Chicago may be informally known as America’s “Second City” — a nod to its rebirth after the Great Fire of 1871 and a nickname kept alive by snarky New Yorkers — but to comedian Stephen Colbert, and to millions of Chicagoans who call it home, it’s simply “the greatest city in the world.”
I grew up in the Chicago area and moved back to the city in 2022 shortly after graduating from college. As a Reuters journalist covering commodity markets and agriculture, I spend most of my working hours in our downtown office and sometimes on farms and rural townsacross the country. My off time, however, is spent enjoying everything the city has to offer, from its sandy beaches and unforgettable bars and restaurants to its towering skyline and rich cultural history.
Here are my tips on how to visit like a local:
When to visit: Our concrete metropolis turns into a beach town whenever the weather is warm. Lake Michigan is like a vast inland ocean, where you can swim and boat in glittering waters and play beach volleyball on the soft sand in the spring and summer. Our freezing winters, however, are so extreme that the Chicago Transit Authority will light train tracks on fire to prevent the steel rails from cracking under the icy cold. While visiting in the winter isn’t ideal, even the cold weather and short days aren’t enough to keep Chicagoans at home, and you can still find nightclubs, restaurants and coffee shops brimming with people.
Getting around: Chicago is a city of more than 200 neighborhoods, and even those right next to each other have wildly different personalities. I live in Boystown, the city’s historically LGBTQ+ neighborhood, which is home to drag brunches, rainbow-colored crosswalks and most of the city’s gay bars. Nightclubs pulse with the sound of Chappell Roan’s “Pink Pony Club,” and on summer days, high-heeled drag queens stop to pet my dog as I walk him to the nearby dog beach. Meanwhile, the Uptown neighborhood directly north has more conservative sensibilities. A longstanding landing spot for new immigrants, itfeatures some of the best Hong Kong barbecue duck, Ethiopian tibs and Vietnamese coffee in the city.
The diversity of neighborhoods makes living in the city an adventure, and visitors with the time shouldtry to venture away from the skyscrapers and into the communities that make Chicagospecial. The best way to get around is to ride the “L,” the city’s train system, or to take the less reliable buses.
Definitive food item: Although Chicago-style deep dish pizza is one of the city’s most iconic dishes, jaded Chicagoans sometimes deride it as overrated. Don’t listen to them. One of the best Chicago-style pizzas in the city is at Labriola, a cozy downtown Italian restaurant. Labriola’s deep-dish is made with a buttery crust and is layered with a thick serving of mozzarella cheese, a tangy tomato sauce and toppings that include anything from pepperoni and sausage to basil and burrata.
Deep-dish can take up to 45 minutes to make, so order it first or even call ahead so the restaurant can start baking it before you arrive. When the weather is nice, try to sit on the patio so you can people-watch and enjoy the metropolitan view while you eat.
Getting away: On one of the last days of summer, my boyfriend and I cruised down the city’s 18-mile (29-km), car-free Lakefront Trail on our bikes, enjoying the sunset over Lake Michigan, views of the glittering city skyline and a warm breeze until we got to Shore Club Chicago, a trendy restaurant and bar next to the trail. The restaurant serves summery dishes and cocktails, but the view and the vibes are the main attraction. It’s easy to forget you’re surrounded by high-rises and skyscrapers when you’re sipping a frozen cocktail and looking out on beaches and shimmering water. Though only open for part of the year, it’s one of the best spots alongside the lake to drink, eat and relax.
If you don’t want to shell out too much money at a beachside restaurant, a blanket, some food and a sweet treat from a popsicle cart at any of the city’s 24 free beaches are an equally lovely way to enjoy a relaxed day in the city.
To buy: Merz Apothecary, a family-owned boutique and pharmacy established in 1857, is one of the most unique shops in the city. In the style of an old-timey European apothecary, the store carries niche skincare products, high-end cosmetics and homeopathic medicines. The walls are lined with hundreds of bottles of essential oils and perfumes as well as herbal teas, European candies and holistic vitamins. Last time we visited, we came away with Danish chocolate-covered licorice, an Indian jasmine perfume and sheep-milk soap.
The surrounding Lincoln Square neighborhood is also charming and laid-back, with a heavy German influence. While you’re there, eat bratwurst and spätzle at some of the nearby German restaurants, explore the cobblestoned pedestrian-only street and visit the historictheater and local museums.
To drink: Chicago’s rich Prohibition-era history of mobsters, clandestine bars and bootleg moonshine have given Chicagoans a singular love for speakeasies. The best cocktails I’ve had in Chicago were at The Alderman, an intimate speakeasy-style bar that you enter through Pilsen Yards, a craft taco restaurant in Chicago’s historically Latino neighborhood. The dark room is lit with a chandelier and tableside candles and smells of the palo santo that is kept burning behind the bar. I particularly enjoyed the Sichuan Panda, a cocktail mostly made of baijiu, a fiery Chinese liquor known for its knife-like flavor and high alcohol content. Though I’m half-Chinese, I’d never had a good cocktail made from baijiu, as the liquor’s sharp taste makes it difficult to mix and hard to drink for the uninitiated. This cocktail, however, was peppery, floral and lightly sweet and matched the dark, romantic vibe of the bar.
Hot ticket: Wrigley Field, home of the Chicago Cubs baseball team, is one of the most popular Major League Baseball stadiums for a reason. The century-old stadium and site of Babe Ruth’s “called shot” has a friendly atmosphere as well as a stubborn sense of tradition and historic detail, with its hand-turned scoreboard, ivy-covered outfield walls and live organ music. One longstanding tradition: Any Cubs fan who catches a ball batted by the opposing team is expected to hurl the ball back into the field – or face a crushing amount of peer pressure and stadium-wide chants to “Throw. It. Back.” Sit in the outfield bleachers if you want the classic experience and a party atmosphere, usually complete with overdrinking and heckling. But maybe sit elsewhere if you actually want to watch the game.
The atmosphere at Wrigley and the surrounding neighborhood is unmatched on spring and summer weekends, especially after the Cubs raise the winning flag over the stadium and the crowds sing the victory song.
DATA POINTS
Population: 2.7 million
Number of skyscrapers: 138. The Sears Tower, sometimes called the Willis Tower, stands at the tallest at 1,451-feet (442 meters).
Price of a cup of coffee: $4.00 for single origin coffee at Metric Coffee in West Loop.
Price of an ice cream: $6.30 for a hand-rolled Thai ice cream at Legend Tasty House in Old Chinatown.
A priceless sunset: Adler Planetarium Skyline Walk (Heather Schlitz/Reuters)
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