Chicago (MDW) to Montego Bay (MBJ), Jul 15, 2027: round trips from $427, one way from $201

Chicago (MDW) to Montego Bay (MBJ), Jul 15, 2027: round trips from $427, one way from $201 on Axel, checked Nov 13, 2026. Lowest published fares: $427 round trip, Axel-exclusive, Frontier Airlines / Southwest Airlines, 1 stop, Jul 15–16, 2027; $201 one way, Axel-exclusive, Frontier Airlines, 1 stop, Jul 15, 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
2027-07-15 · one way Frontier Airlines F92292 + F9125 06:08:00→14:29:00 8h 21m 1 stop via ATL Axel-exclusive $201 Nov 13, 2026
2027-07-15 · one way Southwest Airlines WN2964 + WN292 06:35:00→13:45:00 7h 10m 1 stop via MCO Axel-exclusive $252 Nov 13, 2026
2027-07-15 → 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 $427 Nov 13, 2026
2027-07-15 → 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 $474 Nov 13, 2026
2027-07-15 → 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 $448 Nov 13, 2026
2027-07-15 → 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 $494 Nov 13, 2026
2027-07-15 → 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 $427 Nov 13, 2026
2027-07-15 → 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 $474 Nov 13, 2026
2027-07-15 → 2027-07-19 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 $427 Nov 13, 2026
2027-07-15 → 2027-07-19 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 $474 Nov 13, 2026
2027-07-15 → 2027-07-20 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 $427 Nov 13, 2026
2027-07-15 → 2027-07-20 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 $474 Nov 13, 2026
2027-07-15 → 2027-07-21 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 $427 Nov 13, 2026
2027-07-15 → 2027-07-21 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 $474 Nov 13, 2026
2027-07-15 → 2027-07-22 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 $427 Nov 13, 2026
2027-07-15 → 2027-07-22 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 $474 Nov 13, 2026
2027-07-15 → 2027-07-23 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 $427 Nov 13, 2026
2027-07-15 → 2027-07-23 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 $474 Nov 13, 2026
2027-07-15 → 2027-07-24 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 $448 Nov 13, 2026
2027-07-15 → 2027-07-24 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 $494 Nov 13, 2026
2027-07-15 → 2027-07-25 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 $427 Nov 13, 2026
2027-07-15 → 2027-07-25 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 $474 Nov 13, 2026
2027-07-15 → 2027-07-26 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 $427 Nov 13, 2026
2027-07-15 → 2027-07-26 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 $474 Nov 13, 2026
2027-07-15 → 2027-07-27 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 $427 Nov 13, 2026
2027-07-15 → 2027-07-27 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 $474 Nov 13, 2026
2027-07-15 → 2027-07-28 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 $427 Nov 13, 2026
2027-07-15 → 2027-07-28 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 $474 Nov 13, 2026
2027-07-15 → 2027-07-29 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 $427 Nov 13, 2026
2027-07-15 → 2027-07-29 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 $474 Nov 13, 2026

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

2027-07-15 · one way · Axel-exclusive $201

2027-07-15 · one way · Axel-exclusive $252

2027-07-15 → 2027-07-16 · Axel-exclusive $427

2027-07-15 → 2027-07-16 · Axel-exclusive $474

2027-07-15 → 2027-07-17 · Axel-exclusive $448

2027-07-15 → 2027-07-17 · Axel-exclusive $494

2027-07-15 → 2027-07-18 · Axel-exclusive $427

2027-07-15 → 2027-07-18 · Axel-exclusive $474

2027-07-15 → 2027-07-19 · Axel-exclusive $427

2027-07-15 → 2027-07-19 · Axel-exclusive $474

2027-07-15 → 2027-07-21 · Axel-exclusive $427

2027-07-15 → 2027-07-21 · Axel-exclusive $474

2027-07-15 → 2027-07-22 · Axel-exclusive $427

2027-07-15 → 2027-07-22 · Axel-exclusive $474

2027-07-15 → 2027-07-23 · Axel-exclusive $427

2027-07-15 → 2027-07-23 · Axel-exclusive $474

2027-07-15 → 2027-07-25 · Axel-exclusive $427

2027-07-15 → 2027-07-25 · Axel-exclusive $474

2027-07-15 → 2027-07-26 · Axel-exclusive $427

2027-07-15 → 2027-07-26 · Axel-exclusive $474

2027-07-15 → 2027-07-27 · Axel-exclusive $427

2027-07-15 → 2027-07-27 · Axel-exclusive $474

2027-07-15 → 2027-07-29 · Axel-exclusive $427

2027-07-15 → 2027-07-29 · Axel-exclusive $474

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