Whenever I come home to Chicago from time away, I listen to the song “Chicago” by I Fight Dragons. Although many artists have made songs dedicated to my heart city, this one always hits the strongest.
The jewel beside Lake Michigan, Chicago, is the third largest city in the United States. Also known as the Windy City (because of high falutin egos, not actual wind), it is my favorite city in the world. When you visit Chicago, you’ll understand how I fell in love with it and had to move here.
Chicago famously burned almost to the ground during the Great Chicago Fire in 1871. That is how it got the other nickname of The Second City. It is a city reborn. Chicago is known for its incredible art scene, shopping along the famed Magnificent Mile on Michigan Avenue, and (my favorite) deep-dish pizza. Yet this incredible city is so much more than all that.
“Oh Chicago knows how small we are/How bright she shines in the dark/Oh and though I go, she’s in my heart/Chicago holds me when I fall apart”
-“Chicago” by I Fight Dragons
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Kyle Kroeger / ViaTravelers
Kyle Kroeger / ViaTravelers
Kyle Kroeger / ViaTravelers
Kyle Kroeger / ViaTravelers
Kyle Kroeger / ViaTravelers
Kyle Kroeger / ViaTravelers
Kyle Kroeger / ViaTravelers
Kyle Kroeger / ViaTravelers
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Kyle Kroeger / ViaTravelers
Welcome to Chicago
Best Time to Visit
To me, Chicago is a destination all year long. Seeing the rippling Chicago River in springtime, Lincoln Park Zoo in winter, Millennium Park in autumnal splendor, or downtown Chicago in the bustling summer is just too perfect. But if you aren’t a wintertime wanderer like me, you may want to consider the range of Chicago’s seasons.
June to August: Peak tourist season in Chicago is the summer. The weather is hottest (Midwestern humidity is no joke), and the city is the most crowded. This is our festival season, so there is plenty to do, yet hotels will also be at their most expensive. Hit up North Avenue Beach or Oak Street Beach if you need a dip in the lake.
March to May or September to October: Chicago’s shoulder season, these months offer far cheaper accommodation and activities than the summer. The weather is relatively mild, especially in May or September, with warm temps and lovely spring or fall colors.
November to February: Despite the unpredictable winter months in the city, these are my favorite months for visiting Chicago. Particularly if you’ll be spending time in the city center, it’s much easier to explore Chicago when the weather gets colder. Far fewer tourists, cheaper hotel rates, and the romantic snow? Sold. Just don’t underestimate the bitter wind.
Local Customs and Etiquette
First things first, we are serious about our Chicago-style Dogs. Ketchup? We don’t do that — well, I do if it’s just a plain dog. That’s because an actual Chicago Dog is topped with a ton of things already: white onions, pickle relish, yellow mustard, a dill pickle, tomato, pickled sport peppers, and celery salt. You can put ketchup on a hot dog here, but if you’re in public, you might get side-eyed by a local. Don’t worry about it, our bark is worse than our bite.
We have a reputation for being gruff. What you need to remember, though, is that Chicago is part of the Midwest. So even if we do walk faster because we’re city dwellers, we are genuinely kind. If you’re wandering around Lincoln Park and need directions, we’ll help you out. We are genuinely happy to share our city with visitors. I, for one, want you to have the best visit possible.
That said, please don’t come and talk about how “dangerous” our city is. That’s like walking into someone’s home and talking about how much you hate the wallpaper. No place is perfect, and the rumors of Chicago are greatly exaggerated. It really sucks to be in public and hear someone from out of town railing about the place they’re visiting — a frequent occurrence when I ride the train in the touristy summer. Chicagoans are fierce defenders of their beloved city. We’d prefer if you kept your comments to yourself, we aren’t interested in hearing it.
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Plan Your Trip to Chicago
Embark on an unforgettable journey to Chicago, United States. From its rich cultural heritage to its vibrant neighborhoods, this destination offers a unique blend of experiences for every traveler.