Chicago (MDW) to Montego Bay (MBJ), Jul 4, 2027: round trips from $455, one way from $230

Chicago (MDW) to Montego Bay (MBJ), Jul 4, 2027: round trips from $455, one way from $230 on Axel, checked Nov 13, 2026. Lowest published fares: $455 round trip, Axel-exclusive, Frontier Airlines / Southwest Airlines, 1 stop, Jul 4–6, 2027; $230 one way, Axel-exclusive, Frontier Airlines, 1 stop, Jul 4, 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
2027-07-04 · one way Frontier Airlines F92292 + F9125 06:08:00→14:29:00 8h 21m 1 stop via ATL Axel-exclusive $230 Nov 13, 2026
2027-07-04 · one way Southwest Airlines WN2964 + WN292 06:35:00→13:45:00 7h 10m 1 stop via MCO Axel-exclusive $289 Nov 13, 2026
2027-07-04 → 2027-07-05 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 $490 Nov 13, 2026
2027-07-04 → 2027-07-05 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 $543 Nov 13, 2026
2027-07-04 → 2027-07-06 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 $455 Nov 13, 2026
2027-07-04 → 2027-07-06 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 $508 Nov 13, 2026
2027-07-04 → 2027-07-07 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 $455 Nov 13, 2026
2027-07-04 → 2027-07-07 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 $508 Nov 13, 2026
2027-07-04 → 2027-07-08 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 $455 Nov 13, 2026
2027-07-04 → 2027-07-08 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 $508 Nov 13, 2026
2027-07-04 → 2027-07-09 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 $455 Nov 13, 2026
2027-07-04 → 2027-07-09 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 $508 Nov 13, 2026
2027-07-04 → 2027-07-10 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 $476 Nov 13, 2026
2027-07-04 → 2027-07-10 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 $529 Nov 13, 2026
2027-07-04 → 2027-07-11 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 $455 Nov 13, 2026
2027-07-04 → 2027-07-11 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 $508 Nov 13, 2026
2027-07-04 → 2027-07-12 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 $455 Nov 13, 2026
2027-07-04 → 2027-07-12 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 $508 Nov 13, 2026
2027-07-04 → 2027-07-13 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 $455 Nov 13, 2026
2027-07-04 → 2027-07-13 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 $508 Nov 13, 2026
2027-07-04 → 2027-07-14 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 $455 Nov 13, 2026
2027-07-04 → 2027-07-14 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 $508 Nov 13, 2026
2027-07-04 → 2027-07-15 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 $455 Nov 13, 2026
2027-07-04 → 2027-07-15 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 $508 Nov 13, 2026
2027-07-04 → 2027-07-16 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 $455 Nov 13, 2026
2027-07-04 → 2027-07-16 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 $508 Nov 13, 2026
2027-07-04 → 2027-07-17 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 $476 Nov 13, 2026
2027-07-04 → 2027-07-17 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 $529 Nov 13, 2026
2027-07-04 → 2027-07-18 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 $455 Nov 13, 2026
2027-07-04 → 2027-07-18 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 $508 Nov 13, 2026

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

2027-07-04 · one way · Axel-exclusive $230

2027-07-04 · one way · Axel-exclusive $289

2027-07-04 → 2027-07-05 · Axel-exclusive $490

2027-07-04 → 2027-07-05 · Axel-exclusive $543

2027-07-04 → 2027-07-06 · Axel-exclusive $455

2027-07-04 → 2027-07-06 · Axel-exclusive $508

2027-07-04 → 2027-07-07 · Axel-exclusive $455

2027-07-04 → 2027-07-07 · Axel-exclusive $508

2027-07-04 → 2027-07-08 · Axel-exclusive $455

2027-07-04 → 2027-07-08 · Axel-exclusive $508

2027-07-04 → 2027-07-10 · Axel-exclusive $476

2027-07-04 → 2027-07-10 · Axel-exclusive $529

2027-07-04 → 2027-07-11 · Axel-exclusive $455

2027-07-04 → 2027-07-11 · Axel-exclusive $508

2027-07-04 → 2027-07-12 · Axel-exclusive $455

2027-07-04 → 2027-07-12 · Axel-exclusive $508

2027-07-04 → 2027-07-14 · Axel-exclusive $455

2027-07-04 → 2027-07-14 · Axel-exclusive $508

2027-07-04 → 2027-07-15 · Axel-exclusive $455

2027-07-04 → 2027-07-15 · Axel-exclusive $508

2027-07-04 → 2027-07-16 · Axel-exclusive $455

2027-07-04 → 2027-07-16 · Axel-exclusive $508

2027-07-04 → 2027-07-18 · Axel-exclusive $455

2027-07-04 → 2027-07-18 · Axel-exclusive $508

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