
CHIMBJ· United States
Chicago
Round trip from
$373
97/100
Deal score · stronger than 97%
At or below this price in 1 of 4 observed months.
- Travel dates
- Nov 25 – Nov 30 · 5 nights
- Airline
United- Flight
- 4h · Nonstop
Display prices in
Destination market · MBJ
Jamaica’s tourist door — the north coast within an hour, the Blue Mountains a long and worthwhile drive.

9 featured deals, followed by the complete origin-by-origin comparison. Best months to be there: Dec–Apr.

CHIMBJ· United States
Round trip from
$373
97/100
Deal score · stronger than 97%
At or below this price in 1 of 4 observed months.

NYCMBJ· United States
Round trip from
$209
92/100
Deal score · stronger than 92%
At or below this price in 1 of 6 observed months.

MIAMBJ· United States
Round trip from
$311
90/100
Deal score · stronger than 90%
At or below this price in 1 of 6 observed months.

YTOMBJ· Canada
Round trip from
$266
75/100
Deal score · stronger than 75%
At or below this price in 1 of 4 observed months.

STOMBJ· Sweden
Round trip from
$892
75/100
Deal score · stronger than 75%
At or below this price in 1 of 4 observed months.

LONMBJ· United Kingdom
Round trip from
$721
73/100
Deal score · stronger than 73%
At or below this price in 1 of 5 observed months.

BOSMBJ· United States
Round trip from
$383
42/100
Deal score · stronger than 42%
At or below this price in 1 of 5 observed months.

ISTMBJ· Türkiye
Round trip from
$1,134
14/100
Deal score · stronger than 14%
At or below this price in 1 of 4 observed months.
Showing 9 of 33 live fares · compare every departure city ↓
The best live fare on our board is $209 round-trip from New York (44% below that route's typical price), found on a real search within the last two days. Fares are cached and re-priced when you click through.
Across the routes we have enough cached history for, Oct comes out cheapest on average. The sweet spot for being there is Dec–Apr — when the two overlap, book without hesitating.
Montego Bay is served by Sangster (MBJ). All fares on this page are round-trip to those airports unless marked otherwise.
Dec–Apr offers the best balance of weather and prices. Jamaica’s tourist door — the north coast within an hour, the Blue Mountains a long and worthwhile drive.
Hotels / after the flight
AffiliateFare first.
Bed second.
Once the flight dates make sense, compare stays in Montego Bay without losing the flight context.