Photo of Chicago City


If you are looking for great pizza, cold beer, and friendly faces, Chicago is where you’ll find them. Chicago has so much to offer in each neighborhood, properly exploring the city would take a lifetime. If you are only here for a short while, though, see our list of travel highlights below.

Where to go

Chicago is a city of neighborhoods (more than 200, to be exact) – and while we recommend you visit each one, here are a few must-see spots in the Windy City:

Millennium Park

Catch a concert or simply enjoy the amazing architecture along the lake. There are a thousand ways to enjoy Millennium Park. This area hosts concerts in the summer and features an outdoor ice rink in the winter. It is also home to a sculpture garden and the city’s most iconic sculpture, the Cloud Gate, aka the “Bean”.

Art Institute of Chicago

Recently named the Best Museum in the World, the Art Institute of Chicago is home to more than 300,000 pieces of art and some of the greatest views of Chicago. Sip a latte in their modern art café or enjoy classical masterpieces. The museum is the perfect way to spend a cold winter day.

Willis Tower Skydeck

See the city from a new perspective atop America’s tallest skyscraper. The Willis Tower Skydeck is 103 floors (142 meters) above the street and allows you to face your mortality by standing above air in a glass box. It’s a must-see experience for the Chicago first-timer.


Catch a Cubs baseball game at the famous Wrigley Field or grab a drink from a neighboring bar. While the baseball team hasn’t won a World Series title in over a century, at least the beer is always cold. Walk around the vibrant neighborhood to find some of the best hot dogs and pizza in the city, too.


Nicknamed the Windy City for its long-winded politicians, the weather also lives up to this name. While spring, summer and winter are all beautiful times to visit, Australians might find winter too abrasive. Temperatures often drop to dangerous lows and wind chills make travel downright dangerous. Do not visit Chicago in the winter unless you already own a substantial winter coat.

Travel Tips

Chicago is the murder capital of the United States. Gun violence is incredibly prevalent in some neighborhoods and gang activity is common. While many tourist areas are relatively safe, southern parts of the city should be visited with caution. (This, of course, is with some exceptions: the White Sox stadium is located in South Chicago, as is the world-renowned University of Chicago.) The city’s above-ground subway system, known as the “L” is a safe and inexpensive way to see both of these sites, though it can be slow at times. Some train lines close late at night, so be sure to check schedules and plan trips ahead if you plan to travel by L.

Chicago is a truly diverse and changing city. Do not let its negative reputation scare you away from visiting. Have peace of mind when you purchase an international travel policy from Cover-More Travel Insurance. Let us do the worrying for you.

Image courtesy of Flickr user Jamie McCaffrey