$204 Find Cheap Flights from Montego Bay to Chicago - Compare and Save

Among airlines operating Montego Bay to Chicago flights:

• American Airlines: offers free seat selection
• United Airlines: offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

3 airlines operate flights between Montego Bay and Chicago. The airlines offering nonstop flights on this route include:

• United Airlines
• American Airlines
• Southwest

Flights from Montego Bay to Chicago usually depart from Montego Bay Sangster Intl (MBJ) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

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

• American Airlines: a cabin bag and a checked bag in Business Class
• United Airlines: a cabin bag in Economy Class class
• 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.

Three cabin classes are available on flights from Montego Bay to Chicago:

• Economy Class
• Business Class
• First Class

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $310 round-trip via Houston George Bush Intcntl (IAH), compared to $429 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $35–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

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

• Atlanta Hartsfield-Jackson (ATL) - 24% of one-stop connections
• Fort Lauderdale (FLL) - 21% of one-stop connections
• Miami (MIA) - 17% of one-stop connections
• Washington, D.C. Dulles Intl (IAD) - 14% 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 38% on the Montego Bay to Chicago route. Wednesday is the cheapest departure day at $387 round-trip on average, while Monday is the most expensive at $624, a difference of $237. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Afternoon is the busiest departure period on Montego Bay to Chicago flights, with 100% of flights leaving in that window. Morning departures account for 0%, evening flights for 0%, and night flights for 0%.

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

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

• Earliest: departs at 1:40 pm and lands at 6:17 pm
• Latest: departs at 3:59 pm and lands at 8:36 pm.

The flight takes about 4h 37m.

A nonstop flight from Montego Bay to Chicago takes 4h 37m, covering 1,712 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 $353 to $2,903. That means the highest observed fare was about 8x higher than the lowest one.

One-way fares from Montego Bay to Chicago are currently lower than usual. Average one-way flight prices are about $228, which is 23% 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 6h 55m via Miami (MIA) and 7h 37m via Baltimore/Washington (BWI).

Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

• Routes Car & Truck Rentals
• Europcar
• Hertz
• Dollar
• Ace

Near Chicago Midway Airport (MDW) — daily rates from around $32:

• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

• Alamo
• Enterprise Rent-A-Car
• Budget
• Avis
• National

Round-trip flights from Montego Bay to Chicago range from $341 to $511, with an average of $420 over the past 12 months. Anything below $341 counts as a good deal.

American Airlines is the only airline on the Montego Bay to Chicago route offering in-flight Wi-Fi. Pricing depends on fare class.