Southwest® flights from Las Vegas to Chicago (Midway) from $142

The City of the Big Shoulders is equal parts hustle and bustle and Midwestern charm. Take a colorful stroll or bike ride down a lakeshore path, explore the famous Navy Pier (including museums, restaurants, and the tourist-favorite Ferris wheel), and take in some world-class shopping on the Magnificent Mile. Plan a day—or two, or more—to explore Chicago’s many museums, including the Art Institute of Chicago, the Field Museum, and the Museum of Science and Industry. Museums not your jam? Stargaze at the Adler Planetarium or admire the marine life at the Shedd Aquarium. Architecture buffs can take in a walking tour or a Chicago River boat expedition to view the world-famous skyline from amongst its famous skyscrapers, or venture into one of the city’s many designated neighborhoods to get a peek at the Chicago Bungalow Belts.

Chicago is a sure bet for catching a great show. Broadway hits often take the show on the road and land at one of several theaters in the theater district, but there’s also plenty of home-grown theatrical greatness playing at Chicago’s Steppenwolf Theatre and Piven Theatre in near-north suburb Evanston. Laughter lovers can take in a show at the world-famous Second City and find improv, stand-up, and sketch comedy live in venues from bar back rooms to renowned theaters every night of the week. Hungry for more? Local street food favorites like pizza (thin and crispy, or deep dish for days), hot dogs (no ketchup!), and Italian beefs abound, but foodies in search of world-class cuisine often find themselves on Randolph Street’s Restaurant Row.