Orlando (MCO) to Chicago (MDW) · Jan 9, 2027 · return Jan 19, 2027

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Exact travel dates	Airline	Flights	Total price	Price issued (UTC)
2027-01-09 → 2027-01-19	Frontier Airlines	F91457 / F91536	Axel-exclusive $165.00	2026-10-29T01:28:44Z
2027-01-09 → 2027-01-19	Southwest Airlines	WN2805 / WN1908	Axel-exclusive $260.00	2026-10-29T01:28:44Z
2027-01-09 → 2027-01-19	Delta Air Lines	DL1150 + DL1076 / DL4688 + DL1274	Axel-exclusive $340.00	2026-10-29T01:28:44Z
2027-01-09 → 2027-01-19	Southwest Airlines	WN2803 / WN1908	Axel-exclusive $260.00	2026-10-29T01:28:44Z
2027-01-09 → 2027-01-19	Frontier Airlines	F91563 + F92779 / F91536	Axel-exclusive $190.00	2026-10-29T01:28:44Z
2027-01-09 → 2027-01-19	Southwest Airlines	WN1915 + WN282 / WN1908	Axel-exclusive $270.00	2026-10-29T01:28:44Z
2027-01-09 → 2027-01-19	Southwest Airlines	WN2840 + WN3556 / WN1908	Axel-exclusive $270.00	2026-10-29T01:28:44Z
2027-01-09 → 2027-01-19	Southwest Airlines	WN1789 + WN287 / WN1908	Axel-exclusive $270.00	2026-10-29T01:28:44Z
2027-01-09 → 2027-01-19	Southwest Airlines	WN2777 + WN2106 / WN1908	Axel-exclusive $270.00	2026-10-29T01:28:44Z

Route overview: Orlando to Chicago (MDW) flight deals

2027-01-09 → 2027-01-19 · Axel-exclusive $165.00

Frontier Airlines F91457: MCO 2027-01-09 17:29:00 → MDW 2027-01-09 19:30:00; nonstop; 181 minutes. Local airport times.
Frontier Airlines F91536: MDW 2027-01-19 18:11:00 → MCO 2027-01-19 22:00:00; nonstop; 169 minutes. Local airport times.

2027-01-09 → 2027-01-19 · Axel-exclusive $260.00

Southwest Airlines WN2805: MCO 2027-01-09 16:35:00 → MDW 2027-01-09 18:30:00; nonstop; 175 minutes. Local airport times.
Southwest Airlines WN1908: MDW 2027-01-19 16:25:00 → MCO 2027-01-19 20:00:00; nonstop; 155 minutes. Local airport times.

2027-01-09 → 2027-01-19 · Axel-exclusive $340.00

Delta Air Lines DL1150 / DL1076: MCO 2027-01-09 17:45:00 → MDW 2027-01-09 22:17:00; 1 stop(s) via ATL; 332 minutes. Local airport times.
- DL1150: MCO 2027-01-09 17:45:00 → ATL 2027-01-09 19:25:00; layover at ATL: 115 minutes.
- DL1076: ATL 2027-01-09 21:20:00 → MDW 2027-01-09 22:17:00.
Delta Air Lines DL4688 / DL1274: MDW 2027-01-19 13:31:00 → MCO 2027-01-19 19:34:00; 1 stop(s) via DTW; 303 minutes. Local airport times.
- DL4688: MDW 2027-01-19 13:31:00 → DTW 2027-01-19 15:44:00; layover at DTW: 66 minutes.
- DL1274: DTW 2027-01-19 16:50:00 → MCO 2027-01-19 19:34:00.

2027-01-09 → 2027-01-19 · Axel-exclusive $260.00

Southwest Airlines WN2803: MCO 2027-01-09 10:10:00 → MDW 2027-01-09 12:05:00; nonstop; 175 minutes. Local airport times.
Southwest Airlines WN1908: MDW 2027-01-19 16:25:00 → MCO 2027-01-19 20:00:00; nonstop; 155 minutes. Local airport times.

2027-01-09 → 2027-01-19 · Axel-exclusive $190.00

Frontier Airlines F91563 / F92779: MCO 2027-01-09 07:10:00 → MDW 2027-01-09 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
- F91563: MCO 2027-01-09 07:10:00 → ATL 2027-01-09 09:14:00; layover at ATL: 73 minutes.
- F92779: ATL 2027-01-09 10:27:00 → MDW 2027-01-09 11:33:00.
Frontier Airlines F91536: MDW 2027-01-19 18:11:00 → MCO 2027-01-19 22:00:00; nonstop; 169 minutes. Local airport times.

2027-01-09 → 2027-01-19 · Axel-exclusive $270.00

Southwest Airlines WN1915 / WN282: MCO 2027-01-09 15:40:00 → MDW 2027-01-09 19:50:00; 1 stop(s) via SDF; 310 minutes. Local airport times.
- WN1915: MCO 2027-01-09 15:40:00 → SDF 2027-01-09 18:00:00; layover at SDF: 95 minutes.
- WN282: SDF 2027-01-09 19:35:00 → MDW 2027-01-09 19:50:00.
Southwest Airlines WN1908: MDW 2027-01-19 16:25:00 → MCO 2027-01-19 20:00:00; nonstop; 155 minutes. Local airport times.

2027-01-09 → 2027-01-19 · Axel-exclusive $270.00

Southwest Airlines WN2840 / WN3556: MCO 2027-01-09 16:00:00 → MDW 2027-01-09 20:10:00; 1 stop(s) via PIT; 310 minutes. Local airport times.
- WN2840: MCO 2027-01-09 16:00:00 → PIT 2027-01-09 18:25:00; layover at PIT: 75 minutes.
- WN3556: PIT 2027-01-09 19:40:00 → MDW 2027-01-09 20:10:00.
Southwest Airlines WN1908: MDW 2027-01-19 16:25:00 → MCO 2027-01-19 20:00:00; nonstop; 155 minutes. Local airport times.

2027-01-09 → 2027-01-19 · Axel-exclusive $270.00

Southwest Airlines WN1789 / WN287: MCO 2027-01-09 08:10:00 → MDW 2027-01-09 12:05:00; 1 stop(s) via STL; 295 minutes. Local airport times.
- WN1789: MCO 2027-01-09 08:10:00 → STL 2027-01-09 09:45:00; layover at STL: 70 minutes.
- WN287: STL 2027-01-09 10:55:00 → MDW 2027-01-09 12:05:00.
Southwest Airlines WN1908: MDW 2027-01-19 16:25:00 → MCO 2027-01-19 20:00:00; nonstop; 155 minutes. Local airport times.

2027-01-09 → 2027-01-19 · Axel-exclusive $270.00

Southwest Airlines WN2777 / WN2106: MCO 2027-01-09 10:40:00 → MDW 2027-01-09 15:00:00; 1 stop(s) via RSW; 320 minutes. Local airport times.
- WN2777: MCO 2027-01-09 10:40:00 → RSW 2027-01-09 11:45:00; layover at RSW: 80 minutes.
- WN2106: RSW 2027-01-09 13:05:00 → MDW 2027-01-09 15:00:00.
Southwest Airlines WN1908: MDW 2027-01-19 16:25:00 → MCO 2027-01-19 20:00:00; nonstop; 155 minutes. Local airport times.

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