The Top Things to Do on a Chicago Weekend Trip

For a city that offers incredible theater, art, nightlife, and food, one weekend may not seem like enough time to explore Chicago. While you can’t see everything, don’t be concerned if you only have a weekend to spend in the Windy City—one weekend is plenty of time to be able to see some amazing attractions. No weekend itinerary in Chicago will be complete without considering these options. From iconic Chicago sightseeing spots to popular shopping destinations, these are some of the top things to do on your next weekend trip to Chicago.

Enjoy views from Willis Tower

For some of the best views in the city, spend part of your weekend at Willis Tower. As Chicago’s tallest building, the view is astounding. Looking at it from the ground up and seeing it reach into the sky is mesmerizing on its own, but don’t pass up on a visit to the Willis Tower Skydeck. At the top floor of the building, you’ll be able to see Chicago from 1,000 feet high. Getting photos here is essential. If heights don’t scare you, there’s a transparent, glass floor in one area where you can walk out onto to see the view directly beneath your feet.

The Skydeck stays open until 10 p.m. on Friday, Saturday, and Sunday. Admission for ages 12 and up starts at $30. Tickets to Chicago’s tallest building will be well worth it on your weekend trip to the Windy City.

Shop on The Magnificent Mile

Spending a few hours on your weekend trip walking around Michigan Avenue—otherwise known as the The Magnificent Mile—to experience luxury retailers, culinary options, and some of the best sightseeing spots in Chicago. The Magnificent Mile is home to over 450 stores, as well as famous architectural spots, such as the Chicago Water Tower. Weekend shopping options span from luxury brands like Burberry and Tiffany & Co. to larger department stores such as Bloomingdale’s.

When you need a break from shopping, visit the Albert in Streeterville for an unforgettable culinary experience. Located steps away from Michigan Avenue, the Albert offers an Italian inspired menu with fresh ingredients, creative recipes, and an array of homemade pastas.

Visit Navy Pier

No trip to Chicago is complete without visiting Navy Pier. Open until 10 p.m. each day, the 3,300 foot long pier offers restaurants, rides, boat tours, shows, and shopping options. If you’re looking to catch a show at the pier, check out the Chicago Shakespeare Theater. They have shows throughout the year, leaving you with no shortage of entertainment options.

One of the main Navy Pier attractions is Centennial Wheel. Reaching a height of nearly 200 feet, rides on Centennial Wheel will give you an incredible view of the Chicago skyline as well as Lake Michigan. The wheel operates until 10 p.m. on weekends and can be booked for adults starting at $18.

Explore The Art Institute of Chicago

Founded in 1879, The Art Institute of Chicago offers an incredible collection of artwork, from paintings to ancient Greek artifacts. Current exhibits at The Art Institute of Chicago include a collection of art from Egypt, a David Hockney collection, and dozens of other pieces that will keep art enthusiasts occupied for hours.

However, if you’re on a tight weekend schedule, explore the museum’s guide of what to see in an hour. This quick tour includes some of the most iconic paintings such as American Gothic and some incredible sculptures. The Art Institute of Chicago is sure to be a hit during your short stay, especially if you enjoy viewing collections of art that span centuries and the globe.

Planning your weekend trip to Chicago 

This list will give you options for planning a weekend packed with fun in Chicago. Consider staying at a boutique hotel like Hotel EMC2 for your weekend trip. Located in the heart of the city, Hotel EMC2 puts you in close proximity to many of Chicago’s best attractions.

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