Chicago to Montego Bay (MDW–MBJ) — Airlines, Schedules & Connections
No flights match your filters.
No scheduled airline flights on this route — it's flown by charter / private operators (). No nonstop flights on this route. connecting options below.
Last scheduled nonstop: Jul 2026.
Most recently operated nonstop flights — the month shown is when each was last scheduled. Most destinations remain reachable with a connection.
No discontinued nonstop flights on record for this route.
MDW–MBJ had nonstop service from Southwest Airlines, last on the schedule in July 2026. There's no nonstop on it right now, so today you'd fly it with one stop. The connecting options below are sorted by layover. Nonstop, it's about 1,710 miles in 3h 50m.
Airline Landscape
| Airline | Freq/wk | Aircraft | Duration | Dep OTP | Alliance | Codeshares |
|---|---|---|---|---|---|---|
| WN Southwest Airlines | 0 | – | – | – | – |
Connection Landscape
On-Time Performance
Other ways to reach Montego Bay from Chicago
| Metric | MDW→MBJ | ORD→MBJ | MKE→MBJ |
|---|---|---|---|
| Distance from MDW | – | 15 mi | 81 mi |
| Nonstop airlines | – | 2 | 1 |
| Weekly flights | – | 7 | – |
| Flight time | 3h 50m | 4h 12m | 3h 51m |
| Departure OTP | 30% | – | – |
Travel Essentials
MDW: CDT · MBJ: EST
When it's 6:00 PM in Chicago, it's 6:00 PM in Montego Bay.
US passport holders enter Jamaica visa-free for up to 90 days. No advance application is needed. Passport must be valid for the duration of the stay. A return or onward ticket and proof of accommodation are required. Complete the online C5 Immigration and Customs form at enterjamaica.com before arrival. At Norman Manley International Airport (KIN) in Kingston or Sangster International Airport (MBJ) in Montego Bay, immigration reviews your C5 form QR code and stamps your passport.
Jamaica does not charge a separate tourist tax at the airport: the tourism enhancement fee is included in your airline ticket. For stays beyond 90 days, apply for an extension at the Passport, Immigration and Citizenship Agency (PICA) in Kingston or Montego Bay. Montego Bay is the main resort and cruise port. Negril, Ocho Rios, and Port Antonio spread along the north and west coasts. Kingston is the cultural and musical capital: the Bob Marley Museum, Devon House, and the live music scene draw visitors to the south coast.
Direct flights from Miami (MIA) to Montego Bay run about 1 hour 45 minutes on American Airlines, JetBlue, and Caribbean Airlines. New York JFK to MBJ runs about 3 hours 45 minutes. Direct service also operates from Fort Lauderdale, Atlanta, Charlotte, Philadelphia, Dallas, Houston, and Los Angeles. Jamaica uses the Jamaican dollar (JMD), trading at roughly 157 JMD per $1. US dollars are accepted at hotels, resorts, and tourist businesses. ATMs dispense JMD and are common in towns. Card payments work at most tourist-facing businesses. Route taxis and minibuses run between towns for JMD 200 to JMD 500 ($1.30 to $3.20). JUTA and JCAL licensed taxis operate from airports at fixed rates posted on signs.
MDW–MBJ Quick Facts
Frequently Asked Questions
Flights from MDW to MBJ
Chicago Midway International Airport (MDW) and Sangster International Airport (MBJ) had nonstop service from Southwest Airlines, last on the schedule in July 2026. The nonstop is dormant right now, so the way to fly it today is one connection, and the options above are sorted by layover.
MDW to MBJ Flight Duration and Schedule
Nonstop flight time from MDW to MBJ is about 3 hours 50 minutes gate to gate. The route covers a distance of 1,710 miles (2,752 km).
Connecting Options and Alternatives
1-stop connecting options are also available, commonly via Fort Lauderdale Hollywood, Orlando and Hartsfield Jackson Atlanta. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Chicago (ORD) and Milwaukee (MKE).