Exploring Chicago is an ambitious endeavor. From the bustling streets of the Loop to the historic echoes of the Gold Coast, every corner offers a slice of the city that you’ll undoubtedly want to explore further. Regardless of the time of year, the Windy City’s dynamic energy never wanes, continually beckoning us to experience its allure. Chicago’s enduring charm and diverse offerings consistently place it among America’s most popular destinations.
The culinary scene is particularly vibrant right now, thanks partly to The Bear, which has reminded us of Chicago’s gastronomic richness. This resurgence has highlighted local culinary stars such as Grant Achatz, Anna Posey, and Erick Williams, among others, who continue to push the boundaries of flavor and innovation in the city’s bustling kitchens.
We’ve distilled the essence of Chicago into a collection of must-do experiences, but be warned: you’ll be so captivated by the city’s charms that you’ll be planning your return trip as soon as you board the plane home.
Stay
St. Regis Chicago
Jeanne Gang’s architectural brilliance shines through in the stunning design of the St. Regis, Chicago’s newest luxury hotel. It is also the tallest building in the world, designed by a female architect. The hotel’s silhouette adds a dynamic to the Chicago skyline, seamlessly blending modern aesthetics with classic luxury. The thoughtful use of glass and steel enhances the building’s visual appeal and allows for spectacular views from virtually every room.
The guest rooms are elegantly simple, in grays, white marble, and earth tones with blue accents that enhance the panoramic views of the city, lake, or river. Of course, flattering lighting enhances the soaking tubs and spacious, clean layouts, and a butler is available for every room. Pets are also welcome.
Signature Rituals are central to the St. Regis experience, and each hotel in the collection celebrates distinct daily rituals. In Chicago, The Bloody Mary Ritual pays homage to the classic cocktail with the 1871 Bloody Mary. An homage to the Great Chicago Fire, this version features a locally sourced rye whiskey served in a tall vessel that mirrors the hotel’s stature, presented in a smoking glass and finished with a rim of smoked salt. The Evening Ritual transitions between day and evening with a champagne sabrage. In this ceremonial technique, a bottle of champagne is opened with a saber, slicing off the top of the bottle with the blade. This dramatic method involves sliding the saber along the seam of the bottle to break the neck cleanly at the lip, a practice that dates to the time of Napoleon Bonaparte, who popularized it among his cavalry officers as a celebratory act after victories. Think of it as their way of saying you’ve won the day.
Eat
Smyth
Located in the West Loop, Smyth is a three-Michelin-starred restaurant led by chefs John Shields and Karen Urie Shields. The restaurant emphasizes a farm-to-table philosophy, sourcing ingredients from a nearby sustainable farm. Smyth offers a tasting menu showcasing the chefs’ dedication to quality and innovation, with dishes highlighting the ingredients’ natural flavors. The intimate, rustic-chic setting adds to the charm of this culinary gem. They earned their 3rd Michelin Star in 2023.
Oriole
A hidden gem in the Fulton Market District, Oriole is a two-Michelin-starred restaurant helmed by chef Noah Sandoval. The restaurant offers a 15-course tasting menu that blends global influences with modern techniques. Sandoval’s culinary artistry is evident in every dish, focusing on balance, texture, and flavor. The warm, inviting atmosphere and impeccable service make Oriole a top choice for an unforgettable dining experience.
Lula Cafe
Located in Chicago’s Logan Square, Lula Cafe is helmed by Chef Jason Hammel. Lula has become a beloved staple in the Chicago culinary scene, with specialties like the roasted beet bruschetta and the seasonal vegetable-focused “Farm Dinner” series. Lula Cafe’s cozy, eclectic atmosphere and dedication to sustainable, locally sourced ingredients make it a standout local spot to enjoy any time of day.
Drink
The Aviary
If you have already been to Grant Achatz’s Michelin-starred restaurant Alinea, or if you’re still trying to score a reservation, allow The Aviary to provide you with similar satisfaction, delivered in a cocktail glass. Indeed, a cocktail bar like no other, Achatz founded The Aviary with Nick Kokonas. Known for its avant-garde approach to mixology, The Aviary offers a sensory experience where each drink is a meticulously crafted work of art. Under the leadership of esteemed bartender Micah Melton, the bar presents innovative cocktails that push the boundaries of traditional mixology.
Bisous
Who doesn’t love a mid-century-inspired bar that pays homage to the Martini? This intimate spot blends Parisian elegance with modern flair, featuring a menu crafted by skilled mixologists who excel in both classic and contemporary cocktails, like the L’Jardine—a freezer martini that blends Aqua Perfecta Basil Brandy, Vodka, and Cocchi Americano and is served—as the menu states—VERY COLD.
Do
Architectural Boat Tour
One of the best ways to experience Chicago’s architectural marvels is through a boat tour on the Chicago River. These tours provide an informative and visually stunning journey through the city’s iconic skyline. While gliding along the river, you’ll learn about the history and significance of buildings like the Willis Tower, Tribune Tower, and the Wrigley Building. The experience is especially gorgeous in the fall when the city’s foliage adds color to the skyline. If you prefer to go at your own pace, you can rent a kayak from Urban Kayaks.
Fulton Market
Once a gritty meatpacking district, Fulton Market has transformed into one of Chicago’s most dynamic neighborhoods. The area’s evolution began in the 19th century when it served as a hub for food distribution, surrounded by warehouses and wholesalers. The historical essence is still palpable today, as the district merges its industrial roots with a modern twist. Fulton Market is now a vibrant culinary destination, boasting some of the city’s top dining spots and chic cafes that attract foodies from around the globe. The area also boasts specialty cafes with house-roasted coffee, and unique boutiques selling indie fashion and furnishings, adding to its chic, urban charm.
Live Music
Chicago’s music scene is deeply entrenched in the rich, emotional depth of the blues, a genre that has shaped the city’s cultural identity. Legendary musicians like Muddy Waters, Howlin’ Wolf, and Buddy Guy helped pioneer Chicago blues, creating a distinct sound that thrives in the city today. These artists laid the groundwork at historic venues like the Checkerboard Lounge and Kingston Mines, where the soulful strains of the blues continue to resonate. Today, these clubs and newer spots like Buddy Guy’s Legends serve as stages for a wide array of blues performances and as living museums of musical heritage, drawing in locals and tourists alike to experience the authentic sounds of Chicago blues.
Legendary music venues to visit include Blue Chicago, a staple of the Chicago blues scene for over 30 years, providing a platform for both seasoned and emerging blues artists. Decorated with colorful murals depicting blues legends, Blue Chicago immerses visitors in a visual and auditory feast. It’s particularly noted for spotlighting female blues vocalists, as well as Kingston Mines, a club that is the city’s oldest continuously operating blues club. Since opening its doors in 1968, it has hosted a who’s who of blues greats, from Magic Slim to Koko Taylor, making it a true landmark for die-hard blues fans and newcomers alike. Located in the heart of Lincoln Park, Kingston Mines offers a lively, down-home atmosphere that promises an authentic blues experience seven nights a week. The club features two stages, allowing it to host live performances simultaneously and keep the music going well into the early morning.
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