By Mandy Richardson
Where to Stay
The Peninsula Chicago: Classic elegance, impeccable service and a stunning rooftop terrace are just a few reasons to stay at The Peninsula. The hotel features design and service inspired by Asian traditions to create the most serene and sophisticated atmosphere. Rooms offer high-tech conveniences and gorgeous city views, while the half-Olympic length pool, spa and dining options are top-notch.
Waldorf Astoria: A historic landmark with opulent suites and renowned afternoon tea service is just steps away from Chicago’s Magnificent Mile, shopping, dining and entertainment. The hotel features an award-winning spa, health club and lap pool, as well as a pilates studio and the best personal concierge in town.
The Langham: Beautifully designed rooms — many with floor-to-ceiling windows overlooking the Chicago River, Millennium Park, the Art Institute of Chicago and The Magnificent Mile — are a key highlight of this locale. The Langham houses both the Michelin-starred restaurant Travelle Kitchen + Bar and the award-winning Chuan Spa, and often incorporates the city’s vibrant arts scene into the hotel experience.
Must-Make Reservations
Alinea: The brainchild of chef Grant Achatz, this restaurant offers a truly avant garde and experimental dining experience across three distinct experiences: The Kitchen Table, The Gallery and The Salon. Alinea is known for its artistic and often unexpected presentation of dishes, including Achatz’s famed seasonal tasting menus, and is one of 13 restaurants to have received a Michelin three-star rating.
Cheat code: The Alinea Group also owns Next, which features ever-changing themed or tribute menus, and The Aviary, a swanky cocktail lounge with drinks and small bites presented in eye-catching ways.
Ever: Curtis Duffy and Michael Muser, both formerly of acclaimed restaurant Grace, offer modern American cuisine with a refined and elegant dining experience. The restaurant’s design is meant to enhance the dining experience with wooden walls, museum-quality lighting and sleek black tables to showcase the plating of the food. Ever offers an 8- to 10-course tasting menu that changes seasonally and is meant to last two and a half hours. (And yes, you know Ever from season two of HBO’s “The Bear.”)
Cheat code: Grab post-dinner drinks at After, the lounge next door.
Kasama: This popular Filipino restaurant and bakery is led by chefs Genie Kwon and Timothy Flores. It’s located in the Ukrainian Village and could be the hardest reservation to get right now. It offers breakfast and daytime counter service, which is first come first serve, and dinner by reservation only.
Cheat code: Skip the dinner reservation challenge and order breakfast to-go from 9 a.m.–2 p.m. Wednesday through Sunday.
Monteverde: If you’re craving Italian fare, Monteverde is a must. Watch pasta being made fresh daily at their custom pastificio while you wait for your table, then enjoy chef Sarah Grueneberg’s seasonal dishes and an extensive wine list.
Cheat code: If you can’t get dinner reservations, pop in for lunch. The menus are almost identical.
Oriole: Tucked away in an alley of the West Loop neighborhood, this memorable eatery boasts two Michelin stars. The thoughtful and interactive dining experience focuses on creating an unforgettable culinary journey under the guidance of chef Noah Sandoval.
Between Meals
See an off-Broadway show, visit the Art Institute, experience a performance by the Chicago Symphony Orchestra or Joffrey Ballet, take the architecture tour down the Chicago River, catch a concert at The Salt Shed or go to a major sporting event (Chicago is one of the few U.S. cities that has teams in all five major pro sports: baseball, basketball, football, hockey and soccer).