Welcome to Chicago, IL!

Chi-Town, the Windy City, the home of deep dish and the Cubs. Chicago is an amazing town smack dab in the middle of our country. A big city that thrives with art, theater, history and more, it’s a town that’s easy to fall in love with and hard to leave. The only thing taken more seriously than their food is their sports. Your next few days are going to be full of everything great that you’ve always heard that the town has to offer and maybe a few things you never knew. As ol blue eyes said, bet your bottom dollar that you’ll lose your blues in Chicago…we can’t wait!

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Here's Whym's top ten things to know about Chicago, IL


Welcome to the Windy City, the heart of the Midwest. One of the largest cities in America, constantly abuzz with cutting edge cuisine, die-hard sports fans, and goat based lore. Chicago is a town with big city bustle mixed with Midwestern kindness.

Finding Your Way

Chicago is an absolutely walkable city. When you’re in the heart of the city, many of the main attractions are a short walk away. There are a plethora of cabs and Lyfts are always easy to grab. If you’re looking for the public transportation, the L is the way to go. A 1 day pass is $10, 3 days is $20, and 7 days is $28.

Airport Deets

There are 2 airports in Chicago. From O’Hare, it’s 45 minutes on the Blue L for $5 or a Lyft for $35-45. From Midway, take the Orange L for 25 minutes for $2.25 or a Lyft for $25-35.


Chicago’s history is one of resilience. One of the largest cities in America, it suffered a fire that forced it to completely rebuild which it did quickly - literally upon the ashes of the fire. It would survive strikes, massacres and a baseball team that would spend more than a century trying to win a title. In the end, Chicago couldn’t be kept down and gave us things like the world’s first skyscraper, brownies, cell phones and Walt Disney.

Why Am I Here?

Chicago is centrally located, has incredible architecture, world renowned art, thrilling history, and record setting sports all ensconced in a city with idyllic lakeside views. Chicago is constantly bustling, constantly thriving, and constantly entertaining. A trip here is filled to the brim with excitement, energy, and Midwestern warmheartedness.


Chicago has earned its nickname of “The Windy City” with almost 7 months of blustery conditions. In the winter, the temperature ranges from 22-42°, with lots of snow. In the spring, the temperature climbs steadily, from 43-73° and rain. The summer is beautiful and temperate, ranging from 60-80° and can be humid. Fall is mid-70s to mid-40s with heavy cloud cover.

Local Delicacies

You can’t discuss Chicago without discussing food and there are three key meals that you have to try to really say you’ve been to Chicago. One is Italian beef – roast beef served on a long Italian roll often topped with either hot or sweet peppers and dipped or soaked in au jus. Another is  the Chicago style dog – a hot dog on a poppy seed bun with yellow mustard, relish, tomato, onion, a pickle spear, hot peppers and celery salt. And last but not least, deep dish pizza is a religion in Chicago – cheesy, gooey, and delicious, a visit doesn’t count without trying it!


Chicago is a great town for shopping, so you’ll have no problem bringing home some great things. But probably the most famous souvenir to bring home from Chicago is Garrett Popcorn. A local brand with delicious options, their caramel corn is frequently rated the best in the country. Sure it’s touristy but it’s fun and definitely a thing to do.


Chicago is one of the largest cities in the country and it definitely finds its own approach to style. Chicagoans have a practical approach to fashion, especially with the weather swings. A little more modest with many more layers, Chicagoans pride themselves on ready for any weather – anything goes!

Must Know

Chicago is built on a grid, so don’t forget that if you’re going towards the lake, you’re going east; the center of the grid is the intersection of State & Madison with State dividing the East-West streets and Madison dividing the North-South. The Magnificent Mile is is the premier commercial district with upscale shops, cool restaurants, posh hotels and amazing landmarks including the Willis Tower, which locals still call the Sears Tower. Either way, it’s definitely worth a visit!

She is novelty; for she is never the Chicago you saw when you passed through the last time

- Mark Twain