Delve deeper than pizza: 10 unconventional ways to experience Chicago

January 19, 2016                 6m read time
Kristen Bailey


The Windy City is a flurry of activity—but it’s much more than food and art. Ride the river, ogle at the architecture, and relish the peculiarities of distinct neighborhoods branching from the city’s center. Whether yours will be a whirlwind weekend trip or an extended stay, experiencing Chi-Town is a breeze when the adventures have been vetted for you. 

The Windy City has come a long way since its humble 1837 beginnings as a small trading post at the mouth of the Chicago River. Today, it’s a celebrated mecca of world-class art, gastronomic nirvana, rich history, waterfront spaces and natural escapes. So hold onto your hat: When you blow into the Windy City, nonstop entertainment awaits. Here are 10 distinct activities to put on your itinerary.

1. Sample Homemade Hooch (Ok, Brandy) at Rhine Hall Distillery

Rhine Hall Distillery Brandy in Chicago, Illinois Rhine Hall Distillery

Rhine Hall Distillery Brandy in Chicago, Illinois

Rhine Hall Distillery

 

The specialty handcrafted brandy produced by this father/daughter-owned distillery is made with 100 percent local ingredients from start to finish. Be sure to sample the flagship Rhine Hall Apple Brandy, which tastes exactly like biting into an apple (one that bites right back). Take a 45-minute tour of Rhine Hall Brewery to learn about the distillation process, then taste a rainbow of spirits in magical flavors like mango, plum, pear, peach and cherry. Best of all, you can snag a few bottles (or a case, perhaps?) to take home.

2. Make the Most of Lake Michigan

SUP lessons on Lake Michigan in Chicago, Illinois ash.wu

SUP lessons on Lake Michigan in Chicago, Illinois

ash.wu

 

Chicago’s 31st Street Harbor, which opened in 2012, is known as the Greenest Harbor in the World on account of its elaborate landscaping and a 63,000-square foot green parking garage roof you can mosey around on. For those who want to make the most of Lake Michigan, Chicago Water Sport Rentals is located on-site and rents jet skis, kayaks, and SUPs. Looking for a challenge? Try the one-hour SUP yoga class in the harbor's protected waters.

3. See the City in an Explosive New Light

Romantic fireworks in Chicago, Illinois gary718

Romantic fireworks in Chicago, Illinois

gary718

 

Who says fireworks are strictly Fourth of July? From Memorial Day through Labor Day, Navy Pier puts on a spectacular fireworks show every Wednesday and Saturday night. Top it off with some complimentary champagne while taking in the view during a two-hour fireworks cruise in Monroe Harbor with Offshore Adventure. If you thought the city skyline was magnificent during your morning kayaking adventure, wait until you see it in this light: the city becomes a glowing backdrop for colorful pyrotechnics, and both are fantastically reflected in skyscraper windows and Lake Michigan’s gleaming waters.

4. Bike & Play Along the Lakefront Trail

Walkers, runners, joggers, and bikers along Lakefront Trail in Chicago, Illinois MichelleBikeWalkLincolnPark

Walkers, runners, joggers, and bikers along Lakefront Trail in Chicago, Illinois

MichelleBikeWalkLincolnPark

 

One could easily spend an entire week in Chicago biking along the waterfront and never run out of things to do. Spanning 18.5 miles of premier real estate, the paved Lakefront Trail passes by more areas of interest than you can shake a stick at. Attractions to consider include the Museum of Science and Industry, the Field Museum of Natural History, Shedd Aquarium, Adler Planetarium & Astronomy Museum, the Chicago Children’s Museum, the Peggy Notebaert Nature Museum, the South Shore Cultural Center, Lincoln Park Zoo, Soldier Field, and the 50-acre Navy Pier with its scores of shops, restaurants, and famous 150-foot ferris wheel. The trail also winds through the neighborhoods of Edgewater, Uptown, Lakeview, Lincoln Park, South Loop, Bronzeville, and Hyde Park, serving as your gateway to the sights and eats of each respective area. To make the most of your trip, choose from a variety of rental bikes at Bike and Roll or Lakeshore Bike.

5. Bizarre Meets Beauty in Millennium Park

Lights and sculptures at Millennium Park in Chicago, Illinois Jackman Chiu

Lights and sculptures at Millennium Park in Chicago, Illinois

Jackman Chiu

 

Looking for those quintessential Chicago moments? The famed Millennium Park—which covered 25 acres of rail yards and parking lots until 1998—is the second most popular tourist attraction in the city, for good reason. Larger-than-life interactive art installations, fountains meant for splashing in, and, of course, that iconic, silvery blob will keep you transfixed for hours.

Walk through birds, butterflies, ornamental grasses, and perennials in the Lurie Garden, or splash around in the magnificently bizarre Crown Fountain’s reflective pool. Ogle at the billowing stainless steel curves of world-famous architect Frank Gehry’s Jay Pritzker Pavilion—a project so massive that the city declared the futuristic edifice a “work of art” in order to sidestep local building height ordinances. Then, there’s Anish Kapoor’s legendary Cloud Gate, better known as “the Bean.” Inspired by liquid mercury, this colossal stainless steel sculpture features a concave chamber that warps and multiplies your reflection as you move beneath its 12-foot arch. There’s no better place to take in Chicago’s blue skies and endless horizon: The Bean offers a different reflection of the city, no matter where you stand.

6. Paddle for pints down the Chicago River

Kayakers on the Chicago River in Chicago, Illinois Kunal Mehta

Kayakers on the Chicago River in Chicago, Illinois

Kunal Mehta

 

You’ll be kay-icking yourself if you don’t take a kayaking tour of the Chicago River, a 156-mile system of canals and rivers lazing through the heart of downtown. Originally a utilitarian pathway for commercial vessels, the river is now lined with shops and restaurants and serves as a fantastic sightseeing route. Urban Kayaks offers a number of great options. Enjoy entertaining discourse on Chicago’s deliciously sordid past during a historic dusk tour that takes you through the heart of the city while the sun sets behind the buildings. For kayakers who love kayaking as much as they love cold beer, consider the Paddle for Pints excursion. It concludes at Island Tiki Hut on Tuesdays or Lizzie McNeill’s Irish Pub on Thursdays, and includes two brews.

7. Peaceful or Party-Hardy—Discover Chicago Beach Culture

Beach in Chicago, Illinois, on Lake Michigan gezelle rivera

Beach in Chicago, Illinois, on Lake Michigan

gezelle rivera

 

Chicago has a beach scene to rival Miami, thanks to 26 miles of sandy heaven stretching along Lake Michigan. Spike and dig with the locals by heading to North Avenue Beach near Lincoln Park, where you’ll find abundant volleyball courts amid jovial beach-going crowds. For swimming, sunbathing, and people-watching, Ohio Street Beach is the place to be. Beckoning with more than a mile of shallow water along a seawall, this is where long-distance swimmers do their thing, splashing through reflections of skyscrapers on water. If you’d prefer something a little less “Teen Beach Movie,” try 63rd Street Beach in Jackson Park, home to an interactive splashing fountain and long-distance swimming area.

8. Escape the City—Mountain Bike Through a Glacial Park

Glacial Park Conservatory near Ringwood outside Chicago, Illinois CheepShot

Glacial Park Conservatory near Ringwood outside Chicago, Illinois

CheepShot

 

If the metropolitan sights and sounds become a little dizzying, head to Glacial Park Conservation Area near Ringwood, a small town about an hour north-northwest from the city center. Restore your equilibrium while biking across 3,400 acres of undulating prairie, oak savanna, and delta kames (mounds left behind by retreating glaciers that double as a sweet terrain park). The 26-mile long Prairie Path skirts the eastern edge of the park, offering a leisurely ride with the opportunity to catch glimpses of wildlife such as coyotes, foxes, turtles, and fox snakes. If you’re a birder, and maybe even if you aren’t, you might recognize flocks of finches, orioles, meadowlarks, and cowbirds, as well as circling hawks and turkey vultures that call Glacial Park home.

9. Ascend Swallow Cliff's Limestone Staircase

People walking up and running the limestone staircase at Swallow Cliffs in Chicago, Illinois ChrisHiker.com

People walking up and running the limestone staircase at Swallow Cliffs in Chicago, Illinois

ChrisHiker.com

 

Located on the Sag Valley Forest Preserve just 20 minutes from downtown, Swallow Cliff is a 100-foot high bluff that formed when glacial meltwater carved the Sage Valley 12,000 years ago. Summit the peak by ascending 125 limestone stairs, constructed in 1930 by the Civilian Conservation Corps for winter tobogganers. Once you reach the top, enjoy access to a number of trails, including the 4.75-mile Swallow Cliff Loop trail that winds through oak, hickory and maple forests, across streams, past mammoth oak trees, and low-lying wetlands. In warm weather, take a picnic lunch to enjoy in one of the open-air shelters. If you’re visiting during the winter, fill a thermos with hot cocoa and prepare for a snowy day of sledding down the cliff.

10. Slip Away to an Urban Sanctuary: Humboldt Park

Boathouse at Humboldt Park in Chicago, Illinois Thomas Barrat

Boathouse at Humboldt Park in Chicago, Illinois

Thomas Barrat

 

The 1869 Humboldt Park harbors art and turn-of-the-century architecture that’ll give any museum a run for its money. Ease back into city life with a walk through the 219-acre, lagoon-filled sanctuary, which harbors more than 65 murals depicting the history and diversity of the neighborhood’s predominantly Latino residents. Enjoy lunch with a view at the beautiful Boathouse Cafe, which serves American fare in a 1907 landmark boathouse with a terrace. If you’re hankering for cuisine with a little more flair, head to nearby Bullhead Cantina, a whiskey and taco bar on North California Avenue. Try the sweet potato tacos piled high with cabbage, roasted corn, grilled red onion and avocado salsa. Que rico.

Kristen Bailey

Kristen is a freelance writer based in beautiful Lincoln, Nebraska, which is conveniently located smack in the middle of the country for easy access to both coasts and everywhere in between. When she isn’t writing articles or exploring new cities, you’ll find Kristen building things in the backyard, writing songs for her indie rock band, The Inbetweens, or creating sweet, yet macabre, collages from images found in old textbooks and other ephemera.

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