City guides

Things to know before you go to Chicago

Discover the essential insights for your upcoming trip to the Windy City.

September 19, 2023
 min read
Last updated:
Jan 11
A view of the Chicago skyline, with the Chicago river in the foreground.

Chicago, the third-largest city in the U.S., is a melting pot of culture, history, and iconic landmarks. Nestled on the shores of Lake Michigan, this vibrant city offers a unique blend of architectural marvels, world-class museums, and a culinary scene to die for. Before you pack your bags and head to the heart of the Midwest, here are some top things to know that'll make your visit unforgettable.

The Windy City isn’t just about the breeze

While Chicago is famously known as the "Windy City," the origin of its nickname isn't solely due to the gusts coming off Lake Michigan. Historically, the term was also used to describe the city's politicians, who were often regarded as being full of hot air, boasting about the city's greatness. Over time, the moniker stuck, and today, it serves as a dual reminder of both the city's breezy lakefront and its colorful political history. So, when you're in town, be sure to appreciate both the literal and metaphorical winds that have shaped this incredible city. 

Deep-dish pizza is not the only delicacy

Chicago's deep-dish pizza is legendary, with its thick crust, rich tomato sauce, and gooey cheese. But to limit yourself to just this would be a culinary injustice. The city boasts a diverse food scene, influenced by its rich immigrant history. The Chicago-style hot dog, for instance, is a testament to this, with its array of toppings and strict "no ketchup" rule. Then there's the Italian beef sandwich, dripping in juices and often topped with spicy giardiniera. Each dish tells a story of the people and cultures that have made Chicago their home, making every bite a journey through history. 

Lake Michigan is more than just a lake

Lake Michigan, one of the five Great Lakes, offers more than just a picturesque backdrop to the city. Its shores are lined with beaches, parks, and walking trails, making it a haven for outdoor enthusiasts. In the summer, the lake becomes a hub of activity with locals and tourists alike flocking to its shores for sunbathing, swimming, and water sports. The Navy Pier, jutting out into the lake, offers entertainment, dining, and unparalleled views of the city skyline. As you stand by its shores, it's easy to forget you're by a lake and not an ocean, given its vast expanse and deep blue waters. 

Public transportation is your best friend

Navigating a city as vast as Chicago can seem daunting, but thankfully, the city's public transportation system, especially the 'L' train, makes it a breeze. The elevated train system, affectionately known as the 'L', crisscrosses the city, connecting its various neighborhoods. Not only is it efficient and economical, but it also offers some of the best views of the city's architecture and neighborhoods. Riding the 'L' is an experience in itself, and it's not uncommon to find local musicians serenading passengers during their commute, adding a touch of charm to the journey. 

Chicagoans take their sports seriously

Sports in Chicago is more than just a pastime; it's a way of life. The city is home to some of the most iconic sports teams in the U.S., from the Chicago Bears in football to the Chicago Bulls in basketball. Each team has its own storied history and a dedicated fan base that turns every game into a spectacle. Wrigley Field, home to the Chicago Cubs, is one of the oldest ballparks in the country and offers a nostalgic trip back in time. Whether you're a die-hard sports fan or just looking for a taste of local culture, attending a game is a must. 

It’s a hub for arts and culture

Chicago's cultural scene is as diverse as its population. The Art Institute of Chicago, one of the oldest and largest art museums in the U.S., houses an impressive collection of artworks from around the world. But the city's commitment to the arts doesn't stop at traditional museums. Street art, live music venues, and independent theaters dot the cityscape, offering a platform for emerging artists and performers. The Chicago Symphony Orchestra and the Lyric Opera offer world-class performances for classical music lovers, while the city's many jazz and blues clubs pay homage to its rich musical heritage. 

Summer festivals are the city's specialty

When summer rolls around, Chicago truly comes alive. The city hosts a plethora of festivals, celebrating everything from music and food to art and culture. Events like the Taste of Chicago, Lollapalooza, and the Air and Water Show draw visitors from all over the country. Each festival is a celebration of the city's diversity and creativity, offering a unique blend of experiences. Whether you're looking to sample local delicacies, enjoy live music, or simply soak in the vibrant atmosphere, there's a festival in Chicago that's sure to cater to your tastes. 

The architecture is more than just tall buildings

Chicago's skyline, dotted with iconic skyscrapers, is a testament to its rich architectural history. The city is often credited as the birthplace of the modern skyscraper, and its buildings tell a story of architectural innovation over the years. From the neo-Gothic Tribune Tower to the sleek, modern Willis Tower, each building offers a glimpse into a different era. The Chicago Architecture Center offers boat tours along the Chicago River, providing a unique vantage point to appreciate the city's architectural marvels. As you glide along the river, you'll be treated to stories of the architects and visionaries who shaped the city's skyline. 

It's a city of neighborhoods

Chicago is often described as a city of neighborhoods, each with its own distinct character and charm. From the hipster vibes of Wicker Park to the historic charm of Hyde Park, exploring these neighborhoods offers a more intimate and authentic experience of the city. Each neighborhood has its own set of attractions, eateries, and cultural spots, making them mini cities within the larger metropolis. Taking the time to explore these neighborhoods, interacting with locals, and soaking in their unique vibes can offer insights into the city's soul that's often missed by sticking to just the main tourist spots. 

Winter is cold, but also magical

Chicago's winters are infamous for their brutality, with freezing temperatures and gusty winds. But despite the cold, the city transforms into a magical winter wonderland. The streets are adorned with twinkling lights, ice rinks pop up in parks, and the scent of hot cocoa fills the air. Millennium Park, with its iconic Bean sculpture, becomes a popular spot for ice skating, while the Magnificent Mile, the city's premier shopping district, is decked out in festive decor. While the cold might be biting, the city's festive spirit and winter activities offer plenty of reasons to brave the chill and explore.

Remember that every city has its secrets and quirks. Chicago is no exception. Embrace its diversity, indulge in its offerings, and let the city's charm sweep you off your feet. Safe travels and enjoy every moment in the Windy City!

*Prices fluctuate based on season and day of the week.

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