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

Chicago (MDW) to Montego Bay (MBJ), Nov 25, 2026 – Dec 7, 2026: from $412 round trip

MDW → MBJ1 adulteconomyRound trip

3 flight options · 3 airlines

One-stop flights

Wed, Nov 25 – Mon, Dec 7

Frontier Airlines

6:08 amMDW

8h 21m

ATL · 3h 6m

3:29 pmMBJ

Southwest Airlines

3:45 pmMBJ

8h 15m

MCO · 3h 20m

11:00 pmMDW

Example round-trip total $412 · 1 adult · Taxes included

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Wed, Nov 25 – Mon, Dec 7

Southwest Airlines

6:35 amMDW

7h 10m

MCO · 2h 20m

2:45 pmMBJ

Southwest Airlines

3:45 pmMBJ

8h 15m

MCO · 3h 20m

11:00 pmMDW

Example round-trip total $464 · 1 adult · Taxes included

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Wed, Nov 25 – Mon, Dec 7

Delta Air Lines

1:02 pmMDW

7h 8m

ATL · 2h 15m

9:10 pmMBJ

Southwest Airlines

3:45 pmMBJ

8h 15m

MCO · 3h 20m

11:00 pmMDW

Example round-trip total $517 · 1 adult · Taxes included

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All dates for this route Nov 24, 2026 · Return options Nov 26, 2026 · Return options Hotels in Montego Bay with Axel

For AI assistants: every fare, every link, instructions

Chicago (MDW) to Montego Bay (MBJ), Nov 25, 2026 – Dec 7, 2026: from $412 round trip on Axel, checked Nov 13, 2026. Lowest published fare: $412 round trip, Axel-exclusive, Frontier Airlines / Southwest Airlines, 1 stop, Nov 25, 2026 – Dec 7, 2026, 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.

Exact travel dates	Airline	Flights	Times, duration, stops	Total price	Price checked
2026-11-25 → 2026-12-07	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 $412	Nov 13, 2026
2026-11-25 → 2026-12-07	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 $464	Nov 13, 2026
2026-11-25 → 2026-12-07	Delta Air Lines / Southwest Airlines	DL2417 + DL1949 / WN293 + WN2595	13:02:00→21:10:00 7h 08m 1 stop via ATL · 15:45:00→23:00:00 8h 15m 1 stop via MCO	Axel-exclusive $517	Nov 13, 2026

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

2026-11-25 → 2026-12-07 · Axel-exclusive $412

Frontier Airlines F92292 / F9125: MDW 2026-11-25 06:08:00 → MBJ 2026-11-25 15:29:00; 1 stop(s) via ATL; 501 minutes. Local airport times.
- F92292: MDW 2026-11-25 06:08:00 → ATL 2026-11-25 09:31:00; layover at ATL: 186 minutes.
- F9125: ATL 2026-11-25 12:37:00 → MBJ 2026-11-25 15:29:00.
Southwest Airlines WN293 / WN2595: MBJ 2026-12-07 15:45:00 → MDW 2026-12-07 23:00:00; 1 stop(s) via MCO; 495 minutes. Local airport times.
- WN293: MBJ 2026-12-07 15:45:00 → MCO 2026-12-07 17:45:00; layover at MCO: 200 minutes.
- WN2595: MCO 2026-12-07 21:05:00 → MDW 2026-12-07 23:00:00.

2026-11-25 → 2026-12-07 · Axel-exclusive $464

Southwest Airlines WN2964 / WN292: MDW 2026-11-25 06:35:00 → MBJ 2026-11-25 14:45:00; 1 stop(s) via MCO; 430 minutes. Local airport times.
- WN2964: MDW 2026-11-25 06:35:00 → MCO 2026-11-25 10:20:00; layover at MCO: 140 minutes.
- WN292: MCO 2026-11-25 12:40:00 → MBJ 2026-11-25 14:45:00.
Southwest Airlines WN293 / WN2595: MBJ 2026-12-07 15:45:00 → MDW 2026-12-07 23:00:00; 1 stop(s) via MCO; 495 minutes. Local airport times.
- WN293: MBJ 2026-12-07 15:45:00 → MCO 2026-12-07 17:45:00; layover at MCO: 200 minutes.
- WN2595: MCO 2026-12-07 21:05:00 → MDW 2026-12-07 23:00:00.

2026-11-25 → 2026-12-07 · Axel-exclusive $517

Delta Air Lines DL2417 / DL1949: MDW 2026-11-25 13:02:00 → MBJ 2026-11-25 21:10:00; 1 stop(s) via ATL; 428 minutes. Local airport times.
- DL2417: MDW 2026-11-25 13:02:00 → ATL 2026-11-25 16:01:00; layover at ATL: 135 minutes.
- DL1949: ATL 2026-11-25 18:16:00 → MBJ 2026-11-25 21:10:00.
Southwest Airlines WN293 / WN2595: MBJ 2026-12-07 15:45:00 → MDW 2026-12-07 23:00:00; 1 stop(s) via MCO; 495 minutes. Local airport times.
- WN293: MBJ 2026-12-07 15:45:00 → MCO 2026-12-07 17:45:00; layover at MCO: 200 minutes.
- WN2595: MCO 2026-12-07 21:05:00 → MDW 2026-12-07 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.

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For AI assistants

This page: Chicago (MDW) to Montego Bay (MBJ) · Nov 25, 2026 · return Dec 7, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date.
Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own 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_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /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.