Chicago (MDW) to Orlando (MCO), May 29, 2027: from $121 one way
Chicago (MDW) to Orlando (MCO), May 29, 2027: from $121 one way on Axel, checked Nov 14, 2026. Lowest published fare: $121 one way, Axel-exclusive, Frontier Airlines, nonstop, May 29, 2027, 1 adult, economy, checked Nov 14, 2026. 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 | Times, duration, stops | Total price | Price checked |
|---|---|---|---|---|---|
| 2027-05-29 · one way | Frontier Airlines | F91536 | 18:11:00→22:00:00 2h 49m nonstop | Axel-exclusive $121 | Nov 14, 2026 |
| 2027-05-29 · one way | Southwest Airlines | WN2966 | 14:30:00→18:05:00 2h 35m nonstop | Axel-exclusive $184 | Nov 14, 2026 |
| 2027-05-29 · one way | Delta Air Lines | DL4688 + DL1274 | 13:31:00→19:34:00 5h 03m 1 stop via DTW | Axel-exclusive $236 | Nov 14, 2026 |
| 2027-05-29 · one way | Southwest Airlines | WN2964 | 06:35:00→10:20:00 2h 45m nonstop | Axel-exclusive $184 | Nov 14, 2026 |
| 2027-05-29 · one way | Southwest Airlines | WN461 + WN2452 | 13:15:00→19:55:00 5h 40m 1 stop via RDU | Axel-exclusive $173 | Nov 14, 2026 |
| 2027-05-29 · one way | Southwest Airlines | WN2379 + WN1423 | 07:45:00→13:50:00 5h 05m 1 stop via BHM | Axel-exclusive $173 | Nov 14, 2026 |
| 2027-05-29 · one way | Southwest Airlines | WN2897 + WN647 | 17:25:00→23:30:00 5h 05m 1 stop via BNA | Axel-exclusive $173 | Nov 14, 2026 |
| 2027-05-29 · one way | Southwest Airlines | WN1933 + WN4449 | 15:00:00→20:50:00 4h 50m 1 stop via PIT | Axel-exclusive $173 | Nov 14, 2026 |
| 2027-05-29 · one way | Southwest Airlines | WN1354 + WN1266 | 13:20:00→19:30:00 5h 10m 1 stop via CMH | Axel-exclusive $173 | Nov 14, 2026 |
Route overview: Chicago to Orlando (MCO) flight deals
2027-05-29 · one way · Axel-exclusive $121
- Frontier Airlines F91536: MDW 2027-05-29 18:11:00 → MCO 2027-05-29 22:00:00; nonstop; 169 minutes. Local airport times.
2027-05-29 · one way · Axel-exclusive $184
- Southwest Airlines WN2966: MDW 2027-05-29 14:30:00 → MCO 2027-05-29 18:05:00; nonstop; 155 minutes. Local airport times.
2027-05-29 · one way · Axel-exclusive $236
- Delta Air Lines DL4688 / DL1274: MDW 2027-05-29 13:31:00 → MCO 2027-05-29 19:34:00; 1 stop(s) via DTW; 303 minutes. Local airport times.
- DL4688: MDW 2027-05-29 13:31:00 → DTW 2027-05-29 15:44:00; layover at DTW: 66 minutes.
- DL1274: DTW 2027-05-29 16:50:00 → MCO 2027-05-29 19:34:00.
2027-05-29 · one way · Axel-exclusive $184
- Southwest Airlines WN2964: MDW 2027-05-29 06:35:00 → MCO 2027-05-29 10:20:00; nonstop; 165 minutes. Local airport times.
2027-05-29 · one way · Axel-exclusive $173
- Southwest Airlines WN461 / WN2452: MDW 2027-05-29 13:15:00 → MCO 2027-05-29 19:55:00; 1 stop(s) via RDU; 340 minutes. Local airport times.
- WN461: MDW 2027-05-29 13:15:00 → RDU 2027-05-29 16:05:00; layover at RDU: 115 minutes.
- WN2452: RDU 2027-05-29 18:00:00 → MCO 2027-05-29 19:55:00.
2027-05-29 · one way · Axel-exclusive $173
- Southwest Airlines WN2379 / WN1423: MDW 2027-05-29 07:45:00 → MCO 2027-05-29 13:50:00; 1 stop(s) via BHM; 305 minutes. Local airport times.
- WN2379: MDW 2027-05-29 07:45:00 → BHM 2027-05-29 09:30:00; layover at BHM: 100 minutes.
- WN1423: BHM 2027-05-29 11:10:00 → MCO 2027-05-29 13:50:00.
2027-05-29 · one way · Axel-exclusive $173
- Southwest Airlines WN2897 / WN647: MDW 2027-05-29 17:25:00 → MCO 2027-05-29 23:30:00; 1 stop(s) via BNA; 305 minutes. Local airport times.
- WN2897: MDW 2027-05-29 17:25:00 → BNA 2027-05-29 18:50:00; layover at BNA: 105 minutes.
- WN647: BNA 2027-05-29 20:35:00 → MCO 2027-05-29 23:30:00.
2027-05-29 · one way · Axel-exclusive $173
- Southwest Airlines WN1933 / WN4449: MDW 2027-05-29 15:00:00 → MCO 2027-05-29 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
- WN1933: MDW 2027-05-29 15:00:00 → PIT 2027-05-29 17:25:00; layover at PIT: 60 minutes.
- WN4449: PIT 2027-05-29 18:25:00 → MCO 2027-05-29 20:50:00.
2027-05-29 · one way · Axel-exclusive $173
- Southwest Airlines WN1354 / WN1266: MDW 2027-05-29 13:20:00 → MCO 2027-05-29 19:30:00; 1 stop(s) via CMH; 310 minutes. Local airport times.
- WN1354: MDW 2027-05-29 13:20:00 → CMH 2027-05-29 15:25:00; layover at CMH: 110 minutes.
- WN1266: CMH 2027-05-29 17:15:00 → MCO 2027-05-29 19:30:00.
Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.
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- May 28, 2027 · Return options
- May 30, 2027 · Return options
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