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Orlando → Chicago

Dec 7, 2026 · return Dec 13, 2026

MCO → MDW1 adulteconomyRound trip

8 flight options · 2 airlines

Nonstop flights

Mon, Dec 7 – Sun, Dec 13

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

Round-trip total · 1 adult · Taxes included

Mon, Dec 7 – Sun, Dec 13

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

One-stop flights

Mon, Dec 7 – Sun, Dec 13

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

Mon, Dec 7 – Sun, Dec 13

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

Round-trip total · 1 adult · Taxes included

Mon, Dec 7 – Sun, Dec 13

Southwest Airlines
8:10 amMCO
4h 55m
STL · 1h 10m
12:05 pmMDW
Southwest Airlines
3:00 pmMDW
4h 50m
PIT · 1h
8:50 pmMCO

Round-trip total · 1 adult · Taxes included

Mon, Dec 7 – Sun, Dec 13

Southwest Airlines
10:40 amMCO
5h 20m
RSW · 1h 20m
3:00 pmMDW
Southwest Airlines
3:00 pmMDW
4h 50m
PIT · 1h
8:50 pmMCO

Round-trip total · 1 adult · Taxes included

Mon, Dec 7 – Sun, Dec 13

Southwest Airlines
3:40 pmMCO
5h 10m
SDF · 1h 35m
7:50 pmMDW
Southwest Airlines
3:00 pmMDW
4h 50m
PIT · 1h
8:50 pmMCO

Round-trip total · 1 adult · Taxes included

Mon, Dec 7 – Sun, Dec 13

Southwest Airlines
4:00 pmMCO
5h 10m
PIT · 1h 15m
8:10 pmMDW
Southwest Airlines
3:00 pmMDW
4h 50m
PIT · 1h
8:50 pmMCO

Round-trip total · 1 adult · Taxes included

Make this trip yours

MCO ⇄ MDW

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 24, 2026 → Nov 29, 2026Dec 22, 2026 → Dec 27, 2026Dec 30, 2026 → Jan 2, 2027Jan 15, 2027 → Jan 18, 2027Oct 30, 2026 → Nov 2, 2026Oct 31, 2026 → Nov 7, 2026Nov 27, 2026 → Nov 30, 2026Nov 28, 2026 → Dec 5, 2026Dec 25, 2026 → Dec 28, 2026Dec 26, 2026 → Jan 2, 2027Jan 22, 2027 → Jan 25, 2027Oct 30, 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)
2026-12-07 → 2026-12-13Frontier AirlinesF91457 / F91536$165.002026-10-29T01:28:44Z
2026-12-07 → 2026-12-13Southwest AirlinesWN2806 / WN2964$260.002026-10-29T01:28:44Z
2026-12-07 → 2026-12-13Frontier AirlinesF91563 + F92779 / F91536$190.002026-10-29T01:28:44Z
2026-12-07 → 2026-12-13Southwest AirlinesWN2806 / WN1933 + WN4449$270.002026-10-29T01:28:44Z
2026-12-07 → 2026-12-13Southwest AirlinesWN1789 + WN287 / WN1933 + WN4449$280.002026-10-29T01:28:44Z
2026-12-07 → 2026-12-13Southwest AirlinesWN2777 + WN2106 / WN1933 + WN4449$280.002026-10-29T01:28:44Z
2026-12-07 → 2026-12-13Southwest AirlinesWN1915 + WN282 / WN1933 + WN4449$280.002026-10-29T01:28:44Z
2026-12-07 → 2026-12-13Southwest AirlinesWN2840 + WN3556 / WN1933 + WN4449$280.002026-10-29T01:28:44Z

2026-12-07 → 2026-12-13 · $165.00

  • Frontier Airlines F91457: MCO 2026-12-07 17:29:00 → MDW 2026-12-07 19:30:00; nonstop; 181 minutes. Local airport times.
  • Frontier Airlines F91536: MDW 2026-12-13 18:11:00 → MCO 2026-12-13 22:00:00; nonstop; 169 minutes. Local airport times.

2026-12-07 → 2026-12-13 · $260.00

  • Southwest Airlines WN2806: MCO 2026-12-07 17:40:00 → MDW 2026-12-07 19:30:00; nonstop; 170 minutes. Local airport times.
  • Southwest Airlines WN2964: MDW 2026-12-13 05:15:00 → MCO 2026-12-13 08:45:00; nonstop; 150 minutes. Local airport times.

2026-12-07 → 2026-12-13 · $190.00

  • Frontier Airlines F91563 / F92779: MCO 2026-12-07 07:10:00 → MDW 2026-12-07 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
    • F91563: MCO 2026-12-07 07:10:00 → ATL 2026-12-07 09:14:00; layover at ATL: 73 minutes.
    • F92779: ATL 2026-12-07 10:27:00 → MDW 2026-12-07 11:33:00.
  • Frontier Airlines F91536: MDW 2026-12-13 18:11:00 → MCO 2026-12-13 22:00:00; nonstop; 169 minutes. Local airport times.

2026-12-07 → 2026-12-13 · $270.00

  • Southwest Airlines WN2806: MCO 2026-12-07 17:40:00 → MDW 2026-12-07 19:35:00; nonstop; 175 minutes. Local airport times.
  • Southwest Airlines WN1933 / WN4449: MDW 2026-12-13 15:00:00 → MCO 2026-12-13 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
    • WN1933: MDW 2026-12-13 15:00:00 → PIT 2026-12-13 17:25:00; layover at PIT: 60 minutes.
    • WN4449: PIT 2026-12-13 18:25:00 → MCO 2026-12-13 20:50:00.

2026-12-07 → 2026-12-13 · $280.00

  • Southwest Airlines WN1789 / WN287: MCO 2026-12-07 08:10:00 → MDW 2026-12-07 12:05:00; 1 stop(s) via STL; 295 minutes. Local airport times.
    • WN1789: MCO 2026-12-07 08:10:00 → STL 2026-12-07 09:45:00; layover at STL: 70 minutes.
    • WN287: STL 2026-12-07 10:55:00 → MDW 2026-12-07 12:05:00.
  • Southwest Airlines WN1933 / WN4449: MDW 2026-12-13 15:00:00 → MCO 2026-12-13 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
    • WN1933: MDW 2026-12-13 15:00:00 → PIT 2026-12-13 17:25:00; layover at PIT: 60 minutes.
    • WN4449: PIT 2026-12-13 18:25:00 → MCO 2026-12-13 20:50:00.

2026-12-07 → 2026-12-13 · $280.00

  • Southwest Airlines WN2777 / WN2106: MCO 2026-12-07 10:40:00 → MDW 2026-12-07 15:00:00; 1 stop(s) via RSW; 320 minutes. Local airport times.
    • WN2777: MCO 2026-12-07 10:40:00 → RSW 2026-12-07 11:45:00; layover at RSW: 80 minutes.
    • WN2106: RSW 2026-12-07 13:05:00 → MDW 2026-12-07 15:00:00.
  • Southwest Airlines WN1933 / WN4449: MDW 2026-12-13 15:00:00 → MCO 2026-12-13 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
    • WN1933: MDW 2026-12-13 15:00:00 → PIT 2026-12-13 17:25:00; layover at PIT: 60 minutes.
    • WN4449: PIT 2026-12-13 18:25:00 → MCO 2026-12-13 20:50:00.

2026-12-07 → 2026-12-13 · $280.00

  • Southwest Airlines WN1915 / WN282: MCO 2026-12-07 15:40:00 → MDW 2026-12-07 19:50:00; 1 stop(s) via SDF; 310 minutes. Local airport times.
    • WN1915: MCO 2026-12-07 15:40:00 → SDF 2026-12-07 18:00:00; layover at SDF: 95 minutes.
    • WN282: SDF 2026-12-07 19:35:00 → MDW 2026-12-07 19:50:00.
  • Southwest Airlines WN1933 / WN4449: MDW 2026-12-13 15:00:00 → MCO 2026-12-13 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
    • WN1933: MDW 2026-12-13 15:00:00 → PIT 2026-12-13 17:25:00; layover at PIT: 60 minutes.
    • WN4449: PIT 2026-12-13 18:25:00 → MCO 2026-12-13 20:50:00.

2026-12-07 → 2026-12-13 · $280.00

  • Southwest Airlines WN2840 / WN3556: MCO 2026-12-07 16:00:00 → MDW 2026-12-07 20:10:00; 1 stop(s) via PIT; 310 minutes. Local airport times.
    • WN2840: MCO 2026-12-07 16:00:00 → PIT 2026-12-07 18:25:00; layover at PIT: 75 minutes.
    • WN3556: PIT 2026-12-07 19:40:00 → MDW 2026-12-07 20:10:00.
  • Southwest Airlines WN1933 / WN4449: MDW 2026-12-13 15:00:00 → MCO 2026-12-13 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
    • WN1933: MDW 2026-12-13 15:00:00 → PIT 2026-12-13 17:25:00; layover at PIT: 60 minutes.
    • WN4449: PIT 2026-12-13 18:25:00 → MCO 2026-12-13 20:50:00.

More dates for this route