Chicago (MDW) to Montego Bay (MBJ), Mar 23, 2027: round trips from $460, one way from $243

Chicago (MDW) to Montego Bay (MBJ), Mar 23, 2027: round trips from $460, one way from $243 on Axel, checked Nov 13, 2026. Lowest published fares: $460 round trip, Axel-exclusive, Frontier Airlines / Southwest Airlines, 1 stop, Mar 23, 2027 – Apr 1, 2027; $243 one way, Axel-exclusive, Frontier Airlines, 1 stop, Mar 23, 2027; 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
2027-03-23 · one way Frontier Airlines F92292 + F9125 06:08:00→14:29:00 8h 21m 1 stop via ATL Axel-exclusive $243 Nov 13, 2026
2027-03-23 · one way Southwest Airlines WN2964 + WN292 06:35:00→13:45:00 7h 10m 1 stop via MCO Axel-exclusive $311 Nov 13, 2026
2027-03-23 → 2027-03-24 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→14:29:00 8h 21m 1 stop via ATL · 15:45:00→00:00:00 8h 15m 1 stop via MCO Axel-exclusive $520 Nov 13, 2026
2027-03-23 → 2027-03-24 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→13:45:00 7h 10m 1 stop via MCO · 15:45:00→00:00:00 8h 15m 1 stop via MCO Axel-exclusive $581 Nov 13, 2026
2027-03-23 → 2027-03-25 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→14:29:00 8h 21m 1 stop via ATL · 15:45:00→00:00:00 8h 15m 1 stop via MCO Axel-exclusive $520 Nov 13, 2026
2027-03-23 → 2027-03-25 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→13:45:00 7h 10m 1 stop via MCO · 15:45:00→00:00:00 8h 15m 1 stop via MCO Axel-exclusive $581 Nov 13, 2026
2027-03-23 → 2027-03-26 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→14:29:00 8h 21m 1 stop via ATL · 15:45:00→00:00:00 8h 15m 1 stop via MCO Axel-exclusive $520 Nov 13, 2026
2027-03-23 → 2027-03-26 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→13:45:00 7h 10m 1 stop via MCO · 15:45:00→00:00:00 8h 15m 1 stop via MCO Axel-exclusive $581 Nov 13, 2026
2027-03-23 → 2027-03-27 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN1043 06:08:00→14:29:00 8h 21m 1 stop via ATL · 14:25:00→18:35:00 4h 10m nonstop Axel-exclusive $547 Nov 13, 2026
2027-03-23 → 2027-03-27 Southwest Airlines WN2964 + WN292 / WN1043 06:35:00→13:45:00 7h 10m 1 stop via MCO · 14:25:00→18:35:00 4h 10m nonstop Axel-exclusive $608 Nov 13, 2026
2027-03-23 → 2027-03-28 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→14:29:00 8h 21m 1 stop via ATL · 15:45:00→00:00:00 8h 15m 1 stop via MCO Axel-exclusive $540 Nov 13, 2026
2027-03-23 → 2027-03-28 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→13:45:00 7h 10m 1 stop via MCO · 15:45:00→00:00:00 8h 15m 1 stop via MCO Axel-exclusive $601 Nov 13, 2026
2027-03-23 → 2027-03-29 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→14:29:00 8h 21m 1 stop via ATL · 15:45:00→00:00:00 8h 15m 1 stop via MCO Axel-exclusive $540 Nov 13, 2026
2027-03-23 → 2027-03-29 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→13:45:00 7h 10m 1 stop via MCO · 15:45:00→00:00:00 8h 15m 1 stop via MCO Axel-exclusive $601 Nov 13, 2026
2027-03-23 → 2027-03-30 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→14:29:00 8h 21m 1 stop via ATL · 15:45:00→00:00:00 8h 15m 1 stop via MCO Axel-exclusive $478 Nov 13, 2026
2027-03-23 → 2027-03-30 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→13:45:00 7h 10m 1 stop via MCO · 15:45:00→00:00:00 8h 15m 1 stop via MCO Axel-exclusive $539 Nov 13, 2026
2027-03-23 → 2027-03-31 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→14:29:00 8h 21m 1 stop via ATL · 15:45:00→00:00:00 8h 15m 1 stop via MCO Axel-exclusive $478 Nov 13, 2026
2027-03-23 → 2027-03-31 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→13:45:00 7h 10m 1 stop via MCO · 15:45:00→00:00:00 8h 15m 1 stop via MCO Axel-exclusive $539 Nov 13, 2026
2027-03-23 → 2027-04-01 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→14:29:00 8h 21m 1 stop via ATL · 15:45:00→00:00:00 8h 15m 1 stop via MCO Axel-exclusive $460 Nov 13, 2026
2027-03-23 → 2027-04-01 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→13:45:00 7h 10m 1 stop via MCO · 15:45:00→00:00:00 8h 15m 1 stop via MCO Axel-exclusive $520 Nov 13, 2026
2027-03-23 → 2027-04-02 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→14:29:00 8h 21m 1 stop via ATL · 15:45:00→00:00:00 8h 15m 1 stop via MCO Axel-exclusive $460 Nov 13, 2026
2027-03-23 → 2027-04-02 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→13:45:00 7h 10m 1 stop via MCO · 15:45:00→00:00:00 8h 15m 1 stop via MCO Axel-exclusive $520 Nov 13, 2026
2027-03-23 → 2027-04-03 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN1043 06:08:00→14:29:00 8h 21m 1 stop via ATL · 14:25:00→18:35:00 4h 10m nonstop Axel-exclusive $480 Nov 13, 2026
2027-03-23 → 2027-04-03 Southwest Airlines WN2964 + WN292 / WN1043 06:35:00→13:45:00 7h 10m 1 stop via MCO · 14:25:00→18:35:00 4h 10m nonstop Axel-exclusive $540 Nov 13, 2026
2027-03-23 → 2027-04-04 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→14:29:00 8h 21m 1 stop via ATL · 15:45:00→00:00:00 8h 15m 1 stop via MCO Axel-exclusive $460 Nov 13, 2026
2027-03-23 → 2027-04-04 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→13:45:00 7h 10m 1 stop via MCO · 15:45:00→00:00:00 8h 15m 1 stop via MCO Axel-exclusive $520 Nov 13, 2026
2027-03-23 → 2027-04-05 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→14:29:00 8h 21m 1 stop via ATL · 15:45:00→00:00:00 8h 15m 1 stop via MCO Axel-exclusive $460 Nov 13, 2026
2027-03-23 → 2027-04-05 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→13:45:00 7h 10m 1 stop via MCO · 15:45:00→00:00:00 8h 15m 1 stop via MCO Axel-exclusive $520 Nov 13, 2026
2027-03-23 → 2027-04-06 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→14:29:00 8h 21m 1 stop via ATL · 15:45:00→00:00:00 8h 15m 1 stop via MCO Axel-exclusive $460 Nov 13, 2026
2027-03-23 → 2027-04-06 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→13:45:00 7h 10m 1 stop via MCO · 15:45:00→00:00:00 8h 15m 1 stop via MCO Axel-exclusive $520 Nov 13, 2026

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

2027-03-23 · one way · Axel-exclusive $243

2027-03-23 · one way · Axel-exclusive $311

2027-03-23 → 2027-03-24 · Axel-exclusive $520

2027-03-23 → 2027-03-24 · Axel-exclusive $581

2027-03-23 → 2027-03-25 · Axel-exclusive $520

2027-03-23 → 2027-03-25 · Axel-exclusive $581

2027-03-23 → 2027-03-26 · Axel-exclusive $520

2027-03-23 → 2027-03-26 · Axel-exclusive $581

2027-03-23 → 2027-03-27 · Axel-exclusive $547

2027-03-23 → 2027-03-27 · Axel-exclusive $608

2027-03-23 → 2027-03-29 · Axel-exclusive $540

2027-03-23 → 2027-03-29 · Axel-exclusive $601

2027-03-23 → 2027-03-30 · Axel-exclusive $478

2027-03-23 → 2027-03-30 · Axel-exclusive $539

2027-03-23 → 2027-03-31 · Axel-exclusive $478

2027-03-23 → 2027-03-31 · Axel-exclusive $539

2027-03-23 → 2027-04-02 · Axel-exclusive $460

2027-03-23 → 2027-04-02 · Axel-exclusive $520

2027-03-23 → 2027-04-03 · Axel-exclusive $480

2027-03-23 → 2027-04-03 · Axel-exclusive $540

2027-03-23 → 2027-04-04 · Axel-exclusive $460

2027-03-23 → 2027-04-04 · Axel-exclusive $520

2027-03-23 → 2027-04-06 · Axel-exclusive $460

2027-03-23 → 2027-04-06 · Axel-exclusive $520

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