Sticks on 66.

Medinah Country Club

Start your golf road trip at the premier event, Presidents Cup 2026 at the legendary Medinah Country Club, the only golf course in the world that has hosted US Open, PGA, Ryder Cup an Presidents Cup.

Cog Hill Golf & Country Club

Next, head to one of the most iconic public courses in the country. Cog Hill boasts four 18-hole layouts, but it’s Dubsdread that steals the show. Once a stop for the PGA Tour, it’s a test for any golfer who wants to say they’ve played where the pros have.

When you're ready for a bite, head to Dell Rhea’s Chicken Basket for some of the best fried chicken on Route 66. Or take a quiet stroll along the Illinois & Michigan Canal National Heritage Corridor, where scenic trails and locks recall the early days of Illinois industry.

Bolingbrook Golf Club

Next up is Bolingbrook Golf Club, a modern course with elevated tees, rolling prairie fairways, and unforgettable holes like their signature island green par 3 and 600 yard par 5. It’s a bold, beautiful round from start to finish.

Nearby, you can practice your really short game at Wilderness Falls Mini Golf, or explore aviation history at the Illinois Aviation Museum, where vintage planes and exhibits bring Illinois’ flying past to life.

Naperbrook Golf Course

A short drive brings you to Naperbrook, an 18-hole course known for its excellent conditions and fun, fair layout. One of the more forgiving courses on the list, so whether you're looking to shave a few strokes off your game or just enjoy a relaxed round, this course delivers.

In nearby Naperville, Naper Settlement offers a walk through 19th-century Illinois, with preserved buildings and costumed guides. For younger travelers, the DuPage Children’s Museum is packed with colorful, hands-on exhibits.

Highland Park Golf Course

In Bloomington, tee it up at Highland Park, the city’s oldest course. Its historic charm shines through every hole, offering a nostalgic, walkable layout with tree-lined fairways, a meandering creek, and just enough challenge to make this a local favorite.

After the round, stretch your legs on Route 66 Memory Lane, where restored billboards and classic signs take you back in time. Or pop into the McLean County Museum of History, where interactive exhibits share the story of central Illinois.

North Greens Golf Course

This nine-hole course in the heart of Illinois may be small, but it’s mighty. Water hazards on seven holes and over 20 sand traps keep things interesting, and the peaceful, open setting makes for a great stop mid-trip.

Just off the course, you’ll find the famous Paul Bunyon Statue, holding a giant hot dog and ready for a photo op. Across the street, the Atlanta Museum shares quirky local stories and Route 66 memorabilia.

Piper Glen Golf Club

Arrive in Springfield ready for a championship challenge. Piper Glen has hosted U.S. Amateur and Illinois Amateur qualifiers and stays in top condition year-round. The layout is scenic and smart—just like the rest of this city steeped in history.

Before you leave town, walk through the Lincoln Home National Historic Site, where Abraham Lincoln lived before becoming president. Then stop by the Illinois State Museum for exhibits on natural history, art, and archaeology.

Arlington Greens Golf Course

Finish your trip at Arlington Greens, a sprawling 7,200-yard layout with gently undulating terrain and Bermuda grass fairways. Recently updated irrigation keeps conditions sharp, and the course is welcoming for golfers of all levels.

Before crossing the Mississippi, visit the Chain of Rocks Bridge, one of Route 66’s most unique crossings with its iconic mid-bridge bend. And don’t miss Cahokia Mounds, the site of an ancient Native American city and one of the most significant archaeological sites in the U.S.

From championship greens to giant hot dogs, this one-of-a-kind golf road trip lets you experience Illinois Route 66 like never before. Play a round, take a detour, and see where the road takes you. It should make for a great drive.