It’s always good to plan a short vacation to a new destination. Many people love going to New York, Florida or California. However, they are really missing out on  Illinois. Its capital, Chicago, is famous for being an art and architecture hub as well as a foodie paradise.

This is a smart guide to make the most out of your limited time in the windy city. Despite of what you might hear in the news, Chicago is mostly a safe place to go sightseeing, shopping or eating. But just in case, it is wise to avoid neighborhoods in the south.

Day 1
You should start your trip the right way: head straight to Chicago Loop. This downtown area is also considered a business center. It’s very touristic but not as crowded as Times Square, in NYC. Note: if you find good accommodation in this district, even better. Since most of the tourist attractions are within walking distance, you will save time and money on Uber rides or public transportation.

If you arrive early, go first to the Cloud Gate to snap a picture of the famous giant metal bean. Then, head to Millennium Park and check out the open air theater.

Walk east to see Lake Michigan – the only Great Lake located entirely in the United States. It’s large dimension will make you think you are seeing an ocean. Continue your stroll along the shore on your way to the River Walk. Take in the amazing combination between nature and architecture. Grab a drink in a tiki bar or just sit down on the grass to appreciate the view.

If you are still in the mood to walk, cross the river and make a stop at the Navy Pier. You can grab a bite in one of the restaurants near this area or even go bowling. On the way back, explore the Magnificent Mile region – buildings here are amazing. If you can’t wait to try Chicago’s traditional deep dish, find a Giordano’s for their thick pizza.

Navy Pier and River Walk
Navy Pier and River Walk.

Day 2

Quick breakfast on the go. It’s time to choose a skyscraper to see the city from the top. I’ve been to both Willis Tower and John Hancock building. The first tends to be busier due to the popular crowd looking for great shots of the glass floor. The second has a new attraction that lets you tilt on a glass window.

Next: Field Museum! If you’re lucky,  you’ll get to meet a world-famous Chicagoan resident. I am talking about Sue, the largest, most extensive and best preserved T-rex ever found! The dinosaur’s head is so heavy that it used to be on display separately from its body. I highly advise you to take some time to appreciate this beauty!

If there is enough time, why not explore the Shedd Aquarium? It is right there!

After a lot of intellectual intake, head down Grant Park and contemplate Buckingham Fountain as well as the marvelous skyline. 

Finally, go for some drinks at Miller’s Pub, a historical bar downtown (it’s open since 1935).

View from Chicago 360 John Hancock Building
View from Chicago 360 (John Hancock Building)
Day 3

Make Art Institute of Chicago your first stop. Exploring it takes many hours as it is massive! I only spent a few hours there and I deeply regret it. But if you want to see it all you should do your best to arrive early. Attention: don’t bring big backpacks as you will have to pay to leave them in the locker.

Later, you can stay nearby and visit the American Writers Museum. Travel further to enjoy the peace and quiet of Lincoln Park or see some exotic animals in the Lincoln Zoo.  

Chicago at night
You need to go on some night sightseeing. Chicago looks beautiful anytime of the day.

Many people start to feel tired of so much walking or need to go back home at night, therefore this day has a short itinerary as it is the last one of the journey.

Nevertheless, if you are planning to be in Chicago for a longer time and willing to spend a few more bucks, you can go shopping at the Loop’s stores, attend some baseball game at the Wrigley Field stadium, watch a musical, find a local brewery, go on a river cruise or a film tour.