Poor Mrs. O’Leary was long blamed for the Great Chicago Fire of 1871 after a legend grew that her cow knocked over a lantern and started the blaze. More recent research points to “Peg Leg” Sullivan, who, while feeding his mother’s cow in Mrs. O’Leary’s barn, may have dropped pipe embers into the hay. The resulting fire devastated the city, killing an estimated 130 people and destroying vast swaths of Chicago. Yet from those ashes rose a resilient and rapidly rebuilt metropolis. Today’s Chicago is a testament to reinvention, with a skyline that draws visitors from around the world. If you visit during the warmer months, there are many ways to explore this proud “City of Broad Shoulders.”
I stayed at the centrally located Four Seasons Hotel, where I reserved a corner room overlooking the John Hancock Building and Oak Street Beach. The eighth-floor fitness center also offers a lovely view of the old Water Tower, one of the few structures to survive the 1871 blaze.
From the Four Seasons, head south along Michigan Avenue—The Magnificent Mile—lined with upscale shops such as Nordstrom and the flagship American Girl store, until you reach the Chicago River. Nearby the Chicago Architecture Center runs a popular 90-minute river cruise. The narrated tour highlights a range of architectural styles: the sprawling Art Deco Merchandise Mart, the Beaux-Arts Wrigley Building, and the distinctive eyebrow-shaped balconies of Bertrand Goldberg’s River City, among many others.
After the boat tour, continue down Michigan Avenue to Millennium Park and find Anish Kapoor’s Cloud Gate, more commonly called “The Bean.” This gleaming stainless steel sculpture attracts people of all ages who enjoy seeing distorted reflections of themselves and the city’s skyscrapers on its mirror-like surface.
For lunch, the Park Grill in Millennium Park offers a casual menu with chopped salads, panini and burgers—an easy spot to refuel before more sightseeing. From there, cross the pedestrian bridge to the Art Institute of Chicago. The museum houses one of the world’s largest collections of Monet paintings, Georges Seurat’s iconic A Sunday Afternoon on the Island of La Grande Jatte, and the meticulously crafted Thorne Miniature Rooms, which recreate interior styles from various historical periods in Europe and America.
If you have the energy, take a short taxi ride to Navy Pier, home to its landmark Ferris wheel and a range of entertainment options. Rent a bike and ride south along the Lake Michigan shoreline on a paved trail that passes Buckingham Fountain, the Shedd Aquarium and Soldier Field, where the Chicago Bears play. The ride back toward the city rewards you with spectacular skyline views—perfect for photographs.
After freshening up, make an evening reservation at Next, the innovative restaurant from chef Grant Achatz. Next rotates its theme and menu roughly every three months, offering immersive, prix-fixe dining experiences ranging from historic Parisian cuisine to contemporary Thai. Reservations are booked far in advance, and the unique ticketing system means your meal is prepaid, so you don’t need to worry about carrying a wallet at the table.
Whether you’re discovering Chicago’s architectural landmarks, touring world-class museums, or sampling cutting-edge cuisine, the city offers a rich blend of history and modern culture. With convenient hotels, scenic river and lakefront walks, and a lively food scene, Chicago is easy to explore and endlessly rewarding.