Chicago (MDW) to Montego Bay (MBJ), Jan 19, 2027: round trips from $385, one way from $180

Chicago (MDW) to Montego Bay (MBJ), Jan 19, 2027: round trips from $385, one way from $180 on Axel, checked Nov 13, 2026. Lowest published fares: $385 round trip, Axel-exclusive, Frontier Airlines / Southwest Airlines, 1 stop, Jan 19–20, 2027; $180 one way, Axel-exclusive, Frontier Airlines, 1 stop, Jan 19, 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
2027-01-19 · one way Frontier Airlines F92292 + F9125 06:08:00→15:29:00 8h 21m 1 stop via ATL Axel-exclusive $180 Nov 13, 2026
2027-01-19 · one way Southwest Airlines WN2964 + WN292 06:35:00→14:45:00 7h 10m 1 stop via MCO Axel-exclusive $230 Nov 13, 2026
2027-01-19 → 2027-01-20 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 $385 Nov 13, 2026
2027-01-19 → 2027-01-20 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 $430 Nov 13, 2026
2027-01-19 → 2027-01-21 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 $385 Nov 13, 2026
2027-01-19 → 2027-01-21 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 $430 Nov 13, 2026
2027-01-19 → 2027-01-22 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 $385 Nov 13, 2026
2027-01-19 → 2027-01-22 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 $430 Nov 13, 2026
2027-01-19 → 2027-01-23 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 $405 Nov 13, 2026
2027-01-19 → 2027-01-23 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 $450 Nov 13, 2026
2027-01-19 → 2027-01-24 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 $385 Nov 13, 2026
2027-01-19 → 2027-01-24 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 $430 Nov 13, 2026
2027-01-19 → 2027-01-25 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 $385 Nov 13, 2026
2027-01-19 → 2027-01-25 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 $430 Nov 13, 2026
2027-01-19 → 2027-01-26 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 $385 Nov 13, 2026
2027-01-19 → 2027-01-26 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 $430 Nov 13, 2026
2027-01-19 → 2027-01-27 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 $385 Nov 13, 2026
2027-01-19 → 2027-01-27 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 $430 Nov 13, 2026
2027-01-19 → 2027-01-28 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 $385 Nov 13, 2026
2027-01-19 → 2027-01-28 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 $430 Nov 13, 2026
2027-01-19 → 2027-01-29 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 $385 Nov 13, 2026
2027-01-19 → 2027-01-29 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 $430 Nov 13, 2026
2027-01-19 → 2027-01-30 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 $405 Nov 13, 2026
2027-01-19 → 2027-01-30 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 $450 Nov 13, 2026
2027-01-19 → 2027-01-31 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 $385 Nov 13, 2026
2027-01-19 → 2027-01-31 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 $430 Nov 13, 2026
2027-01-19 → 2027-02-01 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 $391 Nov 13, 2026
2027-01-19 → 2027-02-01 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 $436 Nov 13, 2026
2027-01-19 → 2027-02-02 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 $391 Nov 13, 2026
2027-01-19 → 2027-02-02 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 $436 Nov 13, 2026

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

2027-01-19 · one way · Axel-exclusive $180

2027-01-19 · one way · Axel-exclusive $230

2027-01-19 → 2027-01-20 · Axel-exclusive $385

2027-01-19 → 2027-01-20 · Axel-exclusive $430

2027-01-19 → 2027-01-21 · Axel-exclusive $385

2027-01-19 → 2027-01-21 · Axel-exclusive $430

2027-01-19 → 2027-01-22 · Axel-exclusive $385

2027-01-19 → 2027-01-22 · Axel-exclusive $430

2027-01-19 → 2027-01-23 · Axel-exclusive $405

2027-01-19 → 2027-01-23 · Axel-exclusive $450

2027-01-19 → 2027-01-25 · Axel-exclusive $385

2027-01-19 → 2027-01-25 · Axel-exclusive $430

2027-01-19 → 2027-01-26 · Axel-exclusive $385

2027-01-19 → 2027-01-26 · Axel-exclusive $430

2027-01-19 → 2027-01-27 · Axel-exclusive $385

2027-01-19 → 2027-01-27 · Axel-exclusive $430

2027-01-19 → 2027-01-29 · Axel-exclusive $385

2027-01-19 → 2027-01-29 · Axel-exclusive $430

2027-01-19 → 2027-01-30 · Axel-exclusive $405

2027-01-19 → 2027-01-30 · Axel-exclusive $450

2027-01-19 → 2027-01-31 · Axel-exclusive $385

2027-01-19 → 2027-01-31 · Axel-exclusive $430

2027-01-19 → 2027-02-02 · Axel-exclusive $391

2027-01-19 → 2027-02-02 · Axel-exclusive $436

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