$138 Find Cheap Flights from Chicago Midway Airport to Caribbean - Compare and Save

The cheapest ticket to Caribbean from Chicago Midway Airport found in the last 5 days was to Punta Cana, at $578 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Punta Cana (PUJ), and the cheapest round-trip airline ticket found on this route in the last 5 days was $578.

The cheapest time of day to fly to Caribbean is generally in the morning, when round-trip flights cost $666 on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $666.

No, with an average price for the route of $598, prices are generally cheapest when you fly direct.

The cheapest month for flights from Chicago Midway Airport to Caribbean is October, when tickets cost $394 (return) on average. On the other hand, the most expensive months are June and September, when the average cost of round-trip tickets is $652 and $605 respectively.

Your flight ticket price will generally be cheaper if you fly to Caribbean on a Sunday and more expensive on a Saturday. On your return trip to Chicago Midway Airport, you should consider flying back on a Saturday, and avoid Sundays for better deals.

To get a below average price on the flight from Chicago Midway Airport to Caribbean, you should book around 2 weeks before departure, which saves you about 8% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

There are 2 airlines that fly nonstop from Chicago Midway Airport to Caribbean. They are Frontier and Southwest. The cheapest airline for this route is Frontier, with the best round-trip deal found costing $91 and arriving in San Juan Luis Munoz Marin Intl Airport (SJU). On average, Frontier offers the best prices for nonstop flights between Chicago Midway Airport and Caribbean.

In the past 5 days, the cheapest round-trip tickets from Chicago Midway Airport to Caribbean were found on Southwest ($276) and Delta ($470).

The duration of a flight to Caribbean depends on your arrival airport. The shortest routes to Caribbean from Chicago Midway Airport are to Punta Cana, which takes 4h 25m, San Juan, which takes 4h 40m, and Nassau, which takes 4h 55m.

There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

The earliest flight from Chicago Midway Airport to Caribbean departs at 7:55 am, landing in San Juan at 1:45 pm.

If you prefer to fly at night, the latest flight from Chicago Midway Airport to Caribbean jets off at 8:45 am and lands in San Juan at 2:25 pm.