Chicago to Montego Bay (MDW–MBJ) — Airlines, Schedules & Connections
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No nonstop flights on this route. connecting options below.
MDW–MBJ is served by 1 airline with nonstop service. Southwest Airlines leads the route. The flight covers 1,710 miles in approximately 3h 45m. Beyond nonstop, 21 hubs offer 1-stop connections.
Airline Landscape
| Airline | Freq/wk | Aircraft | Duration | Dep OTP | Alliance | Codeshares |
|---|---|---|---|---|---|---|
| WN Southwest Airlines | 7 | B38M | 3h45 | – | – |
Weekly Schedule Pattern
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 | 1 | 2 | 1 |
| Weekly flights | 7 | 14 | 1 |
| Flight time | 3h 45m | 4h | 3h 42m |
| Departure OTP | 33% | – | – |
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) are connected by nonstop service from Southwest Airlines. With 7 weekly departures, this is a regularly served route.
MDW to MBJ Flight Duration and Schedule
Nonstop flight time from MDW to MBJ ranges from 3 hours 45 minutes. The route covers a distance of 1,710 miles (2,752 km). There are approximately 7 weekly flights outbound and 7 return, totaling 14 flights per week in both directions.
Connecting Options and Alternatives
21 one-stop connections are available, with the fastest taking approximately 6 hours via YYZ. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Chicago (ORD) and Milwaukee (MKE).