Chicago (MDW) to Montego Bay (MBJ), Aug 9, 2027: round trips from $403, one way from $189

Chicago (MDW) to Montego Bay (MBJ), Aug 9, 2027: round trips from $403, one way from $189 on Axel, checked Nov 13, 2026. Lowest published fares: $403 round trip, Axel-exclusive, Frontier Airlines / Southwest Airlines, 1 stop, Aug 9–10, 2027; $189 one way, Axel-exclusive, Frontier Airlines, 1 stop, Aug 9, 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
2027-08-09 · one way Frontier Airlines F92292 + F9125 06:08:00→14:29:00 8h 21m 1 stop via ATL Axel-exclusive $189 Nov 13, 2026
2027-08-09 · one way Southwest Airlines WN2964 + WN292 06:35:00→13:45:00 7h 10m 1 stop via MCO Axel-exclusive $238 Nov 13, 2026
2027-08-09 → 2027-08-10 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 $403 Nov 13, 2026
2027-08-09 → 2027-08-10 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 $446 Nov 13, 2026
2027-08-09 → 2027-08-11 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 $403 Nov 13, 2026
2027-08-09 → 2027-08-11 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 $446 Nov 13, 2026
2027-08-09 → 2027-08-12 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 $403 Nov 13, 2026
2027-08-09 → 2027-08-12 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 $446 Nov 13, 2026
2027-08-09 → 2027-08-13 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 $403 Nov 13, 2026
2027-08-09 → 2027-08-13 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 $446 Nov 13, 2026
2027-08-09 → 2027-08-14 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 $422 Nov 13, 2026
2027-08-09 → 2027-08-14 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 $466 Nov 13, 2026
2027-08-09 → 2027-08-15 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 $403 Nov 13, 2026
2027-08-09 → 2027-08-15 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 $446 Nov 13, 2026
2027-08-09 → 2027-08-16 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 $403 Nov 13, 2026
2027-08-09 → 2027-08-16 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 $446 Nov 13, 2026
2027-08-09 → 2027-08-17 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 $403 Nov 13, 2026
2027-08-09 → 2027-08-17 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 $446 Nov 13, 2026
2027-08-09 → 2027-08-18 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 $403 Nov 13, 2026
2027-08-09 → 2027-08-18 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 $446 Nov 13, 2026
2027-08-09 → 2027-08-19 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 $403 Nov 13, 2026
2027-08-09 → 2027-08-19 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 $446 Nov 13, 2026
2027-08-09 → 2027-08-20 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 $403 Nov 13, 2026
2027-08-09 → 2027-08-20 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 $446 Nov 13, 2026
2027-08-09 → 2027-08-21 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 $422 Nov 13, 2026
2027-08-09 → 2027-08-21 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 $466 Nov 13, 2026
2027-08-09 → 2027-08-22 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 $403 Nov 13, 2026
2027-08-09 → 2027-08-22 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 $446 Nov 13, 2026
2027-08-09 → 2027-08-23 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 $403 Nov 13, 2026
2027-08-09 → 2027-08-23 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 $446 Nov 13, 2026

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

2027-08-09 · one way · Axel-exclusive $189

2027-08-09 · one way · Axel-exclusive $238

2027-08-09 → 2027-08-10 · Axel-exclusive $403

2027-08-09 → 2027-08-10 · Axel-exclusive $446

2027-08-09 → 2027-08-11 · Axel-exclusive $403

2027-08-09 → 2027-08-11 · Axel-exclusive $446

2027-08-09 → 2027-08-12 · Axel-exclusive $403

2027-08-09 → 2027-08-12 · Axel-exclusive $446

2027-08-09 → 2027-08-13 · Axel-exclusive $403

2027-08-09 → 2027-08-13 · Axel-exclusive $446

2027-08-09 → 2027-08-15 · Axel-exclusive $403

2027-08-09 → 2027-08-15 · Axel-exclusive $446

2027-08-09 → 2027-08-16 · Axel-exclusive $403

2027-08-09 → 2027-08-16 · Axel-exclusive $446

2027-08-09 → 2027-08-17 · Axel-exclusive $403

2027-08-09 → 2027-08-17 · Axel-exclusive $446

2027-08-09 → 2027-08-19 · Axel-exclusive $403

2027-08-09 → 2027-08-19 · Axel-exclusive $446

2027-08-09 → 2027-08-20 · Axel-exclusive $403

2027-08-09 → 2027-08-20 · Axel-exclusive $446

2027-08-09 → 2027-08-21 · Axel-exclusive $422

2027-08-09 → 2027-08-21 · Axel-exclusive $466

2027-08-09 → 2027-08-23 · Axel-exclusive $403

2027-08-09 → 2027-08-23 · Axel-exclusive $446

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