A Morning Treat. Chicago is legendary for its gourmet doughnut shops. Indulge at local chain Do-Rite for creative concoctions like Pistachio-Meyer Lemon and Candied Maple Bacon and some of the best coffee in town, courtesy of Dark Matter Coffee.
Get the Waterfront View. For all the bustle of the big city, Chicago has a blissfully undeveloped waterfront. You’ll find mostly parks and green space, and even sand beaches, hugging the scenic Lake Michigan shoreline. Walk along Lakefront Trail, which is actually a paved path, in the morning, when the city is sleepy and the water is calm. From Grant Park, stroll a quarter mile south to where the path rounds the Shedd Aquarium, then look back for one of Chicago’s most beautiful skyline views.
Public Art Must-See. Monumental public art and sculpture abounds in the downtown area known as the Loop. The most famous is Pablo Picasso’s “Untitled” in Daley Plaza. The most Instagram-worthy is in Millennium Park. Locals call the mammoth kidney-bean shaped sculpture “the Bean,” but its official title is “Cloud Gate.” Walk beneath it, admire the skyscrapers reflected in its mirrorlike contours and absolutely have your photograph taken with it.
Visit the World’s Greatest Museum. TripAdvisor named the Art Institute of Chicago the Greatest Museum in the World. Within this historic building you’ll find more than 300,000 pieces of art, including one of the planet’s finest collections of impressionist and post-impressionist art, with works by El Greco, Rembrandt, Picasso, Dali, Renoir, van Gogh, Seurat and Monet. The modern wing, itself an architectural work of art designed by Renzo Piano, is an elegant, delicious venue for lunch. Head to the third floor, to Terzo Piano, for sausage and broccolini flatbread, scallop crudo and heirloom tomato salad.
Get Out on the Ledge. Willis Tower (formerly known as Sears Tower) presides over Chicago from 1,450 feet, making it the second-tallest building in the Western Hemisphere and the city’s high point. Access the Skydeck, 103 stories up, via a high-speed elevator. The concierge at The Ritz-Carlton, Chicago can book you a Fast Pass ticket to avoid the line. On a clear day, expect to see for 50 miles into four states. Be sure to go out on the Ledge, the Skydeck’s glass-bottomed balcony, for a truly singular perspective of the city.
Explore the Magnificent Mile. The roughly mile-long stretch of Michigan Avenue running between the Chicago River and Oak Street rivals Rodeo Drive and Fifth Avenue for shopping. All the major department stores can be found along this vibrant retail promenade — widely considered the American Champs-Élysées — as well as the finest luxury boutiques like Gucci and Louis Vuitton and budget-friendly favorites like H&M. The window-shopping alone is spectacular. Michigan Avenue is also rich with history as the home to iconic buildings like the Water Tower and Pumping Station, dating back to 1869, as well as multiple landmark skyscrapers including the Wrigley Building (look for the clock tower), the neo-Gothic Chicago Tribune Tower and the John Hancock Center.
Relax on the Rooftop. On the 12th story of The Ritz-Carlton, Chicago, overlooking the Magnificent Mile, you’ll find the ultra-modern Rooftop at Torali, a captivating venue for cocktails as the sun starts to dip. Or just kick back in the lounge-style seating and take in the cityscape.
Go Deep. No trip to Chicago is complete without experiencing the city’s famous deep-dish pizza, a hearty pie that’s more akin to a casserole than a flatbread. Local legend credits Pizzeria Uno, in 1943, with creating the high-edged golden crust and filling it to the brim with mozzarella cheese and chunky tomatoes. Visit the original location at 29 E. Ohio St. It’s a Chicago institution, so there may be a line, but the experience is worth the wait. You can also ship a take-and-bake style deep-dish pizza anywhere in the U.S.
Have a Laugh. Improvisational comedy, or improv, that special breed of spontaneous, unscripted hilarity, is a hallmark of Chicago’s nightlife scene. The theater known as The Second City is among the most influential and prolific comedy clubs in the world, having trained favorites like Tina Fey, Bill Murray, Mike Myers and the Belushi brothers. You can catch a live show on one of its three stages any night of the week.