Recreation & Activities
How to spend 36 hours in Chicago, with the Eaglewood Resort & Spa as your base camp.
7 p.m. | Comedy at Laugh Out Loud
This intimate cabaret-style club features improv comedy shows, starting at 7:30 every Friday. The cast relies on totally unscripted prompts from the audience, so come ready to participate – they often pull a few audience members onto the stage. Don’t worry; beer and wine are served, in case you need a little liquid courage.
8 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.
10 a.m. | Visit the Adler Planetarium
The Windy City is home to America’s oldest planetarium. Along with 60,000 square feet of exhibit space devoted to exploring and unraveling the cosmos, its adjacent Doane Observatory features a publically accessible super-powered telescope to peer trillions of miles into space. From 10 a.m. to 1 p.m., the observatory opens for danger-free peeks at the sun.
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. | Wander Through Lurie Garden
Located within Millennium Park and built over parking garages and a commuter rail, these five city-owned acres margined off by 15-foot-high hedges offer beauty through all four seasons. A footbridge divides the garden into two discrete segments: the Dark Plate, dense with a canopy of trees; and the Light Plate, blooming with sun-hungry perennials.
8 p.m. | Comedy Show at The Second City
The list of alumni from The Second City reads like the cast from the world’s funniest sitcom: Bill Murray, Chris Farley, Steve Carell, Tina Fey, Amy Poehler, and other famous names have done time with this sketch and improve comedy group since its inception in 1959. Book your tickets far in advance, and catch a show with the group’s current incarnation at its North Wells Street location.
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. | Shopping on 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, work your way north to East Oak Street, and bring plenty of plastic.
Like a Local
Quirky, under-the-radar highlights only a local could recommend.
RM Champagne Salon
This chic champagne bar, located down a cobblestone alley in West Loop, is a sanctuary for devotees of sparkling white wine. Beyond an artisanal champagne selection served by candlelight – or, in summer months, on the adjacent patio – the menu is a Francophile’s delight, featuring out-of-the-ordinary cheese pairings and desserts made by an in-house pastry chef.
Kona Kai Tiki Lounge
Chicago’s sleepy little northwest suburb of Wood Dale is the last place you’d expect to find authentic Polynesian. Yet, inside an assuming strip mall, is this hidden gem of a restaurant with a thatched-roof bar, vintage Hawaiian decor, live hula music and dancers, and, of course, tropical drinks. Try the Coral Reef, a fishbowl full of rum, pineapple vodka, blue curacao, and a rainbow of fresh fruit.
Founded by proprietor and Michelle Obama stylist Ikram Goldman, this East Huron Street boutique is more than a retail space with a rose-red facade. It’s 16,500 square feet full of high-end designer labels, runway-ready jewelry and handbags, home goods, and art. It even has a café that serves fresh-squeezed juice and farm-to-table fare.
Located in what looks like a modern barn in the Schaumburg Town Center Plaza (another northwest suburb) is Illinois’s only Native American–owned and operated arts institution. Inside, multiple gallery areas and a semi-lofted second level give way to white walls adorned in stunning contemporary Native American art, from paintings and sketches to black-and-white photography and framed beadwork.
The best food artisans, farms, and local markets.
Nestled past Victorian homes down a cobblestone road, this 37-year-old Roselle winery offers daily tastings in its oak tasting room, replete with stained-glass windows and burgundy velvet on the walls. For an easy-drinking introduction to the more than 80 varieties they offer, try the Vin De City Red – a cabernet sauvignon-merlot blend – and the Vin De City White, its signature pinot grigio.
Church Street Brewing Company
Drawing on German brewing methods, this award-winning 30-barrel craft brewery in Itasca specializes in thirst-quenching lagers and ales, alongside seasonal brews and hoppier fare. Swing by between Friday and Sunday for a pint of Heavenly Helles – a lager with a golden body and clean finish – and you might leave with a growler.
Hoosier Mama Pie Company
The 10-plus flavors of sweet pies baking in this cozy Chicago kitchen (and its sister location in Evanston) run the gamut, from pearl coconut custard to rhubarb to chocolate cream depending on the season. Come by each Friday night to sample a flight of three flavors, or start your morning with a slice and a cup of coffee for $6.
Southtown Hot Dogs
This small mom-and-pop hot dog joint in Elmhurst features fast service, friendly staff, and classic Chicago-style dogs without the schlep into the city. While sausage, Italian beef, burgers, gyros, and other fried things are offered, the tried-and-true signature is a nicely cooked juicy Vienna dog served on a steamed poppy seed bun with thin-sliced pickle, celery salt, and sport peppers.
When simply “seeing” a destination just won’t do.
Feature Adventure: Stand on The Ledge
Chicago looks different from 1,354 feet up, especially when there’s nothing – well, nothing visually solid – beneath your feet. Located at the Skydeck of the tallest-in-the-nation Willis Tower, The Ledge is a glass-encased box that juts out more than four feet from the 103rd floor over the bustle of Wacker Drive below, affording a true bird’s-eye view of the Chicago River and the city’s metropolitan contours. And with durable 1,500-pound glass panels arranged according to novel engineering techniques, taking it all in is as safe as it is stunning.
Try Trapeze | Chicago Trapeze School
Take a swing at it
Learn how to swing gracefully between 23-foot-high platforms at TSNY's two-hour beginner-friendly class. The flexible lessons, taught by experts and designed to suit all levels of ability, are sure to satisfy your inner adrenaline junky. This class is open to anyone seeking an adrenaline rush or simply a few hours of thrilling fun.
Indoor Go-Kart Racing | K1 Speed
Start Your Engine
Forgot the lawn mower–powered go-karts of your youth. These European electric go-karts are high-performance machines, producing tremendous torque and horsepower, while also being easier to drive. “Arrive & Drive” sessions at the Addison location last for roughly 10 minutes and allow you to race against the clock or friends.