Travel Guide to Chicago, Illinois

By Caitlin Hornik

You might know it as The Windy City, but Chicago has so much charm and appeal! From history to culture and delicious deep-dish pizza, here’s a list of not-to-be-missed sights, sounds, and activities for your Chicago trip.

What to Know

Situated on Lake Michigan, Chicago was founded in 1830. It was established as a water transit hub and still today remains a large trade center. Airports have replaced the initial methods of transit, but the intention remains the same.

Chicago is known for its jazz music scene. This is a result of many African-Americans relocating to the city from the south after World War I. Many jazz and blues clubs still populate the city today!

In the 1930s, Chicago became famous due to gangers including Al Capone and John Dillinger. They robbed banks and contributed to a significant time of death and crime in the city. But this was also the time when the city’s political “machine” came about. Essentially, the phrase “Chicago politics” refers to this political machine, in which a singular person runs a political party by choosing candidates who will carry out their determined issues. You can actually take Chicago gangster tours during your trip!

Today, Chicago’s population sits at about 8.8 million people in the metro area. It remains an important city for trade, and its history permeates much of the modern-day culture.

When to Go

Early Spring and Early Fall tend to be the best weather months for a Chicago visit. Temperatures are ideal and you’ll have the best chance to soak up some of the city’s premiere activities, including the beautiful Lake Michigan beaches.

For cold-weather lovers, don’t shy away from your chance to visit during the off-season! It’s no secret that the Winter months are cold and blustery, but it should be noted that Chicago during the holiday season is absolutely beautiful!

How to Get Around

Chicago is laid out like a grid, similar to what you’d see in New York CIty. The Chicago Transit Authority (CTA) is the nation’s second-largest public transportation system. They operate 8 “L” trains and over 100 bus routes. You can actually pay cash for single bus rides or purchase a Ventra Transit Card to travel by bus and train around the city. There are also cabs and ride share services available if you’re more comfortable traveling by car!

What to Eat

Deep-dish pizza is the name of the game in Chicago. Lou Malnati's and Giordano’s are two of the more well-known deep-dish chains. Gino’s East and Pizzeria Uno are also well-loved and applauded as mainstays in the city. Go traditional or opt for mountains of toppings -- You can’t go wrong either way!

If you prefer hot dogs over pizza, you’re in luck! Chicago-style hot dogs are all the rage. They’re served on poppyseed buns and are piled high with yellow mustard, sweet green pickle relish, onion, tomato wedges, pickle spear, and a few other toppings depending on where you’re dining. Portillo's Hot Dogs, Wolfy’s, and Chicago’s Dog House are three of the hottest spots in the city.

Pizza and hot dogs aside, Chicago’s dining scene is loaded with top-tier restaurants and all styles of cuisine. You surely won’t be disappointed!

What to See

The Bean is one of Chicago’s signature highlights. Located in AT&T Plaza within Millennium Park, The Bean is formally known as the Cloud Gate sculpture by artist Sir Anish Kapoor. The nickname comes from the statue’s shape. Stroll through the park and snap a selfie in front of The Bean to serve as a lifelong memory!

Regardless of when you visit, strolling along the Chicago River is a great activity morning or night. If you happen to be visiting for St. Patrick’s Day, it’ll likely be dyed green! It might be chilly, but the green hue will put you in the holiday spirit, and also draw you into the nearest bar for a pint.

While you might not think of Chicago as a beach destination, don’t discount the beautiful beaches with clear blue water along Lake Michigan! Definitely pack a beachy outfit if you’re visiting during the summer months.

In terms of entertainment, Chicago has a bustling arts and sports scene. There are plenty of museums to fill your days, including the famous Art Institute Of Chicago. It is not-to-be-missed! Chicago also has a fantastic theater scene. From Broadway musicals to concerts in every style to the comedy scene, there is no shortage of nightly entertainment. Catch a jazz or blues concert one night, a musical the next, and then a late-night comedy show at The Second City! Then throw in a game depending on the timing of your trip. Chicago has two baseball teams, the Cubs and the White Sox, doubling your chances of being able to witness a ballgame in the Summer. You could also catch the Bears football team, the famous Bulls basketball team, or the Blackhawks hockey team.

Tips and Tricks

Packing tip: Layers are helpful in the Windy City. You can bundle up if it’s cooler or easily pair down as the day heats up. Also, definitely bring an umbrella if you’re visiting during the late Spring/early Summer months!

Day Trips

If you’re looking to enhance your trip, there are plenty of cities and destinations within driving distance of Chicago. South Bend, Indiana is home to the University of Notre Dame. Milwaukee and Madison are two Wisconsin cities with lots of delicious food and beer. There’s no shortage of adventure if you’re willing to find it!

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