Chicago

Chicago Architecture River Cruise

One of the most compelling ways to explore Chicago’s architectural heritage is to join an architecture cruise along the Chicago River. Led by expert guides from the Chicago Architecture Center, the approximately 90-minute route traces the city skyline from historic skyscrapers to contemporary towers, exploring different architectural movements and the stories behind the buildings. With the city’s architecture rising directly from the river, the cruise offers a close-up perspective on why Chicago is widely regarded as one of the birthplaces of modern skyscraper architecture.

Pendry Chicago – The Loop

Set within the 1929 Carbide & Carbon Building on Michigan Avenue, Pendry Chicago reinterprets the building’s Art Deco heritage through a contemporary and energetic approach to luxury. Rooms overlooking the city and river, together with the rooftop Château Carbide, make the hotel a distinctive address for experiencing Chicago’s architectural character at close range.

The St. Regis Chicago – Lakeshore East

Rising where the Chicago River meets Lake Michigan, The St. Regis Chicago represents the city’s contemporary skyline through its sculptural tower designed by Jeanne Gang. High-floor rooms, panoramic views, an extensive spa and restaurants including Tre Dita and Miru bring architecture together with a new generation of urban luxury.

The Peninsula Chicago – Magnificent Mile

Located just off the Magnificent Mile, The Peninsula Chicago is one of the city’s established and refined luxury hotels. Renovated rooms, the rooftop Z Bar and a spa extending across the upper floors balance its central location with a calm and highly considered accommodation experience.

Smyth – West Loop

Led by John Shields and Karen Urie Shields, three-Michelin-starred Smyth interprets seasonal produce through experimental techniques and bold flavour combinations. Its open kitchen and refined yet relaxed atmosphere complement a highly creative approach to dining. In 2026, Smyth topped the North America’s 50 Best Restaurants list, taking the title of the continent’s best restaurant.

Alinea – Lincoln Park

Chef Grant Achatz’s two-Michelin-starred Alinea is one of the most influential addresses Chicago has given to the international gastronomic scene. Its tasting menu unfolds through scent, light, tableside presentations and unexpected techniques, transforming dinner into a theatrical and sensory experience.

Kasama – Ukrainian Village

Founded by Tim Flores and Genie Kwon, Kasama reinterprets Filipino cuisine through a contemporary fine-dining approach. Operating as a bakery and café during the day, the restaurant shifts to a tasting menu in the evening, drawing on flavours including adobo, seafood and other Filipino culinary traditions. With two Michelin stars, Kasama is one of the most closely watched restaurants in Chicago for its distinctive culinary identity.

Oak Street ve Magnificent Mile

Chicago’s luxury shopping route stretches from Oak Street in the Gold Coast to the Magnificent Mile along Michigan Avenue. Bringing international fashion houses together with jewellery and watch boutiques and leading department stores, the area reflects the city’s classic and cosmopolitan character through its historic buildings and proximity to the lakefront.

Wicker Park ve Bucktown

Spreading around Milwaukee, Damen and North Avenues, Wicker Park and Bucktown bring independent fashion boutiques together with vintage shops, bookshops and local design brands. Away from the major luxury names, the area is one of Chicago’s most characterful shopping routes for discovering clothing, accessories and lifestyle pieces with a distinctly local identity.

Expo Chicago

Held each spring at Navy Pier, Expo Chicago is one of America’s leading fairs for modern and contemporary art. Bringing international galleries, artists, collectors and curators together, the event also features special exhibitions, talks and art programmes across the city, making it an important fixture on Chicago’s cultural calendar. The 2026 edition took place from 9–12 April.

Chicago Gourmet

Held each September, Chicago Gourmet offers an opportunity to explore the city’s strong gastronomic scene through leading chefs, restaurants and producers. Its programme around Millennium Park includes special dinners, chef demonstrations, tastings and more refined gastronomic experiences such as Grand Cru. The 2026 programme will take place from 23–27 September.

Chicago Symphony Ball

One of the most prestigious events in the Chicago Symphony Orchestra’s calendar, Symphony Ball brings classical music together with the city’s gala culture. The evening begins with a red-carpet arrival and private reception, followed by a concert at Orchestra Hall and celebrations afterwards. The 2026 ball will take place on 10 October with a special programme conducted by Klaus Mäkelä.

The Rookery Building

Located in The Loop, The Rookery Building is one of the most significant examples of Chicago’s early skyscraper architecture. Designed by Burnham & Root in 1888, the building is distinguished by its innovative combination of load-bearing masonry and a steel-frame structure. The marble, iron and glass light court, later redesigned by Frank Lloyd Wright, adds an elegant layer to the building’s historic character.

Aqua Tower

Rising in Lakeshore East, Aqua Tower is one of Chicago’s most recognisable contemporary buildings, designed by Jeanne Gang and Studio Gang. Its undulating concrete balconies vary according to wind, views and functional requirements, giving the façade a distinctly topographical appearance. Bringing residences, a hotel, offices and extensive green space together within an 82-storey tower, Aqua Tower carries Chicago’s tradition of architectural innovation into the present day.

Kumiko – West Loop

Led by Julia Momosé, Kumiko is one of Chicago’s most internationally recognised cocktail destinations. Bringing Japanese drinking culture together with the American bar tradition, the venue combines shochu, Japanese whisky, sake and seasonal cocktails with a refined food programme. Kumiko ranked 11th on the 2026 North America’s 50 Best Bars list and was named the best bar in the Midwest.

The Aviary – Fulton Market

Opened by Alinea Group in 2011, The Aviary is a modern classic of Chicago’s cocktail scene. Approaching cocktails with a technical and experimental sensibility comparable to gastronomy, the bar uses specialised equipment, unconventional presentations and drinks tasting menus to extend the boundaries of the traditional cocktail experience. Celebrating its 15th anniversary, The Aviary remains one of the city’s most distinctive nightlife addresses.

Z Bar – The Peninsula Chicago

Located above The Peninsula Chicago, Z Bar combines a more refined side of the city’s nightlife with panoramic views across Michigan Avenue. Seasonal cocktails inspired by cuisines from around the world, an extensive champagne and spirits selection and a contemporary rooftop atmosphere create a sophisticated urban experience extending from aperitivo into the late evening.