Morning

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. 

Midday

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.

Afternoon

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.

Evening​

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. 

Morning

Have an All-American Brunch. Chicagoans are so brunch-centric that most establishments offer it on both Saturdays and Sundays, but nowhere as visually spectacular as at RL Restaurant by Ralph Lauren. Located adjacent to the world’s largest Ralph Lauren store, RL Restaurant represents Ralph Lauren’s debut into the restaurant industry. The restaurant features the vision and décor of Ralph Lauren and modern city-club cuisine. The food is inspired by American classics—seafood, steaks, chops, salads, and sandwiches.

Midday

See Wrigley Field Up Close. The Windy City is home to not one but two Major League Baseball teams, including the 2016 World Series winner, the Chicago Cubs. The Cubbies’ stadium, Wrigley Field, was built in 1914, and is one of the last old-time baseball stadiums left in the nation. Daily tours take you behind the scenes of this beloved cultural icon, from the press box to the dugout. 

Try an Authentic Chicago Dog. Down the street from Wrigley Field, Wrigleyville Dogs serves classic Chicago-style hot dogs: 100 percent pure Vienna beef on a poppy seed bun slathered in yellow mustard, relish, onion, tomato, pickle and hot peppers, with a dose of celery salt. 

Afternoon

Taste the Mag Mile Sweets. Head to Chi-Town’s swanky shopping district on Michigan Avenue, known as the Magnificent Mile, to sample turmeric- and ginger-infused chocolate bars, among other treats, at Vosges Haut-Chocolat, Chicago’s own designer chocolatier. Be sure to pay your respects to Garrett’s, a Chicago institution that has been selling outrageously good gourmet popcorn since 1949. Order the Garrett Mix, a salty-sweet combination of cheese corn and caramel corn.

Meet Sue. Three of Chicago’s most famous museums sit side by side at the aptly named Museum Campus, including the state-of-the-art science museum known as the Field. Here, you can gaze up at Sue, the largest, best-preserved and most complete Tyrannosaurus rex fossil ever found, spanning 40 feet from snout to tail. Snag a fresh cup of joe inside the museum at the Field Bistro or an ice-cold pint of Tooth & Claw, Sue’s signature beer. 

Evening​

Indulge the Purple Pig. Dine like an in-the-know Chicagoan at the Purple Pig, the darling of the trendy River North neighborhood. This cozy James Beard Award-winning eatery dishes up succulent small plates with big-time flavor. Think: chamomile-tea smoked pork leg steak, house-cured sardines on toast, and octopus with salsa verde. 

Choose Your Music. With two world-class music clubs literally around the corner from each other, you might not have to pick just one. Buddy Guy’s Legends, made famous by namesake Grammy-winning guitarist Buddy Guy, is the home of blues. Jazz Showcase has been proudly presenting the greatest jazz in Chicago since 1947. Both venues host live shows every night of the week.  

Morning

Eat Gourmet Doughnuts. Start the day at Firecakes Donuts, where fried dough reaches new levels with all-natural ingredients and artisan touches like imported cocoa from France. Get Sicilian Pistachio Old Fashioned if it’s in season; otherwise, opt for Butterscotch Praline.  

Visit the Bean. Chicago’s immense lakefront park system knows no equal among the world’s major metropolises. The innovative design dates back to 1909, when forward-thinking civic designers decided to reclaim the lakefront for the public. At Millennium Park, Chicago’s newest, you’ll find the city’s most photographed piece of public art, known locally as “the Bean,” for its kidney-bean shape. The 110-ton steel sculpture’s actual name is “Cloud Gate,” by British artist Anish Kapoor. And yes, you’re supposed to touch its mesmerizing mirrorlike surface. 

Midday

Dig Into a Deep-Dish Pizza. Opened by the son of Rudy Malnati, the man largely responsible for creating the famous Chicago-style deep-dish pizza, Lou Malnati’s Pizzeria has grown to become the quintessential Chicagoland pizza chain. While there are thin-crust pizzas available at Lou Malnati’s, it’s practically a crime not to choose a big, juicy deep-dish on a first visit. 

Visit the Top Museum. With more than 300,000 works displayed in 1 million square feet, the Art Institute of Chicago is the second largest in the country, behind New York’s Metropolitan Museum of Art. Don’t miss “American Gothic,” a national art treasure. Weather permitting, enjoy a glass of rosé on the terrace at Terzo Piano on the third floor of the modern wing. 

Afternoon

Hop Aboard. Take in a whopping 50 famous landmark buildings along the Chicago River on a cruise with the Chicago Architecture Foundation. The 90-minute tours depart every hour on weekends. Purchase your ticket at Chicago’s First Lady boat dock. 

Evening​

Experience the Top Chef. Rick Bayless, the Top Chef Masters Winner in 2009, owns a block of restaurants downtown, including three Mexican-style establishments in the same building on North Clark Street. Depending on preference, diners can choose from Bayless’ flagship Frontera Grill; the artsy, sophisticated Topolobampo; or his take on street food, the fast-casual XOCO. 

End With a Nightcap. 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 with a view.