How to Spend the Perfect Weekend in Chicago

If you’re visiting Chicago for a quick weekend visit, you’ll want to make the most of your trip. There’s plenty of things to do in the city this spring, and many attractions you’ll want to check off on your bucket list. While it’s impossible to tackle everything in one visit—especially if you are just staying in the city for the weekend—it’s a good idea to prioritize the hotspots you most want to see during your travels. If you’re only visiting Chicago for the weekend or a short time, here are the top things you should definitely do to have the best possible trip.

Visit an art museum

Chicago has a fantastic art and design oriented culture, and there are many wonderful art museums to explore throughout the city, including The Art Institute of Chicago. This spring, you’ll be able to see a variety of exhibits at The Art Institute of Chicago, including exhibits such as Monet and Chicago, Jewelry of South Asia’s Nomadic Cultures, and Richard Hunt: Scholar’s Rock or Stone of Hope or Love of Bronze. Other art museums you could visit over the weekend include the Museum of Contemporary Art and the Museum of Illusions. Make sure to buy tickets online before your trip so that you won’t miss out on any of these exciting art museums.

Laugh at a comedy show

Chicago is known for its tremendous comedic talent, and you can’t go wrong with securing tickets to a comedy show at Second City during your weekend stay. Starting May 7, Chicago’s famous The Second City will be offering shows once more again. The Second City is an improvisational comedy enterprise that has been the starting point for many famous comedians and actors such as Steve Carell, Amy Poehler, and Tina Fey.

Dine on an outdoor patio

Now that it is officially springtime and the weather is warmer, restaurants in Chicago are opening their outdoor patios to diners once again. Book a reservation if necessary, and then enjoy dining outside in the spring weather. Plus, it’s the perfect time to snap a selfie with your plate full of delicious food. For both an Instagrammable and delicious dining experience, visit the Albert in Streeterville located conveniently right next to Michigan Avenue, to try signature and innovative dishes.

See the sights from Willis Tower

Willis Tower, which used to be known as Sears Tower, is the second tallest building in the Western hemisphere at 110 stories. Currently, it houses an observation deck, called Skydeck Chicago, which attracts people from all over the world who are visiting the city. Skydeck Chicago offers visitors unobstructed views 1,353 feet straight down through a series of glass bays on the 103rd floor. If you plan to visit Skydeck Chicago in the future, make sure to check their website to see if they are currently open to visitors.

Explore Millennium Park

Millennium Park is one of the most popular bucket list activities in Chicago, and one you can’t miss if you’re visiting for the weekend. The park’s reflective “bean” sculpture is known for its unique shape, as well as its reflection of the city around it. The park also has other art exhibitions, sculptures, and a 3.5-acre garden. This location is perfect for photographers of all skills to take pictures, from professional to amateur. It’s one of the most iconic parks in Chicago, so make sure you plan this activity into your itinerary so that you can show your friends and family photos of this famous landmark after your trip.

Planning your trip to Chicago

Whether you choose to visit Chicago for a short weekend trip or longer, you’ll have a unique and thrilling experience. After you’ve selected your travel dates, you’ll need to decide where you’ll stay on your trip. Consider booking a hotel located in the heart of the city, close to nearly everything. Next up, pack your bags with essentials like comfortable walking shoes and a face covering to keep you safe and healthy. Now you’re ready for your upcoming trip to Chicago filled with breathtaking adventures and spectacular sights. 

Need a place to stay when visiting Chicago? Book your reservation here.