Summer is the best time to visit Chicago — the weather is warm, city patios are buzzing and Lake Michigan is great for swimming. With that said, here’s an itinerary for travelers with only 24 hours to explore one of the greatest cities in the world.
While Chicago has a slew of cool, top-of-the-line hotels to check into, come summertime, we suggest the Forbes Travel Guide Five-Star Trump International Hotel & Tower Chicago in River North. Its location is ideal for people who want to be close to several different Windy City highlights — the lake, the best nightlife scene and even some of the finest museums. Bonus: Trump provides beach services, which includes a pre-packed bag filled with plush towels, sunscreen, fresh fruit and water.
Beyond its proximity to cultural centers and the water, though, the hotel also scores because of how close it sits to the Magnificent Mile. There’s no excuse for skipping a trip down the shopping mecca if you’re staying nearby, especially if you want to hit up stores with serious wow factor, like the Burberry flagship, Barneys New York (just off Michigan Avenue) and the Ralph Lauren mansion. After you’ve given your wallet a workout, stroll down the avenue and then head east to the renowned Museum of Contemporary Art for a quick browse of the museum’s highlights, such as the just-opened peek into African-American creative expression in the 1960s, “The Freedom Principles: Experiments in Art and Music, 1965 to Now.”
Once you’re full on jazz and photography, go a few blocks north to the Gold Coast neighborhood for lunch at Nico Osteria inside the chic Thompson Chicago. This Italian hot spot comes from one of the buzziest restaurant teams (and James Beard Award winners) in Chicago, One Off Hospitality Group, and continues to draw a crowd of beautiful people day in and day out. Even though the cool atmosphere and people watching are why many people book a table here, the food is far from an afterthought. Come lunchtime, you’ll go light but delicious. Our picks: the orzo pasta and quinoa salad with grilled shrimp and Parmesan, and some housemade gelato for dessert.
Walk off your meal by trekking a few more blocks east to pick out your spot in the sand at Oak Street Beach. (Ask your concierge at Trump to reserve you a chair and umbrella before heading out.) While away the afternoon while learning how to paddleboard, watching others play volleyball or just taking in the magnificent skyline.
As tempting as it’ll be to remain at the beach all night, do make sure you’ve carved out enough time for pre-dinner drinks. The first one should be back at the 16th-floor Terrace at Trump, which has, hands down, the best alfresco views of the city. After that initial taste, head to Lone Wolf on Randolph Street in the West Loop for craft cocktails so good you might consider skipping dinner altogether. It’s dark and moody inside, so get with the program by grabbing a booth and ordering the West Loop Smash (Botanist gin, Yellow Chartreuse, lime and mint).
Make your way outside for a walk before dinner to take in the hip, scenic ‘hood. Once you finish, it’ll be time for the highlight of the day — dinner. Five-Star Grace, also in the West Loop, is the ideal place to experience the city’s intense foodie scene. (Again, you’ll want to get the Trump’s help on scoring a seat here well in advance.) Chef Curtis Duffy conceives two eight- to 12-course tasting menus, one vegetarian and another consisting of meats. Ingredients are the freshest. Plates are beautifully constructed. Flavors are precise and well thought out. Tip: Spring for the wine pairings because a meal like this doesn’t come often, whether you’re in the Windy City or not.