Editor’s Note: This is an update to an article published in February 2022. 

Long before French settlers arrived in 1673, tall prairie grass and forests of spruce and poplar covered the land skirting Lake Michigan. Native Americans named this fertile ground “Chicagoua” after the wild garlic that still grows in the region. Rich in history, Chicago is the birthplace of the skyscraper and a seat of creative culture, a veritable feast of art and architecture. Loyal sports fans cheer their teams, blues music fills the air and the city’s flavors are rooted in Chicago’s ethnic and working-class heritage, from deep-dish pizza to Chicago-style hot dogs, Italian beef sandwiches and other signature bites. Welcome to the Windy City. 

Why Chicago 

• The city is easily accessible: Chicago O’Hare (ORD) and Midway (MDW) International Airports are hubs for three major airlines; 14 Amtrak routes arrive at Union Station; and the city is drivable for nearly 50% of the U.S. 

• Intellectual capital abounds with 15 Fortune 500 companies, more than 20 colleges and universities, and some of the country’s top hospitals and tech incubators. 

• Nearly 80 diverse neighborhoods host incredible cultural attractions and events, not to mention dining opportunities. 

What’s New in Chicago 

Photo: Obama.org

• Voted “Best Big City in the U.S.” for nine years in a row by Condé Nast Traveler readers. 

• The new Three Top Lounge at The Salt Shed on Goose Island provides sweeping views of the city’s skyline and can host events of up to 200 guests. 

• The new Home Court athletic and conference center at the Obama Presidential Center is expected to open Spring 2026, complete with an NBA-sized basketball court. 

There are plenty of options when it comes to things to see and do in the Windy City, as well as places to grab a bite to eat, or host a power lunch or dinner. Here, are a few spots to pique your interest and help ensure your clients will make the most of their time in Chicago. 

SEE 

Chicago Board of Trade Building Museum  

A celebration of the spirit of the city, guided tours at the Chicago Board of Trade Building Museum delve into not only the building’s history, but the evolution of its trading pits from outcries to electronic trading; rare trading memorabilia adds to the experience. Group tours are limited to 49 guests due to space capacity. 

Navy Pier Flyover 

Photo: Choose Chicago

Chicago’s lakefront is more accessible and enjoyable thanks to the Navy Pier Flyover, an elevated walking and biking path along Lakefront Trail near Navy Pier. The 18.5-mile trail stretches from Hollywood Avenue to the north, to 71st Street to the south, connecting parks, beaches, gardens and several neighborhoods along the way. The Flyover is lit, too, making for a terrific evening stroll. 

The Obama Presidential Center 

In the heart of Chicago’s South Side is The Obama Presidential Center, slated to open Spring 2026. In addition to an events facility, the 19-acre campus features a fruit and vegetable garden; world-class museum; a branch of the Chicago Public Library; and more. 

For more activities and ideas, ask your ALHI GSO about working with Hosts Global Destination Services and Hosts Chicago, a Hosts Global Member. 

DO 

The Hand & The Eye  

The McCormick Mansion has been masterfully reimagined as The Hand & The Eye, the world’s largest magic venue. Evenings will be filled with experiential interactions as guests are guided through secret passageways, encountering world-class magicians through intimate, personalized performances throughout.  

Chicago Bath House 

Photo: bathhousechicago.com

A traditional bath house since its opening in 1906, Chicago Bath House is the oldest and only traditional bathhouse still in Chicago, and one of only a handful in the U.S. In addition to saunas, the bathhouse features a full bar and restaurant, as well as spa services. 

Chicago Architecture Tours 

Completed in 1885, the Home Insurance Building was the world’s first steel-framed skyscraper. Today, downtown and Chicago’s neighborhoods are filled of high-rise and other landscape-defining landmarks, with loads of Art Deco thrown into the mix. Guided walking and river tours from the Chicago Architecture Center (CAC) and partner First Lady Cruises bring their stories to life. The CAC also offers event rentals. 

For more activities and ideas, ask your ALHI GSO about working with Hosts Global Destination Services and Hosts Chicago, a Hosts Global Member. 

EAT 

Asador Bastian  

A Basque-inspired Chicago chophouse housed in an historic townhouse dating to 1883, the culinary team at Asador Bastian serves the world’s best boutique beef, among other enticing dishes, in a warm and hospitable environment. Begin dinner with a selection of pintxos, small bites served in San Sebastián, Spain, before moving onto fresh fished cooked on the grill; txuleton, or large, bone-in ribeye steaks from the Basque region; or Basian specialties like Black Truffle Steak Tartare, or Spider Crab Arroz Cremoso. Private dining is available.  

Carmine’s 

Photo: Garrett Sweet

An iconic Italian restaurant on Rush Street on Chicago’s Gold Coast for more than 50 years, Carmine’s Chicago is a must-dine for scratch-made recipes, generous portions and warm, heartfelt hospitality. The restaurant’s newly-opened 10,000 square foot space now boasts not only stunning dining rooms and multiple bars, but an expansive, all-weather outdoor terrace overlooking the neighborhood. Settle in and enjoy dishes like Meatballs in Polenta, Parmesean three ways, 14 different pastas, or Carmine’s Famous Veal Chop Milanese or Brick Chicken. Private and semi-private dining is available. 

Iconic Foods of Chicago Tour 

Photo: chicagofoodtours.com

Treat your guests to the flavors of the Windy City when you join the experts at Chicago Food & City Tours, the city’s original, for an Iconic Foods of Chicago. Their most popular, this three-hour tour delivers Chicago’s must-eat dishes, including deep-dish pizza, Italian beef, Chicago-style hot dogs and more; vegetarian requests can be accommodated with advanced notice. Groups are accommodated on tour buyouts for up to 16 guests, or private tours can host up to 30 guests; custom experiences for more than 150 guests are available, too. 

For more activities and ideas, ask your ALHI GSO about working with Hosts Global Destination Services and Hosts Chicago, a Hosts Global Member. 

STAY 

Five ALHI Members are ready to welcome you and your guests to the Windy City: Fairmont Chicago, Millennium Park; InterContinental Chicago Magnificent Mile; Sofitel Chicago Magnificent Mile; The Langham Chicago; and The Peninsula Chicago. 

Fairmont Chicago, Millennium Park 

Centrally located in the heart of downtown, Fairmont Chicago, Millennium Park offers the premier luxury of 687 expansive guest rooms and suites. Groups have 63,000 square feet of creatively designed space, including the 16,100-square-foot Imperial Ballroom. Views of nearby Maggie Daley, Millennium and Grant parks, along with Lake Michigan and the city skyline, set a scenic stage for events. Culinary offerings include Latin Cuisine at Toro Chicago by Chef Richard Sandoval and libations at The Bar, a hybrid coffeehouse-cocktail lounge. When work is done for the day, enjoy time at Leaf Spa. 

InterContinental Chicago Magnificent Mile 

Opened in 1929 as the Medinah Athletic Club, the 792-room InterContinental Chicago Magnificent Mile offers a towering appointment rich in local history. The hotel’s 50,000 square feet of flexible event space includes six regal ballrooms, the most impressive of which may very well be the Grand Ballroom with its six-ton Baccarat crystal chandelier, hand-painted murals and overhanging balcony. Also onsite are Michael Jordan’s Steak House, Casa Chi, a Nikkei concept by Chef Richard Sandoval, and myriad wellness offerings including a fitness facility, Spa InterContinental and junior Olympic-size swimming pool with Dive-In movies. 

Sofitel Chicago Magnificent Mile 

Experience the Windy City through a French lens at Sofitel Chicago Magnificent Mile, where the avant-garde exterior eloquently blends with a chic interior. The hotel’s 412 guest rooms, designed by Pierre-Yves Rochon, combine modern style with luxury appointments that afford the most comfortable of stays. More than 13,000 square feet of meeting and event space wait to be transformed to suit your needs, from intimate board meetings to large-scale celebrations. Dining varies from breakfast and lunch at French-inspired CDA, to seasonal La Terrace and a decidedly chic French alternative to afternoon tea at Un-Tea Afternoon Apéro, complete with bubbles and bites. 

The Langham, Chicago 

Legendary Modernist architect Ludwig Mies van der Rohe’s many contributions to the Chicago skyline include the former IBM Plaza tower from 1972. Today, the 52-story landmark houses The Langham, Chicago on its lower floors. Redesigned by Mies’ grandson, the lobby announces the hotel’s artful Forbes Five-star elegance, and its 316 guest rooms and suites are among the city’s most spacious. Groups have nearly 15,000 square feet of versatile space in 12 meeting rooms, including the Devonshire Ballroom and Cinema Suite. David Rockwell-designed Travelle, featuring seasonal American-driven fare, offers semi-private dining for up to 32 guests. For a bit of relaxation, check into the peaceful Chuan Spa. 

The Peninsula Chicago 

With stellar spaces such as the glass-enclosed Grand Ballroom, boasting an outdoor terrace with panoramic views overlooking the Magnificent Mile, The Peninsula Chicago is a luxurious Forbes Five-Star address in downtown Chicago that has also been recognized as the #1 Hotel in Chicago. From executive meetings to galas, the hotel offers 11,250 square feet of space in 10 venues for up to 350 guests, and 339 guest rooms and suites. Award-winning dining includes the Cantonese and Shanghainese menu at 1930s supper club-inspired Shanghai Terrace. Z Bar offers inventive cocktails and cuisine with outdoor seating, and Pierrot Gourmet serves a taste of Europe. The spa’s 19th-floor Terrace is available for seasonal events. 

For more activities and ideas, ask your ALHI GSO about working with Hosts Global Destination Services and Hosts Chicago, a Hosts Global Member.