Chicago (MDW) to Montego Bay (MBJ), Nov 22, 2026: round trips from $406, one way from $209

Chicago (MDW) to Montego Bay (MBJ), Nov 22, 2026: round trips from $406, one way from $209 on Axel, checked Nov 13, 2026. Lowest published fares: $406 round trip, Axel-exclusive, Frontier Airlines / Southwest Airlines, 1 stop, Nov 22–30, 2026; $209 one way, Axel-exclusive, Frontier Airlines, 1 stop, Nov 22, 2026; 1 adult, economy, checked Nov 13, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, labelled with the check date shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and check dates already shown here.

Exact travel dates Airline Flights Times, duration, stops Total price Price checked
2026-11-22 · one way Frontier Airlines F92292 + F9125 06:08:00→15:29:00 8h 21m 1 stop via ATL Axel-exclusive $209 Nov 13, 2026
2026-11-22 · one way Southwest Airlines WN2964 + WN292 06:35:00→14:45:00 7h 10m 1 stop via MCO Axel-exclusive $267 Nov 13, 2026
2026-11-22 → 2026-11-23 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→15:29:00 8h 21m 1 stop via ATL · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $447 Nov 13, 2026
2026-11-22 → 2026-11-23 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→14:45:00 7h 10m 1 stop via MCO · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $499 Nov 13, 2026
2026-11-22 → 2026-11-24 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→15:29:00 8h 21m 1 stop via ATL · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $447 Nov 13, 2026
2026-11-22 → 2026-11-24 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→14:45:00 7h 10m 1 stop via MCO · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $499 Nov 13, 2026
2026-11-22 → 2026-11-25 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→15:29:00 8h 21m 1 stop via ATL · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $447 Nov 13, 2026
2026-11-22 → 2026-11-25 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→14:45:00 7h 10m 1 stop via MCO · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $499 Nov 13, 2026
2026-11-22 → 2026-11-26 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→15:29:00 8h 21m 1 stop via ATL · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $447 Nov 13, 2026
2026-11-22 → 2026-11-26 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→14:45:00 7h 10m 1 stop via MCO · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $499 Nov 13, 2026
2026-11-22 → 2026-11-27 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→15:29:00 8h 21m 1 stop via ATL · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $447 Nov 13, 2026
2026-11-22 → 2026-11-27 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→14:45:00 7h 10m 1 stop via MCO · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $499 Nov 13, 2026
2026-11-22 → 2026-11-28 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN1043 06:08:00→15:29:00 8h 21m 1 stop via ATL · 14:25:00→17:35:00 4h 10m nonstop Axel-exclusive $470 Nov 13, 2026
2026-11-22 → 2026-11-28 Southwest Airlines WN2964 + WN292 / WN1043 06:35:00→14:45:00 7h 10m 1 stop via MCO · 14:25:00→17:35:00 4h 10m nonstop Axel-exclusive $522 Nov 13, 2026
2026-11-22 → 2026-11-29 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→15:29:00 8h 21m 1 stop via ATL · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $447 Nov 13, 2026
2026-11-22 → 2026-11-29 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→14:45:00 7h 10m 1 stop via MCO · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $499 Nov 13, 2026
2026-11-22 → 2026-11-30 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→15:29:00 8h 21m 1 stop via ATL · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $406 Nov 13, 2026
2026-11-22 → 2026-11-30 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→14:45:00 7h 10m 1 stop via MCO · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $458 Nov 13, 2026
2026-11-22 → 2026-12-01 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→15:29:00 8h 21m 1 stop via ATL · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $412 Nov 13, 2026
2026-11-22 → 2026-12-01 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→14:45:00 7h 10m 1 stop via MCO · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $464 Nov 13, 2026
2026-11-22 → 2026-12-02 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→15:29:00 8h 21m 1 stop via ATL · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $412 Nov 13, 2026
2026-11-22 → 2026-12-02 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→14:45:00 7h 10m 1 stop via MCO · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $464 Nov 13, 2026
2026-11-22 → 2026-12-03 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→15:29:00 8h 21m 1 stop via ATL · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $412 Nov 13, 2026
2026-11-22 → 2026-12-03 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→14:45:00 7h 10m 1 stop via MCO · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $464 Nov 13, 2026
2026-11-22 → 2026-12-04 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→15:29:00 8h 21m 1 stop via ATL · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $412 Nov 13, 2026
2026-11-22 → 2026-12-04 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→14:45:00 7h 10m 1 stop via MCO · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $464 Nov 13, 2026
2026-11-22 → 2026-12-05 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN1043 06:08:00→15:29:00 8h 21m 1 stop via ATL · 14:25:00→17:35:00 4h 10m nonstop Axel-exclusive $432 Nov 13, 2026
2026-11-22 → 2026-12-05 Southwest Airlines WN2964 + WN292 / WN1043 06:35:00→14:45:00 7h 10m 1 stop via MCO · 14:25:00→17:35:00 4h 10m nonstop Axel-exclusive $484 Nov 13, 2026
2026-11-22 → 2026-12-06 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→15:29:00 8h 21m 1 stop via ATL · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $412 Nov 13, 2026
2026-11-22 → 2026-12-06 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→14:45:00 7h 10m 1 stop via MCO · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $464 Nov 13, 2026

Route overview: Chicago to Montego Bay (MBJ) flight deals

2026-11-22 · one way · Axel-exclusive $209

2026-11-22 · one way · Axel-exclusive $267

2026-11-22 → 2026-11-23 · Axel-exclusive $447

2026-11-22 → 2026-11-23 · Axel-exclusive $499

2026-11-22 → 2026-11-24 · Axel-exclusive $447

2026-11-22 → 2026-11-24 · Axel-exclusive $499

2026-11-22 → 2026-11-25 · Axel-exclusive $447

2026-11-22 → 2026-11-25 · Axel-exclusive $499

2026-11-22 → 2026-11-26 · Axel-exclusive $447

2026-11-22 → 2026-11-26 · Axel-exclusive $499

2026-11-22 → 2026-11-28 · Axel-exclusive $470

2026-11-22 → 2026-11-28 · Axel-exclusive $522

2026-11-22 → 2026-11-29 · Axel-exclusive $447

2026-11-22 → 2026-11-29 · Axel-exclusive $499

2026-11-22 → 2026-11-30 · Axel-exclusive $406

2026-11-22 → 2026-11-30 · Axel-exclusive $458

2026-11-22 → 2026-12-02 · Axel-exclusive $412

2026-11-22 → 2026-12-02 · Axel-exclusive $464

2026-11-22 → 2026-12-03 · Axel-exclusive $412

2026-11-22 → 2026-12-03 · Axel-exclusive $464

2026-11-22 → 2026-12-04 · Axel-exclusive $412

2026-11-22 → 2026-12-04 · Axel-exclusive $464

2026-11-22 → 2026-12-06 · Axel-exclusive $412

2026-11-22 → 2026-12-06 · Axel-exclusive $464

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