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Orlando → Chicago

Dec 21, 2026 · return Jan 4, 2027

MCO → MDW1 adulteconomyRound trip

9 flight options · 2 airlines

Nonstop flights

Mon, Dec 21 – Mon, Jan 4

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 21 – Mon, Jan 4

Southwest Airlines
9:05 pmMCO
2h 55m
Nonstop
11:00 pmMDW
Southwest Airlines
5:25 amMDW
2h 35m
Nonstop
9:00 amMCO

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

Southwest Airlines
5:40 pmMCO
2h 55m
Nonstop
7:35 pmMDW
Southwest Airlines
5:25 amMDW
2h 35m
Nonstop
9:00 amMCO

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 21 – 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

Mon, Dec 21 – Mon, Jan 4

Southwest Airlines
5:40 pmMCO
2h 50m
Nonstop
7:30 pmMDW
Southwest Airlines
7:45 amMDW
5h 5m
BHM · 1h 40m
1:50 pmMCO

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

Southwest Airlines
10:40 amMCO
5h 20m
RSW · 1h 20m
3:00 pmMDW
Southwest Airlines
5:25 amMDW
2h 35m
Nonstop
9:00 amMCO

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

Southwest Airlines
3:40 pmMCO
5h 10m
SDF · 1h 35m
7:50 pmMDW
Southwest Airlines
5:25 amMDW
2h 35m
Nonstop
9:00 amMCO

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

Southwest Airlines
4:00 pmMCO
5h 10m
PIT · 1h 15m
8:10 pmMDW
Southwest Airlines
5:25 amMDW
2h 35m
Nonstop
9:00 amMCO

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

Southwest Airlines
8:10 amMCO
4h 55m
STL · 1h 10m
12:05 pmMDW
Southwest Airlines
5:25 amMDW
2h 35m
Nonstop
9:00 amMCO

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 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 → 2027-01-04Frontier AirlinesF91457 / F91536$202.132026-10-29T01:28:44Z
2026-12-21 → 2027-01-04Southwest AirlinesWN2595 / WN2964$318.502026-10-29T01:28:44Z
2026-12-21 → 2027-01-04Southwest AirlinesWN2806 / WN2964$318.502026-10-29T01:28:44Z
2026-12-21 → 2027-01-04Frontier AirlinesF91563 + F92779 / F91536$238.382026-10-29T01:28:44Z
2026-12-21 → 2027-01-04Southwest AirlinesWN2806 / WN2379 + WN1423$328.502026-10-29T01:28:44Z
2026-12-21 → 2027-01-04Southwest AirlinesWN2777 + WN2106 / WN2964$333.002026-10-29T01:28:44Z
2026-12-21 → 2027-01-04Southwest AirlinesWN1915 + WN282 / WN2964$333.002026-10-29T01:28:44Z
2026-12-21 → 2027-01-04Southwest AirlinesWN2840 + WN3556 / WN2964$333.002026-10-29T01:28:44Z
2026-12-21 → 2027-01-04Southwest AirlinesWN1789 + WN287 / WN2964$333.002026-10-29T01:28:44Z

2026-12-21 → 2027-01-04 · $202.13

  • Frontier Airlines F91457: MCO 2026-12-21 17:29:00 → MDW 2026-12-21 19:30:00; nonstop; 181 minutes. Local airport times.
  • Frontier Airlines F91536: MDW 2027-01-04 18:11:00 → MCO 2027-01-04 22:00:00; nonstop; 169 minutes. Local airport times.

2026-12-21 → 2027-01-04 · $318.50

  • Southwest Airlines WN2595: MCO 2026-12-21 21:05:00 → MDW 2026-12-21 23:00:00; nonstop; 175 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.

2026-12-21 → 2027-01-04 · $318.50

  • Southwest Airlines WN2806: MCO 2026-12-21 17:40:00 → MDW 2026-12-21 19:35:00; nonstop; 175 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.

2026-12-21 → 2027-01-04 · $238.38

  • Frontier Airlines F91563 / F92779: MCO 2026-12-21 07:10:00 → MDW 2026-12-21 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
    • F91563: MCO 2026-12-21 07:10:00 → ATL 2026-12-21 09:14:00; layover at ATL: 73 minutes.
    • F92779: ATL 2026-12-21 10:27:00 → MDW 2026-12-21 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.

2026-12-21 → 2027-01-04 · $328.50

  • Southwest Airlines WN2806: MCO 2026-12-21 17:40:00 → MDW 2026-12-21 19:30:00; nonstop; 170 minutes. Local airport times.
  • Southwest Airlines WN2379 / WN1423: MDW 2027-01-04 07:45:00 → MCO 2027-01-04 13:50:00; 1 stop(s) via BHM; 305 minutes. Local airport times.
    • WN2379: MDW 2027-01-04 07:45:00 → BHM 2027-01-04 09:30:00; layover at BHM: 100 minutes.
    • WN1423: BHM 2027-01-04 11:10:00 → MCO 2027-01-04 13:50:00.

2026-12-21 → 2027-01-04 · $333.00

  • Southwest Airlines WN2777 / WN2106: MCO 2026-12-21 10:40:00 → MDW 2026-12-21 15:00:00; 1 stop(s) via RSW; 320 minutes. Local airport times.
    • WN2777: MCO 2026-12-21 10:40:00 → RSW 2026-12-21 11:45:00; layover at RSW: 80 minutes.
    • WN2106: RSW 2026-12-21 13:05:00 → MDW 2026-12-21 15:00:00.
  • Southwest Airlines WN2964: MDW 2027-01-04 05:25:00 → MCO 2027-01-04 09:00:00; nonstop; 155 minutes. Local airport times.

2026-12-21 → 2027-01-04 · $333.00

  • Southwest Airlines WN1915 / WN282: MCO 2026-12-21 15:40:00 → MDW 2026-12-21 19:50:00; 1 stop(s) via SDF; 310 minutes. Local airport times.
    • WN1915: MCO 2026-12-21 15:40:00 → SDF 2026-12-21 18:00:00; layover at SDF: 95 minutes.
    • WN282: SDF 2026-12-21 19:35:00 → MDW 2026-12-21 19:50:00.
  • Southwest Airlines WN2964: MDW 2027-01-04 05:25:00 → MCO 2027-01-04 09:00:00; nonstop; 155 minutes. Local airport times.

2026-12-21 → 2027-01-04 · $333.00

  • Southwest Airlines WN2840 / WN3556: MCO 2026-12-21 16:00:00 → MDW 2026-12-21 20:10:00; 1 stop(s) via PIT; 310 minutes. Local airport times.
    • WN2840: MCO 2026-12-21 16:00:00 → PIT 2026-12-21 18:25:00; layover at PIT: 75 minutes.
    • WN3556: PIT 2026-12-21 19:40:00 → MDW 2026-12-21 20:10:00.
  • Southwest Airlines WN2964: MDW 2027-01-04 05:25:00 → MCO 2027-01-04 09:00:00; nonstop; 155 minutes. Local airport times.

2026-12-21 → 2027-01-04 · $333.00

  • Southwest Airlines WN1789 / WN287: MCO 2026-12-21 08:10:00 → MDW 2026-12-21 12:05:00; 1 stop(s) via STL; 295 minutes. Local airport times.
    • WN1789: MCO 2026-12-21 08:10:00 → STL 2026-12-21 09:45:00; layover at STL: 70 minutes.
    • WN287: STL 2026-12-21 10:55:00 → MDW 2026-12-21 12:05:00.
  • Southwest Airlines WN2964: MDW 2027-01-04 05:25:00 → MCO 2027-01-04 09:00:00; nonstop; 155 minutes. Local airport times.

More dates for this route