Illinois school students learning about Chicago’s origins are taught the acronym “HOMES” — Huron, Ontario, Michigan, Erie and Superior — for good reason. Chicago was formally established as a port city around 1833, with Lake Michigan feeding into the Great Lakes system and, later, the Mississiippi River when the Illionis and Michigan Canal reached completion in 1848, connecting the Chicago River to the Illinois River. The expansion of the nation’s railroad system the same year connected Chicago and the Eastern United States to the American West.

The city’s story as a place of cultural and economic significance continues. On the 100th anniversary of Route 66 (a.k.a. America’s Mother Road) this March, Navy Pier was designated its new starting point, with Santa Monica Pier remaining its California bookend. Thanks to astute urban planning, on the other hand one can easily access Chicago Riverwalk — 26 miles of lakefront walking and bike paths as well as world- class museums such as The Art Institute, Field Museum of Natural History and Barack Obama Presidential Center opening in June 2026 (appointed with community and conference space) — on foot or via public transportation or a short drive.

Chicago is currently home to more than 35 Fortune 500 companies and McCormick Place, the largest convention center in North America. Hotels designed for business with impressive event amenities include the 2,032-room Hyatt Regency Chicago, with 240,000 square feet of meeting space, and the nearly 100-year-old Hilton Chicago, count- ing 1,544 rooms and 235,000 square feet of event space. Conversation-starting boutique hotels in the trending Fulton Market neighborhood include Pendry Chicago (built into the historical Art Deco Carbide & Carbon Building) and neighborhood-based Emily Hotel and The Hoxton, the former noted for apartment-style meeting spaces.

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© CHOOSE CHICAGO

While every city has its signature comfort foods, Chicago’s finest — Vienna Beef hot dogs with the works, Italian beef sandwiches and deep-dish pizza — deserve to be savored in their place of origin. Several neighborhoods near downtown, meanwhile, are regarded as hubs for culinary innovation. Lincoln Park has been a restaurant destination for decades, while the West Loop, Bronzeville, River North and Logan Square added a hipness factor to local dining more recently. Pilsen and Chinatown have undergone glow-ups with new restaurants and chefs adding to their historic Mexican and Asian food landscapes.

Chef-driven Chicago restaurants well-suited for business dining include Girl & the Goat and Avec, while the vibrant Carver’s in Bronzeville proves perfect for more informal occasions. Those visiting Chicago in summer can also explore neighborhood food festivals for the ultimate “eat like a local” experience.

Chicago Architecture Center River Cruise’s boat tours along the Chicago River offer an ideal first-day activity to learn more about the city’s layout and historic touchstones. However, beyond this introduction and after the business activities that follow, one should plan a few extra days to explore the suburbs along Lake Michigan making up the North Shore. Instead of having a suburban feel, they are free-standing towns shaped by Midwestern history, architecture spanning the 19th and 20th centuries, and friendliness that offer a delightful counterpoint to Chicago’s urban vibes. More lakefront bike and walking trails pick up where Chicago’s northern border leaves off.

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Evanston, anchored by the main Northwestern University campus, balances old-money trappings and modern lifestyle businesses in its downtown and along Dempster and Main streets. Find independently owned boutiques; art galleries; coffee bars; yoga studios; and noteworthy restaurants such as Soul & Smoke, The Alcove and a branch of nationally beloved Lou Malnati’s Pizza. Historical landmarks include Charles Gates Dawes House and Grosse Point Lighthouse.

PHOTO: © CHOOSE CHICAGO

Wilmette, Glencoe and Highland Park boast not only stunning residential streets, upscale shopping areas and eateries but also landmarks that give them a unique identity. The Baha’i House of Worship is an essential stop in Wilmette, while Glencoe houses Chicago Botanic Garden; and Highland Park is famous for the 36-acre Ravinia Festival, site of North America’s longest-running outdoor music festival featuring concerts ranging from classical music to jazz and pop from July through September.

Summer months along the North Shore offer more than just carefree days at or alongside the many beaches where locals and visitors can enjoy swimming, hiking, bike riding, sailing and picnicking. Here encounter numerous art festivals with juried artists, fine crafts, live music and street foods from local vendors staged in local parks overlooking the lake throughout the season.

Indeed, there’s no place like “HOMES,” especially with Chicago serving as the front door to the Great Lakes, and the North Shore serving as its lively front yard.