For last-minute reservations, heading to the densely packed restaurants in the city’s West Loop area can mean cocktails and French-inspired dishes at Maude’s, ramen at High Five, Asian-inspired dishes at Embeya or Italian fare at the recently opened Monteverde, which makes its pasta in-house. The city’s newest steakhouses, including Swift & Sons, Maple & Ash and further away Boeufhaus, are a draw for the corporate diner looking for menus that are easier to navigate and a less stuffy atmosphere. Mingling over drinks? Try Green River for some serious cocktails with hard-to-find spirits including small batch whiskey.

Dinner for one? Many restaurants save seating at the bar. However, starting dinner past 21:00 is not the norm, so plan to head out for dinner before 20:00, said Gabrielle McCaig, head of community and communications at Via, a New York-based carpooling app. On her monthly trips to Chicago, McCaig works from WeWork, a co-working space in the River North neighbourhood and stays at the Hotel Felix, a boutique hotel. For a more local food scene, McCaig heads to smaller neighbourhoods that are about a 15-minute drive from downtown including Lincoln Park, Wicker Park and Logan Square.

Off the clock

Chicagoans strive for work-life balance and that means wrapping up business meetings before the 17:00 traffic rush. In the Loop, most offices close by 18:00. “Once the working day is finished, it becomes a little bit of a ghost town,” said Marlene Poynder, general manager at the Waldorf Astoria hotel, a franchise that’s part of Hilton Worldwide.

Situated along Lake Michigan, the sixth-largest freshwater lake in the world, the city has its perks, particularly in the warmer months. The number one question Poynder gets from hotel guests is where to go for a run. “We send them straight down to the lakefront to get a snapshot of the city,” said Poynder about the city’s 18.5-mile linear park and bike path that runs along the waterfront. The path also offers bike rentals. Water sports including sailing, kayaking and paddle boarding are offered at several of the beaches and along the Chicago River.