United Airlines Just Made It Easier to Escape From Chicago to the Caribbean This Fall  

The plane lifts off from Chicago, and just a few hours later, you’re somewhere else entirely. Palm trees replace pavement. Salt replaces cold wind. And suddenly, fall doesn’t feel like fall at all. While most travelers associate peak Caribbean getaways with winter holidays or spring breaks, this fall may just be the smartest time to go. And if you’re flying out of Chicago, it’s never been easier to get there.

We always love visiting the Caribbean in the autumn months for a host of reasons.

More Fall Flights

Starting this October, United Airlines will operate its busiest schedule of the year from Chicago O’Hare—yes, even busier than summer. That means more than 590 flights per day and expanded access to sun-soaked destinations across the U.S., Latin America, and the Caribbean.

For travelers craving the Caribbean, United is extending and expanding weekend service to several in-demand destinations:

Saint Martin (SXM): More weekend flights in November 

Punta Cana (PUJ): Additional service in October

Cozumel (CZM): Extended flights starting in November

These are among the easiest and fastest getaways from the Midwest to turquoise water, white sand, and world-class resorts. Add in extra lift to places like Costa Rica, Guatemala, and Mexico, and the entire region becomes more accessible than ever.

Forget the long lines and high prices of winter travel. Fall offers a different kind of magic. The islands are quieter. The resorts are often more affordable. And the weather? It’s still just about perfect —warm but breezy, with ocean temperatures that invite you to stay in all day.