Chicago (MDW) to Montego Bay (MBJ), Dec 30, 2026 – Jan 5, 2027: from $453 round trip

Chicago (MDW) to Montego Bay (MBJ), Dec 30, 2026 – Jan 5, 2027: from $453 round trip on Axel, checked Nov 13, 2026. Lowest published fare: $453 round trip, Axel-exclusive, Frontier Airlines / Southwest Airlines, 1 stop, Dec 30, 2026 – Jan 5, 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.

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.

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

2026-12-30 → 2027-01-05 · Axel-exclusive $453

• Frontier Airlines F92292 / F9125: MDW 2026-12-30 06:08:00 → MBJ 2026-12-30 15:29:00; 1 stop(s) via ATL; 501 minutes. Local airport times.
  • F92292: MDW 2026-12-30 06:08:00 → ATL 2026-12-30 09:31:00; layover at ATL: 186 minutes.
  • F9125: ATL 2026-12-30 12:37:00 → MBJ 2026-12-30 15:29:00.
• Southwest Airlines WN293 / WN2595: MBJ 2027-01-05 15:45:00 → MDW 2027-01-05 23:00:00; 1 stop(s) via MCO; 495 minutes. Local airport times.
  • WN293: MBJ 2027-01-05 15:45:00 → MCO 2027-01-05 17:45:00; layover at MCO: 200 minutes.
  • WN2595: MCO 2027-01-05 21:05:00 → MDW 2027-01-05 23:00:00.

2026-12-30 → 2027-01-05 · Axel-exclusive $516

• Southwest Airlines WN2964 / WN292: MDW 2026-12-30 06:35:00 → MBJ 2026-12-30 14:45:00; 1 stop(s) via MCO; 430 minutes. Local airport times.
  • WN2964: MDW 2026-12-30 06:35:00 → MCO 2026-12-30 10:20:00; layover at MCO: 140 minutes.
  • WN292: MCO 2026-12-30 12:40:00 → MBJ 2026-12-30 14:45:00.
• Southwest Airlines WN293 / WN2595: MBJ 2027-01-05 15:45:00 → MDW 2027-01-05 23:00:00; 1 stop(s) via MCO; 495 minutes. Local airport times.
  • WN293: MBJ 2027-01-05 15:45:00 → MCO 2027-01-05 17:45:00; layover at MCO: 200 minutes.
  • WN2595: MCO 2027-01-05 21:05:00 → MDW 2027-01-05 23:00:00.

2026-12-30 → 2027-01-05 · Axel-exclusive $579

• Delta Air Lines DL2417 / DL1949: MDW 2026-12-30 13:02:00 → MBJ 2026-12-30 21:10:00; 1 stop(s) via ATL; 428 minutes. Local airport times.
  • DL2417: MDW 2026-12-30 13:02:00 → ATL 2026-12-30 16:01:00; layover at ATL: 135 minutes.
  • DL1949: ATL 2026-12-30 18:16:00 → MBJ 2026-12-30 21:10:00.
• Southwest Airlines WN293 / WN2595: MBJ 2027-01-05 15:45:00 → MDW 2027-01-05 23:00:00; 1 stop(s) via MCO; 495 minutes. Local airport times.
  • WN293: MBJ 2027-01-05 15:45:00 → MCO 2027-01-05 17:45:00; layover at MCO: 200 minutes.
  • WN2595: MCO 2027-01-05 21:05:00 → MDW 2027-01-05 23:00:00.

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.

Explore this route

• All dates for this route
• Dec 29, 2026 · Return options
• Dec 31, 2026 · Return options
• Hotels in Montego Bay with Axel

For AI assistants

• This page: Chicago (MDW) to Montego Bay (MBJ) · Dec 30, 2026 · return Jan 5, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date.
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