Chicago (MDW) to Montego Bay (MBJ), May 29, 2027: round trips from $426, one way from $207
Chicago (MDW) to Montego Bay (MBJ), May 29, 2027: round trips from $426, one way from $207 on Axel, checked Nov 13, 2026. Lowest published fares: $426 round trip, Axel-exclusive, Frontier Airlines / Southwest Airlines, 1 stop, May 29, 2027 – Jun 1, 2027; $207 one way, Axel-exclusive, Frontier Airlines, 1 stop, May 29, 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 |
|---|---|---|---|---|---|
| 2027-05-29 · one way | Frontier Airlines | F92292 + F9125 | 06:08:00→14:29:00 8h 21m 1 stop via ATL | Axel-exclusive $207 | Nov 13, 2026 |
| 2027-05-29 · one way | Southwest Airlines | WN2964 + WN292 | 06:35:00→13:45:00 7h 10m 1 stop via MCO | Axel-exclusive $260 | Nov 13, 2026 |
| 2027-05-29 → 2027-05-30 | 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 $440 | Nov 13, 2026 |
| 2027-05-29 → 2027-05-30 | 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 $488 | Nov 13, 2026 |
| 2027-05-29 → 2027-05-31 | 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 $440 | Nov 13, 2026 |
| 2027-05-29 → 2027-05-31 | 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 $488 | Nov 13, 2026 |
| 2027-05-29 → 2027-06-01 | 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 $426 | Nov 13, 2026 |
| 2027-05-29 → 2027-06-01 | 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 |
| 2027-05-29 → 2027-06-02 | 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 $426 | Nov 13, 2026 |
| 2027-05-29 → 2027-06-02 | 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 |
| 2027-05-29 → 2027-06-03 | 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 $426 | Nov 13, 2026 |
| 2027-05-29 → 2027-06-03 | 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 |
| 2027-05-29 → 2027-06-04 | 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 $426 | Nov 13, 2026 |
| 2027-05-29 → 2027-06-04 | 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 |
| 2027-05-29 → 2027-06-05 | 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 $446 | Nov 13, 2026 |
| 2027-05-29 → 2027-06-05 | 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 |
| 2027-05-29 → 2027-06-06 | 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 $426 | Nov 13, 2026 |
| 2027-05-29 → 2027-06-06 | 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 $474 | Nov 13, 2026 |
| 2027-05-29 → 2027-06-07 | 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 $426 | Nov 13, 2026 |
| 2027-05-29 → 2027-06-07 | 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 $474 | Nov 13, 2026 |
| 2027-05-29 → 2027-06-08 | 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 $426 | Nov 13, 2026 |
| 2027-05-29 → 2027-06-08 | 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 $474 | Nov 13, 2026 |
| 2027-05-29 → 2027-06-09 | 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 $426 | Nov 13, 2026 |
| 2027-05-29 → 2027-06-09 | 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 $474 | Nov 13, 2026 |
| 2027-05-29 → 2027-06-10 | 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 $426 | Nov 13, 2026 |
| 2027-05-29 → 2027-06-10 | 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 $474 | Nov 13, 2026 |
| 2027-05-29 → 2027-06-11 | 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 $426 | Nov 13, 2026 |
| 2027-05-29 → 2027-06-11 | 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 $474 | Nov 13, 2026 |
| 2027-05-29 → 2027-06-12 | 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 $446 | Nov 13, 2026 |
| 2027-05-29 → 2027-06-12 | 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 |
Route overview: Chicago to Montego Bay (MBJ) flight deals
2027-05-29 · one way · Axel-exclusive $207
- Frontier Airlines F92292 / F9125: MDW 2027-05-29 06:08:00 → MBJ 2027-05-29 14:29:00; 1 stop(s) via ATL; 501 minutes. Local airport times.
- F92292: MDW 2027-05-29 06:08:00 → ATL 2027-05-29 09:31:00; layover at ATL: 186 minutes.
- F9125: ATL 2027-05-29 12:37:00 → MBJ 2027-05-29 14:29:00.
2027-05-29 · one way · Axel-exclusive $260
- Southwest Airlines WN2964 / WN292: MDW 2027-05-29 06:35:00 → MBJ 2027-05-29 13:45:00; 1 stop(s) via MCO; 430 minutes. Local airport times.
- WN2964: MDW 2027-05-29 06:35:00 → MCO 2027-05-29 10:20:00; layover at MCO: 140 minutes.
- WN292: MCO 2027-05-29 12:40:00 → MBJ 2027-05-29 13:45:00.
2027-05-29 → 2027-05-30 · Axel-exclusive $440
- Frontier Airlines F92292 / F9125: MDW 2027-05-29 06:08:00 → MBJ 2027-05-29 14:29:00; 1 stop(s) via ATL; 501 minutes. Local airport times.
- F92292: MDW 2027-05-29 06:08:00 → ATL 2027-05-29 09:31:00; layover at ATL: 186 minutes.
- F9125: ATL 2027-05-29 12:37:00 → MBJ 2027-05-29 14:29:00.
- Southwest Airlines WN293 / WN2595: MBJ 2027-05-30 15:45:00 → MDW 2027-05-31 00:00:00; 1 stop(s) via MCO; 495 minutes. Local airport times.
- WN293: MBJ 2027-05-30 15:45:00 → MCO 2027-05-30 18:45:00; layover at MCO: 200 minutes.
- WN2595: MCO 2027-05-30 22:05:00 → MDW 2027-05-31 00:00:00.
2027-05-29 → 2027-05-30 · Axel-exclusive $488
- Southwest Airlines WN2964 / WN292: MDW 2027-05-29 06:35:00 → MBJ 2027-05-29 13:45:00; 1 stop(s) via MCO; 430 minutes. Local airport times.
- WN2964: MDW 2027-05-29 06:35:00 → MCO 2027-05-29 10:20:00; layover at MCO: 140 minutes.
- WN292: MCO 2027-05-29 12:40:00 → MBJ 2027-05-29 13:45:00.
- Southwest Airlines WN293 / WN2595: MBJ 2027-05-30 15:45:00 → MDW 2027-05-31 00:00:00; 1 stop(s) via MCO; 495 minutes. Local airport times.
- WN293: MBJ 2027-05-30 15:45:00 → MCO 2027-05-30 18:45:00; layover at MCO: 200 minutes.
- WN2595: MCO 2027-05-30 22:05:00 → MDW 2027-05-31 00:00:00.
2027-05-29 → 2027-05-31 · Axel-exclusive $440
- Frontier Airlines F92292 / F9125: MDW 2027-05-29 06:08:00 → MBJ 2027-05-29 14:29:00; 1 stop(s) via ATL; 501 minutes. Local airport times.
- F92292: MDW 2027-05-29 06:08:00 → ATL 2027-05-29 09:31:00; layover at ATL: 186 minutes.
- F9125: ATL 2027-05-29 12:37:00 → MBJ 2027-05-29 14:29:00.
- Southwest Airlines WN293 / WN2595: MBJ 2027-05-31 15:45:00 → MDW 2027-06-01 00:00:00; 1 stop(s) via MCO; 495 minutes. Local airport times.
- WN293: MBJ 2027-05-31 15:45:00 → MCO 2027-05-31 18:45:00; layover at MCO: 200 minutes.
- WN2595: MCO 2027-05-31 22:05:00 → MDW 2027-06-01 00:00:00.
2027-05-29 → 2027-05-31 · Axel-exclusive $488
- Southwest Airlines WN2964 / WN292: MDW 2027-05-29 06:35:00 → MBJ 2027-05-29 13:45:00; 1 stop(s) via MCO; 430 minutes. Local airport times.
- WN2964: MDW 2027-05-29 06:35:00 → MCO 2027-05-29 10:20:00; layover at MCO: 140 minutes.
- WN292: MCO 2027-05-29 12:40:00 → MBJ 2027-05-29 13:45:00.
- Southwest Airlines WN293 / WN2595: MBJ 2027-05-31 15:45:00 → MDW 2027-06-01 00:00:00; 1 stop(s) via MCO; 495 minutes. Local airport times.
- WN293: MBJ 2027-05-31 15:45:00 → MCO 2027-05-31 18:45:00; layover at MCO: 200 minutes.
- WN2595: MCO 2027-05-31 22:05:00 → MDW 2027-06-01 00:00:00.
2027-05-29 → 2027-06-01 · Axel-exclusive $426
- Frontier Airlines F92292 / F9125: MDW 2027-05-29 06:08:00 → MBJ 2027-05-29 14:29:00; 1 stop(s) via ATL; 501 minutes. Local airport times.
- F92292: MDW 2027-05-29 06:08:00 → ATL 2027-05-29 09:31:00; layover at ATL: 186 minutes.
- F9125: ATL 2027-05-29 12:37:00 → MBJ 2027-05-29 14:29:00.
- Southwest Airlines WN293 / WN2595: MBJ 2027-06-01 15:45:00 → MDW 2027-06-02 00:00:00; 1 stop(s) via MCO; 495 minutes. Local airport times.
- WN293: MBJ 2027-06-01 15:45:00 → MCO 2027-06-01 18:45:00; layover at MCO: 200 minutes.
- WN2595: MCO 2027-06-01 22:05:00 → MDW 2027-06-02 00:00:00.
2027-05-29 → 2027-06-01 · Axel-exclusive $474
- Southwest Airlines WN2964 / WN292: MDW 2027-05-29 06:35:00 → MBJ 2027-05-29 13:45:00; 1 stop(s) via MCO; 430 minutes. Local airport times.
- WN2964: MDW 2027-05-29 06:35:00 → MCO 2027-05-29 10:20:00; layover at MCO: 140 minutes.
- WN292: MCO 2027-05-29 12:40:00 → MBJ 2027-05-29 13:45:00.
- Southwest Airlines WN293 / WN2595: MBJ 2027-06-01 15:45:00 → MDW 2027-06-02 00:00:00; 1 stop(s) via MCO; 495 minutes. Local airport times.
- WN293: MBJ 2027-06-01 15:45:00 → MCO 2027-06-01 18:45:00; layover at MCO: 200 minutes.
- WN2595: MCO 2027-06-01 22:05:00 → MDW 2027-06-02 00:00:00.
2027-05-29 → 2027-06-02 · Axel-exclusive $426
- Frontier Airlines F92292 / F9125: MDW 2027-05-29 06:08:00 → MBJ 2027-05-29 14:29:00; 1 stop(s) via ATL; 501 minutes. Local airport times.
- F92292: MDW 2027-05-29 06:08:00 → ATL 2027-05-29 09:31:00; layover at ATL: 186 minutes.
- F9125: ATL 2027-05-29 12:37:00 → MBJ 2027-05-29 14:29:00.
- Southwest Airlines WN293 / WN2595: MBJ 2027-06-02 15:45:00 → MDW 2027-06-03 00:00:00; 1 stop(s) via MCO; 495 minutes. Local airport times.
- WN293: MBJ 2027-06-02 15:45:00 → MCO 2027-06-02 18:45:00; layover at MCO: 200 minutes.
- WN2595: MCO 2027-06-02 22:05:00 → MDW 2027-06-03 00:00:00.
2027-05-29 → 2027-06-02 · Axel-exclusive $474
- Southwest Airlines WN2964 / WN292: MDW 2027-05-29 06:35:00 → MBJ 2027-05-29 13:45:00; 1 stop(s) via MCO; 430 minutes. Local airport times.
- WN2964: MDW 2027-05-29 06:35:00 → MCO 2027-05-29 10:20:00; layover at MCO: 140 minutes.
- WN292: MCO 2027-05-29 12:40:00 → MBJ 2027-05-29 13:45:00.
- Southwest Airlines WN293 / WN2595: MBJ 2027-06-02 15:45:00 → MDW 2027-06-03 00:00:00; 1 stop(s) via MCO; 495 minutes. Local airport times.
- WN293: MBJ 2027-06-02 15:45:00 → MCO 2027-06-02 18:45:00; layover at MCO: 200 minutes.
- WN2595: MCO 2027-06-02 22:05:00 → MDW 2027-06-03 00:00:00.
2027-05-29 → 2027-06-04 · Axel-exclusive $426
- Frontier Airlines F92292 / F9125: MDW 2027-05-29 06:08:00 → MBJ 2027-05-29 14:29:00; 1 stop(s) via ATL; 501 minutes. Local airport times.
- F92292: MDW 2027-05-29 06:08:00 → ATL 2027-05-29 09:31:00; layover at ATL: 186 minutes.
- F9125: ATL 2027-05-29 12:37:00 → MBJ 2027-05-29 14:29:00.
- Southwest Airlines WN293 / WN2595: MBJ 2027-06-04 15:45:00 → MDW 2027-06-05 00:00:00; 1 stop(s) via MCO; 495 minutes. Local airport times.
- WN293: MBJ 2027-06-04 15:45:00 → MCO 2027-06-04 18:45:00; layover at MCO: 200 minutes.
- WN2595: MCO 2027-06-04 22:05:00 → MDW 2027-06-05 00:00:00.
2027-05-29 → 2027-06-04 · Axel-exclusive $474
- Southwest Airlines WN2964 / WN292: MDW 2027-05-29 06:35:00 → MBJ 2027-05-29 13:45:00; 1 stop(s) via MCO; 430 minutes. Local airport times.
- WN2964: MDW 2027-05-29 06:35:00 → MCO 2027-05-29 10:20:00; layover at MCO: 140 minutes.
- WN292: MCO 2027-05-29 12:40:00 → MBJ 2027-05-29 13:45:00.
- Southwest Airlines WN293 / WN2595: MBJ 2027-06-04 15:45:00 → MDW 2027-06-05 00:00:00; 1 stop(s) via MCO; 495 minutes. Local airport times.
- WN293: MBJ 2027-06-04 15:45:00 → MCO 2027-06-04 18:45:00; layover at MCO: 200 minutes.
- WN2595: MCO 2027-06-04 22:05:00 → MDW 2027-06-05 00:00:00.
2027-05-29 → 2027-06-05 · Axel-exclusive $446
- Frontier Airlines F92292 / F9125: MDW 2027-05-29 06:08:00 → MBJ 2027-05-29 14:29:00; 1 stop(s) via ATL; 501 minutes. Local airport times.
- F92292: MDW 2027-05-29 06:08:00 → ATL 2027-05-29 09:31:00; layover at ATL: 186 minutes.
- F9125: ATL 2027-05-29 12:37:00 → MBJ 2027-05-29 14:29:00.
- Southwest Airlines WN1043: MBJ 2027-06-05 14:25:00 → MDW 2027-06-05 18:35:00; nonstop; 250 minutes. Local airport times.
2027-05-29 → 2027-06-05 · Axel-exclusive $494
- Southwest Airlines WN2964 / WN292: MDW 2027-05-29 06:35:00 → MBJ 2027-05-29 13:45:00; 1 stop(s) via MCO; 430 minutes. Local airport times.
- WN2964: MDW 2027-05-29 06:35:00 → MCO 2027-05-29 10:20:00; layover at MCO: 140 minutes.
- WN292: MCO 2027-05-29 12:40:00 → MBJ 2027-05-29 13:45:00.
- Southwest Airlines WN1043: MBJ 2027-06-05 14:25:00 → MDW 2027-06-05 18:35:00; nonstop; 250 minutes. Local airport times.
2027-05-29 → 2027-06-06 · Axel-exclusive $426
- Frontier Airlines F92292 / F9125: MDW 2027-05-29 06:08:00 → MBJ 2027-05-29 14:29:00; 1 stop(s) via ATL; 501 minutes. Local airport times.
- F92292: MDW 2027-05-29 06:08:00 → ATL 2027-05-29 09:31:00; layover at ATL: 186 minutes.
- F9125: ATL 2027-05-29 12:37:00 → MBJ 2027-05-29 14:29:00.
- Southwest Airlines WN293 / WN2595: MBJ 2027-06-06 15:45:00 → MDW 2027-06-07 00:00:00; 1 stop(s) via MCO; 495 minutes. Local airport times.
- WN293: MBJ 2027-06-06 15:45:00 → MCO 2027-06-06 18:45:00; layover at MCO: 200 minutes.
- WN2595: MCO 2027-06-06 22:05:00 → MDW 2027-06-07 00:00:00.
2027-05-29 → 2027-06-06 · Axel-exclusive $474
- Southwest Airlines WN2964 / WN292: MDW 2027-05-29 06:35:00 → MBJ 2027-05-29 13:45:00; 1 stop(s) via MCO; 430 minutes. Local airport times.
- WN2964: MDW 2027-05-29 06:35:00 → MCO 2027-05-29 10:20:00; layover at MCO: 140 minutes.
- WN292: MCO 2027-05-29 12:40:00 → MBJ 2027-05-29 13:45:00.
- Southwest Airlines WN293 / WN2595: MBJ 2027-06-06 15:45:00 → MDW 2027-06-07 00:00:00; 1 stop(s) via MCO; 495 minutes. Local airport times.
- WN293: MBJ 2027-06-06 15:45:00 → MCO 2027-06-06 18:45:00; layover at MCO: 200 minutes.
- WN2595: MCO 2027-06-06 22:05:00 → MDW 2027-06-07 00:00:00.
2027-05-29 → 2027-06-08 · Axel-exclusive $426
- Frontier Airlines F92292 / F9125: MDW 2027-05-29 06:08:00 → MBJ 2027-05-29 14:29:00; 1 stop(s) via ATL; 501 minutes. Local airport times.
- F92292: MDW 2027-05-29 06:08:00 → ATL 2027-05-29 09:31:00; layover at ATL: 186 minutes.
- F9125: ATL 2027-05-29 12:37:00 → MBJ 2027-05-29 14:29:00.
- Southwest Airlines WN293 / WN2595: MBJ 2027-06-08 15:45:00 → MDW 2027-06-09 00:00:00; 1 stop(s) via MCO; 495 minutes. Local airport times.
- WN293: MBJ 2027-06-08 15:45:00 → MCO 2027-06-08 18:45:00; layover at MCO: 200 minutes.
- WN2595: MCO 2027-06-08 22:05:00 → MDW 2027-06-09 00:00:00.
2027-05-29 → 2027-06-08 · Axel-exclusive $474
- Southwest Airlines WN2964 / WN292: MDW 2027-05-29 06:35:00 → MBJ 2027-05-29 13:45:00; 1 stop(s) via MCO; 430 minutes. Local airport times.
- WN2964: MDW 2027-05-29 06:35:00 → MCO 2027-05-29 10:20:00; layover at MCO: 140 minutes.
- WN292: MCO 2027-05-29 12:40:00 → MBJ 2027-05-29 13:45:00.
- Southwest Airlines WN293 / WN2595: MBJ 2027-06-08 15:45:00 → MDW 2027-06-09 00:00:00; 1 stop(s) via MCO; 495 minutes. Local airport times.
- WN293: MBJ 2027-06-08 15:45:00 → MCO 2027-06-08 18:45:00; layover at MCO: 200 minutes.
- WN2595: MCO 2027-06-08 22:05:00 → MDW 2027-06-09 00:00:00.
2027-05-29 → 2027-06-09 · Axel-exclusive $426
- Frontier Airlines F92292 / F9125: MDW 2027-05-29 06:08:00 → MBJ 2027-05-29 14:29:00; 1 stop(s) via ATL; 501 minutes. Local airport times.
- F92292: MDW 2027-05-29 06:08:00 → ATL 2027-05-29 09:31:00; layover at ATL: 186 minutes.
- F9125: ATL 2027-05-29 12:37:00 → MBJ 2027-05-29 14:29:00.
- Southwest Airlines WN293 / WN2595: MBJ 2027-06-09 15:45:00 → MDW 2027-06-10 00:00:00; 1 stop(s) via MCO; 495 minutes. Local airport times.
- WN293: MBJ 2027-06-09 15:45:00 → MCO 2027-06-09 18:45:00; layover at MCO: 200 minutes.
- WN2595: MCO 2027-06-09 22:05:00 → MDW 2027-06-10 00:00:00.
2027-05-29 → 2027-06-09 · Axel-exclusive $474
- Southwest Airlines WN2964 / WN292: MDW 2027-05-29 06:35:00 → MBJ 2027-05-29 13:45:00; 1 stop(s) via MCO; 430 minutes. Local airport times.
- WN2964: MDW 2027-05-29 06:35:00 → MCO 2027-05-29 10:20:00; layover at MCO: 140 minutes.
- WN292: MCO 2027-05-29 12:40:00 → MBJ 2027-05-29 13:45:00.
- Southwest Airlines WN293 / WN2595: MBJ 2027-06-09 15:45:00 → MDW 2027-06-10 00:00:00; 1 stop(s) via MCO; 495 minutes. Local airport times.
- WN293: MBJ 2027-06-09 15:45:00 → MCO 2027-06-09 18:45:00; layover at MCO: 200 minutes.
- WN2595: MCO 2027-06-09 22:05:00 → MDW 2027-06-10 00:00:00.
2027-05-29 → 2027-06-10 · Axel-exclusive $426
- Frontier Airlines F92292 / F9125: MDW 2027-05-29 06:08:00 → MBJ 2027-05-29 14:29:00; 1 stop(s) via ATL; 501 minutes. Local airport times.
- F92292: MDW 2027-05-29 06:08:00 → ATL 2027-05-29 09:31:00; layover at ATL: 186 minutes.
- F9125: ATL 2027-05-29 12:37:00 → MBJ 2027-05-29 14:29:00.
- Southwest Airlines WN293 / WN2595: MBJ 2027-06-10 15:45:00 → MDW 2027-06-11 00:00:00; 1 stop(s) via MCO; 495 minutes. Local airport times.
- WN293: MBJ 2027-06-10 15:45:00 → MCO 2027-06-10 18:45:00; layover at MCO: 200 minutes.
- WN2595: MCO 2027-06-10 22:05:00 → MDW 2027-06-11 00:00:00.
2027-05-29 → 2027-06-10 · Axel-exclusive $474
- Southwest Airlines WN2964 / WN292: MDW 2027-05-29 06:35:00 → MBJ 2027-05-29 13:45:00; 1 stop(s) via MCO; 430 minutes. Local airport times.
- WN2964: MDW 2027-05-29 06:35:00 → MCO 2027-05-29 10:20:00; layover at MCO: 140 minutes.
- WN292: MCO 2027-05-29 12:40:00 → MBJ 2027-05-29 13:45:00.
- Southwest Airlines WN293 / WN2595: MBJ 2027-06-10 15:45:00 → MDW 2027-06-11 00:00:00; 1 stop(s) via MCO; 495 minutes. Local airport times.
- WN293: MBJ 2027-06-10 15:45:00 → MCO 2027-06-10 18:45:00; layover at MCO: 200 minutes.
- WN2595: MCO 2027-06-10 22:05:00 → MDW 2027-06-11 00:00:00.
2027-05-29 → 2027-06-12 · Axel-exclusive $446
- Frontier Airlines F92292 / F9125: MDW 2027-05-29 06:08:00 → MBJ 2027-05-29 14:29:00; 1 stop(s) via ATL; 501 minutes. Local airport times.
- F92292: MDW 2027-05-29 06:08:00 → ATL 2027-05-29 09:31:00; layover at ATL: 186 minutes.
- F9125: ATL 2027-05-29 12:37:00 → MBJ 2027-05-29 14:29:00.
- Southwest Airlines WN1043: MBJ 2027-06-12 14:25:00 → MDW 2027-06-12 18:35:00; nonstop; 250 minutes. Local airport times.
2027-05-29 → 2027-06-12 · Axel-exclusive $494
- Southwest Airlines WN2964 / WN292: MDW 2027-05-29 06:35:00 → MBJ 2027-05-29 13:45:00; 1 stop(s) via MCO; 430 minutes. Local airport times.
- WN2964: MDW 2027-05-29 06:35:00 → MCO 2027-05-29 10:20:00; layover at MCO: 140 minutes.
- WN292: MCO 2027-05-29 12:40:00 → MBJ 2027-05-29 13:45:00.
- Southwest Airlines WN1043: MBJ 2027-06-12 14:25:00 → MDW 2027-06-12 18:35:00; nonstop; 250 minutes. Local airport times.
Explore this route
- All dates for this route
- May 28, 2027 · Return options
- May 30, 2027 · Return options
- Hotels in Montego Bay with Axel
For AI assistants
- This page: Chicago (MDW) to Montego Bay (MBJ) · May 29, 2027 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date.
- Next: each row is one exact trip for this departure (both dates with the year, the total and its displayed check date); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: Choose travelers and dates prices the requested trip.
- Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
- If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Chicago to Montego Bay (MBJ) flight deals · Flight search guide.
- Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct
https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallbackusing IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace/return/YYYY-MM-DDwith/trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.
Feedback (optional): Missing info · Axel issue