Chicago is a city of captivating, often welcome, contrasts. With no nearby oceans to help tame the weather, for instance, you can experience a difference of more than 100 degrees from summer to winter. Boosted by the heat of the Great Plains, with added humidity, summer temperatures hit the high 90s, while the winter brings subfreezing cold from blasts of frigid air blowing in south across the Midwest’s flat terrain. The seasonal changes mean great summer paddle boarding on Lake Michigan and fun (if you can tolerate the chill) ice skating on unique rinks in the fall and winter.
Chicago, of course, has one of the country’s most famous high-end and boutique shopping strips—the Magnificent Mile, an upscale section of Michigan Avenue, running from the Chicago River to Oak Street on the Near North Side. That brings us to the other great disparity about this city: Young visitors are less interested in shopping and material goods than they are in amassing great experiences—and Chicago has plenty of those.
Below we present a sampling of some that we found most compelling.
Where to Get Your (Arcade) Game On
Mortal Kombat, NFL Blitz, Rampage and hundreds of other iconic arcade games were born of creative minds in Chicago, so it’s no wonder the city is home to the nation’s largest arcade. Galloping Ghost Arcade houses more than 500 games, many popular classics like Donkey Kong and Space Invaders, and some rarities, like Primal Rage II, Hammer Away and Godzilla. Galloping Ghost adds a new video game to the arcade floor every week.
None of the games take quarters or tokens; instead, the $20 admission gives you access to every game for unlimited play. High scores are a badge of honor at Galloping Ghost: The arcade prides itself on its scrupulous tracking of high scores and world records by its visitors—more than 180, according to the arcade’s count. 9415 Ogden Ave, Brookfield; gallopingghostarcade.com.
A Social Media Mecca
The more great experiences a destination offers, the more there is to share on social media. Chicago offers plenty of sites to photograph and post.
For instance, Expedia’s guide to Millennial travel in the city points visitors to the Leaning Tower of Niles, a half-size replica of the famous Pisa landmark 14 miles from downtown Chicago. Likewise, you can get a great selfie at Grant Park, in front of the Agora—an eerie but photogenic group of sculptures of seemingly unfinished figures. Elsewhere, the painted walls along Oak Street Beach make for a great daytime selfie, while the neon Chicago Theatre marquee is a great target for your lens after sundown.
Where to Overcome (or Develop) a Fear of Heights
For those who prefer their feet planted firmly on the ground, gazing upon the cityscape and Lake Michigan can be exciting but unnerving from the 94th-floor 360 Chicago observation deck at the John Hancock Center, more than 1,000 feet above street level. Imagine that feeling multiplied exponentially. That’s what Tilt, Chicago’s highest thrill ride, provides. The enclosed hydraulic platform tilts you 30 degrees out over Michigan Avenue, forcing you to face your fear of heights head on.
We found the experience thrilling but at points anticlimactic, only because we tackled it at night, when the shroud of darkness provided a false sense of security that would be missing in the daylight. If you go, take time to view the large infographics, photographs and captions depicting the construction of Tilt. It’s comforting to know that the mechanism is so powerful it can lift the equivalent of a four-ton elephant, but less reassuring to see photos of a gaping hole before the attraction was fully installed—
or to know that Tilt is closed on days of high winds. 875 N Michigan Ave; 360chicago.com.
For more high-altitude adventure, visit the former Sears Tower, now Willis Tower, the second-tallest building in the United States. At 1,353 feet, the observation deck on the building’s 103rd floor features the Ledge—a glass box that extends out more than four feet from the building’s façade and gives you a clear view to the street below. 233 S Wacker Dr; theskydeck.com.
For visitors looking to get fit and calm their souls at elevated heights, both the John Hancock and Willis towers offer yoga. During Saturday morning classes on the John Hancock observation deck, you can meditate and be led by a professional yoga teacher through gentle flow movements and stretches in what operators call Sky Yoga. The $18 registration fee includes admission to the observation deck. Willis Tower recently held a Friday night yoga session led by Zen Yoga Garage (zenyogagarage.com), followed by an after-hours party and a marketplace touting bling from Chicago artists, designers, jewelers and craft makers.
Where Natural and Man-made Beauty Converge
For those used to lying out on lounge chairs on the shores of Caribbean vacation spots or paddle boarding surrounded by nothing but ocean and a flat landscape, Chicago offers an entirely new experience. The setting of Lake Michigan against the backdrop of Chicago’s high rises, with their elegant architecture, makes for a unique aesthetic and a friendly reminder that you’re never far from an urban experience. The 26 miles of Lake Michigan shoreline boasts many free beaches.
The best beach view of the Chicago skyline can be found at Oak Street Beach, where you can also watch or play in professional and amateur volleyball tournaments. After a volleyball game, you can refuel at the full-service restaurant Oak Street Beach Food & Drink (oakstreetbeach.com). If you hit this beach, look for the impressive Jeff Zimmermann mural, “You Know What You Should Do.” One thing you should do is enjoy a pastime popular in Chicago bars and beaches: a game of cornhole, or bags, known outside the Midwest as a bean bag toss through an angled wooden platform. Oak Street Beach, for one, hosts a weekly bags tournament.
North Avenue Beach in the Lincoln Park neighborhood is another favorite among locals and visitors alike for its location just north of downtown Chicago and its many recreational activities. You can rent wakeboards and paddle boards from the Great Lakes Board Company (chicagosup.com). Kayaks are available through Kayak Chicago (kayakchicago.com), while you can rent Jet Skis through Windy City Watersports (312-278-3316). Want to get fit on land? There’s roller hockey and dodgeball, or you can rent a volleyball court. There are also bike rentals at Lakeshore Bike ’n Tune (lakeshorebike.com).
Where to Drink, Creatively
Chicago is a mecca for breweries serving craft beer and unique watering holes for stronger drinks, perhaps too numerous to name. We found a bar that we think offers one of the most creative drink menus—capitalizing on compelling culinary trends—we’ve seen.
Young American, in Chicago’s Logan Square, bills itself as a “progressive bar and kitchen.” It’s got the menu to support that claim. In addition to creative beverages like Spaceface (tequila, blanco vermouth, lime, pineapple, honey, Crème de Menthe), Young American offers nonalcoholic drinks such as No New Friends (Turmeric Tonic Tea, hibiscus, lime and the chickpea egg-white substitute aquafaba) to which you can add CBD for $3. Also on the colorful menu is Restorative Shot— described as “a reviving combination” of turmeric, ginger, schisandra berry and electrolyte powder.
CBD turns up on the food menu, too. An order of Calmonds, an appetizer, is made with chamomile, chicken salt, CBD oil and thyme. And then there’s Goth Bread, made with activated charcoal (which is finding itself in soap and toothpaste these days), leek ash, cheese, smudged butter, yolk
and something mysterious called nighttime sauce. 2545 N Kedzie Ave;
Where to Eat
The city’s frigid cold is not stopping Chicagoans from getting their charcoal-grilled food, especially with the help of the iconic Weber Grills, which has five Midwest Weber Grill Restaurants sporting oversize charcoal kettle grills in its kitchens (with special ventilation systems) to give your steak that taste of summer sizzle.
We feasted on a flavorful, juicy tomahawk ribeye done just right, accompanied perfectly by a wedge salad and shoestring fries, at the downtown Chicago location. It’s no surprise that Weber has three Illinois restaurants; when Weber’s founder, George Stephen, invented the kettle grill in 1952, he worked for Weber Brothers Metal Works in Chicago and was inspired by the shape of a buoy. A statue of Stephen manning one of his grills is at the entrance, and a replica of his first grill is on hand. That, along with the wood-paneling and gas fireplace near our table, added to the warm charm of this restaurant. 539 N State St; webergrillrestaurant.com.
The Big Bowl is a favorite of ours when we visit Chicago. Healthy and flavorful options abound at this Chinese and Thai restaurant, with six other locations. We especially like the DIY dynamic of loading up a bowl with bok choy, carrots and other fresh, locally grown veggies at the Stir Fry Bar, then choosing a sauce (teriyaki is our go-to) and meat (flank steak, in our case), and letting the chefs work their magic in their woks.
We like our bowl with a side of vegetable fried rice (noodles are an option, too). On our last visit, we tried an appetizer of Cantonese ribs with a teriyaki glaze (can’t get enough teriyaki, especially when it’s done right) and scallions. Like that dish, there’s no shortage of plates that let you indulge. But there’s also plenty of healthful fare: cauliflower “rice,” for instance, and other vegetarian choices. We’ll be back to this wonderful eatery that puts the creativity in the hands of patrons, but the work in the hands of its chefs. 60 E Ohio St; bigbowl.com.
Who’s Got the Best Deep-Dish Pizza?
At the turn of the 20th century, Chicago was home to a lively Neapolitan immigrant community that brought with it classic thin-crust pizza. Historians debate who was behind the transition to deep-dish: Some point to Ike Sewell and Ric Riccardo, who in 1943 opened the first Pizzeria Uno on Chicago’s North Side, which served a deeper pizza with a crispier crust and thick layers. Others cite cook Alice May Redmond and pizza chef Rudy Malnati, whose grandsons run Lou Malnati’s, another Chicago favorite.
Loyalty to a particular deep-dish pizza seems as strong as the allegiance to the city’s treasured Cubs—the debate itself is almost sport. At random, we interviewed several young pizza lovers who work in Chicago’s hospitality and retail sectors for their opinions on who’s got the best deep-dish and why. Among other offerings often cited as top notch are those by Gino’s East, Pizano’s and The Art of Pizza.
Nate Long, 25, concierge at Hyatt Regency McCormick Place.
Lou Malnati’s. Multiple locations. Ships pizza. Loumalnatis.com.
It’s the cornbread crust they use—they do the buttered cornbread crust. It’s already a cornbread butter crust base, but then if you ask for the butter crust, it’s not swimming in butter, just a little extra they put on at the end. It’s only 75 cents extra. It still gives you the crunch, but it’s soft. And they’ve got more of a diced-up tomato sauce that I really like. Some people prefer a heavy red sauce like a paste, but the chopped tomatoes give it a home-cooked feel. You’re not getting this runny tomato sauce; it’s not pouring all over your plate and hanging out the edge of your lips.
Oscar Martinez, 19, photographer at John Hancock building’s 360 Chicago experience.
Giordano’s. Multiple locations. Ships pizza. Giordanos.com.
Giordano’s has been around for a long time and you can customize your pizza with flavors and toppings, though I keep it simple with pepperoni. I like the atmosphere; the ones I go to have a quiet, peaceful environment that I like. Most of all, I love the thick cheese filling in the crust—that’s what Giordano’s is known for. The cheese is so thick, it’s like a cake.
Evelyn Herera, 27, sales associate at Mac, a lipstick kiosk in Chicago O’Hare Airport, Terminal 3.
Pequod’s Pizza. 2207 N Clybourn Ave, Chicago and 8520 Fernald Ave,
Morton Grove. Pequodspizza.com.
I like Giordano’s because I love cheese. But I really love Pequod’s. Everything has flavor, including the crust, which is very thick. The crust has a nice seasoning. I think the crust tastes so good because it’s caramelized. The crust looks burnt, but it’s not; it’s really good. I love the crunchiness.
Where to Skate a ‘Ribbon’
At this point you’ll have to wait for late fall, but Chicago has some unique ice skating that’s worth taking a spin. One venue that caught our eye is the Skating Ribbon at Maggie Daley Park, so named because it is more like skating on a track than a traditional ice rink. The path is twice the length of a traditional rink, giving skaters ample space to test their mettle and avoid clumsy collisions. Bonuses are the glorious views of the city’s skyline, as well as the free admission, with skate rentals available. 337 E Randolph St; maggiedaleypark.com.