Chicago (MDW) to Montego Bay (MBJ), Aug 26, 2027 – Sep 4, 2027: from $419 round trip
Chicago (MDW) to Montego Bay (MBJ), Aug 26, 2027 – Sep 4, 2027: from $419 round trip on Axel, checked Nov 14, 2026. Lowest published fare: $419 round trip, Axel-exclusive, Frontier Airlines / Southwest Airlines, 1 stop, Aug 26, 2027 – Sep 4, 2027, 1 adult, economy, checked Nov 14, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.
See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.
| Exact travel dates | Airline | Flights | Times, duration, stops | Total price | Price checked |
|---|---|---|---|---|---|
| 2027-08-26 → 2027-09-04 | 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 $419 | Nov 14, 2026 |
| 2027-08-26 → 2027-09-04 | 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 $463 | Nov 14, 2026 |
| 2027-08-26 → 2027-09-04 | Delta Air Lines / Southwest Airlines | DL2417 + DL1949 / WN1043 | 13:02:00→20:10:00 7h 08m 1 stop via ATL · 14:25:00→18:35:00 4h 10m nonstop | Axel-exclusive $507 | Nov 14, 2026 |
Route overview: Chicago to Montego Bay (MBJ) flight deals
2027-08-26 → 2027-09-04 · Axel-exclusive $419
- Frontier Airlines F92292 / F9125: MDW 2027-08-26 06:08:00 → MBJ 2027-08-26 14:29:00; 1 stop(s) via ATL; 501 minutes. Local airport times.
- F92292: MDW 2027-08-26 06:08:00 → ATL 2027-08-26 09:31:00; layover at ATL: 186 minutes.
- F9125: ATL 2027-08-26 12:37:00 → MBJ 2027-08-26 14:29:00.
- Southwest Airlines WN1043: MBJ 2027-09-04 14:25:00 → MDW 2027-09-04 18:35:00; nonstop; 250 minutes. Local airport times.
2027-08-26 → 2027-09-04 · Axel-exclusive $463
- Southwest Airlines WN2964 / WN292: MDW 2027-08-26 06:35:00 → MBJ 2027-08-26 13:45:00; 1 stop(s) via MCO; 430 minutes. Local airport times.
- WN2964: MDW 2027-08-26 06:35:00 → MCO 2027-08-26 10:20:00; layover at MCO: 140 minutes.
- WN292: MCO 2027-08-26 12:40:00 → MBJ 2027-08-26 13:45:00.
- Southwest Airlines WN1043: MBJ 2027-09-04 14:25:00 → MDW 2027-09-04 18:35:00; nonstop; 250 minutes. Local airport times.
2027-08-26 → 2027-09-04 · Axel-exclusive $507
- Delta Air Lines DL2417 / DL1949: MDW 2027-08-26 13:02:00 → MBJ 2027-08-26 20:10:00; 1 stop(s) via ATL; 428 minutes. Local airport times.
- DL2417: MDW 2027-08-26 13:02:00 → ATL 2027-08-26 16:01:00; layover at ATL: 135 minutes.
- DL1949: ATL 2027-08-26 18:16:00 → MBJ 2027-08-26 20:10:00.
- Southwest Airlines WN1043: MBJ 2027-09-04 14:25:00 → MDW 2027-09-04 18:35:00; nonstop; 250 minutes. Local airport times.
Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.
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- Aug 25, 2027 · Return options
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