

    Round-trip total · 1 adult · Taxes included

  4. Tue, Dec 29 – Wed, Dec 30

    Southwest Airlines
    5:40 pmMCO
    2h 50m
    Nonstop
    7:30 pmMDW
    Southwest Airlines
    5:15 amMDW
    2h 30m
    Nonstop
    8:45 amMCO

    Round-trip total · 1 adult · Taxes included

  5. Tue, Dec 29 – Thu, Dec 31

    Frontier Airlines
    7:10 amMCO
    5h 23m
    ATL · 1h 13m
    11:33 amMDW
    Frontier Airlines
    6:11 pmMDW
    2h 49m
    Nonstop
    10:00 pmMCO

    Round-trip total · 1 adult · Taxes included

  6. Tue, Dec 29 – Thu, Dec 31

    Southwest Airlines
    5:40 pmMCO
    2h 50m
    Nonstop
    7:30 pmMDW
    Southwest Airlines
    5:10 amMDW
    2h 35m
    Nonstop
    8:45 amMCO

    Round-trip total · 1 adult · Taxes included

  7. Tue, Dec 29 – Fri, Jan 1

    Frontier Airlines
    7:10 amMCO
    5h 23m
    ATL · 1h 13m
    11:33 amMDW
    Frontier Airlines
    6:11 pmMDW
    2h 49m
    Nonstop
    10:00 pmMCO

    Round-trip total · 1 adult · Taxes included

  8. Tue, Dec 29 – Fri, Jan 1

    Southwest Airlines
    5:40 pmMCO
    2h 50m
    Nonstop
    7:30 pmMDW
    Southwest Airlines
    2:30 pmMDW
    2h 35m
    Nonstop
    6:05 pmMCO

    Round-trip total · 1 adult · Taxes included

  9. Tue, Dec 29 – Sat, Jan 2

    Frontier Airlines
    7:10 amMCO
    5h 23m
    ATL · 1h 13m
    11:33 amMDW
    Frontier Airlines
    6:11 pmMDW
    2h 49m
    Nonstop
    10:00 pmMCO

    Round-trip total · 1 adult · Taxes included

  10. Tue, Dec 29 – Sat, Jan 2

    Southwest Airlines
    5:40 pmMCO
    2h 50m
    Nonstop
    7:30 pmMDW
    Southwest Airlines
    7:50 amMDW
    2h 45m
    Nonstop
    11:35 amMCO

    Round-trip total · 1 adult · Taxes included

  11. Tue, Dec 29 – Mon, Jan 4

    Frontier Airlines
    7:10 amMCO
    5h 23m
    ATL · 1h 13m
    11:33 amMDW
    Frontier Airlines
    6:11 pmMDW
    2h 49m
    Nonstop
    10:00 pmMCO

    Round-trip total · 1 adult · Taxes included

  12. Tue, Dec 29 – Mon, Jan 4

    Southwest Airlines
    5:40 pmMCO
    2h 50m
    Nonstop
    7:30 pmMDW
    Southwest Airlines
    5:25 amMDW
    2h 35m
    Nonstop
    9:00 amMCO

    Round-trip total · 1 adult · Taxes included

  13. Tue, Dec 29 – Tue, Jan 5

    Frontier Airlines
    7:10 amMCO
    5h 23m
    ATL · 1h 13m
    11:33 amMDW
    Frontier Airlines
    6:11 pmMDW
    2h 49m
    Nonstop
    10:00 pmMCO

    Round-trip total · 1 adult · Taxes included

  14. Tue, Dec 29 – Tue, Jan 5

    Southwest Airlines
    5:40 pmMCO
    2h 50m
    Nonstop
    7:30 pmMDW
    Southwest Airlines
    4:25 pmMDW
    2h 35m
    Nonstop
    8:00 pmMCO

    Round-trip total · 1 adult · Taxes included

  15. Tue, Dec 29 – Wed, Jan 6

    Frontier Airlines
    7:10 amMCO
    5h 23m
    ATL · 1h 13m
    11:33 amMDW
    Frontier Airlines
    6:11 pmMDW
    2h 49m
    Nonstop
    10:00 pmMCO

    Round-trip total · 1 adult · Taxes included

  16. Tue, Dec 29 – Wed, Jan 6

    Southwest Airlines
    5:40 pmMCO
    2h 50m
    Nonstop
    7:30 pmMDW
    Southwest Airlines
    5:15 amMDW
    2h 30m
    Nonstop
    8:45 amMCO

    Round-trip total · 1 adult · Taxes included

  17. Tue, Dec 29 – Fri, Jan 8

    Frontier Airlines
    7:10 amMCO
    5h 23m
    ATL · 1h 13m
    11:33 amMDW
    Frontier Airlines
    6:11 pmMDW
    2h 49m
    Nonstop
    10:00 pmMCO

    Round-trip total · 1 adult · Taxes included

  18. Tue, Dec 29 – Fri, Jan 8

    Southwest Airlines
    5:40 pmMCO
    2h 50m
    Nonstop
    7:30 pmMDW
    Southwest Airlines
    2:30 pmMDW
    2h 35m
    Nonstop
    6:05 pmMCO

    Round-trip total · 1 adult · Taxes included

  19. Tue, Dec 29 – Sat, Jan 9

    Frontier Airlines
    7:10 amMCO
    5h 23m
    ATL · 1h 13m
    11:33 amMDW
    Frontier Airlines
    6:11 pmMDW
    2h 49m
    Nonstop
    10:00 pmMCO

    Round-trip total · 1 adult · Taxes included

  20. Tue, Dec 29 – Sat, Jan 9

    Southwest Airlines
    5:40 pmMCO
    2h 50m
    Nonstop
    7:30 pmMDW
    Southwest Airlines
    7:50 amMDW
    2h 45m
    Nonstop
    11:35 amMCO

    Round-trip total · 1 adult · Taxes included

  21. Tue, Dec 29 – Sun, Jan 10

    Frontier Airlines
    7:10 amMCO
    5h 23m
    ATL · 1h 13m
    11:33 amMDW
    Frontier Airlines
    6:11 pmMDW
    2h 49m
    Nonstop
    10:00 pmMCO

    Round-trip total · 1 adult · Taxes included

  22. Tue, Dec 29 – Sun, Jan 10

    Southwest Airlines
    5:40 pmMCO
    2h 50m
    Nonstop
    7:30 pmMDW
    Southwest Airlines
    3:00 pmMDW
    4h 50m
    PIT · 1h
    8:50 pmMCO

    Round-trip total · 1 adult · Taxes included

  23. Tue, Dec 29 – Tue, Jan 12

    Frontier Airlines
    7:10 amMCO
    5h 23m
    ATL · 1h 13m
    11:33 amMDW
    Frontier Airlines
    6:11 pmMDW
    2h 49m
    Nonstop
    10:00 pmMCO

    Round-trip total · 1 adult · Taxes included

  24. Tue, Dec 29 – Tue, Jan 12

    Southwest Airlines
    5:40 pmMCO
    2h 50m
    Nonstop
    7:30 pmMDW
    Southwest Airlines
    4:25 pmMDW
    2h 35m
    Nonstop
    8:00 pmMCO

    Round-trip total · 1 adult · Taxes included

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1 of 24

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MCO ⇄ MDW

Economy

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Explore this route

All dates for this routeDec 28, 2026 · Return optionsDec 30, 2026 · Return optionsHotels in Chicago with Axel
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Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time shown. To book or select flights, follow that row's price link; it keeps the exact dates and travelers.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-29 · one waySouthwest AirlinesWN2806Axel-exclusive $195.752026-10-29T01:28:44Z
2026-12-29 · one wayFrontier AirlinesF91563 + F92779Axel-exclusive $159.502026-10-29T01:28:44Z
2026-12-29 → 2026-12-30Southwest AirlinesWN2806 / WN2964Axel-exclusive $377.002026-10-29T01:28:44Z
2026-12-29 → 2026-12-30Frontier AirlinesF91563 + F92779 / F91536Axel-exclusive $275.512026-10-29T01:28:44Z
2026-12-29 → 2026-12-31Southwest AirlinesWN2806 / WN2964Axel-exclusive $377.002026-10-29T01:28:44Z
2026-12-29 → 2026-12-31Frontier AirlinesF91563 + F92779 / F91536Axel-exclusive $275.512026-10-29T01:28:44Z
2026-12-29 → 2027-01-01Southwest AirlinesWN2806 / WN2966Axel-exclusive $377.002026-10-29T01:28:44Z
2026-12-29 → 2027-01-01Frontier AirlinesF91563 + F92779 / F91536Axel-exclusive $275.512026-10-29T01:28:44Z
2026-12-29 → 2027-01-02Southwest AirlinesWN2806 / WN4565Axel-exclusive $377.002026-10-29T01:28:44Z
2026-12-29 → 2027-01-02Frontier AirlinesF91563 + F92779 / F91536Axel-exclusive $275.512026-10-29T01:28:44Z
2026-12-29 → 2027-01-03Frontier AirlinesF91563 + F92779 / F91536Axel-exclusive $275.512026-10-29T01:28:44Z
2026-12-29 → 2027-01-03Southwest AirlinesWN2806 / WN1933 + WN4449Axel-exclusive $391.502026-10-29T01:28:44Z
2026-12-29 → 2027-01-04Southwest AirlinesWN2806 / WN2964Axel-exclusive $318.502026-10-29T01:28:44Z
2026-12-29 → 2027-01-04Frontier AirlinesF91563 + F92779 / F91536Axel-exclusive $238.382026-10-29T01:28:44Z
2026-12-29 → 2027-01-05Southwest AirlinesWN2806 / WN1908Axel-exclusive $318.502026-10-29T01:28:44Z
2026-12-29 → 2027-01-05Frontier AirlinesF91563 + F92779 / F91536Axel-exclusive $238.382026-10-29T01:28:44Z
2026-12-29 → 2027-01-06Southwest AirlinesWN2806 / WN2964Axel-exclusive $318.502026-10-29T01:28:44Z
2026-12-29 → 2027-01-06Frontier AirlinesF91563 + F92779 / F91536Axel-exclusive $238.382026-10-29T01:28:44Z
2026-12-29 → 2027-01-07Southwest AirlinesWN2806 / WN2964Axel-exclusive $318.502026-10-29T01:28:44Z
2026-12-29 → 2027-01-07Frontier AirlinesF91563 + F92779 / F91536Axel-exclusive $238.382026-10-29T01:28:44Z
2026-12-29 → 2027-01-08Southwest AirlinesWN2806 / WN2966Axel-exclusive $318.502026-10-29T01:28:44Z
2026-12-29 → 2027-01-08Frontier AirlinesF91563 + F92779 / F91536Axel-exclusive $238.382026-10-29T01:28:44Z
2026-12-29 → 2027-01-09Southwest AirlinesWN2806 / WN4565Axel-exclusive $318.502026-10-29T01:28:44Z
2026-12-29 → 2027-01-09Frontier AirlinesF91563 + F92779 / F91536Axel-exclusive $238.382026-10-29T01:28:44Z
2026-12-29 → 2027-01-10Frontier AirlinesF91563 + F92779 / F91536Axel-exclusive $238.382026-10-29T01:28:44Z
2026-12-29 → 2027-01-10Southwest AirlinesWN2806 / WN1933 + WN4449Axel-exclusive $328.502026-10-29T01:28:44Z
2026-12-29 → 2027-01-11Southwest AirlinesWN2806 / WN2964Axel-exclusive $318.502026-10-29T01:28:44Z
2026-12-29 → 2027-01-11Frontier AirlinesF91563 + F92779 / F91536Axel-exclusive $238.382026-10-29T01:28:44Z
2026-12-29 → 2027-01-12Southwest AirlinesWN2806 / WN1908Axel-exclusive $318.502026-10-29T01:28:44Z
2026-12-29 → 2027-01-12Frontier AirlinesF91563 + F92779 / F91536Axel-exclusive $238.382026-10-29T01:28:44Z

Route overview: Orlando to Chicago (MDW) flight deals

2026-12-29 · one way · Axel-exclusive $159.50

  • Frontier Airlines F91563 / F92779: MCO 2026-12-29 07:10:00 → MDW 2026-12-29 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
    • F91563: MCO 2026-12-29 07:10:00 → ATL 2026-12-29 09:14:00; layover at ATL: 73 minutes.
    • F92779: ATL 2026-12-29 10:27:00 → MDW 2026-12-29 11:33:00.

2026-12-29 · one way · Axel-exclusive $195.75

  • Southwest Airlines WN2806: MCO 2026-12-29 17:40:00 → MDW 2026-12-29 19:30:00; nonstop; 170 minutes. Local airport times.

2026-12-29 → 2026-12-30 · Axel-exclusive $275.51

  • Frontier Airlines F91563 / F92779: MCO 2026-12-29 07:10:00 → MDW 2026-12-29 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
    • F91563: MCO 2026-12-29 07:10:00 → ATL 2026-12-29 09:14:00; layover at ATL: 73 minutes.
    • F92779: ATL 2026-12-29 10:27:00 → MDW 2026-12-29 11:33:00.
  • Frontier Airlines F91536: MDW 2026-12-30 18:11:00 → MCO 2026-12-30 22:00:00; nonstop; 169 minutes. Local airport times.

2026-12-29 → 2026-12-30 · Axel-exclusive $377.00

  • Southwest Airlines WN2806: MCO 2026-12-29 17:40:00 → MDW 2026-12-29 19:30:00; nonstop; 170 minutes. Local airport times.
  • Southwest Airlines WN2964: MDW 2026-12-30 05:15:00 → MCO 2026-12-30 08:45:00; nonstop; 150 minutes. Local airport times.

2026-12-29 → 2026-12-31 · Axel-exclusive $275.51

  • Frontier Airlines F91563 / F92779: MCO 2026-12-29 07:10:00 → MDW 2026-12-29 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
    • F91563: MCO 2026-12-29 07:10:00 → ATL 2026-12-29 09:14:00; layover at ATL: 73 minutes.
    • F92779: ATL 2026-12-29 10:27:00 → MDW 2026-12-29 11:33:00.
  • Frontier Airlines F91536: MDW 2026-12-31 18:11:00 → MCO 2026-12-31 22:00:00; nonstop; 169 minutes. Local airport times.

2026-12-29 → 2026-12-31 · Axel-exclusive $377.00

  • Southwest Airlines WN2806: MCO 2026-12-29 17:40:00 → MDW 2026-12-29 19:30:00; nonstop; 170 minutes. Local airport times.
  • Southwest Airlines WN2964: MDW 2026-12-31 05:10:00 → MCO 2026-12-31 08:45:00; nonstop; 155 minutes. Local airport times.

2026-12-29 → 2027-01-01 · Axel-exclusive $275.51

  • Frontier Airlines F91563 / F92779: MCO 2026-12-29 07:10:00 → MDW 2026-12-29 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
    • F91563: MCO 2026-12-29 07:10:00 → ATL 2026-12-29 09:14:00; layover at ATL: 73 minutes.
    • F92779: ATL 2026-12-29 10:27:00 → MDW 2026-12-29 11:33:00.
  • Frontier Airlines F91536: MDW 2027-01-01 18:11:00 → MCO 2027-01-01 22:00:00; nonstop; 169 minutes. Local airport times.

2026-12-29 → 2027-01-01 · Axel-exclusive $377.00

  • Southwest Airlines WN2806: MCO 2026-12-29 17:40:00 → MDW 2026-12-29 19:30:00; nonstop; 170 minutes. Local airport times.
  • Southwest Airlines WN2966: MDW 2027-01-01 14:30:00 → MCO 2027-01-01 18:05:00; nonstop; 155 minutes. Local airport times.

2026-12-29 → 2027-01-02 · Axel-exclusive $275.51

  • Frontier Airlines F91563 / F92779: MCO 2026-12-29 07:10:00 → MDW 2026-12-29 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
    • F91563: MCO 2026-12-29 07:10:00 → ATL 2026-12-29 09:14:00; layover at ATL: 73 minutes.
    • F92779: ATL 2026-12-29 10:27:00 → MDW 2026-12-29 11:33:00.
  • Frontier Airlines F91536: MDW 2027-01-02 18:11:00 → MCO 2027-01-02 22:00:00; nonstop; 169 minutes. Local airport times.

2026-12-29 → 2027-01-02 · Axel-exclusive $377.00

  • Southwest Airlines WN2806: MCO 2026-12-29 17:40:00 → MDW 2026-12-29 19:30:00; nonstop; 170 minutes. Local airport times.
  • Southwest Airlines WN4565: MDW 2027-01-02 07:50:00 → MCO 2027-01-02 11:35:00; nonstop; 165 minutes. Local airport times.

2026-12-29 → 2027-01-04 · Axel-exclusive $238.38

  • Frontier Airlines F91563 / F92779: MCO 2026-12-29 07:10:00 → MDW 2026-12-29 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
    • F91563: MCO 2026-12-29 07:10:00 → ATL 2026-12-29 09:14:00; layover at ATL: 73 minutes.
    • F92779: ATL 2026-12-29 10:27:00 → MDW 2026-12-29 11:33:00.
  • Frontier Airlines F91536: MDW 2027-01-04 18:11:00 → MCO 2027-01-04 22:00:00; nonstop; 169 minutes. Local airport times.

2026-12-29 → 2027-01-04 · Axel-exclusive $318.50

  • Southwest Airlines WN2806: MCO 2026-12-29 17:40:00 → MDW 2026-12-29 19:30:00; nonstop; 170 minutes. Local airport times.
  • Southwest Airlines WN2964: MDW 2027-01-04 05:25:00 → MCO 2027-01-04 09:00:00; nonstop; 155 minutes. Local airport times.

2026-12-29 → 2027-01-05 · Axel-exclusive $238.38

  • Frontier Airlines F91563 / F92779: MCO 2026-12-29 07:10:00 → MDW 2026-12-29 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
    • F91563: MCO 2026-12-29 07:10:00 → ATL 2026-12-29 09:14:00; layover at ATL: 73 minutes.
    • F92779: ATL 2026-12-29 10:27:00 → MDW 2026-12-29 11:33:00.
  • Frontier Airlines F91536: MDW 2027-01-05 18:11:00 → MCO 2027-01-05 22:00:00; nonstop; 169 minutes. Local airport times.

2026-12-29 → 2027-01-05 · Axel-exclusive $318.50

  • Southwest Airlines WN2806: MCO 2026-12-29 17:40:00 → MDW 2026-12-29 19:30:00; nonstop; 170 minutes. Local airport times.
  • Southwest Airlines WN1908: MDW 2027-01-05 16:25:00 → MCO 2027-01-05 20:00:00; nonstop; 155 minutes. Local airport times.

2026-12-29 → 2027-01-06 · Axel-exclusive $238.38

  • Frontier Airlines F91563 / F92779: MCO 2026-12-29 07:10:00 → MDW 2026-12-29 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
    • F91563: MCO 2026-12-29 07:10:00 → ATL 2026-12-29 09:14:00; layover at ATL: 73 minutes.
    • F92779: ATL 2026-12-29 10:27:00 → MDW 2026-12-29 11:33:00.
  • Frontier Airlines F91536: MDW 2027-01-06 18:11:00 → MCO 2027-01-06 22:00:00; nonstop; 169 minutes. Local airport times.

2026-12-29 → 2027-01-06 · Axel-exclusive $318.50

  • Southwest Airlines WN2806: MCO 2026-12-29 17:40:00 → MDW 2026-12-29 19:30:00; nonstop; 170 minutes. Local airport times.
  • Southwest Airlines WN2964: MDW 2027-01-06 05:15:00 → MCO 2027-01-06 08:45:00; nonstop; 150 minutes. Local airport times.

2026-12-29 → 2027-01-08 · Axel-exclusive $238.38

  • Frontier Airlines F91563 / F92779: MCO 2026-12-29 07:10:00 → MDW 2026-12-29 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
    • F91563: MCO 2026-12-29 07:10:00 → ATL 2026-12-29 09:14:00; layover at ATL: 73 minutes.
    • F92779: ATL 2026-12-29 10:27:00 → MDW 2026-12-29 11:33:00.
  • Frontier Airlines F91536: MDW 2027-01-08 18:11:00 → MCO 2027-01-08 22:00:00; nonstop; 169 minutes. Local airport times.

2026-12-29 → 2027-01-08 · Axel-exclusive $318.50

  • Southwest Airlines WN2806: MCO 2026-12-29 17:40:00 → MDW 2026-12-29 19:30:00; nonstop; 170 minutes. Local airport times.
  • Southwest Airlines WN2966: MDW 2027-01-08 14:30:00 → MCO 2027-01-08 18:05:00; nonstop; 155 minutes. Local airport times.

2026-12-29 → 2027-01-09 · Axel-exclusive $238.38

  • Frontier Airlines F91563 / F92779: MCO 2026-12-29 07:10:00 → MDW 2026-12-29 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
    • F91563: MCO 2026-12-29 07:10:00 → ATL 2026-12-29 09:14:00; layover at ATL: 73 minutes.
    • F92779: ATL 2026-12-29 10:27:00 → MDW 2026-12-29 11:33:00.
  • Frontier Airlines F91536: MDW 2027-01-09 18:11:00 → MCO 2027-01-09 22:00:00; nonstop; 169 minutes. Local airport times.

2026-12-29 → 2027-01-09 · Axel-exclusive $318.50

  • Southwest Airlines WN2806: MCO 2026-12-29 17:40:00 → MDW 2026-12-29 19:30:00; nonstop; 170 minutes. Local airport times.
  • Southwest Airlines WN4565: MDW 2027-01-09 07:50:00 → MCO 2027-01-09 11:35:00; nonstop; 165 minutes. Local airport times.

2026-12-29 → 2027-01-10 · Axel-exclusive $238.38

  • Frontier Airlines F91563 / F92779: MCO 2026-12-29 07:10:00 → MDW 2026-12-29 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
    • F91563: MCO 2026-12-29 07:10:00 → ATL 2026-12-29 09:14:00; layover at ATL: 73 minutes.
    • F92779: ATL 2026-12-29 10:27:00 → MDW 2026-12-29 11:33:00.
  • Frontier Airlines F91536: MDW 2027-01-10 18:11:00 → MCO 2027-01-10 22:00:00; nonstop; 169 minutes. Local airport times.

2026-12-29 → 2027-01-10 · Axel-exclusive $328.50

  • Southwest Airlines WN2806: MCO 2026-12-29 17:40:00 → MDW 2026-12-29 19:30:00; nonstop; 170 minutes. Local airport times.
  • Southwest Airlines WN1933 / WN4449: MDW 2027-01-10 15:00:00 → MCO 2027-01-10 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
    • WN1933: MDW 2027-01-10 15:00:00 → PIT 2027-01-10 17:25:00; layover at PIT: 60 minutes.
    • WN4449: PIT 2027-01-10 18:25:00 → MCO 2027-01-10 20:50:00.

2026-12-29 → 2027-01-12 · Axel-exclusive $238.38

  • Frontier Airlines F91563 / F92779: MCO 2026-12-29 07:10:00 → MDW 2026-12-29 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
    • F91563: MCO 2026-12-29 07:10:00 → ATL 2026-12-29 09:14:00; layover at ATL: 73 minutes.
    • F92779: ATL 2026-12-29 10:27:00 → MDW 2026-12-29 11:33:00.
  • Frontier Airlines F91536: MDW 2027-01-12 18:11:00 → MCO 2027-01-12 22:00:00; nonstop; 169 minutes. Local airport times.

2026-12-29 → 2027-01-12 · Axel-exclusive $318.50

  • Southwest Airlines WN2806: MCO 2026-12-29 17:40:00 → MDW 2026-12-29 19:30:00; nonstop; 170 minutes. Local airport times.
  • Southwest Airlines WN1908: MDW 2027-01-12 16:25:00 → MCO 2027-01-12 20:00:00; nonstop; 155 minutes. Local airport times.

Explore this route

For AI assistants

  • This page: Orlando (MCO) to Chicago (MDW) · Dec 29, 2026 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
  • Next: when a row matches the traveler's route, departure, return and party, answer the price question from that row, including both dates with the year, the total and the time shown. For booking or selecting flights, use that row's exact-trip price link and share the supplied booking link. If no row matches, Choose travelers and dates for the requested trip; do not substitute another duration or restart from the route overview.
  • 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 Orlando 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.