$224 Find Cheap Flights from Montego Bay to Chicago Midway Airport - Compare and Save

Only Southwest operates flights between Montego Bay and Chicago Midway Airport.

Flights from Montego Bay to Chicago Midway Airport usually depart from Montego Bay Sangster Intl (MBJ) and arrive at Chicago Midway (MDW).

Here are some options for this route, based on selected ticket types and cabin classes:

• Southwest: a cabin bag in Economy Class class

Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

Only Economy Class is available on flights from Montego Bay to Chicago Midway Airport.

On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $403 round-trip, compared to $463 via a layover through Atlanta Hartsfield-Jackson (ATL).

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $90–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

The Boeing 737 MAX 8 family is used most often on this route, operated mainly by Southwest and United Airlines. Other aircraft seen on the route include Boeing 737 variants.

One-stop flights from Montego Bay to Chicago Midway Airport most commonly connect through:

• Atlanta Hartsfield-Jackson (ATL) - 60% of one-stop connections
• Baltimore/Washington (BWI) - 20% of one-stop connections
• Orlando (MCO) - 20% of one-stop connections

Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

Yes. Being flexible with your travel dates can save you up to 29% on the Montego Bay to Chicago Midway Airport route. Friday is the cheapest departure day at $445 round-trip on average, while Tuesday is the most expensive at $624, a difference of $179. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.

These are the earliest and latest flight times available from Montego Bay to Chicago Midway Airport:

• Earliest: departs at 1:40 pm and lands at 5:50 pm
• Latest: departs at 2:25 pm and lands at 6:35 pm.

The flight takes about 4h 10m.

A nonstop flight from Montego Bay to Chicago Midway Airport takes 4h 10m, covering 1,709 miles.

Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $368 to $1,472. That means the highest observed fare was about 4x higher than the lowest one.

One-way fares from Montego Bay to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $234, which is 27% below the typical average for this route.

Flying via Orlando (MCO) gives the shortest average 1-stop total travel time at 6h 09m, compared with 7h 37m via Baltimore/Washington (BWI) and 10h 06m via Atlanta Hartsfield-Jackson (ATL).

Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:
• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Round-trip flights from Montego Bay to Chicago Midway Airport range from $445 to $548, with an average of $473 over the past 12 months. Anything below $445 counts as a good deal.