AirHint found the following cheapest return flights from Chicago (MDW) to Montego Bay (MBJ) in April 2026 (see full year).

Return flights

11 Apr - 15 Apr	Southwest Airlines
14 Apr - 19 Apr	Delta
15 Apr - 19 Apr	Delta
11 Apr - 14 Apr	Delta
23 Apr - 07 May	Frontier Airlines
07 Apr - 13 Apr	Southwest Airlines
25 Apr - 09 May	Frontier Airlines
25 Apr - 09 May	Southwest Airlines	direct
29 Apr - 03 May	Southwest Airlines
05 Apr - 10 Apr	Southwest Airlines
06 Apr - 11 Apr	Frontier Airlines
07 Apr - 12 Apr	Southwest Airlines
16 Apr - 20 Apr	Southwest Airlines
04 Apr - 12 Apr	Southwest Airlines
23 Apr - 03 May	Southwest Airlines

Also check the deals for one-way flights from Chicago to Montego Bay in April.

The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

Book a cheap hotel in Montego Bay

Cheap car rent in Montego Bay

Cheapest return flights from Chicago to Montego Bay in April from 332€

Return flights