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Orlando → Chicago

Dec 21, 2026 · return Dec 22, 2026

MCO → MDW1 adulteconomyRound trip

9 flight options · 3 airlines

Nonstop flights

Mon, Dec 21 – Tue, Dec 22

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 – Tue, Dec 22

Southwest Airlines
5:40 pmMCO
2h 55m
Nonstop
7:35 pmMDW
Southwest Airlines
4:25 pmMDW
2h 35m
Nonstop
8:00 pmMCO

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Tue, Dec 22

Southwest Airlines
9:05 pmMCO
2h 55m
Nonstop
11:00 pmMDW
Southwest Airlines
4:25 pmMDW
2h 35m
Nonstop
8:00 pmMCO

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 21 – Tue, Dec 22

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

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Tue, Dec 22

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 – Tue, Dec 22

Southwest Airlines
10:40 amMCO
5h 20m
RSW · 1h 20m
3:00 pmMDW
Southwest Airlines
4:25 pmMDW
2h 35m
Nonstop
8:00 pmMCO

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Tue, Dec 22

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

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Tue, Dec 22

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

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Tue, Dec 22

Southwest Airlines
3:40 pmMCO
5h 10m
SDF · 1h 35m
7:50 pmMDW
Southwest Airlines
4:25 pmMDW
2h 35m
Nonstop
8:00 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 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 → 2026-12-22Frontier AirlinesF91457 / F91536$239.262026-10-29T01:28:44Z
2026-12-21 → 2026-12-22Southwest AirlinesWN2806 / WN1908$377.002026-10-29T01:28:44Z
2026-12-21 → 2026-12-22Delta Air LinesDL1150 + DL1076 / DL4688 + DL1274$493.002026-10-29T01:28:44Z
2026-12-21 → 2026-12-22Southwest AirlinesWN2595 / WN1908$377.002026-10-29T01:28:44Z
2026-12-21 → 2026-12-22Frontier AirlinesF91563 + F92779 / F91536$275.512026-10-29T01:28:44Z
2026-12-21 → 2026-12-22Southwest AirlinesWN2777 + WN2106 / WN1908$391.502026-10-29T01:28:44Z
2026-12-21 → 2026-12-22Southwest AirlinesWN1789 + WN287 / WN1908$391.502026-10-29T01:28:44Z
2026-12-21 → 2026-12-22Southwest AirlinesWN2840 + WN3556 / WN1908$391.502026-10-29T01:28:44Z
2026-12-21 → 2026-12-22Southwest AirlinesWN1915 + WN282 / WN1908$391.502026-10-29T01:28:44Z

2026-12-21 → 2026-12-22 · $239.26

  • 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 2026-12-22 18:11:00 → MCO 2026-12-22 22:00:00; nonstop; 169 minutes. Local airport times.

2026-12-21 → 2026-12-22 · $377.00

  • 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 WN1908: MDW 2026-12-22 16:25:00 → MCO 2026-12-22 20:00:00; nonstop; 155 minutes. Local airport times.

2026-12-21 → 2026-12-22 · $493.00

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

2026-12-21 → 2026-12-22 · $377.00

  • 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 WN1908: MDW 2026-12-22 16:25:00 → MCO 2026-12-22 20:00:00; nonstop; 155 minutes. Local airport times.

2026-12-21 → 2026-12-22 · $275.51

  • 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 2026-12-22 18:11:00 → MCO 2026-12-22 22:00:00; nonstop; 169 minutes. Local airport times.

2026-12-21 → 2026-12-22 · $391.50

  • 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 WN1908: MDW 2026-12-22 16:25:00 → MCO 2026-12-22 20:00:00; nonstop; 155 minutes. Local airport times.

2026-12-21 → 2026-12-22 · $391.50

  • 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 WN1908: MDW 2026-12-22 16:25:00 → MCO 2026-12-22 20:00:00; nonstop; 155 minutes. Local airport times.

2026-12-21 → 2026-12-22 · $391.50

  • 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 WN1908: MDW 2026-12-22 16:25:00 → MCO 2026-12-22 20:00:00; nonstop; 155 minutes. Local airport times.

2026-12-21 → 2026-12-22 · $391.50

  • 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 WN1908: MDW 2026-12-22 16:25:00 → MCO 2026-12-22 20:00:00; nonstop; 155 minutes. Local airport times.

More dates for this route