Visiting Chicago: A Guide to America's Windy City

With renowned museums, numerous restaurants and a stunning architecture, Chicago is a city to envy.

We have traveled to this town many times and from our first time to our latest trip, we have found the city to grow in its appeal with ever increasing attractions for new and recurring visitors.

Magnificent Mile, Navy Pier and Wear Comfortable Shoes

There are many ways to see Chicago - open deck buses, boat tours along the Chicago River and Lake Michigan - but no matter the mode of transportation you choose, you will eventually need a good pair of shoes.

I say this because you will have to walk in this city, either along its wide streets or inside its large museums. To tell you the truth, one of the best ways to enjoy Chicago is by walking and by doing so, you will get the real feel for the city.  

So bring your best pair of walking shoes with you on your trip!

When arriving in Chicago for the first time, I recommend taking a walk on North Michigan Avenue, also known as the Magnificent Mile. Numerous shops, indoor malls and department stores line this always busy avenue with most of them closing late evening, so you will have plenty of time to get your shopping fix.

Along the way, head to the top of the John Hancock Observatory and relish widespread views of the entire city.

If spending all day shopping is not your thing, hit the Navy Pier located along Lake Michigan. This 3000 foot-long pier features a variety of entertainment, shopping, restaurants and beautiful views of the extensive lake.

A Day at the Museums

For those who enjoy museums, Chicago is a must go! 

Head to Chicago’s Museum Campus on South Lake Shore, where one could spend a full day just exploring the area. The campus has three big museums: Adler Planetarium, Shedd Aquarium and The Field Museum. 

Our all-time favorite has always been the Filed Museum: It houses renowned permanent exhibits such as ancient Egypt, insects, soil as well as its famous dinosaur collection. This museum should be on anyone’s agenda if they come to Chicago. 

Tip: Make sure to choose which museum you want to see first and start from there – they close early evening and are very extensive.

After a long day inside, the city’s iconic Buckingham Fountain is a great spot for photographs as the skyline stretches in the background. If you are here in the evening, you can sit down on one of the many benches and enjoy beautiful views of the city at night.

Appreciating Art at the Art Institute

The city's celebrated Millennium Park is vast, welcoming a daily influx of tourists and residents that come to enjoy its gardens, fountains, events and its several modern sculptures, including the famous Cloud Gate.

Within the park grounds is the renowned Art Institute of Chicago. This extremely large museum needs an entire day to be fully appreciated; however, a three hour run is what we strive for whenever we come to town.

Tip: If you don't feel like spending your whole day inside the Art Institute, at least make a stop to appreciate their Impressionist and Post-Impressionist permanent collections.

Additional spots that we went and you might enjoy:

  • Richard H. Driehaus Museum is a large three-story mansion built in the 1880’s that has been completely remodeled. Visitors can take guided tours of this gorgeous home and its quarters while learning about its preservation methods.

  • If you want to escape the craziness of the city, take a relaxing stroll through the beautiful Lincoln Park located north of downtown. I recommend going to their free, open year-round Zoo and the nearby Conservatory.

  • Lincoln Park Conservatory displays meticulous gardens, well crafted environments and a comprehensive catalog of plants. It is really worth a visit if you enjoy landscaping, but be warned… you will spend a while inside their large greenhouse.


The Wrap-Up: If you really want to enjoy Chicago to its fullest, it is best to stay for at least three full days. Explore it by foot, get out of the main pedestrian ways and you will certainly discover something new. 

The Pizzeria: Grab a bite at Gino’s East Original Pizzeria. Try their Deep Dish Pizza, one of the most iconic dishes of the city.

The Burger Joint: The Billy Goat Tavern. This famous bar is hard to find since it is tucked away under Michigan Avenue. Once you find it, I recommend ordering their renowned Double Cheeseburger.

The Bar: The Berghoff is located near Millennium Park on West Adams. Sit on its magnificent mahogany bar and order their hand crafted brews and tasty German food.

The Café: Snack at Toni Patisserie and Café. Its precise location is East Washington Street and they offer many European inspired sandwiches and in-house made sweets.