A Comparison of Direct Flights from Chicago to the Caribbean

by Allie d'Almo  |  Published February 26, 2023

Hoping to flee the Windy City for a tropical Caribbean island getaway? You’re in luck. There are now dozens of direct flights to choose from, most with a flight time of less than five hours. 

(Photo: Omar Eagle Clarke via Unsplash)

They say there’s an island for everyone in the Caribbean, whether you’re looking for the endless, empty stretches of white sands of Turks and Caicos or the Reggae rhythms of Jamaica. It’s easier than ever to reach paradise too, with dozens of direct flights departing from Chicago every week. Currently, four airlines offer flights to various destinations in the Caribbean: United Airlines, American Airlines, Southwest Airlines and Frontier Airlines. If you’re considering flying between these two blockbuster destinations, we’ve analysed the best direct flight options between Chicago and the Caribbean below, taking into consideration prices, departure times and onboard facilities and amenities. There are many more indirect flights to choose from, though we’ve omitted these options from our analysis given the carbon impact of take-off and landing, as well as the frequency and convenience of direct flights. 

United Airlines

comparison direct flights NUC Madrid

(Photo: United Airlines)

United Airlines operates flights to the widest range of Caribbean destinations, with routes to 10 different islands. For the most part, travellers will need to travel on a Saturday to fly to smaller islands. Travellers with less flexibility should opt to travel to Puerto Rico, the Bahamas, Dominican Republic or Jamaica since these are the only destinations served by daily flights. San Juan, Puerto Rico is the cheapest destination to fly to in the Caribbean with United Airlines.  

Customers can choose from Basic Economy, Economy, Premium Economy and Business. The cheapest ticket includes one personal item, but customers will need to pay extra for a carry-on bag and checked bags. Meals are not offered on this flight but snacks are available to purchase on board. We’ve summarised the best United Airlines options below: 

United Airlines: Chicago (ORD) to Aruba  (AUA)

United Airlines operates two flights to Aruba per week, both at the weekend. Both depart in the morning and arrive in the late afternoon. Journey times average 5 hours and 7 minutes and prices average $455 for a one-way ticket. 

United Airlines: Chicago (ORD) to Grand Cayman (GCM)

There are three United Airlines flights between Chicago and Grand Cayman per week, departing on Friday, Saturday and Sunday. Flights average $440 and take roughly four hours. 

United Airlines: Chicago (ORD) to Montego Bay (MBJ)

United operates daily flights to Jamaica at prices as low as $160. All flights depart in the morning and land just before 13:00. 

United Airlines: Chicago (ORD) to Nassau (NAS)

United Airlines operates one daily flight to Nassau, the Bahamas,  which departs at 10:35 and arrives at 15:00. Journey times average just under 3 hours 30 minutes and ticket prices average $420 for a one-way ticket. 

United Airlines: Chicago (ORD) to Providenciales (PLS) 

Travellers can choose from three weekly flights to Turks and Caicos, with options to fly on Friday, Saturday or Sunday. Flights average $325 for a one-way ticket and journey times average four hours. All flights depart at 08:45 in the morning. 

United Airlines: Chicago (ORD) to Punta Cana (PUJ)

Travellers can travel to the Dominican Republic with United Airlines on any day of the week. There are two flights to choose from every Saturday, though both depart in the morning. The cheapest ticket we found cost $180 for a one-way ticket. 

United Airlines: Chicago (ORD) to Saint Lucia (UVF)

United Airlines offers one direct flight to Saint Lucia every Saturday. Flights depart at 08:47 and arrive at Hewanorra International Airport at 15:35. Prices average $320 for a one-way ticket. 

United Airlines: Chicago (ORD) to Saint Thomas (STT)

United Airlines offers Saturday and Sunday flights to Saint Thomas in the U.S. Virgin Islands. Both depart at 07:36 and land at 13:20, just in time for lunch. Flight prices average $520. 

United Airlines: Chicago (ORD) to San Juan (SJU)

United Airlines operates regular flights to Puerto Rico, with at least one or two flights every day. Travellers can choose from a morning (09:30) or evening (18:00) flight, and both journeys average 4 hours and 40 minutes. Tickets can be purchased for as little as $150 one-way, making it the cheapest United Airlines offering to the Caribbean. 

United Airlines: Chicago (ORD) to Sint Maarten (SXM)

Flights depart weekly from Chicago on a Saturday morning. The journey takes roughly five hours with prices ranging from $300 to $840, depending on the time of year.

Find the lowest rates at Kayak

American Airlines 

Photo by Riik@mctr via Flickr (CC BY-SA 2.0)

American Airlines offers direct flights from Chicago to seven Caribbean destinations, slightly less than United Airlines. Flights tend to be slightly pricier than those operated by United Airlines too. Like United Airlines, travellers can choose from three types of ticket: Basic, Main Cabin and Business. Unlike United Airlines, basic rate tickets include full-size carry-on bags, so you could end up paying less for your ticket than with United Airlines. Beyond this, there is little advantage to travelling with American Airlines, since flights depart at similar times and there’s little difference in journey times. 

American Airlines: Chicago (ORD) to Aruba  (AUA)

American Airlines offers one direct flight to Aruba per week, on a Saturday. Flights depart at 08:30 and arrive at 15:30, with an average journey time of five hours. Prices tend to be slightly higher than United Airlines, with an average price of $670. 

American Airlines: Chicago (ORD) to Montego Bay (MBJ)

American Airlines operates daily flights to Montego Bay departing at 09:00. Journey times average 3 hours and 55 minutes and cost an average of $200. 

American Airlines: Chicago (ORD) to Nassau (NAS)

American Airlines offers one flight per week to Nassau, which departs on a Saturday morning at 08:25. Journey times average 3 hours 16 minutes and range between $450-1000. 

American Airlines: Chicago (ORD) to Providenciales (PLS) 

American Airlines offers a weekly Saturday flight to Turks and Caicos. Flights depart at 10:50 and average 3 hours and 50 minutes. Prices average $320. 

American Airlines: Chicago (ORD) to Punta Cana (PUJ)

American Airlines operates daily direct flights to Punta Cana that depart at 08:30 each day. Prices average between $250-300. 

American Airlines: Chicago (ORD) to Saint Thomas (STT)

United Airlines offers one flight per week on a Saturday to  Saint Thomas in the U.S. Virgin Islands. Flights depart at 08:10 and average $815.

American Airlines: Chicago (ORD) to San Juan (SJU)

American Airlines operates one flight to San Juan on most days and two flights on Saturdays. Flights depart at 16:40 and arrive at 22:10. The cheapest one-way ticket we found online costs $160. 

Find the lowest rates at Kayak

Southwest Airlines 

(Photo: Southwest Airlines)

Southwest Airlines operates direct flights to three Caribbean destinations: Montego Bay, Punta Cana and San Juan. On average, tickets to these three destinations are cheaper than those offered by United Airlines and American Airlines, though travellers are more limited by departure times. 

Southwest Airlines: Chicago (MDW) to MontegoBay (MBJ)

Southwest Airlines operates one direct flight to Jamaica per week, which departs at 08:25 am. The cheapest ticket available costs $228 one-way. 

Southwest Airlines: Chicago (MDW) to Punta Cana (PUJ)

Southwest Airlines offers two weekly flights to Punta Cana on a Saturday and Sunday. Journey times average 4 hours and 20 minutes and the cheapest one-way tickets cost $273. 

Southwest Airlines: Chicago (MDW) to San Juan (SJU) 

Southwest Airlines operates one flight per day from Chicago to San Juan. Flight prices range from $156 to $624. 

Find the lowest rates at Kayak

Frontier Airlines 

(Photo: Frontier Airlines)

Frontier Airlines offers one direct flight from Chicago to the Caribbean, with one weekly flight to Montego Bay. However, if you’re looking to travel to Jamaica and you aren’t too picky about flight times, this is the cheapest way to get there. There’s only one type of ticket available to purchase (Standard) and this includes one free personal item. Any additional carry-on or checked baggage will need to be purchased at checkout. 

Frontier Airlines: Chicago (MDW) to Montenegro Bay (MBJ)

Frontier Airlines operates one weekly flight to Jamaica for prices as low as $99. Flights depart at 10:00 and average 3 hours 55 minutes.

Find the lowest rates at Kayak