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Chicago → Orlando

Dec 9, 2026 · return Dec 14, 2026

MDW → MCO1 adulteconomyRound trip

9 flight options · 3 airlines

Nonstop flights

Wed, Dec 9 – Mon, Dec 14

Frontier Airlines
6:11 pmMDW
2h 49m
Nonstop
10:00 pmMCO
Frontier Airlines
5:29 pmMCO
3h 1m
Nonstop
7:30 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 9 – Mon, Dec 14

Southwest Airlines
5:15 amMDW
2h 30m
Nonstop
8:45 amMCO
Southwest Airlines
5:40 pmMCO
2h 55m
Nonstop
7:35 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 9 – Mon, Dec 14

Southwest Airlines
3:00 pmMDW
2h 40m
Nonstop
6:40 pmMCO
Southwest Airlines
5:40 pmMCO
2h 55m
Nonstop
7:35 pmMDW

Round-trip total · 1 adult · Taxes included

One-stop flights

Wed, Dec 9 – Mon, Dec 14

Delta Air Lines
1:31 pmMDW
5h 3m
DTW · 1h 6m
7:34 pmMCO
Delta Air Lines
5:45 pmMCO
5h 32m
ATL · 1h 55m
10:17 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 9 – Mon, Dec 14

Southwest Airlines
1:15 pmMDW
5h 40m
RDU · 1h 55m
7:55 pmMCO
Southwest Airlines
5:40 pmMCO
2h 55m
Nonstop
7:35 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 9 – Mon, Dec 14

Southwest Airlines
3:00 pmMDW
4h 50m
PIT · 1h
8:50 pmMCO
Southwest Airlines
5:40 pmMCO
2h 55m
Nonstop
7:35 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 9 – Mon, Dec 14

Southwest Airlines
5:25 pmMDW
5h 5m
BNA · 1h 45m
11:30 pmMCO
Southwest Airlines
5:40 pmMCO
2h 55m
Nonstop
7:35 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 9 – Mon, Dec 14

Southwest Airlines
1:20 pmMDW
5h 10m
CMH · 1h 50m
7:30 pmMCO
Southwest Airlines
5:40 pmMCO
2h 55m
Nonstop
7:35 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 9 – Mon, Dec 14

Southwest Airlines
7:45 amMDW
5h 5m
BHM · 1h 40m
1:50 pmMCO
Southwest Airlines
5:40 pmMCO
2h 55m
Nonstop
7:35 pmMDW

Round-trip total · 1 adult · Taxes included

Make this trip yours

MDW ⇄ MCO

Economy

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

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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)
2026-12-09 → 2026-12-14Frontier AirlinesF91536 / F91457$160.002026-10-29T01:29:09Z
2026-12-09 → 2026-12-14Southwest AirlinesWN2964 / WN2806$270.002026-10-29T01:29:09Z
2026-12-09 → 2026-12-14Delta Air LinesDL4688 + DL1274 / DL1150 + DL1076$350.002026-10-29T01:29:09Z
2026-12-09 → 2026-12-14Southwest AirlinesWN2966 / WN2806$270.002026-10-29T01:29:09Z
2026-12-09 → 2026-12-14Southwest AirlinesWN461 + WN2452 / WN2806$260.002026-10-29T01:29:09Z
2026-12-09 → 2026-12-14Southwest AirlinesWN1933 + WN4449 / WN2806$260.002026-10-29T01:29:09Z
2026-12-09 → 2026-12-14Southwest AirlinesWN2897 + WN647 / WN2806$260.002026-10-29T01:29:09Z
2026-12-09 → 2026-12-14Southwest AirlinesWN1354 + WN1266 / WN2806$260.002026-10-29T01:29:09Z
2026-12-09 → 2026-12-14Southwest AirlinesWN2379 + WN1423 / WN2806$260.002026-10-29T01:29:09Z

2026-12-09 → 2026-12-14 · $160.00

  • Frontier Airlines F91536: MDW 2026-12-09 18:11:00 → MCO 2026-12-09 22:00:00; nonstop; 169 minutes. Local airport times.
  • Frontier Airlines F91457: MCO 2026-12-14 17:29:00 → MDW 2026-12-14 19:30:00; nonstop; 181 minutes. Local airport times.

2026-12-09 → 2026-12-14 · $270.00

  • Southwest Airlines WN2964: MDW 2026-12-09 05:15:00 → MCO 2026-12-09 08:45:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN2806: MCO 2026-12-14 17:40:00 → MDW 2026-12-14 19:35:00; nonstop; 175 minutes. Local airport times.

2026-12-09 → 2026-12-14 · $350.00

  • Delta Air Lines DL4688 / DL1274: MDW 2026-12-09 13:31:00 → MCO 2026-12-09 19:34:00; 1 stop(s) via DTW; 303 minutes. Local airport times.
    • DL4688: MDW 2026-12-09 13:31:00 → DTW 2026-12-09 15:44:00; layover at DTW: 66 minutes.
    • DL1274: DTW 2026-12-09 16:50:00 → MCO 2026-12-09 19:34:00.
  • Delta Air Lines DL1150 / DL1076: MCO 2026-12-14 17:45:00 → MDW 2026-12-14 22:17:00; 1 stop(s) via ATL; 332 minutes. Local airport times.
    • DL1150: MCO 2026-12-14 17:45:00 → ATL 2026-12-14 19:25:00; layover at ATL: 115 minutes.
    • DL1076: ATL 2026-12-14 21:20:00 → MDW 2026-12-14 22:17:00.

2026-12-09 → 2026-12-14 · $270.00

  • Southwest Airlines WN2966: MDW 2026-12-09 15:00:00 → MCO 2026-12-09 18:40:00; nonstop; 160 minutes. Local airport times.
  • Southwest Airlines WN2806: MCO 2026-12-14 17:40:00 → MDW 2026-12-14 19:35:00; nonstop; 175 minutes. Local airport times.

2026-12-09 → 2026-12-14 · $260.00

  • Southwest Airlines WN461 / WN2452: MDW 2026-12-09 13:15:00 → MCO 2026-12-09 19:55:00; 1 stop(s) via RDU; 340 minutes. Local airport times.
    • WN461: MDW 2026-12-09 13:15:00 → RDU 2026-12-09 16:05:00; layover at RDU: 115 minutes.
    • WN2452: RDU 2026-12-09 18:00:00 → MCO 2026-12-09 19:55:00.
  • Southwest Airlines WN2806: MCO 2026-12-14 17:40:00 → MDW 2026-12-14 19:35:00; nonstop; 175 minutes. Local airport times.

2026-12-09 → 2026-12-14 · $260.00

  • Southwest Airlines WN1933 / WN4449: MDW 2026-12-09 15:00:00 → MCO 2026-12-09 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
    • WN1933: MDW 2026-12-09 15:00:00 → PIT 2026-12-09 17:25:00; layover at PIT: 60 minutes.
    • WN4449: PIT 2026-12-09 18:25:00 → MCO 2026-12-09 20:50:00.
  • Southwest Airlines WN2806: MCO 2026-12-14 17:40:00 → MDW 2026-12-14 19:35:00; nonstop; 175 minutes. Local airport times.

2026-12-09 → 2026-12-14 · $260.00

  • Southwest Airlines WN2897 / WN647: MDW 2026-12-09 17:25:00 → MCO 2026-12-09 23:30:00; 1 stop(s) via BNA; 305 minutes. Local airport times.
    • WN2897: MDW 2026-12-09 17:25:00 → BNA 2026-12-09 18:50:00; layover at BNA: 105 minutes.
    • WN647: BNA 2026-12-09 20:35:00 → MCO 2026-12-09 23:30:00.
  • Southwest Airlines WN2806: MCO 2026-12-14 17:40:00 → MDW 2026-12-14 19:35:00; nonstop; 175 minutes. Local airport times.

2026-12-09 → 2026-12-14 · $260.00

  • Southwest Airlines WN1354 / WN1266: MDW 2026-12-09 13:20:00 → MCO 2026-12-09 19:30:00; 1 stop(s) via CMH; 310 minutes. Local airport times.
    • WN1354: MDW 2026-12-09 13:20:00 → CMH 2026-12-09 15:25:00; layover at CMH: 110 minutes.
    • WN1266: CMH 2026-12-09 17:15:00 → MCO 2026-12-09 19:30:00.
  • Southwest Airlines WN2806: MCO 2026-12-14 17:40:00 → MDW 2026-12-14 19:35:00; nonstop; 175 minutes. Local airport times.

2026-12-09 → 2026-12-14 · $260.00

  • Southwest Airlines WN2379 / WN1423: MDW 2026-12-09 07:45:00 → MCO 2026-12-09 13:50:00; 1 stop(s) via BHM; 305 minutes. Local airport times.
    • WN2379: MDW 2026-12-09 07:45:00 → BHM 2026-12-09 09:30:00; layover at BHM: 100 minutes.
    • WN1423: BHM 2026-12-09 11:10:00 → MCO 2026-12-09 13:50:00.
  • Southwest Airlines WN2806: MCO 2026-12-14 17:40:00 → MDW 2026-12-14 19:35:00; nonstop; 175 minutes. Local airport times.

More dates for this route