Chicago Area

Chicago is the rare American golf trip where the city itself earns a slot in the itinerary. Most golf-only destinations ask you to fly into a regional airport, rent a car, and disappear into a resort for three days. Chicago inverts that: you stay downtown, eat and drink in one of the country's best food cities, and drive out to the courses in the morning. The three anchor courses sit in genuinely different parts of the metro, south, north, and east, giving each day its own setting and character.

The trip works because the public-access inventory here is legitimately exceptional, not just by big-city standards. Two courses rank on Golf Digest's America's 100 Greatest Public list. A third offers lakefront golf with downtown skyline views. The southwest suburban cluster adds a second tier of quality that would anchor a trip in most other markets.

Cog Hill Course 4, known as Dubsdread, is the trip anchor. Dick Wilson and Joe Lee designed the layout in 1964; Rees Jones renovated it in 2008, narrowing landing zones and hardening the green complexes without disrupting the original routing logic. The result is a demanding parkland test: bentgrass fairways winding through mature oaks, push-up greens that punish aggressive approaches, and a closing stretch that has broken confident scorecards for six decades. It hosted the BMW Championship on the PGA Tour, and the conditioning still reflects a course built for that level of scrutiny. Groups wanting a second round at the facility can book Course 2, called The Ravines, which adds genuine elevation change and ravine carries in the afternoon.

The Glen Club in Glenview is the second anchor, and it deserves more attention than it typically gets in Chicago trip planning. Tom Fazio designed the course in 2001 on the former site of Naval Air Station Glenview, which operated for seven decades before closing in 1993. The land was almost entirely flat when Fazio started: military runways require it. He worked in enough fill and shaping to create genuine movement throughout the routing, and the result is a rolling, tree-lined layout with the kind of green-complex sophistication that defines the best Fazio work anywhere. Golf Digest ranks it among the top 35 public-access courses in the country. It sits 15 miles north of downtown on I-94, an easy 30-minute drive from the Loop.

Harborside International is the third day and the most distinctly Chicago experience of the three. The facility sits on the south lakefront, 15 minutes from the Loop, with two Dick Nugent courses that opened in 1995. The Port Course and Starboard Course share the same property, which means a group of eight or twelve can split into simultaneous foursomes on separate courses and finish within the same window. Starboard is the stronger of the two by most rankings, but the full 36-hole day is the right call for groups that have the legs for it.

The fourth day, if the trip extends, belongs to the southwest suburban corridor. Mistwood in Romeoville is the standout pick: Ray Hearn's 1998 design includes 20 St. Andrews-style sod-wall bunkers that give the course a visual identity unlike anything else in the region. Bolingbrook Golf Club, a municipal Arthur Hills and Steve Forrest design operated by the Bolingbrook Park District, hosts LIV Golf events and maintains conditioning that punches well above park-district pricing. Prairie Landing in West Chicago, an RTJ Jr. design from 1994, delivers the prairie-and-links experience that rounds out the week architecturally. Any one of the three would anchor the trip in a lesser market; in Chicago they become the fourth day.

Downtown Chicago is the right lodging anchor. River North, the Loop, and the West Loop all sit within reach of every course on this list, and the morning commutes to Cog Hill, The Glen Club, and Harborside are manageable with early tee times that beat the rush hour window. Groups staying downtown pay more for rooms than they would in the western suburbs, but the city itself is part of what makes Chicago worth the trip. Staying in Wheaton to save on hotels misses the point.