Friday
6 p.m. | Bowl at Kegler’s Bowling Alley
Whether you’re a league champion or you haven’t played a game of tenpin since high school, Eaglewood’s six lanes (located in the resort’s recreation building) are the perfect place to get reacquainted with the finer points of strikes and spares. Along with a retro bowling experience, the alley features pool tables, darts, a bar, and an outdoor patio.
8 p.m. | Improv Comedy Club
This comedy club attracts some of standups most well-known acts like Joel McHale, Whitney Cummings, and Shawn Wayans. Plenty of table seating makes it the ultimate place to grab a late-night dinner during the show and wash it down with a “Barrel of Laughs,” the club’s signature drink of vodka, gin, and white rum mixed with blueberry schnapps, blue curacao, and sprite.
Saturday
10 a.m. | Stroll Cantigny Park
Just 14 miles from the resort, this 500-acre park is marked by vast formal gardens, two miles of trails, playgrounds, and movies and music in the park. But the real showstopper is the property’s McCormick House. The grand 1896 Beaux Arts–style estate was home to the family that started The Chicago Tribune but now serves as a preserved museum containing original furnishings and antiques in its 27 rooms open to the public.
1 p.m. | Chicago Pizza at Lou Malnati’s
It wouldn’t be a visit to Windy City without a deep-dish pizza. Considered the oldest family name in Chicago Pizza, Lou Malnati’s opened in 1971, but the pizza itself dates back to the 1940s when Grandpa Malnati started making his signature hearty pies with a buttery crust, special sausage blend, vine-ripened plum tomato sauce, and Wisconsin cheese. With several locations all over the city, their South Loop location is no more than two miles from the Adler Planetarium.
3 p.m. | Visit the Arlington Race Track
This historic horse racing park hosts thoroughbred races from May through September, where you can get close to the action or watch from the comfort of any of the track’s nine dining venues like the Terrace Cafe or the Million Room Restaurant.
8 p.m. | Walk the Magnificent Mile
With some 460 stores squeezed into 13 blocks, this stretch of Michigan Avenue is a shopaholic’s paradise, full of clothiers from Neiman Marcus to Patagonia, department stores, jewelers, confectioners, a doggy boutique, and all other forms of retail therapy. Start at its southerly origins by the Chicago River and work your way north to East Oak Street.
Sunday
9:30 a.m. | Massage at Eaglewood’s Spa
Spend a quiet morning in Eaglewood’s 10,000-square-foot spa, home to eight rooms and a generous menu of massages facials and skin treatments. Try the Eaglewood Indulgence, a signature 90-minute massage that combines four styles of massage in one.
12 p.m. | Play a Round
Set in a captivating atmosphere of rolling greens and majestic old oak trees, Eaglewood Resort’s 18-hole private course boasts fantastic views of its many sparkling lakes. Sand traps are a strong feature of the layout, as the 65 sculpted bunkers provide aesthetic beauty and demand precision from every tee. Accuracy, not distance, is key.
