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An Insider's Guide to Chicago

Ngoc Ngoc Follow Dec 11, 2023 · 4 mins read
An Insider's Guide to Chicago
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Arriving in Winter

The depths of a Chicago winter had been nothing short of brutal. While temperatures usually hover around the freezing mark in January, periodic Arctic blasts can plunge the mercury well below zero, creating a bone-chilling environment that demands extreme layers of clothing. During my last winter in the city back in 1986, the cold was so intense it felt dangerous to even step outside for brief periods without bundling up like an explorer heading to the South Pole. Staying indoors near blasting heaters was the only true refuge from the biting wind and subzero conditions. Thankfully, by July I had escaped to much warmer pastures in South San Francisco.

Beware of the Biting Wind

What makes Chicago winters especially harsh is the relentless prairie wind that seems to find any gap or opening in your many layers. Without adequate protection from the elements, prolonged exposure can lead to frostbite or hypothermia within a startlingly short time frame. Visitors unaccustomed to such Arctic conditions are wise to take local advice seriously when bundling up with scarves, hats, gloves and multiple layers of insulating clothing. Pay special attention to covering any exposed skin and protecting sensitive areas like the ears, nose, hands and feet. A windproof and waterproof outer layer is essential for warding off the slicing gusts.

Finding Friendliness Despite the Frigid Temps

However, what Chicago lacks in mild winters it more than makes up for with the warmth of its people. Residents take pride in being friendly and helpful towards visitors, even during the coldest months. Don’t be afraid to ask locals for directions or recommendations, as most will gladly offer assistance. Exploring popular neighborhoods like River North and Wicker Park presents opportunities to chat with locals in cafes or pubs over a hot drink. Make an effort to learn about the city’s history and you’ll find Chicagoans enjoy sharing their passion and insights with outsiders braving the chill. Although it may be frigid outside, the city’s residents will help thaw your spirits with their trademark Midwestern hospitality.

Savoring Chicago-Style Pizza

No trip to the Windy City is complete without indulging in its signature deep-dish pizza. Loaded with molten cheese, hearty chunks of meat and a thick crust that acts as more of a casserole dish, eating an entire pie oneself is no small feat. My friend who worked at a downtown hotel saw this folly play out repeatedly with visitors unfamiliar with proper portioning.

Resisting the Urge to Conquer the Whole Pie

Each individual slice of Chicago-style pizza is essentially an entire meal on its own. With an average pie containing 8 such hefty slices, attempting to take one down solo is a guaranteed way to end up in a food coma. Out-of-towners with return flights should exercise serious restraint, as finishing even half a pie would be difficult for most. The better strategy is splitting an order with traveling companions so no one feels obligated to force-feed themselves for the sake of not wasting food. Remember, Chicago pizza travels well reheated at home as leftovers too.

Opting for Slice Shop Sampling

A safer option for single diners or those with less vigorous appetites is stopping at one of Chicago’s many pizza slice shops. Here you can taste three or four different slices from specialty pies without overindulging. Some excellent slice shop options include Giordano’s, Louis Pizza and Pizza Pitstop, where prices are very reasonable given the portion sizes. Not only will you avoid the shame of abandoning unfinished pizza, but sampling various slices lets you truly experience the diversity of Chicago’s deep-dish pizza styles.

Experiencing Other Classic Chicago Cuisine

Beyond pizza, Chicago’s food scene offers many iconic dishes worth seeking out. Whether it’s a casual meal or fine dining, trying some local specialties is a must during any visit. Here are a few top recommendations beyond pizza to round out any Chicago culinary tour:

Savoring Italian Beef Sandwiches

A city staple are Italian beef sandwiches - thin-sliced roast beef simmered in broth and topped with giardiniera peppers served on a crusty roll. Local legend claims this sandwich was invented by Chicago Italian immigrants as a way to use less prized cuts of meat. Some of the best in the city include Buona Beef and Portillo’s, where you’ll often see long lines of loyal patrons. Be sure to request it “dipped” to fully soak the bread before consuming.

Enjoying Hot Dogs Chicago-Style

For pure Chicago patriotism, there’s nothing better than an classic hot dog from renowned stands like Hot Doug’s and Mr. Beef on Orchard. What distinguishes a Chicago dog is its popped yellow mustard, chopped white onions, bright green sweet pickle relish, a dill pickle spear and tomato wedges - all nested inside a steamed poppy seed bun. Coupled with non-alcoholic beverage like Chicago Cream Soda, it’s the ultimate ballpark meal on the go.

Indulging in Desserts

The city is also legendary for its tooth-rottingly sweet desserts. Must-tries include deep-dish cookie pies from Xoco; tall fluffy cups of chocolate cake from Floriole Bakery; and creamy rolls of cannoli stuffed with sweet ricotta from Mr. Guido’s Pasta. Chicagoans believe there’s no better way to digest a heavy meal than ending on a high note of decadent sweets.

An Insider's Guide to Chicago

Ngoc
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