Chicago (MDW) to Montego Bay (MBJ), Jan 3, 2027: round trips from $453, one way from $252

Chicago (MDW) to Montego Bay (MBJ), Jan 3, 2027: round trips from $453, one way from $252 on Axel, checked Nov 13, 2026. Lowest published fares: $453 round trip, Axel-exclusive, Frontier Airlines / Southwest Airlines, 1 stop, Jan 3–4, 2027; $252 one way, Axel-exclusive, Frontier Airlines, 1 stop, Jan 3, 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
2027-01-03 · one way Frontier Airlines F92292 + F9125 06:08:00→15:29:00 8h 21m 1 stop via ATL Axel-exclusive $252 Nov 13, 2026
2027-01-03 · one way Southwest Airlines WN2964 + WN292 06:35:00→14:45:00 7h 10m 1 stop via MCO Axel-exclusive $322 Nov 13, 2026
2027-01-03 → 2027-01-04 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 $453 Nov 13, 2026
2027-01-03 → 2027-01-04 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 $516 Nov 13, 2026
2027-01-03 → 2027-01-05 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 $453 Nov 13, 2026
2027-01-03 → 2027-01-05 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 $516 Nov 13, 2026
2027-01-03 → 2027-01-06 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 $453 Nov 13, 2026
2027-01-03 → 2027-01-06 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 $516 Nov 13, 2026
2027-01-03 → 2027-01-07 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 $453 Nov 13, 2026
2027-01-03 → 2027-01-07 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 $516 Nov 13, 2026
2027-01-03 → 2027-01-08 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 $453 Nov 13, 2026
2027-01-03 → 2027-01-08 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 $516 Nov 13, 2026
2027-01-03 → 2027-01-09 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 $473 Nov 13, 2026
2027-01-03 → 2027-01-09 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 $536 Nov 13, 2026
2027-01-03 → 2027-01-10 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 $453 Nov 13, 2026
2027-01-03 → 2027-01-10 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 $516 Nov 13, 2026
2027-01-03 → 2027-01-11 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 $453 Nov 13, 2026
2027-01-03 → 2027-01-11 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 $516 Nov 13, 2026
2027-01-03 → 2027-01-12 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 $453 Nov 13, 2026
2027-01-03 → 2027-01-12 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 $516 Nov 13, 2026
2027-01-03 → 2027-01-13 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 $453 Nov 13, 2026
2027-01-03 → 2027-01-13 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 $516 Nov 13, 2026
2027-01-03 → 2027-01-14 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 $453 Nov 13, 2026
2027-01-03 → 2027-01-14 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 $516 Nov 13, 2026
2027-01-03 → 2027-01-15 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 $453 Nov 13, 2026
2027-01-03 → 2027-01-15 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 $516 Nov 13, 2026
2027-01-03 → 2027-01-16 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 $473 Nov 13, 2026
2027-01-03 → 2027-01-16 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 $536 Nov 13, 2026
2027-01-03 → 2027-01-17 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 $453 Nov 13, 2026
2027-01-03 → 2027-01-17 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 $516 Nov 13, 2026

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

2027-01-03 · one way · Axel-exclusive $252

2027-01-03 · one way · Axel-exclusive $322

2027-01-03 → 2027-01-04 · Axel-exclusive $453

2027-01-03 → 2027-01-04 · Axel-exclusive $516

2027-01-03 → 2027-01-05 · Axel-exclusive $453

2027-01-03 → 2027-01-05 · Axel-exclusive $516

2027-01-03 → 2027-01-06 · Axel-exclusive $453

2027-01-03 → 2027-01-06 · Axel-exclusive $516

2027-01-03 → 2027-01-07 · Axel-exclusive $453

2027-01-03 → 2027-01-07 · Axel-exclusive $516

2027-01-03 → 2027-01-09 · Axel-exclusive $473

2027-01-03 → 2027-01-09 · Axel-exclusive $536

2027-01-03 → 2027-01-10 · Axel-exclusive $453

2027-01-03 → 2027-01-10 · Axel-exclusive $516

2027-01-03 → 2027-01-11 · Axel-exclusive $453

2027-01-03 → 2027-01-11 · Axel-exclusive $516

2027-01-03 → 2027-01-13 · Axel-exclusive $453

2027-01-03 → 2027-01-13 · Axel-exclusive $516

2027-01-03 → 2027-01-14 · Axel-exclusive $453

2027-01-03 → 2027-01-14 · Axel-exclusive $516

2027-01-03 → 2027-01-15 · Axel-exclusive $453

2027-01-03 → 2027-01-15 · Axel-exclusive $516

2027-01-03 → 2027-01-17 · Axel-exclusive $453

2027-01-03 → 2027-01-17 · Axel-exclusive $516

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