Plan your next trip with our new Crash Course series, which gives you the best recommendations for golf courses, hotels, restaurants, and sightseeing–so you can relax and focus on your round instead of your itinerary. Now on the tee: Chicago.
With the sports world focused on Chicago and the 2016 World Series, it’s worth remembering that the Windy City is also surprisingly strong golf destination. Cook County boasts the greatest collection of private and public golf courses of any metropolitan region in the U.S. Toss in myriad cultural attractions as well as endless options for drinking and dining, and you’re guaranteed to leave happy.
1 p.m. Worth the Green
After retrieving your bags and rental car from O’Hare, drive 25 minutes north to the Glen Club ($100-$160; theglenclub.com) in Glenview, a rolling, robust Tom Fazio design built atop an old Naval Air Station. Ranked Number 90 in our Top 100 Courses You Can Play, The Glen Club benefitted from Fazio’s creative wizardry. By its 2001 opening, Fazio had taken a dead flat property and moved two million cubic yards of dirt, brought in 4,000 trees and peppered the layout with lakes, streams and fescue-topped hills. Standout holes include the superbly framed par-3 fourth, the stream-guarded, par-4 eighth and the risk/reward par-5 18th. Yes, the Glen Club is one of the Chicago area’s priciest plays, but it delivers on value, with curb-to-curb service, an outstanding restaurant and terrific education, as it’s home to both top instruction and to the memorabilia-filled Illinois Golf Hall of Fame. For a bargain alternative to the Glen Club, try Orchard Valley ($49-$69; orchardvalleygolf.com) in Aurora, ranked sixth in Illinois in our 2016 state-by-state listing of Best Courses Near You.
5 p.m. Game Room
For a traditional, full-service experience in the downtown area, the Peninsula (weekend rates from $488 per night; chicago.peninsula.com) is without peer for location, service and facilities. During a stay a few years back, there was a DVD player in the room and one night when I had a dinner engagement I couldn’t avoid, they taped the Cubs playoff game downstairs, stuck it on a disk and delivered it to my room before I had finished dessert.
7 p.m. Pizza Pilgrimage
Start your trip with a true taste of Chicago by feasting on deep dish pizza. Many pay homage at Pizzeria Uno’s original 1943 location at Ohio and Wabash, though others swear by Lou Malnati’s (more than 40 locations in Greater Chicago).
9 a.m. Public Treasure
Cog Hill (No. 4) ($135; coghillgolf.com) in the southwestern suburb of Lemont has long been the region’s top public-access track. It ranks as Best in Illinois and Number 31 in the U.S. 1989 British Open winner Mark Calcavecchia once praised this 52-year-old Dick Wilson/Joe Lee design, stating, “It could host a U.S. Open tomorrow.” Well, it won’t be the 2017 U.S. Open, because that event was awarded to Erin Hills in Wisconsin, but the fact that Cog Hill was runner-up is testament to its quality. The longtime home to the PGA Tour’s Western Open and then BMW Championship, Cog Hill was toughened in 2008 by Rees Jones, who deepened and repositioned bunkers and stretched it to nearly 7,400 yards. In 2009, Tiger Woods won for the fifth time here—by eight shots. For budget-conscious golfers, Cog Hill (No. 2), a scintillating sibling to Number 4, offers almost all of the character as its brawnier brother, at a fraction of the cost ($46-$62).
2 p.m. Must-See Museum
If you’re into culture—or just run into a rainy day—the Art Institute of Chicago ($19-$25; artic.edu) is a can’t-miss attraction. Located downtown on Michigan Avenue in Grant Park, the 137-year-old treasure trove is one of America’s largest and best art museums. Among its 30,000-plus works of art are Grant Wood’s iconic “American Gothic” and masterpieces by Monet, Rembrandt and Renoir.
7 p.m. Prime Location
My colleague Josh Sens summed up the truth about Gibson’s steakhouse best: “it’s an old-school haunt serving linebacker-sized portions of the classics, ranging from lobster tails in spicy cocktail sauce to prime rib glazed in roasted bone marrow. The atmosphere is exactly how you’d want it: upscale but unpretentious, with red booths, wood-paneled walls, and lively, martini-lubricated conversation. Tables book up quickly, so make a reservation well in advance. Show up without one, and odds are you’ll be forced to call an audible.”
10 a.m. A Course with a View
Harborside International (57-$75; harborsidegolf.com) features two faux-links courses near the downtown loop. Both are Dick Nugent designs draped atop landfill sites that serve up breeze-fueled shotmaking challenges and outstanding views of the city skyline. The Port and Starboard courses offer near-equal experiences in challenge and scenery. The Port played host to the Champions Tour in 2002, when Ben Crenshaw compared it to Muirfield in Scotland and its par-3 sixth hole witnessed an ace by former president Bill Clinton in 2001.