show performed at a historic Loop Theater District venue. In Old Town, check out rising stars of comedy at The Second City , the improv club where comic legends like Steve Carell and Amy Poehler got their start. Dare to see Chicago from a new (and very high) perspective with TILT at 360 Chicago , a one-of-a-kind thrill ride that tilts you out more than 1,000 feet above the city. You can also get a bird’s-eye view from 103 stories up at The Ledge at Skydeck Chicago . Whatever you do, don’t skip a meal in Chicago. Fill up on classic Chicago eats, like deep dish pizza from Lou Malnati’s , hot dogs from Portillo’s , and Italian beef sandwiches from Mr. Beef on Orleans . And don’t forget the many trailblazers that put Chicago on the world’s culinary map, such as Michelin-starred Alinea and James Beard Award winners like Parachute . And the city is rife with neighborhood breweries and distilleries, especially in areas like Malt Row or the Chicago Brewing District . Don’t go home empty handed. There are loads of notable shops and designer showrooms along The Magnificent Mile and historic State Street in the Loop. Be sure to branch out into Chicago’s diverse neighborhoods to explore local boutiques and one-of-a-kind artisan workshops. One last tip: With a CityPASS or Go Chicago card, you can get easy access to a bundle of top sights at a discounted rate — essential whether it’s your first trip to Chicago or your fifth. The Second City Learn about Chicago’s health and sanitation practices to keep visitors safe at choosechicago.com/updates . The Magnificent Mile Route 66 in Chicago Route 66, known as the Main Street of America, originates in Chicago and spans nearly 2,500 miles west across the country to California. Look for the Historic Route 66 sign, on Adams Street near Michigan Avenue, that marks the start of the Mother Road. Before you begin your journey, visit one of the route’s most spectacular landmarks — Buckingham Fountain — and fuel up at Lou Mitchell’s diner in the Loop, which has been serving up hearty breakfasts to Route 66 travelers since 1923. Buckingham Fountain 10 choosechicago.com TOP TO BOTTOM: CLAYTON HAUCK; DENNIS LEE/FACTOR WOMEN; CITY OF CHICAGO