Southwest® flights from Chicago (O'Hare) to Denver from $80

When you trade the sky-high skyline of the Windy City for the Rocky Mountains, you’ll be in the perfect place to experience life on the mountain. When you deplane at Denver International Airport, you’re not just standing in a travel hub larger than Manhattan—you’re well on your way to exploring this Rocky Mountain metropolis, hitting the slopes, or simply unplugging from the hustle and bustle back home.

Denver boasts great walkability for a city its size, as well as a mass transit bus system, but grabbing a rental car will open both the city and parts beyond for easy adventuring access. Swishing down a mountainside will require a short drive out of town, but that doesn’t mean there aren’t plenty of mountaineering options closer. Visitors often marvel at Red Rocks Park, home to iconic red sandstone outcrops and the world-famous Red Rocks Amphitheatre. If there isn’t a show playing during your stay, there’s plenty else to explore at the park including public art, the Colorado Music Hall of Fame museum, and lots of opportunities for hiking and biking.