A Pocket Guide for Exploring Chicago

Looking for some fun things to do in Chicago over the weekend? Luckily, the city is full of hidden gems, excellent museums, fantastic eateries, awesome public art, inspiring architecture, and not to mention one seriously impressive shopping strip.

We take a look at some of the top things to do if you’re planning on spending a weekend in this wonderful city.

First, plan your trip

This may seem a bit obvious, but before you travel to the Windy City, be sure to plan your trip out properly. If you’re only spending a couple of days somewhere, then you want to make sure that you make the most of your short stay.

Besides the obvious, such as buying your plane ticket or booking accommodation, you should also list some locations you’re interested in visiting. You can then make an itinerary for what to see on what day, considering things like opening hours, distance from one location to the next, and budget.

Now, two days doesn’t give you much time to explore a city, so a great way to check out some of the top attractions is to purchase a hop on, hop off bus tour ticket. You can get a 1 or 2-day ticket, which is pretty handy as the tour takes you past some of the famous spots around Chicago including the Magnificent Mile, Millennium Park, John Hancock Center, The Wrigley Building, and more.

Image source: Pixabay

To save some money on your ticket, pre-book online instead of buying it on-street, or purchase a Go Chicago card where you can get access to several attractions for a single low price. They give you the option to build your own pass too, so if you already know which attractions you want to visit, you can pick and choose only what you’re interested in.

Here, we’ve put together a sample itinerary to give you some ideas.

Day 1

Start off at the John Hancock Tower and head up to the 360 Chicago Observatory to experience awe-inspiring views of the city from the observation deck located on the 94th floor. There’s a tilting glass lookout 1000 feet up if you’re up for a thrill ride.

The Magnificent Mile, a mile-long stretch between Lake Shore Drive and the Chicago River, is just a short walk from there. With about 900 stores and nearly 300 restaurants, you could spend the whole day here! Besides shopping, be sure to take in the incredible architecture and history this spot has to offer.

Image source: Pixabay

After that, head over to Millennium Park for a selfie at “The Bean,” a public sculpture by artist Sir Anish Kapoor, which is actually called Cloud Gate. The polished stainless-steel sculpture reflects the city’s skyline beautifully, capturing some of its best-known buildings.

Image source: Pixabay

Next stop on your list should be the Art Institute of Chicago, which is the second largest art museum in the U.S. and considered to be one of the best museums in the world. Some of the highlights include The Thorne Miniature Room, and paintings by Matisse, Georgia O’Keeffe, Renoir, and Van Gogh.

If you time it right, you can stay there for some dinner. There are a few places to choose from, but the Terzo Piano has excellent food and stunning views of the city, which can be enjoyed from the outdoor rooftop, as well as indoors. We recommend booking in advance as it’s a popular spot, and also requesting a window seat if you’re eating indoors for the best views.

Day 2

Start your second day off at Grant Park, where you’ll find the magnificent Buckingham Fountain. It’s one of the largest fountains in the world and puts on some pretty impressive choreographed displays, with water shooting up as high as 150 feet into the air.

Image source: Pixabay

From there, you can visit The Field Museum, one of the best natural history museums in the world. Learn about different cultures and fascinating history, including things like evolution, Egyptian mummies, dinosaurs, and ancient American art.

Shedd Aquarium is another popular attraction a short walk from the museum, which houses around 32,000 creatures. To make the most of your day, be sure to check out some of their special experiences, including the aquatic presentations, animal chats, and animal encounters.   

If stars are more your thing, or if you feel you have the time, then check out Adler Planetarium. All three attractions are within walking distance to each other, so it’s easy to hop from one place to the next. You’ll find some pretty impressive views of Chicago’s skyline here, too.

Image source: Pixabay

After a long day of museum hopping, you’ll probably be looking forward to a nice dinner. We all know the city is best known for its deep-dish pizza, so why not head over to Gino’s Pizza and tuck into some delicious, Chicago-style pizza? You may have to stand in line for a while, but trust us, it will be worth the wait!