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

Chicagoland is very flat. If you find yourself missing the heights of being back home in the Mile High City, buy a ticket to reach the summit of Willis Tower (or Sears Tower, as Chicagoans still call it). Step out into the glass balconies of the observation deck for panoramic views of the city, the lake, and beyond. It’s not the kind of view you’re used to from summits back home, to be sure, but just as breathtaking.

Sightseeing can be done with feet planted firmly on the ground, of course. Walking tours abound, whether you choose to tour the Loop (what Chicagoans call their downtown) or one of the city’s dozens of neighborhoods. Or take to the water for a riverboat architecture tour or a boat ride along the city’s Lake Michigan waterfront for a unique view of the skyline. The lakefront has plenty to explore while downtown, including Museum Campus, Grant Park, and Millennium Park. Can’t get enough of aquatics? Visit the Shedd Aquarium. Want more sky and less skyline? Explore the Adler Planetarium. Seeking opportunities for snap-worthy selfies? Walk through the public art at Millennium Park.